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oxalicacid|C2H2O4PubChem

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CHEMISTRY
D A T A B A S E

PUBCHEM COMPOUND OXALICACID

OxalicAcid

CitethisRecord

Vendors

Drug Information

Pharmacology

Literature

Patents

Bioactivities

PubChemCID:

971
OxalicacidEthanedioicacid144627AktisalAquisalOxiric

ChemicalNames:

acid More...

MolecularFormula:

C2H2O4

MolecularWeight:

90.03488g/mol

InChIKey:

MUBZPKHOEPUJKRUHFFFAOYSAN

UNII:

9E7R5L6H31

SafetySummary:

LaboratoryChemicalSafetySummary(LCSS)

ModifyDate:

20151031

CreateDate:

20040916

Oxalicacidisastrongdicarboxylicacidoccurringinmanyplantsandvegetables.Itisproducedinthebodyby
metabolismofglyoxylicacidorascorbicacid.Itisnotmetabolizedbutexcretedintheurine.Itisusedasan
analyticalreagentandgeneralreducingagent.
fromMeSH
Oxalicacidisanodorlesswhitesolid.Sinksandmixeswithwater.(USCG,1999)
PhysicalDescriptionfromCAMEOChemicals

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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Contents
12DStructure
23DConformer
3NamesandIdentifiers
4ChemicalandPhysicalProperties
5RelatedRecords
6ChemicalVendors
7DrugandMedicationInformation
8PharmacologyandBiochemistry
9UseandManufacturing
10Identification
11SafetyandHazards
12Toxicity
13Literature
14Patents
15BiomolecularInteractionsandPathways
16BiologicalTestResults
17Classification
18InformationSources

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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1 2DStructure
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Download

GetImage

Magnify

fromPubChem

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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2 3DConformer
Search

Download

GetImage

ShowHydrogens

ShowAtoms

Magnify

Animate
fromPubChem

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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3 NamesandIdentifiers
3.1 ComputedDescriptors
3.1.1 IUPACName
oxalicacid
fromPubChem

3.1.2 InChI
InChI=1S/C2H2O4/c31(4)2(5)6/h(H,3,4)(H,5,6)
fromPubChem

3.1.3 InChIKey
MUBZPKHOEPUJKRUHFFFAOYSAN
fromPubChem

3.1.4 CanonicalSMILES
C(=O)(C(=O)O)O
fromPubChem

3.2 OtherIdentifiers
3.2.1 CAS
144627
fromDrugBank,EPAChemicalDataReport,ILOICSC,NIOSHPocketGuide,OSHAOccupationalChem

3.2.2 ECNumber
2056343
fromILOICSC
2056343
fromECHA
2089321
fromECHA
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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2139508
fromECHA

3.2.3 ICSCNumber
0529
fromILOICSC

3.2.4 RTECSNumber
RO2450000
fromILOICSC
RO2450000
fromNIOSHPocketGuide

3.2.5 UNNumber
3261
fromILOICSC,CAMEOChemicals
1759
fromNJDOHRTKHazardousSubstanceList

3.2.6 UNII
9E7R5L6H31
fromFDA/SPLIndexingdata

3.2.7 Wikipedia
Oxalicacid
fromWiki

3.3 Synonyms
3.3.1 MeSHSynonyms
1. Acid,Oxalic

11. FerricOxalate

21. MonosodiumOxalate

31. Oxalate,

2. AluminumOxalate

12. Iron(2+)Oxalate(1:1)

22. Oxalate,Aluminum

32. Oxalate,

3. AmmoniumOxalate

13. Iron(3+)Oxalate

23. Oxalate,Chromium

33. Oxalate,

4. Chromium(2+)Oxalate

14. IronOxalate

24. Oxalate,Diammonium

34. Oxalate,

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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5. Chromium(3+)Oxalate(3:2)

15. MagnesiumOxalate

25. Oxalate,Dilithium

35. Oxalate,

6. ChromiumOxalate

16. MagnesiumOxalate(1:1)

26. Oxalate,Dipotassium

36. Oxalate,

7. DiammoniumOxalate

17. Manganese(2+)Oxalate(1:1)

27. Oxalate,Disodium

37. Oxalate,

8. DilithiumOxalate

18. MonoammoniumOxalate

28. Oxalate,Ferric

38. OxalicA

9. DipotassiumOxalate

19. MonohydrogenMonopotassiumOxalate

29. Oxalate,Iron

39. Potassiu

20. MonopotassiumOxalate

30. Oxalate,Magnesium

40. Potassiu

10. DisodiumOxalate

fromMeSH

3.3.2 DepositorSuppliedSynonyms
1. oxalicacid

11. Acidumoxalicum

21. Acidoossalico[Italian]

31. CHEBI:16995

2. ethanedioicacid

12. Acideoxalique

22. Kyselinastavelova[Czech]

32. MUBZPKHOEPUJ

3. 144627

13. Acidoossalico

23. EPAPesticideChemicalCode009601

33. EINECS2056343

4. Aktisal

14. CaswellNo.625

24. HOOCCOOH

34. STK379550

5. Aquisal

15. Ethanedionicacid

25. CCRIS1454

35. Oxalicacid

6. Oxiricacid

16. Oxaalzuur[Dutch]

26. AI326463

36. DSSTox_CID_581

7. oxalate

17. NCIC55209

27. HSDB1100

37. C00209

8. Oxaalzuur

18. Oxalsaeure[German]

28. NSC62774

38. DSSTox_RID_779

9. Oxalsaeure

19. Acideoxalique[French]

29. BRN0385686

39. DSSTox_GSID_25

20. Ethane1,2dioicacid

30. UNII9E7R5L6H31

40. Oxalicacidstanda

10. Kyselinastavelova

fromPubChem

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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4 ChemicalandPhysicalProperties
4.1 ComputedProperties
MolecularWeight

90.03488g/mol

MolecularFormula

C2H2O4

XLogP3

0.3

HydrogenBondDonorCount

HydrogenBondAcceptorCount

RotatableBondCount

ExactMass

89.995309g/mol

MonoisotopicMass

89.995309g/mol

TopologicalPolarSurfaceArea

74.6A^2

HeavyAtomCount

FormalCharge

Complexity

71.5

IsotopeAtomCount

DefinedAtomStereocenterCount

UndefinedAtomStereocenterCount

DefinedBondStereocenterCount

UndefinedBondStereocenterCount

CovalentlyBondedUnitCount

1
fromPubChem

4.2 ExperimentalProperties
4.2.1 PhysicalDescription
1. DryPowder
2. OtherSolid
3. PelletsLargeCrystals
fromEPAChemicalDataReport
HYGROSCOPICCOLOURLESSCRYSTALSORWHITEPOWDER.
fromILOICSC
Colorless,odorlesspowderorgranularsolid.
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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fromNIOSHPocketGuide,OSHAOccupationalChemicalDB
Oxalicacidisanodorlesswhitesolid.Sinksandmixeswithwater.(USCG,1999)
fromCAMEOChemicals

4.2.2 Color
ANHYDROUSOXALICACID,CRYSTALLIZEDFROMGLACIALACETICACIDISORTHORHOMBIC,
CRYSTALSBEINGPYRAMIDALORELONGATEDOCTAHEDRA
Budavari,S.(ed.).TheMerckIndexEncyclopediaofChemicals,DrugsandBiologicals.Rahway,NJ:MerckandCo.,Inc.,
1989.,p.1093

fromHSDB
Colorlesspowderorgranularsolid[Note:Theanhydrousform(COOH)2isawhitepowder].
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.94116.Washington,D.C.:U.S.
GovernmentPrintingOffice,June1994.,p.238

fromHSDB

4.2.3 Odor
Odorless.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.94116.Washington,D.C.:U.S.
GovernmentPrintingOffice,June1994.,p.238

fromHSDB

4.2.4 BoilingPoint
Sublimes
fromNIOSHPocketGuide,OSHAOccupationalChemicalDB

4.2.5 MeltingPoint
189.5DEGC(DECOMPOSES)
Budavari,S.(ed.).TheMerckIndexEncyclopediaofChemicals,DrugsandBiologicals.Rahway,NJ:MerckandCo.,Inc.,
1989.,p.1093

fromHSDB
189.5decC
PhysProp

fromDrugBank
189.5C
fromILOICSC
215F
fromNIOSHPocketGuide,OSHAOccupationalChemicalDB
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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372F(Decomposes)
(NTP,1992)

fromCAMEOChemicals

4.2.6 Solubility
100GAQSOLNSATURATED@15DEGCCONTAINS6.71G100GAQSOLNSATURATED@20DEGC
CONTAINS8.34G100GAQSOLNSATURATED@25DEGCCONTAINS9.81G
Budavari,S.(ed.).TheMerckIndexEncyclopediaofChemicals,DrugsandBiologicals.Rahway,NJ:MerckandCo.,Inc.,
1989.,p.1093

fromHSDB
VERYSOLINETHANOLSLIGHTLYSOLINETHERINSOLINBENZENE,CHLOROFORM,PETROLEUM
ETHER
Weast,R.C.(ed.).HandbookofChemistryandPhysics.60thed.BocaRaton,Florida:CRCPressInc.,1979.,p.C409

fromHSDB
Watersolubilityof220,000mg/lat25degC
YalkowskySHetalArizonaDataBaseofWaterSolubility(1989)

fromHSDB
WaterSolubility
220000mg/L(at25C)
YALKOWSKY,SH&DANNENFELSER,RM(1992)

fromDrugBank
Solubilityinwater,g/100mlat20C:910(moderate)
fromILOICSC
14%[g/100mL]
fromNIOSHPocketGuide
50to100mg/mLat75F
(NTP,1992)

fromCAMEOChemicals

4.2.7 Density
1.90@17DEG/4DEGC,ALPHA
Budavari,S.(ed.).TheMerckIndexEncyclopediaofChemicals,DrugsandBiologicals.Rahway,NJ:MerckandCo.,Inc.,
1989.,p.693

fromHSDB
Density(atC):1.9g/cm
fromILOICSC
1.9
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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fromNIOSHPocketGuide,OSHAOccupationalChemicalDB
1.9at59F
(USCG,1999)

fromCAMEOChemicals

4.2.8 VaporDensity
4.3
(NTP,1992)

fromCAMEOChemicals

4.2.9 VaporPressure
0.54mm@105degC
Clayton,G.D.andF.E.Clayton(eds.).Patty'sIndustrialHygieneandToxicology:Volume2A,2B,2C:Toxicology.3rded.New
York:JohnWileySons,19811982.,p.4936

fromHSDB
<0.001mmHg
fromNIOSHPocketGuide
<0.001
fromOSHAOccupationalChemicalDB
0.001mmHgat68F
(NTP,1992)

fromCAMEOChemicals

4.2.10 LogP
0.81
fromILOICSC

4.2.11 LogS
0.38
ADMEResearch,USCD

fromDrugBank

4.2.12 Stability
OXALICACIDCANBEDEHYDRATEDBYCAREFULDRYING@100DEGC,BUTLOSSESOCCUR
THROUGHSUBLIMATION/OXALICACIDDIHYDRATE/
Budavari,S.(ed.).TheMerckIndexEncyclopediaofChemicals,DrugsandBiologicals.Rahway,NJ:MerckandCo.,Inc.,
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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1989.,p.897

fromHSDB

4.2.13 Decomposition
...DECOMPPRODUCTSINCLCARBONMONOXIDE&FORMICACID.
NationalFireProtectionAssociation.FireProtectionGuideonHazardousMaterials.7thed.Boston,Mass.:NationalFire
ProtectionAssociation,1978.,p.49224

fromHSDB
seeNotes.
fromILOICSC

4.2.14 HeatofCombustion
245.61KJ/mol
KirkOthmerEncyclopediaofChemicalTechnology.3rded.,Volumes126.NewYork,NY:JohnWileyandSons,19781984.,p.
V16619(1981)

fromHSDB

4.2.15 DissociationConstants
pKa1:1.46pKa2:4.40
Clayton,G.D.andF.E.Clayton(eds.).Patty'sIndustrialHygieneandToxicology:Volume2A,2B,2C:Toxicology.3rded.New
York:JohnWileySons,19811982.,p.4936

fromHSDB

4.2.16 KovatsRetentionIndex
Semistandardnonpolar

748
fromNIST

4.3 CrystalStructures
CrystalStructures:1of5
CCDCNumber

929767

CrystalStructureData

DOI:10.5517/cc106hh6

AssociatedArticle

DOI:10.1021/cg400668w
fromTheCambridgeStructuralDatabase

CrystalStructures:2of5
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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CCDCNumber

929768

CrystalStructureData

DOI:10.5517/cc106hj7

AssociatedArticle

DOI:10.1021/cg400668w
fromTheCambridgeStructuralDatabase

CrystalStructures:3of5
CCDCNumber

929769

CrystalStructureData

DOI:10.5517/cc106hk8

AssociatedArticle

DOI:10.1021/cg400668w
fromTheCambridgeStructuralDatabase

CrystalStructures:4of5
CCDCNumber

929770

CrystalStructureData

DOI:10.5517/cc106hl9

AssociatedArticle

DOI:10.1021/cg400668w
fromTheCambridgeStructuralDatabase

CrystalStructures:5of5
CCDCNumber

929771

CrystalStructureData

DOI:10.5517/cc106hmb

AssociatedArticle

DOI:10.1021/cg400668w
fromTheCambridgeStructuralDatabase

4.4 SpectralProperties
IR:8279(SadtlerResearchLaboratoriesIRGratingCollection)
Weast,R.C.andM.J.Astle.CRCHandbookofDataonOrganicCompounds.VolumesIandII.BocaRaton,FL:CRCPressInc.
1985.,p.V1946

fromHSDB
NMR:17060(SadtlerResearchLaboratoriesSpectralCollection)
Weast,R.C.andM.J.Astle.CRCHandbookofDataonOrganicCompounds.VolumesIandII.BocaRaton,FL:CRCPressInc.
1985.,p.V1946

fromHSDB
MASS:52(NationalBureauofStandardsEPANIHMassSpectraDataBase,NSRDSNBS63)
Weast,R.C.andM.J.Astle.CRCHandbookofDataonOrganicCompounds.VolumesIandII.BocaRaton,FL:CRCPressInc.
1985.,p.V1946

fromHSDB

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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4.4.1 GCMS

1of3

NISTNumber

229396

Library

Mainlibrary

TotalPeaks

20

m/zTopPeak

45

m/z2ndHighest

46

m/z3rdHighest

29
CLICKTOLOAD...

Thumbnail

fromNIST

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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5 RelatedRecords
CLICKTOLOAD...

fromNCBI

5.1 RelatedCompoundswithAnnotation
CLICKTOLOAD...

fromPubChem

5.2 RelatedCompounds
SameConnectivity

7records

SameParent,Connectivity

930records

SameParent,Exact

920records

Mixtures,Components,and
NeutralizedForms

37111records

SimilarCompounds

279records

SimilarConformers

396records
fromPubChem

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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5.3 Substances
5.3.1 RelatedSubstances
All

139987records

Same

391records

Mixture

139596records
fromPubChem

5.3.2 SubstancesbyCategory
CLICKTOLOAD...

fromPubChem

5.4 EntrezCrosslinks
PubMed

3531records

ProteinStructures

77records

Taxonomy

2records

Gene

11records
fromPubChem

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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6 ChemicalVendors
CLICKTOLOAD...

fromPubChem

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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7 DrugandMedicationInformation
7.1 DrugWarning
Ascorbicacidingestioninhighdosesisassociatedwithoxalatedepositionintissueindialysispatients./Oxalates/
Haddad,L.M.,ClinicalManagementofPoisoningandDrugOverdose.2nded.Philadelphia,PA:W.B.SaundersCo.,1990.,p.
702

fromHSDB

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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8 PharmacologyandBiochemistry
8.1 MeSHPharmacologicalClassification
ReducingAgents
Materialsthataddanelectrontoanelementorcompound,thatis,decreasethepositivenessofitsvalence.(From
McGrawHillDictionaryofScientificandTechnicalTerms,5thed) SeealistofPubChemcompoundsmatching
thiscategory.
fromMeSH

