10,13-epoxy-11-methyl-Octadecadienoic Acid (Synonyms: F2 Furan Fatty Acid, 3-methyl-5-pentyl-2-Furannonanoic Acid, 9M5)

10,13-epoxy-11-methyl-Octadecadienoic acid is a furan fatty acid.^1,2,3,4,5 It prevents the formation of primary and secondary lipid oxidation products during the storage of ω-3 PUFA-enriched fish oil when used at concentrations of 50, 100, and 250 µM.¹ 10,13-epoxy-11-methyl-Octadecadienoic acid (20 µM) induces transcriptional activation of peroxisome proliferator-activated receptor γ (PPARγ) in a reporter assay.² It increases lipid accumulation during the differentiation of 3T3-L1 preadipocytes to adipocytes when used at a concentration of 10 µM. 10,13-epoxy-11-methyl-Octadecadienoic acid has been found in marine bacteria, Adriatic fish, and butter.^3,4,5

1.Buscato, M.H.H., MÜller, F., Vetter, W., et al.Furan fatty acids in enriched ω-3 fish oil: Oxidation kinetics with and without added monomethyl furan fatty acid as potential natural antioxidantFood Chem.327127087(2020) 2.Lauvai, J., Becker, A.-K., Lehnert, K., et al.The furan fatty acid 9M5 acts as a partial ligand to peroxisome proliferator-activated receptor gamma and enhances adipogenesis in 3T3-L1 preadipocytesLipids54277-288(2019) 3.Shirasaka, N., Nishi, K., and Shimizu, S.Occurrence of a furan fatty acid in marine bacteriaBiochimica et Biophysica Acta1258225-227(1995) 4.Pacetti, D., Alberti, F., Boselli, E., et al.Characterisation of furan fatty acids in Adriatic fishFood Chemistry122(1)209-215(2010) 5.Wendlinger, C., and Vetter, W.High concentrations of furan fatty acids in organic butter samples from the German marketJ. Agric. Food Chem.62(34)8740-8744(2014)