Borneol
| Borneol | |
|---|---|
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| 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 |
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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.
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.
Use in organic chemistry
Derivatives of isoborneol are used as chiral ligands in asymmetric synthesis:
- (2S)-(−)-3-exo-(morpholino)isoborneol or MIB[1] with a morpholine substituent in the α-hydroxyl position
- (2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB[2] with a dimetylamino substituent in the α-hydroxyl position
External links
- NIST datasheet including full spectroscopic data
- Datasheet
- Dynamic 3D model borneol
- Dynamic 3D model isoborneol
- Reduction of Borneol oxidation with sodium hypochlorite
- Borneol in Chinese medicine
References
- ^ 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.
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