Synthesis of both enantiomers of cis-α-Irone (cas 1335-94-0) and cis-γ-Irone (cas 1335-94-0), principal constituents of iris oil, via resolution of (±)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid

Add time:09/01/2019    Source:sciencedirect.com

The principal constituents of iris oil, (−)-cis-α-irone and (−)-cis-γ-irone, and their enantiomers, were synthesized from (−)- and (+)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acids. The racemic acid was resolved by recrystallization of its salt with a chiral amine, or by enzymatic hydrolysis of the corresponding alcohol. The fragrances of (−)-(1R,5S)-cis-α-irone and (−)-(1R,5S)-cis-γ-irone were superior to those of (+)-(1S,5R)-cis-α-irone and (+)-(1S,5R)-cis-γ-irone.

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