Fatty Acids

cis-9-Heptadecenoic acid is a monounsaturated fatty acid that is a major constituent of ruminant fat and milk. The levels of cis-9-heptadecenoic acid in milk are negatively correlated with methane production in cows fed a high-lipid diet.

cis-8-Octadecenoic acid is a monounsaturated fatty acid and an isomer of oleic acid (HY-N1446), trans-vaccenic acid (HY-113427), trans-petroselinic acid, and cis-petroselinic acid. It has been found in partially hydrogenated vegetable oil and milk fat.

Anandamide (AEA) is an endogenous cannabinoid that binds to both central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors. The biological actions of AEA are terminated by cellular uptake and hydrolysis of the amide bond by the enzyme fatty acid amide hydrolase. Arachidonoyl-N-methyl amide is an analog of anandamide that binds to the human central cannabinoid (CB1) receptor with a Ki of 60 nM. It inhibits rat glial gap junction cell-cell communication 100% at a concentration of 50 μM.

Very long chain polyunsaturated fatty acids (VLCPUFA) are present in retina, sperm, and brain. Though little is known of their biosynthesis or functional roles in these tissues, recent studies using the elongation of very long-chain FA-4 protein suggest a unique role for VLCPUFA in retinal development and macular degeneration. Dotriaconta-14,17,20,23,26,29-hexaenoic acid is a C32:6 VLCPUFA whose specific biological actions are largely unknown, but are thought to involve normal photoreceptor cell function in the retina.

13(R)-HODE is the opposite enantiomer of the 13(S)-HODE produced when linoleic acid is incubated with soybean lipoxygenase. The presence of 13(R)-HODE in the supernatants and membranes of cultured bovine endothelial cells has been attributed to COX metabolism.1 13(R)-HODE is a weak (IC₅₀=2.7 μM) inhibitor of U-46619-induced platelet aggregation.

8(Z)-Eicosenoic acid is a cis-unsaturated free fatty acid with a 20-carbon chain. It potentiates acetylcholine (ACh) receptor channel currents without depression and enhances PCKε phosphorylation of a substrate peptide in Xenopus oocytes. 8(Z)-Eicosenoic acid constitutes 6% of the fatty acid pool in seed oil isolated from B. collina.

9(R)-HODE is a monohydroxy fatty acid and metabolite of linoleic acid. It is formed from linoleic acid by COX and lipoxygenase (LO).9(R)-HODE induces chemotaxis, increases the levels of chemokine (C-C motif) receptor 9 (CCR9) and chemokine (C-X-C motif) receptor 4 (CXCR4), and inhibits IL-6 release in primary human monocytes. It inhibits CD3α- and CD28-induced proliferation of isolated human peripheral blood lymphocytes when used at a concentration of 25 μg/mL.

12,15-epoxy-13-methyl-12,14-Eicosadienoic acid is a furan fatty acid originally isolated from northern pike (E. lucius).1 Levels of 12,15-epoxy-13-methyl-12,14-eicosadienoic acid are increased in the liver of starving cod.

7-epi Jasmonic acid is the isomer of (±)-Jasmonic acid (HY-122464). (±)-Jasmonic acid is a plant growth regulator and a derivative of α-linolenic acid. (±)-Jasmonic acid decreases chlorophyll levels in green and etiolated barley leaf segments and inhibits elongation of rice seedlings.

11-Dodecenyl acetate is a insect sex pheromone, which is involved in attraction behavior of male moths.

(E,E)-9,11-Tetradecadienyl acetate is a female sex pheromone isolated from light-induced isomerization products in female coastal noctuid moths.

(E,Z)-4,7-Tridecadienyl acetate is a sex pheromone that can be isolated from potato tuber moths (Phthorimaea opercucella).

(E,Z)-3,13-Octadecadienyl acetate (E3,Z13-18:Ac) is an insect sex pheromone that elicits attraction in male lesser peachtree borers (Lesser Peachtree Borer), which can be isolated from female lesser peachtree borers.

E12-Tetradecenyl acetate is a pheromone produced by Ostrinia nubilalis.

Z12-Tetradecenyl acetate is a pheromone produced by Ostrinia nubilalis.

(Z)-11-Hexadecenoic acid is a sex pheromone capable of attracting male pine processionary moths (Thaumetopoea pityocampa).

(Z)-7,11-Hexadecadienyl acetate is a female sex pheromone used to attract male insects, isolated from Plutella xylostella.

(E,E)-8,10-dodecadienyl acetate is isolated from attractants of pine shoot moths (Rhyacionia rigidana).

(Z)-7-Decenyl acetate is a synthetic insect sex pheromone used for attracting turnip moths (Agrotis segetum), which can be isolated from analogs with lower activity than natural pheromones.