Alpha-linolenic acid

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α-Linolenic acid is an organic compound found in many common vegetable oils. In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid.[2] In physiological literature, it is given the name 18:3 (n−3).

α-Linolenic acid is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is an isomer of gamma-linolenic acid, a polyunsaturated n−6 (omega-6) fatty acid.

Contents

History

Alpha-linolenic acid was first isolated by Rollett[3] as cited in J. W. McCutcheon's synthesis in 1942.[4] and referred to in Green and Hilditch's 1930's survey.[5]

Alpha-linolenic was first artificially synthesized in 1995 from C6 homologating agents. A Wittig reaction of the phosphonium salt of [(Z-Z)-nona-3,6-dien-1-yl]triphenylphosphonium bromide with methyl 9-oxononanoate, followed by saponification, completed the synthesis.[6]

Dietary sources

Seed oils are the richest sources of α-linolenic acid, notably those of rapeseed (canola), soybeans, walnuts, flaxseed (Linseed oil), perilla, chia, and hemp. α-Linolenic acid is also obtained from the thylakoid membranes of the green leaves of broadleaf plants (the membranes responsible for photosynthesis).[7] Green vegetables, and therefore, animals that eat greens, are often a good source of α-linolenic acid.[citation needed]

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