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Borneol



Borneol
IUPAC name endo-1,7,7-trimethyl- bicyclo[2.2.1]heptan-2-ol
Identifiers
CAS number [507-70-0] (+)
[464-45-9] (-)
SMILES CC1(C2(C)C)C(O)CC2CC1
Properties
Molecular formula C10H18O
Molar mass 154.25 g/mol
Density 1.011 g/cm3 @ 20oC
Melting point

208 °C

Boiling point

sublimes

Hazards
MSDS External MSDS
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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.

Additional recommended knowledge

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 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 [1].

Use in organic chemistry

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

References

  1. ^ Plants containing borneol (Dr. Duke's Phytochemical and Ethnobotanical Databases)]
  2. ^ Young K. Chen, Sang-Jin Jeon, Patrick J. Walsh, and William A. Nugent Organic Syntheses, Vol. 82, p.87 (2005) Article
  3. ^ James D. White, Duncan J. Wardrop, and Kurt F. Sundermann Organic Syntheses, Coll. Vol. 10, p.305 (2004); Vol. 79, p.130 (2002) Article.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Borneol". A list of authors is available in Wikipedia.
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