Methyl Dihydrojasmonate and Its Stereoisomers: Sensory Properties and Enantioselective Analysis

Abstract

Enantiomeric methyl dihydrojasmonates (MDHJs) were separated by chiral gas chromatography (GC) and high performance liquid chromatography. Organoleptical evaluation clearly revealed that all four stereoisomers are odor-active and differ in their olfactory properties. Using enantio-multidimensional capillary GC -mass spectrometry with heptakis(2,3-di-O-methyl-6-O-tert butyldimethylsilyl)-b-cyclodextrin as the chiral stationary phase, the direct enantioselective analysis of all four stereoisomers of MDHJ in numerous natural products was achieved for the first time.

Jasminum grandiflorum flowers—Phytochemical complexity and its capture in extracts: a review

“…Whereas methyl dihydrojasmonate has been identified in several natural sources, 182 its presence as a trace element in JA has been cited only once but never confirmed on the grounds of reliable evidence. 136,149 On one occasion only, this author has detected traces of methyl (E)-dihydrojasmonate in JA from Grasse, but without being able to rule out any possible exogenous contamination.…”

“…Another route to methyl jasmonate involves artificial photo‐oxidation of polyunsaturated C18 acid (as methyl ester), 181 but it is not expected to occur significantly at any stage of JA processing. Whereas methyl dihydrojasmonate has been identified in several natural sources, 182 its presence as a trace element in JA has been cited only once but never confirmed on the grounds of reliable evidence 136,149 . On one occasion only, this author has detected traces of methyl ( E )‐dihydrojasmonate in JA from Grasse, but without being able to rule out any possible exogenous contamination.…”

Preparation and odour properties of the four stereoisomers of 2‐hexyl‐4‐acetoxytetrahydrofuran

“…The olfactory properties of over 1348 enantiomers have been reported since Rienäcker and Ohloff published the first data regarding the enantioselective perception of β ‐citronellol in 1961 . Many studies have shown that stereostructure of odorants greatly affects the odour properties either in terms of feature or odour intensity …”

Efficient synthesis of the cyclopentanone fragrances (Z)-3-(2-oxopropyl)-2-(pent-2-en-1-yl)cyclopentanone and Magnolione®

“…Currently, 2 is a highly prized fragrance ingredient for the manufacture of high grade perfumes and also finds utility in fruit flavors, tea, tobacco, and laundry products. 1,4 …”