Borneol - Wikipedia https://en.wikipedia.

org/wiki/Borneol

Borneol
Borneol is a bicyclic organic compound and a terpene
derivative. The hydroxyl group in this compound is Borneol
placed in an endo position. Being chiral, borneol exists as
two enantiomers. Both (+)-borneol (older name
d-borneol) and (−)-borneol (l-borneol) are found in
nature.

Contents
Reactions
Occurrence
Synthesis
Uses
Use in organic chemistry Names

Toxicology IUPAC name

Skin Irritation rel-(1R,2S,4R)-1,7,7-
Phototoxicity and photoallergy Trimethylbicyclo[2.2.1]heptan-2-ol
Other names
Derivatives
1,7,7-Trimethylbicyclo[2.2.1]heptan-
Notes and references 2-endo-ol
External links endo-2-Bornanol
Identifiers

Reactions CAS Number 507-70-0 (+/-)

3D model Interactive image (https://c
Borneol is easily oxidized to the ketone (camphor). One (JSmol) hemapps.stolaf.edu/jmol/j
historical name for borneol is Borneo camphor which mol.php?model=O%5BC%
explains the name. 40H%5D1C%5BC%40H%
5D2CC%5BC%40%5D1%
Occurrence 28C%29C2%28C%29C)
ChEBI CHEBI:15393 (https://ww
The compound was named in 1842 by the French
w.ebi.ac.uk/chebi/searchId.
chemist Charles Frédéric Gerhardt.[2] Borneol can be
do?chebiId=15393)
found in several species of Heterotheca,[3] Artemisia,
Callicarpa,[4] Dipterocarpaceae, Blumea balsamifera ChEMBL ChEMBL486208 (https://w
and Kaempferia galanga.[5] ww.ebi.ac.uk/chembldb/ind
ex.php/compound/inspect/
It is one of the chemical compounds found in castoreum.
ChEMBL486208)
This compound is gathered from the beaver's plant
food.[6]

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Synthesis ChemSpider 5026296 (http://www.chem

spider.com/Chemical-Struc
Borneol can be synthesized by reduction of camphor by ture.5026296.html)
the Meerwein–Ponndorf–Verley reduction (a reversible
process). Reduction of camphor with sodium ECHA InfoCard 100.006.685 (https://echa.
borohydride (fast and irreversible) gives instead the europa.eu/substance-infor
isomer isoborneol as the kinetically controlled reaction mation/-/substanceinfo/10
product. 0.006.685)
EC Number 207-352-6
IUPHAR/BPS 6413 (http://www.guidetop
harmacology.org/GRAC/Li
gandDisplayForward?tab=
summary&ligandId=6413)
KEGG C01411 (https://www.kegg.
jp/entry/C01411)
PubChem CID 6552009 (https://pubchem.
ncbi.nlm.nih.gov/compoun
d/6552009)
UNII M89NIB437X (https://fdasi
s.nlm.nih.gov/srs/srsdirect.j
sp?regno=M89NIB437X)
UN number 1312
CompTox DTXSID2058700 (https://c
Dashboard (EPA) omptox.epa.gov/dashboar
d/DTXSID2058700)
InChI
InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11
H,4-6H2,1-3H3/t7-,8+,10+/m1/s1
Key: DTGKSKDOIYIVQL-WEDXCCLWSA-N

InChI=1/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,
4-6H2,1-3H3/t7-,8+,10+/m1/s1
Key: DTGKSKDOIYIVQL-WEDXCCLWBQ

SMILES
O[C@H]1C[C@H]2CC[C@]1(C)C2(C)C

Properties
Chemical formula C10H18O
Molar mass 154.253 g·mol−1
Appearance colorless to white lumps
Odor pungent, camphor-like
Density 1.011 g/cm3 (20 °C)[1]
Melting point 208 °C (406 °F; 481 K)
Boiling point 213 °C (415 °F; 486 K)

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Solubility in water slightly soluble (D-form)

Solubility soluble in chloroform,
ethanol, acetone, ether,
benzene, toluene, decalin,
tetralin
Magnetic −1.26 × 10−4 cm3/mol
susceptibility (χ)
Hazards
Safety data sheet External MSDS (https://fsci
mage.fishersci.com/msds/
33824.htm)
GHS pictograms

GHS Signal word Warning

GHS hazard H228
statements
GHS P210, P240, P241, P280,
precautionary P370+378
statements
NFPA 704
(fire diamond)
2
2 0

Flash point 65 °C (149 °F; 338 K)

Related compounds
Related Bornane (hydrocarbon)
compounds
Except where otherwise noted, data are given
for materials in their standard state (at 25 °C
[77 °F], 100 kPa).
verify (what is ?)
Infobox references

Uses

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Whereas d-borneol was the enantiomer that used to be the most readily available commercially, the
more commercially available enantiomer now is l-borneol, which also occurs in nature.

Borneol is used in traditional Chinese medicine. An early description is found in the Bencao Gangmu.

Borneol is a component of many essential oils[7] and it is a natural insect repellent.[8]

Laevo-borneol is used as an aroma chemical in perfumery. It has a balsamic odour type with pine,
woody and camphoraceous facets.

