(1S*,3S*)-[1α,2α,4α,6α]-3-(5,5,6-Trimethylbicyclo[2.2.1]hept-2-yl)cyclohexan-1-ol

3-trans-Isocamphylcyclohexanol Chemische Eigenschaften,Einsatz,Produktion Methoden

• Chemische Eigenschaften

  3-trans-Isocamphylcyclohexanol is the component responsible for the sandalwood odor of a synthetic mixture of terpenylcyclohexanol isomers. A commercially available mixture containing 3-trans-isocamphylcyclohexanol is prepared by reacting camphene and guaiacol in the presence of an acidic catalyst (e.g., boron trifluoride), followed by catalytic hydrogenation of the resulting terpenylguaiacols. In the alkylation reaction, camphene rearranges to the isobornyl, isofenchyl, and isocamphyl skeletons. These substituents may be introduced in guaiacol at four positions. In the subsequent hydrogenation with simultaneous elimination of the methoxy group, additional possibilities for isomerism arise because the hydroxy group may be either axial or equatorial to the terpenyl moiety. Therefore, the actual content of the desired isomer, 3-trans-isocamphylcyclohexanol, is low in most products.The other isomers are either weak in odor or odorless.
  A process starting from catechol, instead of guaiacol, yields a mixture with a higher content of 3-trans-isocamphylcyclohexanol, especially if the hydrogenation of the terpenylcatechols is carried out continuously under high pressure on a cobalt catalyst.
  Themixture is used as such in large amounts as a fixative with sandalwood odor in a broad range of fragrances.

• Handelsname

  Sandela® (Givaudan), RhodiantalTM IBCH (Rhodia), RhodiantalTM Candalum (Rhodia).