Borneol
| Borneol | |
|---|---|
 |
 |
| IUPAC name endo-1,7,7-Trimethyl- bicyclo[2.2.1]heptan-2-ol | |
| Identifiers | |
| CAS number | 507-70-0  |
| PubChem | 6552009 |
| ChemSpider | 5026296 |
| UNII | M89NIB437X |
| KEGG | C01411 |
| ChEBI | CHEBI:15393 |
| ChEMBL | CHEMBL486208 |
| Jmol-3D images | {{#if:O[C@H]1C[C@H]2CC[C@]1(C)C2(C)C|Image 1 |
| |
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| Properties | |
| Molecular formula | C10H18O |
| Molar mass | 154.25 g mol−1 |
| Appearance | colorless to white lumps |
| Odor | pungent, camphor-like |
| Density | 1.011 g/cm3 (20 °C)[1] |
| Melting point | 208 °C; 406 °F; 481 K |
| Boiling point | 213 °C; 415 °F; 486 K |
| Solubility in water | slightly soluble (D-form) |
| Solubility | soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin |
| Hazards | |
| MSDS | External MSDS |
| NFPA 704 |
 2
2
0
|
| Flash point | 65 °C; 149 °F; 338 K |
| Related compounds | |
| Related compounds | Bornane (hydrocarbon) |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Borneol is a bicyclic organic compound and a terpene. The hydroxyl group in this compound is placed in an endo position. Borneol exists as two enantiomers which have two different CAS numbers. Naturally occurring d-(+)-borneol is optically active.
Reactions
Borneol is easily oxidized to the ketone (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 (a reversible process). Reduction of camphor with sodium borohydride (fast and irreversible) gives instead the isomer isoborneol as the kinetically controlled reaction product.
Synthesis of the borneol isomer isoborneol via reduction of camphor.
Natural occurrences
Borneol can be found in several species of Artemisia, Dipterocarpaceae, Blumea balsamifera and Kaempferia galanga.[2]
It is also one of the chemical compounds found in castoreum. This compound is gathered from the beaver plant food.[3]
Uses
Whereas d-borneol was the antipode that formerly was the most readily available commercially, the currently more commercially available antipode is l-Borneol, which also occurs in nature.
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,[4] and it is a natural insect repellent.[5]
Use in organic chemistry
Derivatives of isoborneol are used as chiral ligands in asymmetric synthesis:
- (2S)-(−)-3-exo-(morpholino)isoborneol or MIB[6] with a morpholine substituent in the α-hydroxyl position
- (2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB[7] with a dimethylamino substituent in the α-hydroxyl position
Toxicology
Borneol is an eye, skin, and respiratory irritant; and is harmful if swallowed.[8]
Notes and references
- ↑ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. p. 3.56. ISBN 0-8493-0486-5.
- ↑ Wong, K. C.; Ong, K. S.; Lim, C. L. (2006). "Composition of the essential oil of rhizomes of Kaempferia Galanga L.". Flavour and Fragrance Journal 7 (5): 263–266. doi:10.1002/ffj.2730070506.
- ↑ The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (book at google books)
- ↑ Plants containing borneol (Dr. Duke's Phytochemical and Ethnobotanical Databases)]
- ↑ "Chemical Information". sun.ars-grin.gov. Retrieved 2008-03-02.
- ↑ Chen, Y. K.; Jeon, S.-J.; Walsh, P. J.; Nugent, W. A. (2005), "(2S)-(–)-3-exo-(MORPHOLINO)ISOBORNEOL [(–)-MIB]", Org. Synth. 82: 87; Coll. Vol. 11: 702
- ↑ White, J. D.; Wardrop, D. J.; Sundermann, K. F. (2002), "(2S)-(−)-3-exo-(DIMETHYLAMINO)ISOBORNEOL [(2S)-(−)-DAIB]", Org. Synth. 79: 130; Coll. Vol. 10: 305
- ↑ Material Safety Data Sheet, Fisher Scientific
External links
- NIST datasheet including full spectroscopic data
- Dynamic 3D model borneol
- Dynamic 3D model isoborneol
- Borneol in Chinese medicine