8.2 Absorption,DistributionandExcretion
TARTARIC&OXALICACIDSAREEXCRETEDINURINEUNCHANGED.
Parke,D.V.TheBiochemistryofForeignCompounds.Oxford:PergamonPress,1968.,p.141

fromHSDB
Theabsorptionof(14)ClabelledoxalicacidwasstudiedinWistarrats,CD1miceandNMRImice.Oxalicacidin
solutionwasgiventotheanimalsbygavageeitherwithwateraloneorwith0.625g/kgbodywtofxylitol.Both
xylitoladaptedanimalsandanimalsnotpreviouslyexposedtoxylitolwereused.Adaptationtoxylitoldiets
enhancedtheabsorptionandurinaryexcretionofthelabel(oxalicacid)inbothstrainsofmicebutnotinrats.
Earlierstudieshaveindicatedahighincidenceofbladdercalculiinmicebutnotinratsfedhighamountsofxylitol.
Theresultsofthepresentstudyofferonelikelyexplanationfortheincreasedformationofbladdercalculiasaresult
ofoversaturationofurinewithoxalate. Abstract:PubMed
SalminenSetalToxicolLett44(12):11320(1988)

fromHSDB

8.3 Metabolism/Metabolites
INRABBIT,MAJORENDPRODUCTOFMETABOF(14)CETHYLENEGLYCOLISRESPCARBONDIOXIDE
(60%OFDOSEIN3DAYS),&METABOLITESEXCRETEDINURINEAREUNCHANGEDETHYLENE
GLYCOL(10%)&OXALICACID(0.1%)....GLYCOLALDEHYDE,GLYCOLLICACID&GLYOXYLICACIDARE
INTERMEDIATESINCONVERSIONTOCARBONDIOXIDE.
Parke,D.V.TheBiochemistryofForeignCompounds.Oxford:PergamonPress,1968.,p.214

fromHSDB
INOXIDATIVEMETABOFETHYLENEGLYCOLINMAMMALS,SPECIESVARIATIONSOCCURWHICH
EXPLAIN...DIFFERENCESINTOXICITY.GLYCOLISOXIDIZEDBYMAJORPATHWAYINTOCARBON
DIOXIDE,&BYMINORPATHWAYTO...OXALICACID.EXTENTOFFORMATIONOFOXALICACIDIS
DEPENDENTONDOSELEVEL,BUTHAS...BEENSHOWNTOVARYWITHSPECIES...
Parke,D.V.TheBiochemistryofForeignCompounds.Oxford:PergamonPress,1968.,p.118

fromHSDB
INITIALSTEPSINOXIDATIONOFETHYLENEGLYCOLTODIALDEHYDE(GLYOXAL)&TOGLYOXYLIC
ACIDSEEMTOBEMEDIATEDBYALCDEHYDROGENASEDECARBOXYLATIONOFGLYOXYLICACID
YIELDSCARBONDIOXIDE&FORMICACID.GLYOXYLICACIDISALSOOXIDIZEDTOOXALICACID.
Gilman,A.G.,L.S.Goodman,andA.Gilman.(eds.).GoodmanandGilman'sThePharmacologicalBasisofTherapeutics.7thed.
NewYork:MacmillanPublishingCo.,Inc.,1985.,p.1637

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fromHSDB
Piridoxilateisanassociationofglyoxylicacidandpyridoxineinwhichpyridoxineissupposedtofacilitateinvivo
transformationofglyoxylicacidtoglycineratherthantooxalicacid.However,ithasrecentlybeenshownthatlong
termtreatmentwithpiridoxilatemayresultinoverproductionofoxalicacidandincalciumoxalatenephrolithiasis.A
patientinwhompiridoxilateinducedbothoxalatenephrolithiasisandchronicoxalatenephropathywithrenal
insufficiency,anassociationthathasnotbeenpreviouslydescribed,wasreported.Therefore,piridoxilateshouldbe
addedtothelistofchemicalsresponsibleforchronicoxalatenephropathy. Abstract:PubMed
VigeralPetalNephrolDialTransplant2(4):2758(1987)

fromHSDB
CyclosporinAinterfereswithoxalatemetabolismand,therefore,shouldbegivenwithutmostcautioninpatients
withprimaryhyperoxaluria. Abstract:PubMed
DrachmanRetalChildNephrolUrol9(12):902(1988)

fromHSDB

8.4 MechanismofAction
Metabolicallyitstoxicityisbelievedduetothecapacityofoxalicacidtoimmobilizecalciumandthusupsetthe
calciumpotassiumratioincriticaltissues.
AmericanConferenceofGovernmentalIndustrialHygienists.DocumentationoftheThresholdLimitValuesandBiological
ExposureIndices.5thed.Cincinnati,OH:AmericanConferenceofGovernmentalIndustrialHygienists,1986.,p.451

fromHSDB

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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9 UseandManufacturing
9.1 Uses
9.1.1 IndustryUses
1. Paintadditivesandcoatingadditivesnotdescribedbyothercategories
2. Photosensitivechemicals
3. Surfaceactiveagents
fromEPAChemicalDataReport

9.1.2 ConsumerUses
1. CleaningandFurnishingCareProducts
2. LaundryandDishwashingProducts
3. PaintsandCoatings
4. PhotographicSupplies,Film,andPhotochemicals
fromEPAChemicalDataReport

9.2 MethodsofManufacturing
MADEBYPASSINGCARBONMONOXIDEINTOCONCENTRATEDSODIUMHYDROXIDEORBYHEATING
SODIUMFORMATEINPRESENCEOFSODIUMHYDROXIDEORSODIUMCARBONATE.
Budavari,S.(ed.).TheMerckIndexEncyclopediaofChemicals,DrugsandBiologicals.Rahway,NJ:MerckandCo.,Inc.,
1989.,p.1093

fromHSDB
OXALICACIDISPRODUCEDCOMMERCIALLYBYNITRICACIDOXIDATIONOFSTARCH,SUGAR,OR
ETHYLENEGLYCOL
CHEMICALPRODUCTSSYNOPSIS:OXALICACID,1984

fromHSDB
OXALICACIDISACOPRODUCTOFTHEFERMENTATIONOFMOLASSESTOCITRICACID.OXALICACID
CANBEMADEBYFUSINGSAWDUST(OROTHERFORMSOFCELLULOSE)WITHAMIXTUREOF
SODIUMHYDROXIDEANDPOTASSIUMHYDROXIDE.TEXACOWASGRANTEDAPATENTIN1973FOR
THEELECTROLYTICSYNTHESISOFOXALICACIDFROMCARBONDIOXIDEANDHYDROGEN.
CHEMICALPRODUCTSSYNOPSIS:OXALICACID,1984

fromHSDB

9.3 Formulations/Preparations
Technical(crystalsandpowder)chemicallypure:agradedesignationsignifyingaminimumofimpurities,butnot
100%purity.
Sax,N.I.andR.J.Lewis,Sr.(eds.).Hawley'sCondensedChemicalDictionary.11thed.NewYork:VanNostrandReinholdCo.,
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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1987.,p.862

fromHSDB
THECOMMERCIALPRODUCTISCOMPRISEDOFWHITETOCOLORLESSMONOCLINICPRISMSOR
GRANULESCONTAINING71.42wt%ANHYDROUSOXALICACIDAND28.58wt%WATER
KirkOthmerEncyclopediaofChemicalTechnology.3rded.,Volumes126.NewYork,NY:JohnWileyandSons,19781984.,p.
V16618(1981)

fromHSDB

9.4 Consumption
27%FORTEXTILEFINISHING,STRIPPINGANDCLEANING27%FORMETALANDEQUIPMENT
CLEANING25%ASACHEMICALINTERMEDIATE2%FORLEATHERTANNING19%FORMISC
APPLICATIONS(1971)
SRI

fromHSDB
33%FORTEXTILE/APPLICATIONS/20%FORMETAL7%FORLEATHER20%FOROXALATESAND20%
FOROTHERUSE(1983)
CHEMICALPRODUCTSSYNOPSIS:OXALICACID,1984

fromHSDB

9.5 U.S.Production
(1972)1.0X10+10G
SRI

fromHSDB
(1974)8.17X10+9G
SRI

fromHSDB
(1982)9.08X10+8G(EST)
CHEMICALPRODUCTSSYNOPSIS:OXALICACID,1984

fromHSDB

9.6 U.S.Imports
(1972)8.6X10+8G
SRI

fromHSDB
(1975)1.73X10+9G
SRI

fromHSDB
(1984)9.31X10+9g
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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BUREAUOFTHECENSUS.U.S.IMPORTSFORCONSUMPTIONANDGENERALIMPORTS1984p.1357

fromHSDB

9.7 U.S.Exports
(1972)NEGLIGIBLE
SRI

fromHSDB
1.68X10+8g
BUREAUOFTHECENSUS.U.S.EXPORTS,SCHEDULEE,1984p.279

fromHSDB

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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10 Identification
10.1 AnalyticLaboratoryMethods
VEGETABLEPRODUCTS:TITRATIONORATOMICABSORPTIONSPECTROPHOTOMETRY.
AssociationofOfficialAnalyticalChemists.OfficialMethodsofAnalysis.15thed.andSupplements.Washington,DC:
AssociationofAnalyticalChemists,1990,p.15/994974.24

fromHSDB
AIRSAMPLE.PROCEDURE:TITRATION.
Sunshine,I.(ed.).CRCHandbookofAnalyticalToxicology.Cleveland:TheChemicalRubberCo.,1969.,p.649

fromHSDB

10.2 ClinicalLaboratoryMethods
APPLICATION:SERUMORURINE.METHOD:FLUORESCENCEANALYSIS.
Sunshine,I.(ed.).CRCHandbookofAnalyticalToxicology.Cleveland:TheChemicalRubberCo.,1969.,p.927

fromHSDB

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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11 SafetyandHazards
11.1 HazardsIdentification
11.1.1 GHSClassification

Signal:Danger
Harmfulifswallowed
Causessevereskinburnsandeyedamage
Maycauserespiratoryirritation
fromILOICSC

Signal:Wng
H312Harmfulincontactwithskin
H302Harmfulifswallowed
fromREGULATION(EC)No1272/2008

11.1.2 CLPHazardClassandCategoryCodes
CLPHazardClasssandCategoryCodes
AcuteTox.4*
AcuteTox.4*
fromREGULATION(EC)No1272/2008

11.1.3 HealthHazard
Asdustorasasolution,cancausesevereburnsofeyes,skin,ormucousmembranes.Ingestionof5gramshas
causeddeathwithsymptomsofnausea,shock,collapse,andconvulsionscomingonrapidly.Repeatedor
prolongedskinexposurecancausedermatitisandslowhealingulcers.(USCG,1999)
fromCAMEOChemicals
Corrosive
fromNJDOHRTKHazardousSubstanceList

11.1.4 FireHazard
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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Combustible.Givesoffirritatingortoxicfumes(orgases)inafire.
fromILOICSC

11.1.5 SkinHazard
Redness.Pain.Skinburns.
fromILOICSC

11.1.6 InhalationHazard
Cough.Sorethroat.Burningsensation.Shortnessofbreath.Labouredbreathing.Headache.
fromILOICSC

11.1.7 EyeHazard
Redness.Pain.Blurredvision.Burns.
fromILOICSC

11.1.8 IngestionHazard
Sorethroat.Burningsensation.Abdominalpain.Labouredbreathing.Convulsions.Paralysis.Cardiacdysrhythmia.
Shockorcollapse.
fromILOICSC

11.1.9 Skin,Eye,andRespiratoryIrritations
Thechiefeffectsofinhalationofthedustorvaporareirritationoftheeyesandupperrespiratorytract.
Sax,N.I.DangerousPropertiesofIndustrialMaterials.6thed.NewYork,NY:VanNostrandReinhold,1984.,p.2098

fromHSDB

11.2 SafetyandHazardProperties
11.2.1 Flammability
CombustibleSolid
fromNIOSHPocketGuide

11.2.2 NFPAHazardClassification
Health:3.3=Materialsthat,onshortexposure,couldcauseserioustemporaryorresidualinjury,includingthose
requiringprotectionfromallbodilycontact.Firefightersmayentertheareaonlyiftheyareprotectedfromall
contactwiththematerial.Fullprotectiveclothing,includingselfcontainedbreathingapparatus,coat,pants,gloves,
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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boots,andbandsaroundlegs,arms,andwaist,shouldbeprovided.Noskinsurfaceshouldbeexposed.
FireProtectionGuidetoHazardousMaterials.12ed.Quincy,MA:NationalFireProtectionAssociation,1997.,p.4999

fromHSDB
Flammability:1.1=Thisdegreeincludesmaterialsthatmustbepreheatedbeforeignitionwilloccur,suchasClass
IIIBcombustibleliquidsandsolidsandsemisolidswhoseflashpointexceeds200degF(93.4degC),aswellas
mostordinarycombustiblematerials.Watermaycausefrothingifitsinksbelowthesurfaceoftheburningliquid
andturnstosteam.However,awaterfogthatisgentlyappliedtothesurfaceoftheliquidwillcausefrothingthat
willextinguishthefire.
FireProtectionGuidetoHazardousMaterials.12ed.Quincy,MA:NationalFireProtectionAssociation,1997.,p.4999

fromHSDB
Reactivity:0.0=Thisdegreeincludesmaterialsthatarenormallystable,evenunderfireexposureconditions,and
thatdonotreactwithwater.Normalfirefightingproceduresmaybeused.
FireProtectionGuidetoHazardousMaterials.12ed.Quincy,MA:NationalFireProtectionAssociation,1997.,p.4999

fromHSDB

11.2.3 NFPAFireRating
1
fromOSHAOccupationalChemicalDB,CAMEOChemicals

11.2.4 NFPAReactivityRating
0
fromOSHAOccupationalChemicalDB

11.2.5 NFPAHealthRating
2
fromOSHAOccupationalChemicalDB
3
fromCAMEOChemicals

11.2.6 PhysicalDanger
Nodata.
fromILOICSC

11.2.7 ChemicalDanger
500mg/cum
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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fromHSDB
Decomposesoncontactwithhotsurfacesorflames.Thisproducesformicacidandcarbonmonoxide.Thesolution
inwaterisamediumstrongacid.Reactsviolentlywithstrongoxidants.Thisgeneratesfireandexplosionhazard.
Reactswithsomesilvercompounds.Thisproducesexplosivesilveroxalate.Attackssomeformsofplastic.
fromILOICSC

