8-Methyl-6-nonenoic acid

Capsaicin, the major capsaicinoid, is the N-vanillyl amide of 8-methyl-6-nonenoic acid. Related dihydro-, homo-, and dihydrohomo- isomers have also been reported. Most research efforts on red pepper have been concerned with determining the capsaicinoid makeup and concentration in various red pepper varieties and products 0 8). 

Capsaicin is a bioactive molecule synthesized by enzymatic (putative capsaicin synthase) condensation of vanillylamine, a phenyl propanoid intermediate with 8-methyl-nonenoic acid, a fatty acid derivative from the leucine/valine pathway. Analysis of levels of 8-methyl-nonenoic acid and phenyl propanoid intermediates in high-, medium- and low-pungent Capsicum genotypes revealed that the 8-methyl-nonenoic acid pool plays a crucial role in determining the efficacy of capsaicin levels. Cerulenin-mediated inhibition of 8-methyl-nonenoic... 

Prasad, B.C.N., Cururaj, H.B., Kumar, V., Ciridhar, P., Parimalan, R., Sharma, A. and Ravishankar, G.A. (2006) Influence of 8-methyl-nonenoic acid on capsaicin biosynthesis in in vivo and in vitro cell cultures of Capsicum spp. Journal of Agricultural and Food Chemistry 54(5), 1 854-1859. 

Synonyms Methyl non-2-enoate Methyl nonylenate Neofolione 2-Nonenoic acid, methyl ester Non-2-enoic acid methyl ester... 

Bromo-9-[[4-(methylthio)-1 //-imidazol-3-y I] methyl]-9//-pyrido[3,4-/)]indole, see D-30074 3-Bromo-2-nonenoic acid, B-30081 10-Bromoobtusallene, in 0-10003... 

Investigations of the structure/effect relationship show that the intensity of the pungency does not change when 8-methyl- ran5-6-nonenoic acid in capsaicin is replaced by nonanoic acid (9 0). However, it decreases when shorter, e.g., 8 0 (75%), 7 0 (25%), 6 0 (5%), or longer fatty acids, e.g., 10 0 (50%), 11 0 (25%), are introduced. 

The oxidation of unsaturated esters to unsaturated keto esters is accomplished with chromium trioxide in acetic acid and acetic anhydride. Methyl 2-nonenoate is thus converted in benzene solution at 0-20 °C into methyl 4-keto-2-nonenoate in 86% yield [553],... 

Methylnonanoic acid. See Isodecanoic acid Methyl 2-nonenoate... 

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