Borneol

Chembox new
Name = Borneol
ImageFileL1 = Borneol_Structure.png ImageSizeL1 = 120px
ImageNameL1 = Borneol
ImageFileR1 = Borneol-3D-balls.png ImageSizeR1 = 140px
IUPACName = "endo"-1,7,7-Trimethyl- bicyclo [2.2.1] heptan-2-ol
Section1 = Chembox Identifiers
CASOther = [507-70-0] (+)
[464-45-9] (-)
SMILES = CC1(C2(C)C)C(O)CC2CC1
Section2 = Chembox Properties
C=10|H=18|O=1
Density = 1.011 g/cm³ @ 20^oC
MeltingPt = 208 °C
BoilingPt = sublimes
Section7 = Chembox Hazards
ExternalMSDS = [http://physchem.ox.ac.uk/MSDS/BO/borneol.html External MSDS]

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

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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.

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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 and Dipterocarpaceae.

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, [ [http://www.ars-grin.gov/cgi-bin/duke/highchem.pl?chem=borneol&allchems=x Plants containing borneol] (Dr. Duke's Phytochemical and Ethnobotanical Databases)] ] and it is a natural insect repellent. [cite web
url=http://sun.ars-grin.gov:8080/npgspub/xsql/duke/chemdisp.xsql?chemical=BORNEOL
title=Chemical Information
publisher=sun.ars-grin.gov
accessdate=2008-03-02
last=
first=]

Use in organic chemistry

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

* (2S)-(−)-3-exo-(morpholino)isoborneol or MIB [Young K. Chen, Sang-Jin Jeon, Patrick J. Walsh, and William A. Nugent Organic Syntheses, Vol. 82, p.87 (2005) [http://www.orgsynth.org/orgsyn/prep.asp?prep=v82p0087 Article] ] with a morpholine substituent in the α-hydroxyl position
* (2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB [James D. White, Duncan J. Wardrop, and Kurt F. Sundermann Organic Syntheses, Coll. Vol. 10, p.305 (2004); Vol. 79, p.130 (2002) [http://www.orgsynth.org/orgsyn/prep.asp?prep=v79p0130 Article] .] with a dimethylamino substituent in the α-hydroxyl position

External links

* [http://webbook.nist.gov/cgi/cbook.cgi?ID=507-70-0&Units=SI&Mask=100 NIST datasheet including full spectroscopic data]
* [http://www.flavornet.org/info/507-70-0.html Dynamic 3D model borneol]
* [http://www.flavornet.org/info/124-76-5.html Dynamic 3D model isoborneol]
* [http://www.itmonline.org/arts/borneol.htm Borneol in Chinese medicine]

References