11.2.8 OSHAStandards
PermissibleExposureLimit:TableZ18hrTimeWeightedAvg:1mg/cum.
29CFR1910.1000(7/1/98)

fromHSDB
Vacated1989OSHAPELTWA1mg/cumSTEL2mg/cumisstillenforcedinsomestates.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.369

fromHSDB

11.2.9 NIOSHRecommendations
RecommendedExposureLimit:10HrTimeWeightedAvg:1mg/cum.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.238

fromHSDB
RecommendedExposureLimit:15MinShortTermExposureLimit:2mg/cum.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.238

fromHSDB

11.3 FirstAidMeasures
11.3.1 FirstAid
Eye:Irrigateimmediately
Skin:Waterflushpromptly
Breathing:Respiratorysupport
Swallow:Medicalattentionimmediately Moreinformation...
fromNIOSHPocketGuide
EYES:Firstcheckthevictimforcontactlensesandremoveifpresent.Flushvictim'seyeswithwaterornormal
salinesolutionfor20to30minuteswhilesimultaneouslycallingahospitalorpoisoncontrolcenter.Donotputany
ointments,oils,ormedicationinthevictim'seyeswithoutspecificinstructionsfromaphysician.IMMEDIATELY
transportthevictimafterflushingeyestoahospitalevenifnosymptoms(suchasrednessorirritation)develop.
SKIN:IMMEDIATELYfloodaffectedskinwithwaterwhileremovingandisolatingallcontaminatedclothing.Gently
washallaffectedskinareasthoroughlywithsoapandwater.IMMEDIATELYcallahospitalorpoisoncontrolcenter
evenifnosymptoms(suchasrednessorirritation)develop.IMMEDIATELYtransportthevictimtoahospitalfor
treatmentafterwashingtheaffectedareas.INHALATION:IMMEDIATELYleavethecontaminatedareatakedeep
breathsoffreshair.Ifsymptoms(suchaswheezing,coughing,shortnessofBreathing,orburninginthemouth,
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throat,orchest)develop,callaphysicianandbepreparedtotransportthevictimtoahospital.Provideproper
respiratoryprotectiontorescuersenteringanunknownatmosphere.Wheneverpossible,SelfContainedBreathing
Apparatus(SCBA)shouldbeusedifnotavailable,usealevelofprotectiongreaterthanorequaltothatadvised
underProtectiveClothing.INGESTION:DONOTINDUCEVOMITING.Corrosivechemicalswilldestroythe
membranesofthemouth,throat,andesophagusand,inaddition,haveahighriskofbeingaspiratedintothe
victim'slungsduringvomitingwhichincreasesthemedicalproblems.Ifthevictimisconsciousandnotconvulsing,
give1or2glassesofwatertodilutethechemicalandIMMEDIATELYcallahospitalorpoisoncontrolcenter.
IMMEDIATELYtransportthevictimtoahospital.Ifthevictimisconvulsingorunconscious,donotgiveanythingby
mouth,ensurethatthevictim'sairwayisopenandlaythevictimonhis/hersidewiththeHeadachelowerthanthe
body.DONOTINDUCEVOMITING.TransportthevictimIMMEDIATELYtoahospital.(NTP,1992)
fromOSHAOccupationalChemicalDB

11.3.2 FireFirstAid
Usewaterspray,powder,foam,carbondioxide.
fromILOICSC

11.3.3 ExplosionFirstAid
Incaseoffire:keepdrums,etc.,coolbysprayingwithwater.
fromILOICSC

11.3.4 InhalationFirstAid
Freshair,rest.Halfuprightposition.Referimmediatelyformedicalattention.
fromILOICSC

11.3.5 SkinFirstAid
Removecontaminatedclothes.Rinseskinwithplentyofwaterorshowerforatleast15minutes.Referformedical
attention.
fromILOICSC

11.3.6 EyeFirstAid
Rinsewithplentyofwater(removecontactlensesifeasilypossible).Referimmediatelyformedicalattention.
fromILOICSC

11.3.7 IngestionFirstAid
Rinsemouth.DoNOTinducevomiting.Referimmediatelyformedicalattention.
fromILOICSC

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11.4 FireFightingMeasures
USEWATERSPRAY,DRYCHEM,"ALCRESISTANT"FOAM,ORCARBONDIOXIDE.DUSTMAYBE
REDUCEDWITHWATERSPRAY.AQUEOUSSOLUTIONMUSTBECONTAINEDFORDISPOSAL.USE
WATERTOKEEPFIREEXPOSEDCONTAINERSCOOL.WATERMAYCAUSEFOAMINGOFMOLTEN
MATERIAL./OXALICACIDDIHYDRATE/
FireProtectionGuidetoHazardousMaterials.12ed.Quincy,MA:NationalFireProtectionAssociation,1997.,p.4999

fromHSDB

11.4.1 FireFighting
Firesinvolvingthiscompoundmaybecontrolledwithadrychemical,carbondioxideorHalonextinguisher.(NTP,
1992)
fromOSHAOccupationalChemicalDB

11.5 AccidentalReleaseMeasures
11.5.1 SpillageDisposal
Personalprotection:particulatefilterrespiratoradaptedtotheairborneconcentrationofthesubstance,protective
glovesandsafetygoggles.Sweepspilledsubstanceintocoveredplasticcontainers.Ifappropriate,moistenfirstto
preventdusting.Washawayremainderwithplentyofwater.
fromILOICSC

11.5.2 CleanupMethods
Coverwithsodaashorsodiumbicarbonate.Mixandaddwater.Neutralizeanddrainintoadrainwithsufficient
water.
ITII.ToxicandHazardousIndustrialChemicalsSafetyManual.Tokyo,Japan:TheInternationalTechnicalInformationInstitute,
1988.,p.389

fromHSDB

11.5.3 DisposalMethods
Oxalicacidisawastechemicalstreamconstituentwhichmaybesubjectedtoultimatedisposalbycontrolled
incineration.Pretreatmentinvolveschemicalreactionwithlimestoneorcalciumoxideformingcalciumoxalate.This
maythenbeincineratedutilizingparticulatecollectionequipmenttocollectcalciumoxideforrecycling.
USEPAEngineeringHandbookforHazardousWasteIncinerationp.218(1981)EPA68033025

fromHSDB

11.5.4 OtherPreventativeMeasures
Adequateventilation.
ITII.ToxicandHazardousIndustrialChemicalsSafetyManual.Tokyo,Japan:TheInternationalTechnicalInformationInstitute,
1988.,p.389
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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fromHSDB
Theworkershouldimmediatelywashtheskinwhenitbecomescontaminated.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239

fromHSDB
Workclothingthatbecomeswetorsignificantlycontaminatedshouldberemovedandreplaced.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239

fromHSDB
Workerswhoseclothingmayhavebecomecontaminatedshouldchangeintouncontaminatedclothingbefore
leavingtheworkpremises.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239

fromHSDB
SRP:Contaminatedprotectiveclothingshouldbesegregatedinsuchamannersothatthereisnodirectpersonal
contactbypersonnelwhohandle,dispose,orcleantheclothing.Qualityassurancetoascertainthecompletenessof
thecleaningproceduresshouldbeimplementedbeforethedecontaminatedprotectiveclothingisreturnedforreuse
bytheworkers.Contaminatedclothingshouldnotbetakenhomeatendofshift,butshouldremainatemployee's
placeofworkforcleaning.
fromHSDB
SRP:Thescientificliteraturefortheuseofcontactlensesinindustryisconflicting.Thebenefitordetrimental
effectsofwearingcontactlensesdependnotonlyuponthesubstance,butalsoonfactorsincludingtheformofthe
substance,characteristicsanddurationoftheexposure,theusesofothereyeprotectionequipment,andthe
hygieneofthelenses.However,theremaybeindividualsubstanceswhoseirritatingorcorrosivepropertiesaresuch
thatthewearingofcontactlenseswouldbeharmfultotheeye.Inthosespecificcases,contactlensesshouldnot
beworn.Inanyevent,theusualeyeprotectionequipmentshouldbewornevenwhencontactlensesareinplace.
fromHSDB

11.6 HandlingandStorage
11.6.1 NonfireSpillResponse
NeutralizingAgentsforAcidsandCaustics:Limeorsodaash(USCG,1999)
fromOSHAOccupationalChemicalDB

11.6.2 SafeStorage
Separatedfromstrongoxidantsandfoodandfeedstuffs.Dry.Wellclosed.
fromILOICSC

11.6.3 StorageConditions
STOREINCOOL,DRY,WELLVENTILATEDLOCATION./OXALICACIDDIHYDRATE/
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Reynolds,J.E.F.,Prasad,A.B.(eds.)MartindaleTheExtraPharmacopoeia.28thed.London:ThePharmaceuticalPress,1982.,
p.49131

fromHSDB

11.7 ExposureControlandPersonalProtection
11.7.1 REL
TWA1mg/m3ST2mg/m3
fromNIOSHPocketGuide

11.7.2 PEL
TWA1mg/m3
fromNIOSHPocketGuide

11.7.3 PELTWA
1mg/m3
fromOSHAOccupationalChemicalDB

11.7.4 RELTWA
1mg/m3
fromOSHAOccupationalChemicalDB

11.7.5 RELSTEL
2mg/m3
fromOSHAOccupationalChemicalDB

11.7.6 IDLH
500mg/m3
fromNIOSHPocketGuide

11.7.7 ThresholdLimitValues
8hrTimeWeightedAvg(TWA):1mg/cum15minShortTermExposureLimit(STEL):2mg/cum.
AmericanConferenceofGovernmentalIndustrialHygienistsTLVsandBEIs.ThresholdLimitValuesforChemicalSubstances
andPhysicalAgentsandBiologicalExposureIndices.Cincinnati,OH,2008,p.45

fromHSDB
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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11.7.8 OccupationalExposureLimits
TLV:1mg/masTWA(ACGIH2009).
EUOEL(selected):1mg/masTWA.
fromILOICSC

11.7.9 InhalationRisk
Evaporationat20Cisnegligibleaharmfulconcentrationofairborneparticlescan,however,bereachedquickly
whendispersed.
fromILOICSC

11.7.10 EffectsofShortTermExposure
Thesubstanceiscorrosivetotheeyes,skinandrespiratorytract.Corrosiveoningestion.Thesubstancemaycause
effectsonthecalciumbalanceafteringestion.Exposureathighlevelscouldcausedeath.
fromILOICSC

11.7.11 EffectsofLongTermExposure
Repeatedorprolongedcontactwithskinmaycausedermatitis.Exposuremayresultinkidneystones,slowhealing
ulcersandblackfingernails.
fromILOICSC

11.7.12 AllowableTolerances
Residuesofoxalicacidareexemptedfromtherequirementofatolerancewhenusedasacalciumchelatinghard
waterinhibitorinaccordancewithgoodagriculturalpracticesasinert(oroccasionallyactive)ingredientsinpesticide
formulationsappliedtogrowingcropsortorawagriculturalcommoditiesafterharvest.Limits:Nomoreoxalicacid
shouldbeusedthanisnecessarytochelatecalciumand,innocase,shouldmorethan2lboxalicacidperacrebe
used.
40CFR180.1001(c)(7/1/90)

fromHSDB

11.7.13 PersonalProtection
Skin:Preventskincontact
Eyes:Preventeyecontact
Washskin:Whencontaminated
Remove:Whenwetorcontaminated
Change:Daily
Provide:Eyewash Moreinformation...
fromNIOSHPocketGuide

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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11.7.14 RespiratorRecommendations
NIOSH/OSHA
Upto25mg/m3:(APF=25)Anysuppliedairrespiratoroperatedinacontinuousflowmode(APF=25)Any
powered,airpurifyingrespiratorwithahighefficiencyparticulatefilter.
Upto50mg/m3:(APF=50)Anyairpurifying,fullfacepiecerespiratorwithanN100,R100,orP100filter.Click
hereforinformationonselectionofN,R,orPfilters.(APF=50)Anyselfcontainedbreathingapparatuswithafull
facepiece(APF=50)Anysuppliedairrespiratorwithafullfacepiece
Upto500mg/m3:(APF=2000)Anysuppliedairrespiratorthathasafullfacepieceandisoperatedinapressure
demandorotherpositivepressuremode
EmergencyorplannedentryintounknownconcentrationsorIDLHconditions:(APF=10,000)Anyselfcontained
breathingapparatusthathasafullfacepieceandisoperatedinapressuredemandorotherpositivepressuremode
(APF=10,000)Anysuppliedairrespiratorthathasafullfacepieceandisoperatedinapressuredemandorother
positivepressuremodeincombinationwithanauxiliaryselfcontainedpositivepressurebreathingapparatus
Escape:(APF=50)Anyairpurifying,fullfacepiecerespiratorwithanN100,R100,orP100filter.Clickherefor
informationonselectionofN,R,orPfilters.Anyappropriateescapetype,selfcontainedbreathingapparatus
Moreinformation...
fromNIOSHPocketGuide

11.7.15 FirePrevention
NOopenflames.
fromILOICSC

11.7.16 ExposurePrevention
PREVENTDISPERSIONOFDUST!
fromILOICSC

11.7.17 InhalationPrevention
Useventilation(notifpowder),localexhaustorbreathingprotection.
fromILOICSC

11.7.18 SkinPrevention
Protectivegloves.Protectiveclothing.
fromILOICSC

11.7.19 EyePrevention
Wearfaceshieldoreyeprotectionincombinationwithbreathingprotection.
fromILOICSC

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11.7.20 IngestionPrevention
Donoteat,drink,orsmokeduringwork.Washhandsbeforeeating.
fromILOICSC

11.7.21 ProtectiveEquipmentandClothing
...EYE&SKINPROTECTION/MUST/BEPROVIDEDFORPERSONSWORKINGWITHOXALICACID.
InternationalLabourOffice.EncyclopediaofOccupationalHealthandSafety.Vols.I&II.Geneva,Switzerland:International
LabourOffice,1983.,p.984

fromHSDB
Wearspecialprotectiveclothingandpositivepressureselfcontainedbreathingapparatus./Oxalicaciddihydrate/
FireProtectionGuidetoHazardousMaterials.12ed.Quincy,MA:NationalFireProtectionAssociation,1997.,p.49122

fromHSDB
Ifmistsofoxalicacidshouldbeencounteredfromhotsolutions...adequateventilationshouldbeprovidedor
properrespiratoryprotectivedevicesworn.
InternationalLabourOffice.EncyclopediaofOccupationalHealthandSafety.Vols.I&II.Geneva,Switzerland:International
LabourOffice,1983.,p.1574

fromHSDB
Respiratorfordustormistprotectionrubber,neoprene,orvinylgloveschemicalsafetyglassesrubbers,over
leatherorrubbersafetyshoesapronorimperviousclothingforsplashprotection.
U.S.CoastGuard,DepartmentofTransportation.CHRISHazardousChemicalData.VolumeII.Washington,D.C.:U.S.
GovernmentPrintingOffice,19845.

fromHSDB
Wearappropriatepersonalprotectiveclothingtopreventskincontact.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239

fromHSDB
Wearappropriateeyeprotectiontopreventeyecontact.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239

fromHSDB
Eyewashfountainsshouldbeprovidedinareaswherethereisanypossibilitythatworkerscouldbeexposedtothe
substancethisisirrespectiveoftherecommendationinvolvingthewearingofeyeprotection.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239

fromHSDB
Recommendationsforrespiratorselection.Maxconcnforuse:25mg/cum.RespiratorClass(es):Anysuppliedair
respiratoroperatedinacontinuousflowmode.Eyeprotectionneeded.Anypowered,airpurifyingrespiratorwitha
dustandmistfilter.Eyeprotectionneeded.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239

fromHSDB
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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Recommendationsforrespiratorselection.Maxconcnforuse:50mg/cum.RespiratorClass(es):Anyairpurifying,
fullfacepiecerespiratorwithahighefficiencyparticulatefilter.Anyselfcontainedbreathingapparatuswithafull
facepiece.Anysuppliedairrespiratorwithafullfacepiece.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239

fromHSDB
Recommendationsforrespiratorselection.Maxconcnforuse:500mg/cum.RespiratorClass(es):Anysuppliedair
respiratorthathasafullfacepieceandisoperatedinapressuredemandorotherpositivepressuremode.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239

fromHSDB
Recommendationsforrespiratorselection.Condition:EmergencyorplannedentryintounknownconcnorIDLH
conditions:RespiratorClass(es):Anyselfcontainedbreathingapparatusthathasafullfacepieceandisoperatedin
apressuredemandorotherpositivepressuremode.Anysuppliedairrespiratorthathasafullfacepieceandis
operatedinapressuredemandorotherpositivepressuremodeincombinationwithanauxiliaryselfcontained
breathingapparatusoperatedinpressuredemandorotherpositivepressuremode.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239

fromHSDB
Recommendationsforrespiratorselection.Condition:Escapefromsuddenlyoccurringrespiratoryhazards:
RespiratorClass(es):Anyairpurifying,fullfacepiecerespiratorwithahighefficiencyparticulatefilter.Any
appropriateescapetype,selfcontainedbreathingapparatus.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239

fromHSDB

11.8 StabilityandReactivity
11.8.1 AirandWaterReactions
Watersoluble.Hygroscopic
fromCAMEOChemicals

11.8.2 ReactiveGroup
Acids,Carboxylic
fromCAMEOChemicals

11.8.3 ReactivitiesandIncompatibilities
Reactswithstrongalkalies,strongoxidizingmaterials,chlorites,andhypochlorites./Oxalicaciddihydrate/
FireProtectionGuidetoHazardousMaterials.12ed.Quincy,MA:NationalFireProtectionAssociation,1997.,p.49122

fromHSDB
Strongoxidizers,silvercompounds,strongalkalis,chlorites[Note:Givesoffwaterofcrystallizationat215degrees
Fandbeginstosublime].
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.238

fromHSDB
Strongoxidizers,silvercompounds,strongalkalis,chlorites[Note:Givesoffwaterofcrystallizationat215Fand
beginstosublime.]
fromNIOSHPocketGuide
STABILITY:Thischemicalishygroscopicandsensitivetoheat.Solutionsofthischemicalshouldbestablefor24
hoursundernormallabconditions.REACTIVITY:Thiscompoundmayreactviolentlywithfurfurylalcohol,silver,
sodium,perchlorate,sodiumhypochlorite,strongoxidizers,sodiumchlorite,acidchlorides,metalsandalkalimetals.
(NTP,1992)
fromOSHAOccupationalChemicalDB

