U. S. DEPARTMENT oP CoMMERCB NATIONAL BURl!

AU OP STANDARDS

RESEARCH PAPER RP1680

Part of Jourrial of Research of the N_ational Bureau of Staridards, Volume 35
N_ovember 1945

OXIDATION OF GALACTURONIC ACID AND OF 5-KETO­

G LUCONIC ACID IN ALKALINE SOLUTION
By Horace S. lsbell and Nancy B. Holt

ABSTRACT
In thc present investigation detcrminations wcre madc of the quantities of
oxalate, tartrate, and trihydroxyglutarate formed by the oxidation of galactnronic
acid and of 5-keto-gluconic acid in the presenee of various bases and ve.rious
concentrations of the base. Although preliminary measur<'mcnls indicate that
the proportions of the products can be altcred by use of catalysts, tl>is roport is
restricted to the results obtaincd witl'out thc addition of catalytic substanc<'s.
Oxidation of sodium galacturonate with oxygcn in 1-N sodium hydroxide s0]1,tion
gave oxalate, n-tartrate (levo), and n-arabo-trihydroxyglu (arate in yiclds of 0.10,
0.10, and 0.45 mole, rcspectively, per mole oí galacturonate. Oxidation of sodium
5-keto-gluconate under Jike eonditions gave oxalatc, L-tartrate (dextro), and xylo­
trihydroxyglutarate in yields of 0.20, 0.10, and 0.45 mole, respectively, per mole oí
sodium 5-keto-gluconate. Dírectíons are included for the preparalion of potas­
sium n-arabo-trihydroxyglutaratc from galaeturonic acid.
CONTENTS
Pege
I. Introduetíon____________________________________________________ 433
IJ. Experimental methods___________________________________________ 435
l. Oxidation mcthod________________________________________ 435
2. Determination or oxalate, tartrate, and trihydroxyglutarate_____ 435
3. Pr<'paration of potassium acid D-tartrale (levo) and potassium
D-arabo-trihydroxyglutaratc from sodium galacturonate______ 436
4. Preparation of potassium acid L-tartrate (dextro) and potassium
xylo-trihydroxyglutarate from calcium 5-keto-gluconate ______ 437
III. Discussion of results_____________________________________________ 437
IV. Referenccs _____________________________________________________ 438

I. INTRODUCTION
Tbe development of relativcly simple methods for thc prcparation
of salts of galacturonic acid [I] 1 and of 5-keto-gluconic acid (2] makes
these substances readily available for the investigation of possible
uses. The prcparation of L-tartaric acid (dextrorotaLory) 2 from
5-keto-gluconic acid and the preparation of n-arabo-trihydroxyglu­
taric acid from galacturonic acid are reported in thc patent literature
[3, 4]. The processes for the preparation of thc two products aro
• Figures in brackcts indicatc the Jiternture reíerenccs at the cnd ol this paper.
• Dextrorotntory tartnric ncid is comrnonly callcd d-tartaric acid. 'I'hc "d" relcrs to the direction of
oplical rotntion, and should not be conlused with tbc "o" used to indicntc conflguration in tbe carbobydrato
ficld. Dcxtrorotatory tartaric acid is configuratlonaliy rclatcd to L-glyceraldehyde, the substancc used for
thc n and L classification ol the carbobydratcs. In this paper it is dcsignated L-tartaric acid,
670468-45--fl 433