Isoborneol
Chemical compound
From Wikipedia, the free encyclopedia
Isoborneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an exo position. The endo diastereomer is called borneol. Being chiral, isoborneol exists as enantiomers.
| Names | |
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| IUPAC names
+: (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol -: (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol | |
| Identifiers | |
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3D model (JSmol) |
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| ChEBI |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.285 |
PubChem CID |
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| UNII |
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| UN number | 1312 |
CompTox Dashboard (EPA) |
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| Properties | |
| C10H18O | |
| Molar mass | 154.253 g·mol−1 |
| Appearance | white or colorless solid |
| Melting point | 212–214 °C (414–417 °F; 485–487 K) + or -; 210–215 °C for rac |
| Hazards | |
| GHS labelling:[1] | |
| Warning | |
| H228 | |
| P210, P240, P241, P280, P370+P378 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
Isoborneol is synthesized commercially by hydrolysis of isobornyl acetate. The latter is obtained from treatment of camphene with acetic acid in the presence of a strong acid catalyst.[2]
It can also be produced by reduction of camphor:
Isoborneol derivatives as chiral ligands
Derivatives of isoborneol are used as ligands in asymmetric synthesis.[3]
- (2S)-(−)-3-exo-(morpholino)isoborneol or MIB[4] with a morpholine substituent in the α-hydroxyl position.
- (2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB[5] with a dimethylamino substituent in the α-hydroxyl position