11.9 TransportInformation
11.9.1 DOTLabel
Corrosive
fromCAMEOChemicals

11.9.2 PackagingandLabelling
Donottransportwithfoodandfeedstuffs.
fromILOICSC

11.9.3 ECClassification
Symbol:XnR:21/22S:(2)24/25
fromILOICSC

11.9.4 UNClassification
UNHazardClass:8UNPackGroup:III
fromILOICSC

11.9.5 EmergencyResponse
NFPACode:H3F1R0.
fromILOICSC

11.10 RegulatoryInformation
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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11.10.1 FIFRARequirements
Residuesofoxalicacidareexemptedfromtherequirementofatolerancewhenusedasacalciumchelatinghard
waterinhibitorinaccordancewithgoodagriculturalpracticesasinert(oroccasionallyactive)ingredientsinpesticide
formulationsappliedtogrowingcropsortorawagriculturalcommoditiesafterharvest.Limits:Nomoreoxalicacid
shouldbeusedthanisnecessarytochelatecalciumand,innocase,shouldmorethan2lboxalicacidperacrebe
used.
40CFR180.1001(c)(7/1/90)

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11.11 OtherSafetyInformation
11.11.1 ToxicCombustionProducts
Combustionmayproduceirritantsandtoxicgases,includingformicacid./Oxalicaciddihydrate/
FireProtectionGuidetoHazardousMaterials.12ed.Quincy,MA:NationalFireProtectionAssociation,1997.,p.4999

fromHSDB

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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12 Toxicity
12.1 ToxicologicalInformation
12.1.1 ExposureRoutes
Thesubstancecanbeabsorbedintothebodybyinhalationofitsaerosolandbyingestion.Seriouslocaleffectsby
allroutesofexposure.
fromILOICSC
inhalation,ingestion,skinand/oreyecontact
fromNIOSHPocketGuide

12.1.2 Symptoms
irritationeyes,skin,mucousmembraneeyeburnslocalizedpain,cyanosisshock,collapse,convulsionskidney
damage
fromNIOSHPocketGuide

12.1.3 TargetOrgans
Eyes,skin,respiratorysystem,kidneys
fromNIOSHPocketGuide

12.1.4 Interactions
AnumberofsulfhydrylcompoundswereshowntoinhibitCO2andoxalateformationfromglyoxylatebyratliver
homogenatesandhepatocytes.Themostsignificantinhibitionoccurredwithcysteineandthisinhibitionwas
concentrationdependent.Inratsmadehyperoxaluricbyadministeringethyleneglycolintheirdrinkingwater,daily
intraperitonealinjectionsofcysteinecausedarapidandmarkeddecreaseinurinaryoxalateexcretionwhichwas
maintainedoverthedurationofthetreatment(28days).Overthistimeperiod,thelevelofurinaryoxalateexcretion
intheseethyleneglycoltreatedratswasreducedtothatofthecontrols.Itispostulatedthatthedecreaseisdueto
theformationofacysteineglyoxylateadduct,2carboxy4thiazolidinecarboxylate,whichpreventsglyoxylatebeing
furtheroxidizedtooxalate.Cysteineorsimilarsulphydrylcompoundsmaythereforehavepotentialastherapeutic
agentsinthepreventionofrenalstones. Abstract:PubMed
BaisRetalJUrol145(6):13025(1991)

fromHSDB
ThestudywasconductedtoinvestigatetheeffectofvitaminA,B1andB6deficiencyonoxalatemetabolismin
rats.Asignificanthyperoxaluriawasthecommonobservationinallthethreevitamindeficiencies(vitaminB6
greaterthanvitaminAgreaterthanvitaminB1).Theactivitiesofhepaticglycolateoxidaseandglycolate
dehydrogenaseweremarkedlyenhancedinvitaminAandvitaminB6deficientrats.However,lactate
dehydrogenaselevelsremainedunalteredinthesedeficienciesascomparedtotheirrespectivepairfedcontrols.
VitaminB1deficiencyof4weeksdurationcouldaugmenttheactivityofglycolateoxidaseonly,withnoalterations
intheglycolatedehydrogenaseandlactatedehydrogenaselevels.Intestinaloxalateuptakestudiesrevealed
increasedbioavailabilityofoxalatefromthegutinvitaminAandvitaminB6deficientrats.Thus,theresultssuggest
therelativecontributionofbothexogenousaswellasendogenousoxalateintheprocessofcalculogenesisunder
variousnutritionalstressconditionsinrat. Abstract:PubMed
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SharmaSetalAnnNutrMetab34(2):10411(1990)

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HyperoxalemiacanbeaggravatedbyvitaminCsupplementationinregularhemodialysispatients.Thepresent
studywasundertakentoexaminethevalidityofthisobservationinanexperimentalsetting.Fiftyfivesixths
nephrectomizedratsweredividedintotwogroups:30ratswereallowedfreeaccesstowatercontaining8mg/mlof
vitaminC(100160mg/100g/24hr)andtheremaindergiventapwaterwithoutvitaminC.Theserumcreatinine
increasedandthehematocritdecreasedgraduallyhowever,therewasnodifferencebetweenthetwogroups.
PlasmavitaminC,oxalateandurinaryoxalatelevelswerehigherinthevitamintreatedgroupthanthenontreated
rats.Histologicalexaminationrevealedglomerularandinterstitialfibrosisandroundcellinfiltrationaswellastubular
cystformation.OxalatedepositsinrenaltubuleswerefoundonlyinvitaminCtreatedratswithadvancedrenal
failure.Nontreatedanimalswithequallyadvancedrenalimpairmentshowednooxalatedeposits.Theseresults
confirmpreviousclinicalfindingsthatvitaminCsupplementationaggravatesthesecondaryoxalosisofchronicrenal
failure. Abstract:PubMed
OnoKetalNephron51(4):5369(1989)

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MaleWistarstrainratswhichhadbeenfedaglycolicaciddietdevelopedseverenephrocalcinosiswithurinary
calculiwithin4weeks.Ratsfedthesamedietwithcitratesaltsaddedhad,however,eitherslightorno
nephrocalcinosiswithoutanystonesintheurinarysystem.Nephrocalcinosisintermediatebetweenthoseinthe
citrategroupsandtheglycolicacidgroup,withsomeurinarycalculi,wasobservedinthecitricacidgroup.During
theexperiment,theurinaryoxalateconcentrationincreasedmarkedlyandwashigherinthecitrateandcitricacid
thanintheglycolicacidgroup.Theurinarycitrateconcentrationwassignificantlyhigherinthecitrategroupsand
lowerinthecitricacidandglycolicacidgroups.Therefore,citratesaltscanbeconcludedtoinhibitnephrocalcinosis
andcalculiformationasaresultofdecreasedurinarysaturationbymeansofincreaseinurinarycitrate,inspiteofa
slightincreaseintheurinaryoxalate. Abstract:PubMed
OgawaYetalHinyokikaKiyo33(11):17727(1987)

fromHSDB
Theadditionofoxalatetobloodstoredincitratephosphatedextroseproducesamarkedimprovementin2,3
diphosphoglyceratepreservationanincreasein2,3diphosphoglyceratelevelscanalsobedocumentedinshort
termincubationstudies.Oxalateisapotentinvitroinhibitorofredcelllactatedehydrogenase,
monophosphoglyceratemutase,andpyruvatekinase.Inthepresenceoffructose1,6diphosphatethelatter
inhibitoryeffectiscompetitivewithphospho(enol)pyruvate.Determinationofthelevelsofintermediatecompounds
inredcellsincubatedwithoxalatesuggestthepresenceofinhibitionatthepyruvatekinasestep,indicatingthatthis
isthesiteofoxalateaction.Apparentinhibitionattheglyceraldehydephosphatedehydrogenasestepisapparently
duetoanincreaseintheNADH/NADratio.Oxalatehadnoeffectontheinvivoviabilityofrabbitredcellsstoredin
citratephosphatedextrosepreservativesfor21days.Greaterunderstandingofthetoxicityofoxalateisrequired
beforeitcanbeconsideredsuitableasacomponentofpreservativemedia,butappreciationofthemechanismby
whichitaffects2,3diphosphoglyceratelevelsmaybeimportantindesignofotherbloodadditives.Malonate,the3
carbondicarboxylicacidanalogofoxalatedidnotinhibitpyruvatekinasenoraffect2,3diphosphoglyceratelevels.
Abstract:PubMed
BeutlerEetalBlood70(5):138993(1987)

fromHSDB
Twentytworecurrentcalciumstoneformershad24hrurinaryoxalateexcretionsontheirhomedietswhichwere
significantlygreaterthanthoseof30normalsubjects(0.48+or0.23mmol/daymean+orstandarddeviation
comparedwith0.31+or0.11p<0.01).Thestoneformersalsodemonstratedmarkeddaytodayvariabilityin
oxalateexcretionindicatingthatasinglenormalurinaryoxalatemeasurementdidnotexcludesignificant
hyperoxaluriaatothertimes.Onahospitaldietcontaining1000mgcalciumperday,urinaryoxalateexcretionfell
significantlyfrom0.48+or0.23mmol/dayto0.32+or0.12(p<0.01).Astheurinarycalciumexcretioninand
outofhospitalwassimilar,itseemsunlikelythatlowcalciumintakeathomewasresponsibleforthehyperoxaluria.
Allpatientshadrecurrentsymptomaticstonediseaseandhadbeenadvisedtoavoidfoodsrichinoxalate.Whilst
poorcomplianceisapossibleexplanationforthevariabilityinoxalateexcretion,itismorelikelythatthereisan
inadvertentintakeofoxalogenicprecursorsintheirdiet.Asnormalsubjectsdonotdemonstratehyperoxaluriaon
similarhomediets,stoneformersmayhaveametabolicdefectinthehandlingoftheseprecursors. Abstract:
PubMed
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BrownJMetalAnnClinBiochem24(Pt4):38590(1987)

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12.1.5 AntidoteandEmergencyTreatment
Treatmentshouldberapidlyinstitutedbygivingadilutesolutionofcalciumlactate,limewater,finelypulverized
chalk,plaster,and/ormilktosupplylargeamountsofcalciumtoinactivateoxalatebyforminganinsolublecalcium
saltinthestomach.Gastriclavageiscontroversial,sincethismaycompoundanalreadyseverecorrosivelesionin
theesophagusorstomach.However,ifused,gastriclavageshouldbedonewithlimewater(calciumhydroxide).
Intravenousgluconateorcalciumchloridesolutionsshouldbegiventopreventhypocalcemictetanyinseverecases
parathyroidextractalsohasbeengiven....Additionally,acuterenalfailureshouldbeanticipated,andcarefulfluid
managementisnecessary./Oxalates/
Haddad,L.M.,ClinicalManagementofPoisoningandDrugOverdose.2nded.Philadelphia,PA:W.B.SaundersCo.,1990.,p.
702

fromHSDB
Metabolicallyitstoxicityisbelieved/tobe/duetothecapacityofoxalicacidtoimmobilizecalciumandthusupset
thecalciumpotassiumratioincriticaltissues.Effectivetherapyagainstburnsfromoxalicacidinvolvesreplacement
ofcalcium.
AmericanConferenceofGovernmentalIndustrialHygienists.DocumentationoftheThresholdLimitValuesandBiological
ExposureIndices.5thed.Cincinnati,OH:AmericanConferenceofGovernmentalIndustrialHygienists,1986.,p.451

fromHSDB

12.1.6 MedicalSurveillance
CAREFULCONSIDERATIONSHOULDBEGIVENTOPLACEMENTOFANYINDIVIDUALSWHOHAVE
PERIPHERALVASCULARDISEASEOFTHEHANDS,&ITWOULDSEEMBESTTOAVOIDEXPOSUREOF
SUCHPERSONSTOOXALICACID....
InternationalLabourOffice.EncyclopediaofOccupationalHealthandSafety.Vols.I&II.Geneva,Switzerland:International
LabourOffice,1983.,p.1574

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12.1.7 HumanToxicityExcerpts
SYMPTOMATOLOGY:1.BURNINGPAININTHROAT,ESOPHAGUS,&STOMACH.EXPOSEDAREASOF
MUCOUSMEMBRANETURN...OPAQUEWHITE...2.VOMITING(OFTENBLOODYORWITHCOFFEE
GROUNDAPPEARANCE),INTENSEBURNINGPAIN,SEVEREPURGING.3.PULSEBECOMESWEAK,
IRREGULAR,SOMETIMESIMPERCEPTIBLE.HYPOTENSIONANDUSUALSIGNSOFCARDIOVASCULAR
COLLAPSEAPPEAR.4.IFDEATHISDELAYEDFORFEWHR,NERVOUSORNEUROMUSCULAR
SYMPTOMSDEVELOP:HEADACHE...TETANY,SOMETIMESCONVULSIONS,STUPOR,COMA,AND
DEATH.5.RENALDAMAGE,ASEVIDENCEDBYOLIGURIA,ALBUMINURIA,ANDHEMATURIA,MAY
PERSISTFORWEEKS./ORALOXALATE/
Gosselin,R.E.,R.P.Smith,H.C.Hodge.ClinicalToxicologyofCommercialProducts.5thed.Baltimore:WilliamsandWilkins,
1984.,p.III327

fromHSDB
CHRONICSKINEXPOSURETOSOLNOFOXALICACID.../HAS/BEENREPORTEDTOHAVECAUSED
LOCALIZEDPAIN&CYANOSISINFINGERSOREVENGANGRENOUSCHANGES...APPARENTLYDUE
TOLOCALIZEDABSORPTION...&RESULTANTARTERITIS.
InternationalLabourOffice.EncyclopediaofOccupationalHealthandSafety.Vols.I&II.Geneva,Switzerland:International
LabourOffice,1983.,p.1574
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THENEUROMUSCULAREFFECTSCANBEEXPLAINEDLARGELYBYCALCIUMCOMPLEXINGACTIONOF
OXALATE,WHICHDEPRESSESTHELEVELOFIONIZEDCALCIUMINBODYFLUIDS.THIS
HYPOCALCEMIAPRODUCESSEVEREDISTURBANCESINACTIONSOFHEART&NERVOUSSYSTEM
DEATHMAYRESULT.../OXALATE/
Gosselin,R.E.,R.P.Smith,H.C.Hodge.ClinicalToxicologyofCommercialProducts.5thed.Baltimore:WilliamsandWilkins,
1984.,p.II71

