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.

Quick facts Names, Identifiers ...
Isoborneol
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.285 Edit this at Wikidata
UNII
UN number 1312
  • +: InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1
    Key: DTGKSKDOIYIVQL-OYNCUSHFSA-N
  • -: InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1
    Key: DTGKSKDOIYIVQL-MRTMQBJTSA-N
  • +: C[C@]12CC[C@H](C1(C)C)C[C@@H]2O
  • -: C[C@@]12CC[C@@H](C1(C)C)C[C@H]2O
  • rac: CC1(C2CCC1(C(C2)O)C)C
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]
GHS02: Flammable
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]

References

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