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 name (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) | |
ChEBI |
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ChEMBL | |
ChemSpider | |
PubChem CID | |
UNII |
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UN number | 1312 |
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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). |
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
References
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