fromHSDB
...HASCAUSEDBURNSOFHUMANEYE...WHENSOLNACCIDENTALLYCAMEINCONTACTWITHEYE.
Grant,W.M.ToxicologyoftheEye.3rded.Springfield,IL:CharlesC.ThomasPublisher,1986.,p.685

fromHSDB
TOXICBYINHALATIONANDINGESTION,STRONGIRRITANT.
Sax,N.I.andR.J.Lewis,Sr.(eds.).Hawley'sCondensedChemicalDictionary.11thed.NewYork:VanNostrandReinholdCo.,
1987.,p.862

fromHSDB
Oxalicacidisregardedasastrongpoisonwhentakeninternallyaslittleas5gramshaveprovedfatal.
AmericanConferenceofGovernmentalIndustrialHygienists.DocumentationoftheThresholdLimitValuesandBiological
ExposureIndices.5thed.Cincinnati,OH:AmericanConferenceofGovernmentalIndustrialHygienists,1986.,p.451

fromHSDB
Oxalateproductionbymoldsinfectingmaizesilagearebelievedtohavecausedintoxicationinahorse./Oxalates/
Humphreys,D.J.VeterinaryToxicology.3rded.London,England:BailliereTindell,1988.,p.200

fromHSDB
Symptoms:Local:Conjunctivitis,cornealdamagegangrenousulcerationsofskin.Inhalation:Irritationofrespiratory
tractulcerationofmucousmembranes,epistaxis,headache,nausea,vomiting,muscularirritability,weakness,
albuminuria.Swallowing:Burning&corrosionofthemouth,esophagus,stomachnausea&vomitingwith
hematemesisabdominalpain,diarrhea,bloodystool,numbness&tinglingoffingers&toesmuscularirritability,
tetany,convulsionsshock,oliguria,anuria,hematuria,albuminuriacardiacirregularities&circulatorycollapse.
ITII.ToxicandHazardousIndustrialChemicalsSafetyManual.Tokyo,Japan:TheInternationalTechnicalInformationInstitute,
1988.,p.388

fromHSDB
Studieswithbothunlabeledandlabeledagentsinhumanshaveprovidedbothstrongcircumstantialanddirect
evidencefortheexistenceofminorpathwaysofcarbohydratemetabolismandofoxidativedealkylationand
dehalogenationreactionsindrugbiotransformationsthatlinkxylitol,glycerol,polysorbateemulsifiers,
methoxyflurane,andpossiblydichloroacetatetoendogenousoxalateproduction.Becauseurinaryoxalateisnow
consideredtobeacriticalfactorinstoneformationandbecauseitisincreasinglyacceptedthat8090%ofurinary
oxalateisproducedendogenously,itisnowpossibletoformulatepathwaysthatlinkoxalateproductionwithdietary
macronutrients.Therapeuticmodificationsofdiet,invivohormonalmilieu,andintracellularmetaboliccontrolsin
relationtoendogenousoxalateproductionmayprovidenewformsoftreatmentforurolithiasis. Abstract:PubMed
ConyersRAetalClinChem36(10):171730(1990)

fromHSDB
Patientswithchronicrenalfailurewhoundergohemodialysisexperienceacceleratedatherosclerosisandpremature
death.Sincetheendmetabolite,oxalicacid,accumulatesinplasmainproportiontotheseverityofrenalfailure,/a
studywasconductedtodetermine/whethersodiumoxalate(0to300uM)isanendothelialtoxinand,therefore,
mightenhanceatherogenesis.Exposuretouremiclevelsofoxalate(greaterthan30uM)for9to28daysdepressed
endothelialcellreplicationby33%to84%(mean+orstandarddeviation,54%+or15.7%,n=17experiments,p
=0.002).Incontrast,replicationoffibroblastsexposedto200uMoxalatefor45dayswasnotinhibited.The
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inhibitoryeffectofoxalateonendothelialcellreplicationwasbothdoseandtimedependent(bothp<0.0001)and
wasfirstdetected3to7daysaftertheinitialexposuretooxalate.Further,theinhibitoryeffectwasfullyreversible
uponremovalofoxalate,butonlyifexposurewaslimitedto5daysorless.Sodiumsaltsofothercarboxylicacids
(citric,succinic,glyoxylic,andmalonic200uM)aswellashydrochloricacid(200uM)didnotsuppressendothelial
cellreplication.Oxalatealsoinhibitedendothelialcellmigrationbuthadnoeffectonbasal,thrombininduced,or
arachidonateinducedprostacyclinproductionbyendothelialcells.Exposureofendothelialcellstosodiumoxalate
(200uM)foraslittleas24hratimeperiodsufficienttoinducedelayed,transientinhibitionofreplicationnot
detectableuntilapproximately1weekafterexposureinhibitedincorporationof(3)Hleucineintoproteinby40%(p=
0.009).Itwasconcludedthatsodiumoxalateactsasauremictoxin,inhibitingendothelialcellreplicationand
migration,functionswhichmaybeimportantforconstitutiveinhibitionofatherosclerosis. Abstract:PubMed
LevinRIetalArteriosclerosis10(2):198207(1990)

fromHSDB
Theefficacyoflongtermtherapywithallopurinol,100mg3timesdaily,inthepreventionofrecurrentcalcium
oxalatecalculiofthekidneywasevaluatedinadoubleblindplacebocontrolledstudyin60patients.Afterthestudy,
theplacebogrouphad63.4%fewercalculi,whereastheallopurinolgrouphad81.2%fewercalculi.Duringthestudy
period,themeanrateofcalculouseventswas0.26perpatientperyearintheplacebogroupand0.12inthe
allopurinolgroup.Whenthetreatmentgroupswerecomparedbyactuarialanalysis,theallopurinolgroupwasfound
tohaveasignificantlylongertimebeforerecurrenceofcalculi.Itwasconcludedthatallopurinoliseffectiveinthe
preventionofcalciumoxalatestonesinpatientswithhyperuricosuria. Abstract:PubMed
EttingerBetalNEnglJMed315(27):13869(1986)

fromHSDB
Theeffectsoflongtermtreatmentwithoralpotassiumcitrate,3080meq/day,werestudiedin37patients(aged
2868yr)withidiopathichypocitraturiccalciumoxalateneprholithiasisforaperiodof2yr.Potassiumcitrate
treatmentproducedasustainedincreaseinurinarycitrateexcretionfrominitiallylowvaluestowithinnormallimits.
UrinarypHrosesignificantlyandwasmaintainedat6.5to7.0.Alongwiththesechanges,urinarysaturationof
calciumoxalatedeclinedsignificantlytonormallimits.Furtherstoneformationceasedin89.2%ofpatientsduring
treatment,andthestoneformationratedeclinedfrom2.11to0.28stones/patientyr.Itwasconcludedthat
potassiumcitraterepresentsarationaltreatmentforpatientswithidiopathihypocitraturiccalciumoxalate
nephrolithiasisbecauseitprovidesphysiologiccorrection(restorationofnormalurinarycitrate)andinhibitsnew
stoneformation./Calciumoxalate/ Abstract:PubMed
PakCYC,FullerCAnnInternMed104(Jan):337(1986)

fromHSDB
A14.5yearoldboywithendstagerenalfailureduetofamilialprimaryhyperoxaluriaunderwentcadaverdonorrenal
transplantation.Thegraftfunctionwasstableforaperiodof22months,whilehewasonconventional
immunosuppressivetherapy(prednisoloneandazathioprine)andadditionaloralpyridoxine,phosphorus,and
magnesiumsupplementation.WhenCyclosporinAwasintroducedinsteadofazathioprine,thebloodlevelsof
oxalaterose,andoxalatedepositionintherenaltubulibecameevident.Theseobservationssuggestthat
CyclosporinAinterfereswithoxalatemetabolismand,therefore,shouldbegivenwithutmostcautioninpatients
withprimaryhyperoxaluria. Abstract:PubMed
DrachmanRetalChildNephrolUrol9(12):902(1988)

fromHSDB
A34yearoldwomandevelopedacrystallineretinopathyafter2yrofinhalationalabuseofmethoxyflurane.After
thewomandevelopedrenalfailure,arenalbiopsyshowedmultiplebirefringentcrystalsintherenaltubularlumens,
epithelialcells,andinterstitiumcompatiblewithcalciumoxalate.Multiplebrightyellowwhitecrystalswere
depositedthroughouttheretinaandattheleveloftheretinalpigmentepitheliumwitharetinalarterialand
periarterialpredilection./Calciumoxalate/ Abstract:PubMed
NovakMAetalRetina8(4):2306(1988)

fromHSDB
Duringthelast4yr27specimensofcalciumoxalatenephrolithiasisinpatientsreceivinglongtermtreatmentwith
piridoxilate,adrugcomposedofanequimolarcombinationofglyoxylateandpyridoxine,werecollected.Themean
durationoftreatmentwas3.6yr(range4monthsto10yr)andthemeandailydosewas580mgpiridoxilate,which
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contained160mgglyoxylate.Calculioftenrecurred,withanaveragenumberof9.9perpatient,andanopen
operation,shockwavelithotripsyorpercutaneousnephrolithotomywasrequiredin22patients(81%).Oxalate
excretionwas727+or246umoleperdaywhileonthedrugand382+or201umoleperdayafterthedrugwas
withdrawn.Whewellitewasthemajorcomponentofcalculiinallcasesbutthestonesexhibitedapeculiar
morphologicalarrangement,withmultiplesmallindentationsandafinemamillarystructure.Freshlyvoidedurine
specimenscontainedunusualcrystals,whichoninfraredspectroscopywerecomposedofcalciumoxalatetrihydrate,
avarietyofcrystalneverobservedpreviouslyinhumanurine.Piridoxilateinducedcalciumoxalatenephrolithiasisis
anewvarietyofmetabolicdruginducednephrolithiasis.Observationssuggestthatevenlargedosesofpyridoxine
maybeunabletopreventtheexcessiveproductionofoxalatefromglyoxylate. Abstract:PubMed
DaudonMetalJUrol138(2):25861(1987)

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12.1.8 NonHumanToxicityExcerpts
...OXALATEMAYUPSETCALCIUMMETABOLISMSUFFICIENTLYTOINTERFEREWITHMILK
PRODUCTIONANDBONEGROWTHINLACTATINGANDPREGNANTANIMALS./OXALATE/
Clarke,E.G.,andM.L.Clarke.VeterinaryToxicology.Baltimore,Maryland:TheWilliamsandWilkinsCompany,1975.,p.258

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...MOSTCOMMONEFFECTOFOXALATESISTOCAUSEKIDNEYDAMAGEOWINGTOBLOCKINGOF
TUBULESBYCRYSTALSOFCALCIUMOXALATE....OXALATESMAYCRYSTALLIZEOUTINBRAIN
TISSUE&CAUSESYMPTOMSOFPARALYSIS&OTHERDISORDERSOFCENTRALNERVOUSSYSTEM.
OXALATESMAYLEADTOBREAKDOWNOFREDBLOODCELLS./OXALATES/
Clarke,E.G.,andM.L.Clarke.VeterinaryToxicology.Baltimore,Maryland:TheWilliamsandWilkinsCompany,1975.,p.258

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FIRSTSYMPTOMSINCLUDEDULLNESSANDLOSSOFAPPETITE.HEADISLOWERED&ANIMALIS
UNWILLINGTOKEEPWITHFLOCK.WITHACUTEPOISONINGTHEREMAYBESALIVATIONANDNASAL
DISCHARGEWITHPROGRESSIVEWEAKNESS,RAPIDSHALLOWBREATHINGANDCOLLAPSE.
/OXALATE/
Clarke,E.G.,andM.L.Clarke.VeterinaryToxicology.Baltimore,Maryland:TheWilliamsandWilkinsCompany,1975.,p.259

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ATPOSTMORTEMANINVARIABLEFINDINGISACCUMULATIONOFCALCIUMOXALATECRYSTALSIN
KIDNEYSANDURINARYTRACT.LUNGSMAYBEDARKRED&FILLEDWITHBLOODANDTHEREMAYBE
PETECHIALORLARGERHEMORRHAGES./OXALATE/
Clarke,E.G.,andM.L.Clarke.VeterinaryToxicology.Baltimore,Maryland:TheWilliamsandWilkinsCompany,1975.,p.259

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TOXICDOSEOFOXALICACIDTOTHEDOGISABOUT1G&TOTHECAT,ABOUT0.2G.
Clarke,E.G.,andM.L.Clarke.VeterinaryToxicology.Baltimore,Maryland:TheWilliamsandWilkinsCompany,1975.,p.259

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INATTEMPTSTOINDUCEOXALATEPOISONINGINHORSES...2DOSESOF454GOFOXALICACID,
SODIUMOXALATEORAMMONIUMOXALATE/HADTOBEGIVEN/WITHIN24HR,OR200GOF
AMMONIUMOXALATEDAILYFOR5DAYSINORDERTOKILLTHEANIMALS.DOSEOF200GOFOXALIC
ACID/DAYFOR8DAYSINDUCEDNONFATALPOISONING....
Clarke,E.G.,andM.L.Clarke.VeterinaryToxicology.Baltimore,Maryland:TheWilliamsandWilkinsCompany,1975.,p.259

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DOSEOF340GOFHALOGETONOR900GOFGREASEWOOD/BOTHOXALATECONTAININGPLANTS/
ISALETHALDOSEFORAFASTINGSHEEP.
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Clarke,E.G.,andM.L.Clarke.VeterinaryToxicology.Baltimore,Maryland:TheWilliamsandWilkinsCompany,1975.,p.259

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MALE&FEMALELONGEVANSRATSMAINTAINEDFOR70DAYSONDIETSCONTAINING2.5&5.0%
OXALICACIDHADDECRBODYWT&RESTRICTEDGROWTHRATES.5.0%DEPRESSEDABSOLUTE
ORGANWTBUTENHANCEDORGAN/BODYWTRATIO.VAGINALSMEARSINDICATEDDISRUPTED
ESTROUSCYCLES. Abstract:PubMed
GOLDMANETALRESCOMMUNCHEMPATHOLPHARMACOL18(2):369(1977)

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SIGNIFICANTREDNINTHYROIDWT,24HRTHYROIDUPTAKEOF(125)I&PLASMARADIOACTIVITY
OBSERVEDWITHINCRINPLASMATHYROIDSTIMULATINGHORMONEINLONGEVANSRATS
INGESTINGDIETARY5.0%OXALICACID.5.0%CANLEADTOHYPOTHYROIDISM.INCRIN
TRIIODOTHYRONINE. Abstract:PubMed
GOLDMANM,DOERINGGJTOXICOLAPPLPHARMACOL48(3):409(1979)

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2SHEEP&1COWCHANGEDFROMALFALFAHAYTODIETSWITH12%WT/WTOXALICACID.ADAPTED
ANIMALSTOLERATEDOXALATEWITHOUTSIGNSOFTOXICITY.HOWEVER,2OTHERSHEEPDIED
BECAUSETHEYWEREUNABLETOTOLERATETHEINFUSIONOFINCRAMTOFSODIUMOXALATE
INTOTHERUMENS. Abstract:PubMed
ALLISONETALJANIMSCI45(5):1173(1977)

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Oxaliscernua(OxalispescapraeBermudabuttercup,soursob)hascausedchronicoxalatepoisoninginsheepin
Australia.ThisplantoftencausesintoxicationinsheepgrazinginoliveorchardsinSardiniawhereitgrowsfreely.
Calvesfedexclusivelyonmilkfromcowsgiventhisplanthavebeenreportedtohavedevelopedcatarrhalenteritis,
markedeosinophilia,submucosalintestinalhemorrhages,folliculitisofthemesentericlymphnodesandnephrosis
withcrystallinedeposits./Oxalates/
Humphreys,D.J.VeterinaryToxicology.3rded.London,England:BailliereTindell,1988.,p.253

