Borneol

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Borneol
Borneol 140px
Systematic name endo-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol
Chemical formula C10H18O
Molecular mass 154.25 g/mol
Density 1.011 g/cm3 @ 20oC
Specific rotation 37.7 °
Melting point 208 °C
Boiling point sublimes
CAS number [507-70-0] (+) <br\> [464-45-9] (-)
SMILES CC1(C2(C)C)C(O)CC2CC1
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.

Isoborneol

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.

Reduction of camphor to isoborneol

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.

Use in organic chemistry

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


External links

References

  1. Young K. Chen, Sang-Jin Jeon, Patrick J. Walsh, and William A. Nugent Organic Syntheses, Vol. 82, p.87 (2005) Article
  2. James D. White, Duncan J. Wardrop, and Kurt F. Sundermann Organic Syntheses, Coll. Vol. 10, p.305 (2004); Vol. 79, p.130 (2002) Article.

da:Borneol de:Borneol


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