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 exo isomer.

Borneol is easily oxidized to the kinetically controlled reaction product.

Borneol exists as two optically active. It can be found in several species of Artemisia and Dipterocarpaceae.

Borneol is used in Bencao Gangmu.

Borneol is a component of many essential oils [1].

Use in organic chemistry

Derivatives of isoborneol are used as chiral asymmetric synthesis:

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

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.