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Theoxalatecontentofplantsishighestattheleafystageofgrowth,andplantswhicharenormallynotdangerous
tostockmaybecomesoatcertaintimesoftheyear.Halogetonmaycontainasmuchas34.5%ofoxalate,
mangelsupto12%andsoursob5.9%(dryweight).Unfortunately,mostoxalatecontainingplantsareverypalatable
tostock.Althoughsugarbeettopsareharmfultoanimalswhenfresh,theycanbefedwithoutilleffectoncethe
topshavewilted.Thisissaidtobeduetoconversionofharmfulsolublesaltsintoharmlessinsolubleonesduring
theprocess,butthereiscontraryevidenceonthispointandthequestioniscomplicatedbythefactthatoxalateis
nottheonlytoxicsubstanceinsugarbeettopstheycancontainlethalquantitiesofnitrate./Oxalates/
Humphreys,D.J.VeterinaryToxicology.3rded.London,England:BailliereTindell,1988.,p.199

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2SHEEP&1COWCHANGEDFROMALFALFAHAYTODIETSWITH12%OXALICACID.10FOLD&
GREATERINCRININVITRORATEOFOXALATEMETABBYRUMINALMICROBES.OXALATE
DEGRADINGCAPACITYNEGLIGIBLEINCELLFREERUMINALFLUIDOFADAPTEDSHEEPBUTASSOC
WITHFRACTIONSWITHBACTERIALCELLS. Abstract:PubMed
ALLISONETALJANIMSCI45(5):1173(1977)

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Tenof100matureeweswereafflictedwithacuteoxalatetoxicosiswithin40hoursafterbeingtemporarilypenned
inalotthatcontainedconsiderablegrowingRumexcrispus(curlydock).Clinicalsignsoftoxicosisincludedexcess
salivation,tremors,ataxia,andrecumbency.Affectedewesweremarkedlyhypocalcemicandazotemic.Oxalate
crystalswerenotobservedinurine.Grosspostmortemlesionswereminimalandnondiagnosticin2ewesthatdied
peracutely,butperirenaledemaandrenaltubulardegenerationwereclearlyobservableineweseuthanatizedonthe
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thirddayoftoxicosis.Diagnosisofoxalatetoxicosiswasconfirmedbyhistopathologicfindings.SamplesofRumex
sppcontained6.6to11.1%oxalicacidonadryweightbasis,aconcentrationcomparablewiththatinotheroxalate
containingplantsthathavecausedacuteoxalatetoxicosis. Abstract:PubMed
PancieraRJetalJAmVetMedAssoc196(12):19814(1990)

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Inaperiodof21days,sixsubcutaneousinjectionsofcalciumchlorideanddibutyloxalatesolutionproduceda
flecklike,polymorphouscornealopacityandaslightstromalcloudinginchinchillarabbits,asseenwiththeslitlamp.
Infrontoftheendothelium,opaquestructurescouldbeseenwiththespecularmicroscope.NewZealandwhite
rabbitsshowedonlyadiffusecornealclouding.Lightmicroscopyrevealedareticularalterationofthecytoplasmin
thebasallayersofthecornealepitheliumprimarilyinchinchillabastardrabbits.Incentralcornealareasanirregular
structureofthebasalepithelialcellsandapapillalikealterationofthestromalepithelialborderwasseen.Inthe
endotheliumanincreasedformationofvacuoleswasobservedinbothspecies.Scanningelectronmicroscopy
demonstratedendothelialcellloss./Dibutyloxalate/ Abstract:PubMed
WeberUetalGraefesArchClinExpOphthalmol224(5):44751(1986)

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Depositionofcalciumoxalateisresponsibleforthepathologicmanifestationsofoxalosisandmaycontributeto
multiorgandysfunctioninuremiaandtotheprogressionofrenaldamageafterrenalfailureisestablished.Arat
modelofoxalosisusingasingleintravenousinjectionofsodiumoxalate,0.3mmol/kgbodyweight,inratshasbeen
developed.Polarizedlightmicroscopyandsectionfreezedryautoradiographywereusedtoidentify(14)Coxalate
withintherenalparenchymaandinextrarenalorgans.(14)Coxalatecrystalsunder3uinlengthwereidentified
withinoneminofinjectioninproximaltubulelumens.Sectionfreezedryautoradiographyshowedoccasionalminute
crystalswithinglomeruli,heart,lungandliveratonehr.Incontrasttoconcentrativecellularuptakedemonstratedin
ratrenalcorticalslicesinvitro,intracellularaccumulationof(14)Coxalatecouldnotbedetectedinvivo.Withinthe
first24hr,renaloxalateretentionreachedamaximumof25+or4%oftheinjecteddose/gmkidneycomparedto
amaximumofonly7+or3%/gmkidneyafteripadministration.Althoughlessthan1%dose/gmkidney
remainedafteroneweek,crystalfragmentswerescatteredthroughoutthecortexandmedulla,oftensurroundedby
fociofinterstitialnephritis.Theretentionofcrystalsinkidneyandotherbodyorgansfollowingivoxalateprovidesa
modelofoxalosiswhichstimulatespathophysiologiceventsinavarietyofclinicalsituationscharacterizedby
transientlyorpersistentlyelevatedserumoxalate. Abstract:PubMed
BlumenfruchtMJetalJUrol135(6):12749(1986)

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12.1.9 NonHumanToxicityValues
LDLoDogoral1000mg/kg
ITII.ToxicandHazardousIndustrialChemicalsSafetyManual.Tokyo,Japan:TheInternationalTechnicalInformationInstitute,
1988.,p.388

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12.1.10 NationalToxicologyProgramReports
Oxalicacid(OA)ametaboliteofethyleneglycol,wasselectedfortestingintheRACBprotocolbasedonthe
biologicalactivityoftheparentcompound....Datacollectedonbodyweights,clinicalsigns,&food/water
consumptionduringthedoserangefindingsegment(Task1)wereusedtosetconcnsforthemainstudy(Task2)at
0.05%,0.10%,&0.2%OAindrinkingwater.Theseconcnsreducedwaterconsumptioninthemiddle&highdose
groupsbyapprox25%,&yieldedcalculatedconsumptionestimatesofnearly=89,162,&275mgOA/kg/day.
Therewerenoadverseclinicalsigns.Onefemalediedinboththelow&middledosegroups.At0.2%OA,the
numberoflitters/pairwasreducedby5%&thepupweightadjustedforlittersizewasreducedbynearly=4%sire
&damweightswerenotaffectedduringTask2.ForthelastlitterborninTask2,bodyweights&pupnumberwere
recordedforthecontrols&0.1&0.2%OAgroupstherewerenotreatmentrelatedchangesinpupsurvivalor
weightgaintopostnatalday14.BecauseamodestdegreeofeffectseenatthetopdosegroupinTask2was
identifiedonlyaftersummingalltheTask2litterdata,itwaspredictedthatthesinglelitterproducedinTask3
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wouldbeinsufficienttohelpdeterminetheaffectedsex.Thus,thelastlitterfromthecontrol&highdoseanimals
wererearedfortestinginTask4,&Task3wasnotconducted.AftertheTask4micewereweaned,10F0mice
fromthecontrol&0.2%groupswerekilled&necropsied.Nochangeswereseeninbodyororganweightsfrom
females.Formales,theonlysignificanteffectwasa19%decrinprostateweightat0.2%OA.Totalcalciumlevels
inbloodweremeasuredfor10miceofeachsexinthecontrol&0.2%OAgroupsthecontrollevelof9.4mg/dl
wasunchangedbyOAconsumption.IntheTask4onewkmatingtrial,therewasa20%reductioninthenumberof
livepups/litterdeliveredbythe0.2%OAgroup.Nootherdifferenceswereobserved.After7daysofvaginallavage,
theF1micewerekilled&necropsied.Whileterminalbodyweightwasunchangedineithersex,femalekidney
weight(adjustedforbodyweight)wasincreasedby10%intheOAtreatedfemales.Therewerenootherchangesin
organweights.The%ofabnormalspermformsincreasedfrom2.2%incontrolsto4.0%inthe0.2%OAgroup.
Serumcalciumlevelsineithersexwereunchangedfromcontrollevelsof7.9mg/dl.Insummary,intheF0mice,
OAattheselevelsreducedwaterconsumption,&reducedthenumberoflitters/pair,adjustedpupweight,&
prostateweightintheabsenceofdetectedsomaticorganchanges.InF1mice,anincrinkidneyweightoccurred
concomitantwithareductioninthenumberoflivepups/litter,&increasedabnormalspermforms.Ifthekidney
weighteffectistheresultofreducedwaterconsumption,thenitcanbeconcludedthatOxalicAcidisareproductive
toxicantinSwissmiceatconcnsthatreduceparentalwaterconsumption,butthatcausefewothersomaticeffects.
DepartmentofHealth&HumanServices/NationalInstituteofEnvironmentalHealthSciences,NationalToxicologyProgram
OxalicAcid(CAS#144627):ReproductionandFertilityAssessmentinCD1MiceWhenAdministeredinDrinkingWater,NTP
StudyNo.RACB84064(September1985)Availablefrom,asofAugust14,2002:http://ntp.niehs.nih.gov/index.cfm?
objectid=0847F35A0850D1E7B02ED4DDD150F990

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12.2 EcologicalInformation
12.2.1 EnvironmentalFate/ExposureSummary
Oxalicacidisnaturallycontainedasthepotassiumorcalciumsaltinplants,vegetables,humanurine,animalurine,
andkidneystones.Itisalsotheproductofthemetabolismofmanymolds.Oxalicacidmaybereleasedtothe
environmentintobaccosmoke,automobileexhaust,rendering,inwastestreamsfrompulpbleaching,andby
photochemicaloxidationsofanthropogeniccompoundsduringlongrangetransport.Ifreleasedtosoil,oxalicacid
underenvironmentalconditions(pH59)willbeintheformoftheoxalateion(pKa1andpKa2of1.25and4.28,
respectively)andisexpectedtoleachinsoil.Photolysisisexpectedtobeanimportantfateprocessthedaytime
persistenceofoxalicacidonsoilsurfacesisnotexpectedtoexceedafewhours.Baseduponscreening
biodegradationtests,biodegradationinsoilisexpectedtobeimportant.Ifreleasedtowater,oxalicacidwillnot
volatilize,adsorbtosediment,bioconcentrateinaquaticorganisms,oxidizeorhydrolyze.Thepredominantaquatic
fateprocessesareexpectedtobephotolysisinsurfacewatersandaerobicandanaerobicbiodegradation.If
releasedtotheatmosphere,removalfromairviawetdeposition,drydeposition,andphotolysisislikelytooccur.
Exposureofthegeneralpopulationtooxalicacidisexpectedtooccurthroughconsumptionoffoodsinwhichitis
naturallycontained,inhalationofcontaminatedair,andconsumptionofcontaminatedgroundwater.Inoccupational
settings,exposuretooxalicacidmayoccurthroughinhalationofvaporsandthrougheyeandskincontact.(SRC)
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12.2.2 NaturalOccurringSources
MANYPLANTSCONTAINOXALATE,NOTABLYRHUBARBLEAVES,DIEFFENBACHIAORDUMBCANE,
BEETS,SPINACH,MANGOLD,HALOGETON,SORREL,PURSLANE,DOCK,GREASEWOOD&RUSSIAN
THISTLE./OXALATES/
Gosselin,R.E.,R.P.Smith,H.C.Hodge.ClinicalToxicologyofCommercialProducts.5thed.Baltimore:WilliamsandWilkins,
1984.,p.III326

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PLANTSCONTAININGOXALATES:ATRIPLEXSPECIES,BETAVULGARIS,CALANDRINIASPECIES,
EMEXAUSTRALIS,ENCHYLAENATOMENTOSA,HALOGETONGLOMERATUS,OXALISSPECIES,
PORTULACASPECIES,RHEUMRHAPONTICUM,RUMEXSPECIES,SALSOLAKALI,SARCOBATUS
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VERMICULATUS,THRELKELDIAPROCERIFLORA,TRIANTHEMASPECIES./FROMTABLEOXALATES/
Clarke,M.L.,D.G.HarveyandD.J.Humphreys.VeterinaryToxicology.2nded.London:BailliereTindall,1981.,p.260

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Oxalicacidispresentinmanyplantsandvegetables,notablyinthoseoftheOxalisandRumexfamilies,whereit
occursintheleaves,roots,rhizomes,andsapoftheplantasthepotassiumorcalciumsalt(12).Forexample,
waterliliesandduckweedareoxylatecontainingplants(3)andthesefrequentlycolonizelakesandotheraquatic
environments.Furthermore,oxylatemayconstituteasmuchas50%ofthedryweightofsomeplantorgans,serving
bothanexcretoryandastoragefunctionbychelatingandprecipitatingexcesscalciumions(3).Itistheproductof
themetabolismofmanymolds(1).SeveralspeciesofPenicilliumandAspergillusconvertsugarintocalciumoxylate
with90%yieldsunderoptimumconditions(1).Italsooccursinhumanandanimalurineandthecalciumsaltisa
majorconstituentofkidneystones(2).
(1)WindholzMetalTheMerckIndex10thed.Rahway,NJ:Merck&CoIncp.991(1983)(2)BernalesCAetalKirkOthmer
EncyclChemTech.3rdNY:Wiley16:61836(1981)(3)SmithRL,OremlandRSApplEnvironMicrobiol46:10613(1983)

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12.2.3 ArtificialSources
Oxalicacidmaybereleasedtotheenvironmentasemissionsfromrendering,tobaccosmoke(1),andautomobile
exhaust(2).Oxalicacidmaybeproducedintheatmospherebyphotochemicaloxidationsofanthropogenic
compoundsduringlongrangetransport(3).Oxalicacidhasbeenidentifiedinpulpkraftmilleffluents(46)therefore,
itmaybereleasedtotheenvironmentinwastestreamsresultingfrompulpbleaching(SRC).Theestimated
emissionrateofoxalicacidintheSouthEastAirBasin,CAis87kg/day(7).
(1)GraedelTEetalAtmosphericChemicalCompoundsNY:AcademicPressp.346(1986)(2)KawamuraK,KaplanIR
EnvironSciTechnol21:10510(1987)(3)SatsumabayashiH,KuritaHAtmosphericEnviron24A:144350(1990)(4)SuntioLR
etalChemosphere17:124990(1988)(5)LindstromK,OsterbergFEnvironSciTechnol2:1338(1986)(6)KringstadKP,
LindstromKEnvironSciTechnol18:236A48A(1984)(7)GrosjeanDetalMeasurementsofOrganicAcidsintheSouthEast
AirBasin.StateofCaliforniaAirResourcesBoardNTISPB89145411p.43(1988)

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12.2.4 EnvironmentalFate
TERRESTRIALFATE:AnestimatedKocvalueof5(1,SRC)foroxalicacidindicateshighmobilityinsoil(2)and
oxalicacidhasbeendetectedingroundwater(3).Volatilizationfrommoistsoilsisnotexpectedtoberapidbased
uponalowHenry'sLawconstant.Severalscreeningstudiesindicaterapidbiodegradationofoxalicacid(48).
Althoughthesestudiesarenotspecifictosoilmedia,theysuggestthatoxalicacidwillreadilybiodegradeinsoil.
Theoxalicacidconcninanotherstudywasdeterminedtodecreasefrom30mg/kgonasoilsurfacetoabout6
mg/kg540cmbelowthesoilsurface(3)whichsuggeststhatbiodegradationmayhaveoccurred(SRC).Photolysisis
expectedtobeanimportantterrestrialfateprocessthedaytimepersistenceofoxalicacidonsoilsurfacesisnot
expectedtoexceedafewhours(9).
(1)LymanWJetalHandbookofChemicalPropertyEstimationMethods.WashingtonDC:AmerChemSocpp.49,510,74,
1515to1532(1990)(2)SwannRLetalResRev85:1728(1983)(3)CordtT,KussmaulHVomWasser74:28798(1990)(4)
GaffneyPE,HeukelekianHSewIndustWastes30:503(1958)(5)HeukelekianH,RandMCJWaterPollutContrAssoc29:
104053(1955)(6)MadsenEL,AlexanderMApplEnvironMicrobiol50:3429(1985)(7)TakemotoetalSuishitsuOdaku
Kenkyu4:8090(1981)(8)YoungetalJWaterPollutContrFed40:35468(1968)(9)GrosjeanDetalMeasurementsof
OrganicAcidsintheSouthCoastAirBasinARBR88/375PB89145441)GovRepAnnounceIndex(U.S.)89(9)AbstrNo.
921,946(1989)

