Decynoic acid

Decyl tetradecanol, in cosmetic molded sticks, 7 840t 9-Decynoic acid, 5 34t Dedicated facility design, 11 47 DEDM hydantoin, antimicrobial used in cosmetics, 7 831t... 

A closely related E. coli protein is a 79-kDa multifunctional enzyme that catalyzes four different reactions of fatty acid oxidation (Chapter 17). The amino-terminal region contains the enoyl hydratase activity.32 A quite different enzyme catalyzes dehydration of thioesters of (3-hydroxyacids such as 3-hydroxydecanoyl-acyl carrier protein (see Eq. 21-2) to both form and isomerize enoyl-ACP derivatives during synthesis of unsaturated fatty acids by E. coli. Again, a glutamate side chain is the catalytic base but an imidazole group of histidine has also been implicated.33 This enzyme is inhibited irreversibly by the N-acetylcysteamine thioester of 3-decynoic acids (Eq. 13-8). This was one of the first enzyme-activated inhibitors to be studied.34... 

In a beaker-type cell (Figure 2) equipped with two platinum electrodes (area 10 cm, thickness 0.05 mm, supported on a teflon frame), a solution of 14.3 mmol 5-decynoic acid and 86 mmol methyl sube-rate in 40 mL methanol, neutralized to 5% with KOH, was electrolyzed at 22 C and a current density of 100 mA cm 2, provided from a regulated d.c. power supply, until a pH of 8-9 was reached. After evaporation of the methanol the crude product was refluxed with equimolar amounts of KOH in 100-200 mL methanol for 24 h thereafter the mixture was evaporated to dryness and extracted with petroleum ether. The remaining salt was dissolved in water, acidified with 15% HCl, and continuously extracted with petroleum ether. The precipitated tetradecanoic dicarboxylic acid (72%, m.p. 126 C) was filtered off, and after evaporation of the petroleum ether 8.43 mmol (59%) 11-hexadecynoic acid was isolated by bulb to bulb distillation m.p, (from pentane) 40-41... 

These procedures have been extensively employed and the following examples (p. 288) are taken from the work of Gunstone and Ismail (1967) and Barve and Gunstone (1971) who prepared all the octa-decynoic acids and from them all the cis- and trans-octadecenoic acids and of Gilman and Holland (1974) who prepared all the Cio, Cn, C12, C13 and Ci4 monoynoic acids. 

Malvaceae Hibiscus rosa-sinensis 8-nonynoic acid, 9-decynoic acid 319... 

Kawashima H, Yajima K, Kuge Y, Hashimoto N, Miyake Y (1997) Synthesis of l-[ C]-2-octynoic acid, l-[ C]-2-decynoic acid and 1-[ C]-3-(R,S)-methyloctanoic acid as potential markers for PET studies of fatty acid metabolism. J Labelled Compd Radiopharm 39 181-193... 

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