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Many hydroperoxides derived from fatty acids, steroids, and terpenes are also formed via the Schenck ene reaction. For instance, the generation of cis-3-hexenal from linolenic acid: Cis-3-hexenal is generated by conversion of linolenic acid to the hydroperoxide by the action of a lipoxygenase followed by the lyase-induced formation of the ...
cis-3-Hexenal, also known as (Z)-3-hexenal and leaf aldehyde, is an organic compound with the formula CH 3 CH 2 CH=CHCH 2 CHO. It is classified as an unsaturated aldehyde. It is a colorless liquid and an aroma compound with an intense odor of freshly cut grass and leaves. [1] [2]
Its scent resembles freshly cut grass, like cis-3-hexenal. [5] It is potentially useful as a natural extract that prevents fruit spoilage. [6] It occurs naturally, and contributes to a hay-like "off-note" flavor in green peas. [7] The first synthesis of hexanal was published in 1907 by P. Bagard. [8]
Pathway for biosynthesis of the GLV cis-3-hexenal from linolenic acid. The first step involves formation of the hydroperoxide by the action of a lipoxygenase . Subsequently a hydroperoxide lyase induces formation of the hemiacetal, the precursor to a volatile C6 compound.
cis-3-Hexen-1-ol, also known as (Z)-3-hexen-1-ol and leaf alcohol, is a colorless oily liquid with an intense grassy-green odor of freshly cut green grass and leaves. It is produced in small amounts by most plants and it acts as an attractant to many predatory insects .
2-Hexyne can be semihydrogenated to yield 2-hexene or fully hydrogenated to hexane. [3] With appropriate noble metal catalysts it can selectively form cis-2-hexene. [4] 2-Hexyne can act as a ligand on gold atoms. [5] With strong sulfuric acid, the ketone 2-hexanone is produced. However this reaction also causes polymerization and charring. [6]
With cycloheptene, the cis-isomer is always assumed but the trans-isomer does also exist. One procedure for the organic synthesis of trans-cycloheptene is by singlet photosensitization of cis-cycloheptene with methyl benzoate and ultraviolet light at −35 °C. [2] The double bond in the trans isomer is very strained. [3]
3 I. (Similar procedures can give cis,trans isomers of 1,4-cyclooctadiene and 1,5-cyclooctadiene). [2] In addition, a photochemical method exists for the direct cis–trans isomerisation. Although this equilibrium strongly favours the more stable cis form, the reaction can be driven towards the trans form by trapping with silver ions. [11] [12]