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AQUATICFATE:Severalscreeningstudies(48)andgrabsampletests(9)indicatethatunderaerobicand
anaerobicconditions,oxalicacidwillreadilybiodegradeinaquaticecosystems.BasedonanexperimentalHenry's
Lawconstantof1.4X1010atmcum/moleat25degC(2),oxalicacidisexpectedtobeessentiallynonvolatilefrom
water(1).Adsorptiontosedimentandbioconcentrationinaquaticorganismsmaynotbeimportantfateprocesses
foroxalicacidinwatersystems.BasedonpKa1andpKa2valuesof1.25and4.28(3),respectively,oxalicacidwill
existprimarilyastheoxalateionunderenvironmentalconditions(pH59,SRC).Aquaticoxidationisnotlikelytobe
animportantfateprocessbasedonahalflifeof285yrsinwaterundercontinuoussunlight(3,SRC).Oxalicacid
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mayreactslowlyinwaterwithphotochemicallyproducedOHradicals,butitisexpectedtoberemovedrapidlyfrom
surfacewaterbydirectphotolysisthedaytimepersistenceofoxalicacidisnotexpectedtoexceedafewhours(10).
(1)LymanWJetalHandbookofChemicalPropertyEstimationMethods.WashingtonDC:AmerChemSocpp.49,510,154,
1515to1532(1990)(2)GaffneyJSetalEnvironSciTechnol21:51924(1987)(3)BuxtonGVetalJPhysChemRefData
17(2):517882(1988)(4)GaffneyPE,HeukelekianHSewIndustWastes30:503(1958)(5)HeukelekianH,RandMCJWater
PollutContrAssoc29:104053(1955)(6)MadsenEL,AlexanderMApplEnvironMicrobiol50:3429(1985)(7)Takemotoetal
SuishitsuOdakuKenkyu4:8090(1981)(8)YoungetalJWaterPollutContrFed40:35468(1968)(9)SmithRL,Oremland
RSApplEnvironMicrobiol46:106113(1983)(10)GrosjeanDetalMeasurementsofOrganicAcidsintheSouthCoastAir
BasinARBR88/375PB89145411GovRepAnnounceIndex(U.S.)89(9)AbstrNo.921,946(1989)

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ATMOSPHERICFATE:Basedonameasuredvaporpressureof2.34104mmHgat25degC(2),oxalicacidis
expectedtoexistalmostentirelyinthevaporphaseintheambientatmosphere(3).Inthevaporphase,oxalicacid
intheambientatmosphereisveryslowlydegradedbyreactionwithphotochemicallyformedhydroxylradicalsthe
halflifeforthisreactioninaircanbeestimatedtobeabout223days(1).Oxalicacidintheambientatmosphere
mayreactslowlywithOHradicals,butitisremovedrapidlybyphotolysisthedaytimepersistenceofoxalicacidis
notexpectedtoexceedafewhours(4).Basedonitshighwatersolubility,removalfromairviawetdepositionis
likelytooccur(4,SRC).Oxalicacidmayalsoberemovedfromairviadrydepositionwith11%ofthetotaldeposition
beingdrydeposition(4).
(1)AtkinsonREnvironToxicolChem7:43542(1988)(2)BernalesCAetalKirkOthmerEncyclChemTech.3rdNY:Wiley
16:61836(1981)(3)EisenreichSJetalEnvironSciTechnol15:308(1981)(4)GrosjeanDetalMeasurementsofOrganic
AcidsintheSouthCoastAirBasinARBR88/375PB89145411GovRepAnnounceIndex(U.S.)89(9)AbstrNo.921,946(1989)

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12.2.5 Biodegredation
Sixtestsatoxalicacidinitialconcnsof3.3to10ppmexhibited75to202%BODToveranincubationperiodof5
daysinanaerobicscreeningstudyusingsewageinoculum(1).A78and55.5%BODTforoxalicacidwasmeasured
underaerobicconditionsoveraperiodof5daysinscreeningtestsat20degCusingsewageinoculum(2).Oxalic
acidatinitialconcnsof0.00375,0.0375,and0.375ppmexhibited95,99,and100%degradation,respectively,in
anaerobicscreeningstudyat25degCusingsewageinoculum(3).Inanotherscreeningstudyusingsewage
inoculum,68and64%BODTweremeasuredforoxalicacidatinitialconcnsof10and20ppm,respectively,overa
5dayincubationperiod(4).An89%BODTwasmeasuredforoxalicacid(10ppminitialconcn)inanaerobic
screeningstudyusingsewageinoculumat19.520.5degCoveranincubationperiodof5days(5).
(1)GaffneyPE,HeukelekianHSewIndustWastes30:503(1958)(2)HeukelekianH,RandMCJWaterPollutContrAssoc29:
104053(1955)(3)MadsenEL,AlexanderMApplEnvironMicrobiol50:3429(1985)(4)TakemotoetalSuishitsuOdaku
Kenkyu4:8090(1981)(5)YoungetalJWaterPollutContrFed40:35468(1968)

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Ultimateanaerobicbiodegradationratesweredeterminedinamarinewater/sedimentgrabsampletakenfromasalt
marshinPaloAlto,CAtobe0.41,0.92,and0.76/daywhichcorrespondtoanaerobicdegradationhalflivesof1.7,
0.75,and0.9days,respectively.Inanothermarinewater/sedimentgrabsamplefromBigSodaLake,NV,anaerobic
biodegradationratesof0.004and0.22/dayweredeterminedwhichcorrespondtohalflivesof173and3.15days,
respectively.Usingthesamemethod(14CO2evolution,GC),ultimateanaerobicbiodegradationratesof0.55,0.31,
5.45,1.73,and1.96/day(halflivesof1.26,2.23,0.13,0.4,and0.35days,respectively)weremeasuredin
freshwater/sedimentgrabsamplestakenfromSearsvilleLake,PaloAlto,CA.Inafreshwater/sedimentgrab
sampletakenfromLakeTahoe,CA,ultimateanaerobicbiodegradationratesweremeasuredtobe0.01and
0.13/daywhichcorrespondtorespectivehalflivesof69and5.3day(1).[(1)SmithRL,OremlandRSApplEnviron
Microbiol46:10613(1983)] Fulltext:PMC239274 Abstract:PubMed
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12.2.6 AbioticDegredation
Therateconstantforthevaporphasereactionofoxalicacidwithphotochemicallyproducedhydroxylradicalscanbe
estimatedtobe7.2X1014cucm/moleculesecat25degCwhichcorrespondstoanatmospherichalflifeofabout
223daysatanatmosphericconcnof5X10+5hydroxylradicalspercucm(1,SRC).Acidsaregenerallyresistentto
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hydrolysis(4)therefore,oxalicacidisnotexpectedtohydrolyzeinaquaticenvironments.Basedondissociation
constantvaluespKa1andpKa2of1.25and4.28(1),respectivelyoxalicacidisexpectedtoexistasanionunder
environmentalconditions(pH59).Theaquaticoxidationrateforthereactionofhydroxylradicalsinwaterwiththe
oxalateionhasbeenexperimentallydeterminedtobe7.7X10+6L/molesatpH6(1).Basedonthisrateanda
hydroxylradicalconcnof1X1017mole/Linwaterundercontinuoussunlight(3),thehalflifefortheaquatic
oxidationofoxalicacidcanbeestimatedtobe285yrs(SRC).OxalicacidmayreactslowlywithOHinwater,butit
isremovedrapidlybydirectphotolysisthedaytimepersistenceofoxalicacidisnotexpectedtoexceedafew
hours(5).
(1)BuxtonGVetalJPhysChemRefData17:517882(1988)(2)AtkinsonREnvironToxicolChem7:43542(1988)(3)MillT
etalScience2078867(1980)(4)LymanWJetalHandbookofChemicalPropertyEstimationMethods.WashingtonDC:
AmerChemSocpp.49,54,510,74,75,1515to1532(1990)(5)GrosjeanDetalMeasurementsofOrganicAcidsinthe
SouthCoastAirBasinARBR88/375PB89145411GovRepAnnounceIndex(U.S.)89(9)AbstrNo.921,946(1989)

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12.2.7 Bioconcentration
Basedonanaverageexperimentalwatersolubilityof220,000mg/Lat25degC(1)andaregressionderived
equation(2),theBCFforoxalicacidcanbeestimatedtobeapproximately0.6(SRC)andthereforeshouldnotbe
expectedtobioconcentrateinaquaticorganisms(SRC).
(1)YalkowskySHetalArizonaDataBaseofWaterSolubility(1989)(2)LymanWJetalHandbookofChemicalProperty
EstimationMethods.WashingtonDC:AmerChemSocpp.49,54,510,74,75,1515to1532(1990)

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12.2.8 SoilAdsorption/Mobility
Basedonanaverageexperimentalwatersolubilityof220,000mg/Lat25degC(1)andaregressionderived
equation(2),theKocforundissociatedoxalicacidcanbeestimatedtobeapproximately5.ThisKocvalueindicates
thatoxalicacidwillhaveveryhighmobilityinsoil(3)therefore,adsorptiontosoilandsedimentmaynotbean
importantfateprocess.BasedonpKa1andpKa2valuesof1.25and4.28(4)respectively,oxalicacidwillexist
primarilyastheoxalateionunderenvironmentalconditions(pH59).Noexperimentaldataareavailableto
determinewhethertheoxalateionwilladsorbtosedimentorsoilmorestronglythanitsestimatedKocvalue
indicates(SRC).
(1)YalkowskySHetalArizonaDataBaseofWaterSolubility(1989)(2)LymanWJetalHandbookofChemicalProperty
EstimationMethods.WashingtonDC:AmerChemSocpp.49,54,510,74,75,1515to1532(1990)(3)SwannRLetalRes
Rev85:1728(1983)(4)BuxtonGVetalJPhysChemRefData17:517882(1988)

fromHSDB

12.2.9 VolatilizationfromWater/Soil
BasedonanexperimentalHenry'sLawconstantof1.4X1010atmcum/moleat25degC(1),oxalicacidis
essentiallynonvolatilefromwater(2).
(1)GaffneyJSetalEnvironSciTechnol21:51924(1987)(2)LymanWJetalHandbookofChemicalPropertyEstimation
Methods.WashingtonDC:AmerChemSocpp.49,54,510,74,75,1515to1532(1990)

fromHSDB

12.2.10 WaterConcentrations
GROUNDWATER:OxalicacidwasdetectedatasiteinGermanyataconcnofabout1mg/kgingroundwater610
to640cmbelowthesurfacehowever,itwasnotdetectedingroundwater640to670cmbelowthesurface(1).
(1)CordtT,KussmaulHVomWasser74:28798(1990)

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fromHSDB
RAIN/SNOW:OxalicacidwasdetectedintwosamplesofmistcollectedinLosAngeles,CAonJune9,1983and
June11,1983atconcnsof23.3and4uM,respectively(1).Inthesamestudy,oxalicacidwasdetectedin4fog
samplesinJuneof1983atconcnsrangingfrom17.3to18.7uMatanaverageconcnof18uM(1).Also,oxalicacid
wasdetectedin8rainsamplescollectedinLosAngeles,CAinAugustandSeptemberof1983atconcnsranging
from2.8to20.7uMatanaverageconcnof15.9uM(1).
(1)SteinbergSetalInternJEnvironAnalChem19:25160(1985)

fromHSDB

12.2.11 EffluentsConcentrations
Oxalicacidhasbeenqualitativelydetectedinpulpmilleffluents(1).Oxalicacidwasidentifiedintwoprebleaching
spentliquorsofkraftpulpmilleffluentsatconcnsof0.5and6g/tonofpulp(2).Itwasdetectedduringkraftpulp
bleachingataconcnof130g/toninaspentchlorinationliquorand590g/toninaspentalkaliextractionliquor(3).
Oxalicacidwasidentifiedintheautomobileexhaustofa1982ToyotaCorollaataconcnof182nmole/cum(4).It
wasalsoidentifiedataconcnof482nmole/cuminautomobileexhaustfroma1971MercedesBenz(4).
(1)SuntioLRetalChemosphere17:124990(1988)(2)LindstromK,OsterbergFEnvironSciTechnol2:1338(1986)(3)
KringstadKP,LindstromKEnvironSciTechnol18:236A48A(1984)(4)KawamuraK,KaplanIREnvironSciTechnol21:105
10(1987)

fromHSDB

12.2.12 Sediment/SoilConcentrations
Oxalicacidwasdetectedatconcnsrangingfrom30to6mg/kginsoil0to540cm,respectively,belowthesurface
atasiteinGermany(1).Oxalicacidwasidentifiedin2soilsamplestakenfromtheUCLAcampus(LosAngeles,
CA)atconcnsof166and156nmol/g(2).Oxalicacidwasdetectedin2fractionsofbogsedimentfromtheLos
Angeles,CAareaatconcnsof1,410(humicacidfraction)and3,350(fulvicacidfraction)nmol/g(2).Significant
concnsofoxylate(dissolvedplusparticulate)werepresentinsedimentstakenfromadiversityofaquatic
environments,rangingfrom0.1to0.7mmol/lofsediment(3).Theseincludedpelagicandlittoralsedimentsfrom
twofreshwaterlakes(SearsvilleLake,CAandLakeTahoe,CA),ahypersaline,meromictic,alkalinelake(BigSoda
Lake,NV),andasouthSanFranciscoBaymudflatandsaltmarsh(3).
(1)CordtT,KussmaulHVomWasser74:28798(1990)(2)KawamuraK,KaplanIREnvironSciTechnol21:10510(1987)(3)
SmithRL,OremlandRSApplEnvironMicrobiol46:10613(1983)

fromHSDB

12.2.13 AtmosphericConcentrations
URBAN/SUBURBAN:OxalicacidwasthedominantspeciesofdicarboxylicacidsintherangeC2C10identifiedin
theLosAngeles,CAambientatmosphere(1).InJune,1984,oxalicacidwasdetectedinwestLosAngelesairat
concnsof6.38and2.12nmol/cum(1).OxalicacidwasdetectedinwestLosAngelesambientairin6samplesata
concnrangeof3.40to8.65nmol/cumandanaverageconcnof5.4nmol/cuminOctober,1984(1).Inthesame
studyduringOctoberof1984,itwasdetectedin2samplestakenfromdowntownLosAngelesatconcnsof6.60
and8.31nmol/cum(1).OxalicacidwasalsodetectedingreenhouseairatUCLA(LosAngeles,CA)inDecember
of1984atconcnsof1.31and2.83nmol/cum(1).OxalicacidwasdetectedinairborneaerosolsaboveTakasaki
andKaruizawa,Japanataverageconcnsof5.1and3.8ng/cum,respectively,duringJulyof1986(2).Oxalicacid
wasdetectedataconcnofapproximately3ng/cuminairborneparticulatematterinasuburbanareainJapan(3).
InSeptemberof1985,oxalicacidwasdetectedintheambientatmosphereofClaremont,CAin12of12samples
takenataconcnrangeof<0.12to0.94ug/cum(4).
(1)KawamuraK,KaplanIREnvironSciTechnol21:10510(1987)(2)SatsumabayashiH,KuritaHAtmosEnviron24A:1443
50(1990)(3)YokouchiY,AmbeYAtmosEnviron20:172734(1986)(4)GrosjeanDAtmosEnviron22:163748(1988)

