Borneol

Borneol

IUPAC name endo-1,7,7-Trimethyl- bicyclo[2.2.1]heptan-2-ol
Identifiers
CAS number	507-70-0^Y
PubChem	6552009
ChemSpider	5026296^Y
UNII	M89NIB437X^Y
KEGG	C01411^Y
ChEBI	CHEBI:15393^Y
ChEMBL	CHEMBL486208^Y
Jmol-3D images	Image 1
SMILES O[C@H]1C[C@H]2CC[C@]1(C)C2(C)C
InChI InChI=1S/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^Y Key: DTGKSKDOIYIVQL-WEDXCCLWSA-N^Y 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
Properties
Molecular formula	C₁₀H₁₈O
Molar mass	154.25 g mol⁻¹
Density	1.011 g/cm³ (20 °C)^[1]
Melting point	208 °C, 481 K, 406 °F
Boiling point	213 °C
Hazards
MSDS	External MSDS
Related compounds
Related compounds	Bornane (hydrocarbon)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Borneol is a bicyclic organic compound and a terpene. The hydroxyl group in this compound is placed in an endo position.

Borneol is easily oxidized to the ketone yielding camphor. One historical name for borneol is Borneo camphor which explains the name. Borneol can be synthesized by reduction of camphor by the Meerwein-Ponndorf-Verley Reduction. The same reduction but then fast and irreversible with sodium borohydride gives isoborneol as the kinetically controlled reaction product.

Borneol exists as two enantiomers which have two different CAS numbers. Naturally occurring d-(+)-borneol is optically active. It can be found in several species of Artemisia, Dipterocarpaceae, Blumea balsamifera and Kaempferia galanga^[2] .

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

Borneol is a component of many essential oils,^[3] and it is a natural insect repellent.^[4]

Use in organic chemistry

Derivatives of isoborneol are used as chiral ligands in asymmetric synthesis:

(2S)-(−)-3-exo-(morpholino)isoborneol or MIB^[5] with a morpholine substituent in the α-hydroxyl position
(2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB^[6] with a dimethylamino substituent in the α-hydroxyl position

The related isoborneol is the exo isomer.

Borneol is an eye, skin, and respiratory irritant; and is harmful if swallowed.^[7]

^ 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.
^ Wong, K. C. et al.; Ong, K. S.; Lim, C. L. (2006). "Compositon of the essential oil of rhizomes of kaempferia galanga L.". Flavour and Fragrance Journal 7 (5): 263–266. doi:10.1002/ffj.2730070506.
^ Plants containing borneol (Dr. Duke's Phytochemical and Ethnobotanical Databases)]
^ "Chemical Information". sun.ars-grin.gov. http://sun.ars-grin.gov:8080/npgspub/xsql/duke/chemdisp.xsql?chemical=BORNEOL. Retrieved 2008-03-02.
^ Young K. Chen, Sang-Jin Jeon, Patrick J. Walsh, and William A. Nugent Organic Syntheses, Vol. 82, p.87 (2005) Article
^ James D. White, Duncan J. Wardrop, and Kurt F. Sundermann Organic Syntheses, Coll. Vol. 10, p.305 (2004); Vol. 79, p.130 (2002) Article.
^ Material Safety Data Sheet, Fisher Scientific