Цис-3-гексенол (листовий спирт)

Identity and occurrence

Cis-3-hexen-1-ol, also called leaf alcohol, has the molecular formula C₆H₁₂O and the IUPAC name (Z)-hex-3-en-1-ol. It is produced in small amounts by most plants.

Formation in plants

It belongs to the green leaf volatiles, which are organic compounds released by plants. On mechanical damage, plants form (Z)-3-hexenal, a C6 aldehyde, which is quickly reduced to the C6 alcohol (Z)-3-hexenol. The alcohol can be further converted to (Z)-3-hexenyl acetate by an acetyl transferase. Green leaf volatiles include the C6 aldehydes (Z)-3-hexenal and n-hexanal and their derivatives, among them (Z)-3-hexenol and (Z)-3-hexen-1-yl acetate.

Chemistry

Leaf alcohol is very slightly soluble in water and soluble in ethanol and ether. The related aldehyde cis-3-hexenal smells similar and even stronger, but it is relatively unstable and isomerizes into conjugated trans-2-hexenal.

Uses and perception

The global production volume is about 3000 tonnes. The esters of cis-3-hexen-1-ol are also important flavor and fragrance raw materials. A pair of single-nucleotide polymorphisms in the gene for the OR2J3 odor receptor strongly reduces human sensitivity to this odorant. The Joint FAO/WHO Expert Committee on Food Additives found no safety concern at current levels of intake when cis-3-hexen-1-ol is used as a flavouring agent.

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