fromHSDB
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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12.2.14 FoodSurveyValues
Oxalicacidispresentinmanyplantsandvegetables,notablyinthoseoftheOxalisandRumexfamilies,whereit
occursinthesapoftheplantasthepotassiumorcalciumsalt(2).Oxalicacidwasqualitativelydetectedinraw
cassava(Manihotesculenta,Crantz)whichisoneofthemajorstaplefoodsofthetropics(1).GariandFarine
(Farinhademandioca),bothproductsofcassava,weredeterminetobe0.04%and0.2%oxalicacid,respectively(1).
(1)DouganJetalJSciFoodAgric34:87484(1983)(2)WindholzMetalTheMerckIndex10thedRahway,NJ:Merck&Co
Incp.991(1983)

fromHSDB

12.2.15 PlantConcentrations
OXALATECONTENTOFPLANTSISHIGHESTATLEAFYSTAGEOFGROWTH&PLANTSWHICHARE
NORMALLYNOTDANGEROUSTOSTOCKMAYBECOMESO@CERTAINTIMESOFYR.HALOGETON
MAYCONTAIN...34.5%OFOXALATE,MANGELSUPTO12%&SOURSOB5.9%(DRYWT)./OXALATE/
Clarke,M.L.,D.G.HarveyandD.J.Humphreys.VeterinaryToxicology.2nded.London:BailliereTindall,1981.,p.258

fromHSDB
Oxalicacidispresentinmanyplantsandvegetables,notablyinthoseoftheOxalisandRumexfamilies,whereit
occursintheleaves,roots,rhizomes,andsapoftheplantasthepotassiumorcalciumsalt(12).Forexample,
waterliliesandduckweedareoxylatecontainingplants(3).Furthermore,oxylatemayconstituteasmuchas50%of
thedryweightofsomeplantorgans,servingbothanexcretoryandastoragefunctionbychelatingandprecipitating
excesscalciumions(3).Oxylateconcnsrangedfrom0.1to5.0%inseveralplantspeciesthatarepotentialsources
oftheoxylatesinsedimentsofSearsvilleLake,CA,LakeTahoe,CA,BigSodaLake,NV,andasouthSan
FranciscoBaymudflatandsaltmarsh(3).
(1)WindholzMetalTheMerckIndex10thedRahway,NJ:Merck&CoIncp.991(1983)(2)BernalesCAetalKirkOthmer
EncyclChemTech.3rdNY:Wiley16:61836(1981)(3)SmithRL,OremlandRSApplEnvironMicrobiol46:10613(1983)

fromHSDB

12.2.16 AnimalConcentrations
Oxalicacidoccursinhumanandanimalurineandthecalciumsaltisamajorconstituentofkidneystones(1).
(1)BernalesCAetalKirkOthmerEncyclChemTech.3rdNY:Wiley16:61836(1981)

fromHSDB

12.2.17 OtherEnvironmentalConcentrations
OxalicacidwasidentifiedingreenhousedustanddustfromdowntownLosAngeles,CAataconcnsof2,330and
2,510nmol/g,respectively(1).
(1)KawamuraK,KaplanIREnvironSciTechnol21:10510(1987)

fromHSDB

12.2.18 ProbableRoutesofHumanExposure
Exposureofthegeneralpopulationtooxalicacidisexpectedtooccurthroughconsumptionoffoodsinwhichitis
naturallycontained,inhalationofcontaminatedairandconsumptionofcontaminatedgroundwater(17,SRC).In
occupationalsettings,exposuretooxalicacidmayoccurthroughinhalationofvaporsandthrougheyeandskin
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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contact(SRC).
(1)KawamuraK,KaplanIREnvironSciTechnol21:10510(1987)(2)SatsumabayashiH,KuritaHAtmosphericEnviron24A:
144350(1990)(3)YokouchiY,AmbeYAtmosEnviron20:172734(1986)(4)GrosjeanDAtmosEnviron22:163748(1988)
(5)DouganJetalJSciFoodAgric34:87484(1983)(6)WindholzMetalTheMerckIndex10thedRahway,NJ:Merck&Co
Incp.991(1983)(7)CordtT,KussmaulHVomWasser74:28798(1990)

fromHSDB
NIOSH(NOHSSurvey19721974)hasstatisticallyestimatedthat705,215workersarepotentiallyexposedtooxalic
acidintheUSA(1).NIOSH(NOESSurvey19811983)hasstatisticallyestimatedthat130,128workersare
potentiallyexposedtooxalicacidintheUSA(2).
(1)NIOSHNationalOccupationalHazardSurvey(NOHS)(1974)(2)NIOSHNationalOccupationalExposureSurvey(NOES)
(1983)

fromHSDB

12.2.19 BodyBurdens
Oxalicacidcalciumsaltisamajorconstituentofkidneystones(1).
(1)BernalesCAetalKirkOthmerEncyclChemTech.3rdNY:Wiley16:61836(1981)

fromHSDB

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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13 Literature
13.1 DepositorProvidedPubMedCitations
DepositorProvidedPubMed
Citations

3531records
fromPubChem

13.2 NLMCuratedPubMedCitations
CLICKTOLOAD...

fromPubChem

13.3 SynthesisReferences
GiuseppeMessina,GiovanniM.Sechi,LorenoLorenzoni,GiovanniChessa,"Methodofpreparationofoxalicacid
estersandamides."U.S.PatentUS4981963,issuedJuly,1971.
fromDrugBank

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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14 Patents
14.1 DepositorSuppliedPatentIdentifiers
CLICKTOLOAD...

fromPubChem

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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15 BiomolecularInteractionsandPathways
15.1 ProteinBound3DStructures
CLICKTOLOAD...

fromPubChem

15.2 BiosystemsandPathways
CLICKTOLOAD...

fromPubChem

15.3 DrugBankInteractions
DrugBankInteractions:1of3
Target

ProtooncogenetyrosineproteinkinaseSrc Moreinformation...

GeneralFunction

Involvedinproteinkinaseactivity

GeneName

SRC

GenBankGene

AL133293

GenBankProtein

10635153
1. OveringtonJP,AlLazikaniB,HopkinsAL:Howmanydrugtargetsare
there?NatRevDrugDiscov.2006Dec5(12):9936.Pubmed
2. ImmingP,SinningC,MeyerA:Drugs,theirtargetsandthenatureand

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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References

oxalicacid|C2H2O4PubChem

numberofdrugtargets.NatRevDrugDiscov.2006Oct5(10):82134.
Pubmed
3. BermanHM,WestbrookJ,FengZ,GillilandG,BhatTN,WeissigH,
ShindyalovIN,BournePE:TheProteinDataBank.NucleicAcidsRes.
2000Jan128(1):23542.Pubmed
fromDrugBank

DrugBankInteractions:2of3
Transporter

Solutecarrierorganicaniontransporterfamilymember2B1

Action

inhibitor

GeneralFunction

Involvedinaniontransporteractivity

SpecificFunction

MediatestheNa(+)independenttransportoforganicanionssuchas
taurocholate,theprostaglandinsPGD2,PGE1,PGE2,leukotrieneC4,
thromboxaneB2andiloprost

GeneName

SLCO2B1

GenBankGene

AB026256

GenBankProtein

5006263

References

KobayashiD,NozawaT,ImaiK,NezuJ,TsujiA,TamaiI:Involvementof
humanorganicaniontransportingpolypeptideOATPB(SLC21A9)inpH
dependenttransportacrossintestinalapicalmembrane.JPharmacolExpTher.
2003Aug306(2):7038.Epub2003Apr30.Pubmed
fromDrugBank

DrugBankInteractions:3of3
Transporter

Solutecarrierfamily22member8

Action

substrate

GeneralFunction

Carbohydratetransportandmetabolism

SpecificFunction

Playsanimportantroleintheexcretion/detoxificationofendogenousand
exogenousorganicanions,especiallyfromthebrainandkidney.Involvedinthe
transportbasolateralofsteviol,fexofenadine.Transportsbenzylpenicillin
(PCG),estrone3sulfate(E1S),cimetidine(CMD),2,4dichloro
phenoxyacetate(2,4D),paminohippurate(PAH),acyclovir(ACV)and
ochratoxin(OTA)

GeneName

SLC22A8

GenBankGene

AF097491

GenBankProtein

4378059

References

RaceJE,GrasslSM,WilliamsWJ,HoltzmanEJ:Molecularcloningand
characterizationoftwonovelhumanrenalorganicaniontransporters(hOAT1
andhOAT3).BiochemBiophysResCommun.1999Feb16255(2):50814.
Pubmed
fromDrugBank

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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16 BiologicalTestResults
16.1 BioAssayResults
CLICKTOLOAD...

fromPubChem

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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17 Classification
17.1 Ontologies
17.1.1 MeSHTree
CLICKTOLOAD...

fromMeSH

17.1.2 ChEBIOntology
CLICKTOLOAD...

fromChEBI

17.1.3 GeneOntology:BiologicalProcess
CLICKTOLOAD...

fromGeneOntology

17.1.4 GeneOntology:MolecularFunction
CLICKTOLOAD...

fromGeneOntology

17.1.5 KEGG:Metabolite
CLICKTOLOAD...

fromKEGG

17.1.6 WIPOIPC
CLICKTOLOAD...

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

fromWIPO

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18 InformationSources
1. OXALICACIDfromHSDB1100http://toxnet.nlm.nih.gov/cgibin/sis/search/r?
dbs+hsdb:@term+@rn+@rel+144627
2. OxalicAcidfromDrugBankDB03902http://www.drugbank.ca/drugs/DB03902
3. OXALICACIDfromILOICSC0529http://www.ilo.org/dyn/icsc/showcard.display?p_card_id=0529
PeerReviewStatus:24.11.2009Validated

4. OxalicacidfromNIOSHPocketGuidenpgd0474http://www.cdc.gov/niosh/npg/npgd0474.html
5. OXALICACIDfromOSHAOccupationalChemicalDB270
http://www.osha.gov/chemicaldata/chemResult.html?RecNo=270
6. OxalicacidfromCAMEOChemicalsCBNOAA00000000008966
http://cameochemicals.noaa.gov/chemical/8966
7. EPAChemicalDataReport144627http://www.epa.gov/cdr/
8. DrugBankDB03902interaction#1http://www.drugbank.ca/drugs/DB03902#targets
9. DrugBankDB03902interaction#2http://www.drugbank.ca/drugs/DB03902#transporters
10. DrugBankDB03902interaction#3http://www.drugbank.ca/drugs/DB03902#transporters
11. oxalicacidfromNJDOHRTKHazardousSubstanceList1445
http://nj.gov/health/eoh/rtkweb/documents/fs/1445.pdf

NewJerseyDepartmentofHealth,RighttoKnowHazardousSubstanceList

12. ECHA2056343http://echa.europa.eu/
13. ECHA2089321http://echa.europa.eu/
14. ECHA2139508http://echa.europa.eu/
15. REGULATION(EC)No1272/20086070060081http://www.reach
compliance.eu/english/compliance/CLP/CLPInitialVersion.html
16. Wiki772http://en.wikipedia.org/wiki/Oxalic_acid
17. FDA/SPLIndexingdata9E7R5L6H31
http://www.fda.gov/ForIndustry/DataStandards/StructuredProductLabeling/ucm377913.htm
18. TheCambridgeStructuralDatabaseCCDC929767http://www.ccdc.cam.ac.uk/pages/Home.aspx

TheCambridgeStructuralDatabaseprovidesaccessto3Dstructuresofmoleculesdeterminedexperimentallyusingdiffraction
techniques.

19. TheCambridgeStructuralDatabaseCCDC929768http://www.ccdc.cam.ac.uk/pages/Home.aspx

TheCambridgeStructuralDatabaseprovidesaccessto3Dstructuresofmoleculesdeterminedexperimentallyusingdiffraction
techniques.

20. TheCambridgeStructuralDatabaseCCDC929769http://www.ccdc.cam.ac.uk/pages/Home.aspx

TheCambridgeStructuralDatabaseprovidesaccessto3Dstructuresofmoleculesdeterminedexperimentallyusingdiffraction
techniques.

21. TheCambridgeStructuralDatabaseCCDC929770http://www.ccdc.cam.ac.uk/pages/Home.aspx

TheCambridgeStructuralDatabaseprovidesaccessto3Dstructuresofmoleculesdeterminedexperimentallyusingdiffraction
techniques.

22. TheCambridgeStructuralDatabaseCCDC929771http://www.ccdc.cam.ac.uk/pages/Home.aspx

TheCambridgeStructuralDatabaseprovidesaccessto3Dstructuresofmoleculesdeterminedexperimentallyusingdiffraction
techniques.

23. OxalicacidfromNISTRIforMUBZPKHOEPUJKRUHFFFAOYSANhttp://www.nist.gov/srd/nist1a.cfm
24. OxalicacidfromNISTGCMSforMUBZPKHOEPUJKRUHFFFAOYSANhttp://www.nist.gov/srd/nist1a.cfm
25. PubChemhttp://pubchem.ncbi.nlm.nih.gov
DatadepositedinorcomputedbyPubChem

26. OxalicAcidfromMeSH68019815http://www.ncbi.nlm.nih.gov/mesh/68019815
27. MeSHTreefromMeSHDescTreehttp://www.nlm.nih.gov/mesh/meshhome.html

MeSH(MedicalSubjectHeadings)istheNLMcontrolledvocabularythesaurususedforindexingarticlesforPubMed.

28. ChEBIOntologyfromChEBIOBOhttp://www.ebi.ac.uk/chebi/userManualForward.do#ChEBI%20Ontology
TheChEBIOntologyisastructuredclassificationoftheentitiescontainedwithinChEBI.

29. MetabolitefromKEGGbr08001http://www.genome.jp/dbgetbin/www_bget?brite:br08001
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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Compoundswithbiologicalroles

30. biologicalprocessfromGeneOntologyGO_ROOT_486550
http://amigo.geneontology.org/amigo/term/GO:0008150

TheGeneOntology(GO)http://www.geneontology.org/projectprovidesacontrolledvocabularyoftermsfordescribingthe
functionsofgeneproducts,andisdividedintothreedomains.Eachterminthebiologicalprocessesdomain,shownhere,
representsrecognizedseriesofevents,oracollectionofmoleculareventswithadefinedbeginningandend.Mutant
phenotypesoftenreflectdisruptionsinbiologicalprocesses.Thetermsbelowapplytothegene/proteintarget(s)testedby
theBioAssay.

31. molecularfunctionfromGeneOntologyGO_ROOT_486552
http://amigo.geneontology.org/amigo/term/GO:0003674

TheGeneOntology(GO)http://www.geneontology.org/projectprovidesacontrolledvocabularyoftermsfordescribingthe
functionsofgeneproducts,andisdividedintothreedomains.Eachterminthemolecularfunctionsdomain,shownhere,
representaprotein'sjobsorabilities.Thesemayincludetransportingthingsaround,bindingtothings,holdingthingstogether
andchangingonethingintoanother.Thisisdifferentfromthebiologicalprocessesthegeneproductisinvolvedin,which
involvemorethanoneactivity.Thetermsbelowapplytothegene/proteintarget(s)testedbytheBioAssay.

32. InternationalPatentClassification2015fromWIPOIPChttp://www.wipo.int/classifications/ipc/

TheWorldIntellectualPropertyOrganization(WIPO)InternationalPatentClassification(IPC)providesforahierarchical
systemoflanguageindependentsymbolsfortheclassificationofpatentsandutilitymodelsaccordingtothedifferentareasof
technologytowhichtheypertain.

33. ReducingAgentsfromMeSH68019163http://www.ncbi.nlm.nih.gov/mesh/68019163
34. NCBILinkOuthttp://www.ncbi.nlm.nih.gov/projects/linkout

LinkOutisaservicethatallowsonetolinkdirectlyfromNCBIdatabasestoawiderangeofinformationandservicesbeyond
NCBIsystems.

http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties

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