Use in organic chemistry

Derivatives of isoborneol are used as ligands in asymmetric synthesis:

(2S)-(−)-3-exo-(morpholino)isoborneol or MIB[9] with a morpholine substituent in the α-hydroxyl

position.
(2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB[10] with a dimethylamino substituent in the
α-hydroxyl position

Toxicology
Borneol may cause eye, skin, and respiratory irritation; it is harmful if swallowed. [11]

Skin Irritation

Borneol has been shown to have little to no irritation effect when applied to the human skin at a small
dose.[12] However, a long term exposure to borneol may cause mild irritation.[13]

Phototoxicity and photoallergy

Since Borneol does not absorb UV light at 290 nm to 400 nm, it doesn't have any phototoxic or
photoallergic potential.[12]

Derivatives
The bornyl group is a univalent radical C10H17 derived from borneol by removal of hydroxyl and is
also known as 2-bornyl.[14] Isobornyl is the univalent radical C10H17 that is derived from
isoborneol.[15] The structural isomer fenchol is also a widely used compound derived from certain
essential oils.

Bornyl acetate is the acetate ester of borneol.

Notes and references

1. Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL):
CRC Press. p. 3.56. ISBN 0-8493-0486-5.

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2. C. Gerhardt (1842) "Sur la transformation de l'essence de valériane en camphre de Bornéo et en

camphre des laurinées" (On the transformation of the essence of valerian into Borneo camphor
and into laurel camphor), Comptes rendus, 14 : 832-835. From p. 834 (http://gallica.bnf.fr/ark:/121
48/bpt6k2973d/f838.item.r=.zoom): "Je donne, par cette raison, à l'hydrogène carboné de
l'essence de valériane, le nom de bornéène, et, au camphre lui-même, celui de bornéol." (I give,
for this reason [namely, that the compound that Gerhardt had obtained from valerian oil was
identical to that obtained by Pelouze from camphor from Borneo], to the hydrocarbon from
valerian essence, the name bornéène, and, to camphor itself, that of borneol.)
3. Lincoln, D.E., B.M. Lawrence. 1984. "The volatile constituents of camphorweed, Heterotheca
subaxillaris". Phytochemistry 23(4): 933-934
4. "Species Information". sun.ars-grin.gov. Retrieved 2008-03-02.
5. Wong, K. C.; Ong, K. S.; Lim, C. L. (2006). "Composition of the essential oil of rhizomes of
Kaempferia Galanga L.". Flavour and Fragrance Journal. 7 (5): 263–266.
doi:10.1002/ffj.2730070506 (https://doi.org/10.1002%2Fffj.2730070506).
6. The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (book at google books
(https://books.google.com/books?id=HZ5WjXB5Pr8C&pg=PA43))
7. Plants containing borneol (http://www.ars-grin.gov/cgi-bin/duke/highchem.pl?chem=borneol&allch
ems=x) Archived (https://web.archive.org/web/20150923174038/http://www.ars-grin.gov/cgi-bin/du
ke/highchem.pl?chem=borneol&allchems=x) 2015-09-23 at the Wayback Machine (Dr. Duke's
Phytochemical and Ethnobotanical Databases)]
8. "Chemical Information" (https://web.archive.org/web/20041107161247/http://sun.ars-grin.gov:8080
/npgspub/xsql/duke/chemdisp.xsql?chemical=BORNEOL). sun.ars-grin.gov. Archived from the
original (http://sun.ars-grin.gov:8080/npgspub/xsql/duke/chemdisp.xsql?chemical=BORNEOL) on
2004-11-07. Retrieved 2008-03-02.
9. "(2S)-(−)-3-exo-(MORPHOLINO)ISOBORNEOL [(−)-MIB]". Organic Syntheses. 82: 87. 2005.
doi:10.15227/orgsyn.082.0087 (https://doi.org/10.15227%2Forgsyn.082.0087).
10. "(2S)-(−)-3-exo-(DIMETHYLAMINO)ISOBORNEOL [(2S)-(−)-DAIB]". Organic Syntheses. 79: 130.
2002. doi:10.15227/orgsyn.079.0130 (https://doi.org/10.15227%2Forgsyn.079.0130).
11. Material Safety Data Sheet, Fisher Scientific (https://fscimage.fishersci.com/msds/33824.htm)
12. Bhatia, S.P.; Letizia, C.S.; Api, A.M. (November 2008). "Fragrance material review on borneol" (htt
ps://linkinghub.elsevier.com/retrieve/pii/S0278691508003219). Food and Chemical Toxicology. 46
(11): S77–S80. doi:10.1016/j.fct.2008.06.031 (https://doi.org/10.1016%2Fj.fct.2008.06.031).
13. HAZARDOUS SUBSTANCE FACT SHEET (https://nj.gov/health/eoh/rtkweb/documents/fs/0242.p
df)
14. "Definition of BORNYL" (https://www.merriam-webster.com/dictionary/bornyl). www.merriam-
webster.com.
15. "Definition of ISOBORNYL" (https://www.merriam-webster.com/dictionary/isobornyl).
www.merriam-webster.com.

External links
NIST datasheet including full spectroscopic data (http://webbook.nist.gov/cgi/cbook.cgi?ID=507-7
0-0&Units=SI&Mask=100)
Borneol in Chinese medicine (http://www.itmonline.org/arts/borneol.htm)

Retrieved from "https://en.wikipedia.org/w/index.php?title=Borneol&oldid=1011562079"

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