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.

Isoborneol
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
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).

Preparation

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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

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Derivatives of isoborneol are used as ligands in asymmetric synthesis.[3]

References

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  1. ^ "(+)-Isoborneol". pubchem.ncbi.nlm.nih.gov. Retrieved 1 December 2022.
  2. ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  3. ^ Yus, Miguel; Ramón, Diego (2007). "Chiral Ligands with an Isoborneol-10-sulfonamide Structure: A Ten-Year Odyssey". Synlett. 2007 (15): 2309–2320. doi:10.1055/s-2007-985602.
  4. ^ Chen, Y. K.; Jeon, S.-J.; Walsh, P. J.; Nugent, W. A. (2005). "(2S)-(−)-3-exo-(Morpholino)isoborneol". Organic Syntheses. 82: 87. doi:10.15227/orgsyn.082.0087.
  5. ^ White, J. D.; Wardrop, D. J.; Sundermann, K. F. (2002). "(2S)-(−)-3-exo-(Dimethylamino)isoborneol". Organic Syntheses. 79: 130. doi:10.15227/orgsyn.079.0130.