204916-72-3

Upstream product

• 204916-68-7 (S)-Methoxy-phenyl-acetic acid 2-((R)-4-methyl-2-oxo-cyclohex-3-enyl)-allyl ester 
• 477717-71-8 (-)-(3R,4R)-p-mentha-1,8⁽¹⁰⁾diene-3,9-diol diacetate 
• 52062-24-5 (E)-1-acetoxy-3-methyl-1,3-butadiene 

Relevant academic research and scientific papers

Enzyme-mediated preparation of enantiomerically pure p-menthan-3,9-diols and their use for the synthesis of natural p-menthane lactones and ethers

The diastereoselective preparation of the p-menthane-3,9-diols (±)-12, (±)-13a, (±)-13b, and (±)-18 and the study of their enzymic resolution is described (Scheme 1). The corresponding enantiomer-enriched diols obtained by means of the lipase-mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p-menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e., of the enantiomeric form of 3-hydroxy-p-menthan-9-oic acid lactone 1, of mintlactone 2, of the 3,9-epoxy-p-menth-1,8(10)-diene 10, and of the pheromone vesperal 11 (Schemes 2 and 3).

Identification and Synthesis of Vesperal, the Female Sex Pheromone of the Longhorn Beetle Vesperus xatarti

10-Oxoisopiperitenone and 10-hydroxyisopiperitenone (for which the trivial names vesperal and vesperol are proposed) were identified using various EIMS (or MS-MS), CIMS data and GC-Fourier transform infrared obtained from the female-specific semiochemicals of the longhorn beetle Vesperus xatarti.Their structure was confirmed by synthesis via a Diels-Alder reaction and appropriate oxidation steps.The role of the female sex pheromone for vesperal was demonstrated.Comparison of the HPLC retention time of natural vesperal with those of synthesized pure enantiomers revealed that the natural compound has (S)-stereochemistry.- Keywords: 10-oxoisopiperitenone; 10-hydroxyisopiperitenone; mass spectrometry, pheromone; Cerambycidae; Vesperus xatarti.