Synthesis and olfactory evaluation of homologous series of (+)‐ and (−)‐carvone oxime ethers

Abstract

Novel semi‐synthetic fragrant compounds were prepared from both isomers of carvone. Deprotonation of (+) and (−)‐carvone oximes with sodium hydride and subsequent O‐Alkylation with various alkyl halides in DMSO resulted in 18 ethers. Scents of most synthesized compounds are agreeable. A shift of fragrance is observed between substrates. The scent of (−)‐carvone resembles that of spearmint and (+)‐carvone – caraway. The fragrance of carvone oximes is similar, vegetable‐like. Significant differences were observed between homologous series of carvone oxime ethers. Their odours range from vegetable‐like (pickled cucumber, leaves of horseradish and carrot, scallion and onion) and herbaceous to sulphuric, floral (lily) and fruity (blackcurrant and pear). Copyright © 2015 John Wiley & Sons, Ltd.

Preliminary ecotoxicity assessment of selected flavour and fragrance compounds using Microtox assay

“…Over the last years, a constantly growing request for synthesis of new fragrance components has been observed [1]. The olfactory potential depends mainly on the structure of the designed molecules and an osmophore (functional group) [2,3]. The chemical groups responsible for a pleasant smell include: ester, ketone, aldehyde, ether and hydroxyl groups, whereas the presence of thiocarbonyl, thioformyl, thioether, thiol and amine groups result most often in unobjectionable smell.…”

“…Due to the high cost of scents isolated from natural sources, more often aroma compounds are prepared via synthesis [4]. Upwards of 3000 scent-bearing compounds are applied in perfumery industry [3]. The largest amount of fragrance compounds is present in cosmetics, perfumes and household chemicals [6].…”

Study of the Room‐Temperature Synthesis of Oxime Ethers by using a Super Base

“…There has also been research performed on the use of oxime ethers as fragrances. [16] Oxime ethers can be obtained from the aminohydroxylation reaction of ketones [17,18] and reactions of the oximes with alcohols with triphenylphosphine, [9,19] alkenes, [9] aryl halogens, [20,21] appropriate alkyl halogens, functionalized alkyl halogens, and benzylh alogens. For the synthesis of oxime ethers in latter method,b ases in different solvents are usually used, for example CH 3 ONa in CH 3 OH, [14] NaH in DMF, [22] K 2 CO 3 in acetone/ DMF, [6] NaOH (aq) /toluene, [15] as the halogensu sed are cheap and readily available chlorides.…”

“…They exhibit anticancer, anti‐aggregation, antidepressant, anticonvulsant, antimicrobial, antiviral, acaricidal, anti‐protozoal, and herbicidal effects. There has also been research performed on the use of oxime ethers as fragrances …”

Synthesis, lipase catalyzed kinetic resolution, and determination of the absolute configuration of enantiomers of the Morita-Baylis-Hillman adduct 3-hydroxy-2-methylenebutanenitrile

“…Our previous research focused on the synthesis and evaluation of biological activities of novel terpenoid derivatives. [12][13][14][15] We have focused recently on the possibility of using MBH adducts in the synthesis of novel δ-lactones with potential olfactory properties. We chose 3-(RS)-hydroxy-2-methylenebutanenitrile 1(RS) as a model substrate for further studies.…”