Borneol
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| Names | |||
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| IUPAC name
endo-1,7,7-Trimethyl- bicyclo[2.2.1]heptan-2-ol
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| Identifiers | |||
507-70-0  |
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| ChEBI | CHEBI:15393 |
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| ChEMBL | ChEMBL486208 |
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| ChemSpider | 5026296 |
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| 6413 | |||
| Jmol 3D model | Interactive image | ||
| KEGG | C01411 |
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| PubChem | 6552009 | ||
| UNII | M89NIB437X |
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| Properties | |||
| 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) | ||
| slightly soluble (D-form) | |||
| Solubility | soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin | ||
| Vapor pressure | {{{value}}} | ||
| Related compounds | |||
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Related compounds
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Bornane (hydrocarbon) | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |||
Borneol is a bicyclic organic compound and a terpene. The hydroxyl group in this compound is placed in an endo position. There are two different enantiomers of borneol. Both d-(+)-borneol and l-(–)-borneol are found in nature.
Contents
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.
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File:Synthesis of isoborneol from camphor.svgSynthesis 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 enantiomer that formerly was the most readily available commercially, the currently more commercially available enantiomer 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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 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)]
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Material Safety Data Sheet, Fisher Scientific
