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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 hemiacetal. [ 5 ] It must be noted, however, that this enzyme catalyzed path follows a different mechanism from the usual Schenck ene reaction.
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.
The related aldehyde cis-3-hexenal (leaf aldehyde) has a similar and even stronger smell but is relatively unstable and isomerizes into the conjugated trans-2-hexenal. This compound has been recognized as a semiochemical involved in mechanisms and behaviors of attraction in diverse animals such as insects and mammals.
[2] An illustrative transformation involving a hydroperoxide lyase. Here 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 hemiacetal.
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In an α,β-unsaturated enal, the alkene is conjugated to the carbonyl group of the aldehyde (formyl group). [3] The simplest enal is acrolein (CH 2 =CHCHO). Other examples include cis-3-hexenal (essence of mowed lawns) and cinnamaldehyde (essence of cinnamon). Other α,β-unsaturated carbonyls