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Methyl hiragonate has been prepared from Japanese sardine oil, and it was subjected to the oxidation by the permanganate method and by the ozonide method. Among the oxidation products obtained by the permanganate method, succinic acid, acetic acid and methyl hydrogen adipate were identified. The products obtained by the ozonide method contained, besides the above-mentioned three acidic compounds, acetaldehyde and semialdehyde of methyl hydrogen adipate, and also the presence of semialdehyde of succinic acid and succinic aldehyde (or its polymerised products) was indicated. Accordingly, the constitution of hiragonic acid is Δ6:7, 10:11, 14:15-hexadecatrienoic acid as expressed by the following formula: CH_3·CH=CH·(CH_2)_2·CH=CH·(CH_2)_2·CH=CH·(CH_2)_4·COOH
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Toyama et al. (1935) studied this question.
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