Arachidonic acid ethyl ester

Arachidonic acid ethyl ester (C22H3g02 MW = 332.52) T(K) P(bar) y lxlO ... 

Arachidonic acid, ethyl ester. See Ethyl arachidonate Arachidyl alcohol... 

Synonyms Ethyl arachidonate (all -Z)-5,8,11,14-Eicosatetraenoic acid ethyl ester Source Liong, K. Foster, N. Ting, S. 

Polyunsaturated fatty acids (PUFAs) have various physiological functions and are widely used as pharmaceuticals, neutraceuticals, and as food additives. The ethyl ester of eicosapentaenoic acid (EPA) has been used for the treatment of arteriosclerosis and hyperlipemia since 1991 in Japan (Hara, 1993). DHA possesses not only similar physiological activities to those of EPA, but also an important function in the brain and retina (Hung, 2007). In addition, DHA accelerates the growth of preterm infants as does arachidonic acid (Carlson et al., 1993 Lanting et al., 1994). From these reasons, DHA ethyl ester (DHAEE) is currently expected to be used as a medicine, and the development of the purification methods is desired. 

Resolution of alcohols (c/., l-(naphthyl)ethyl isocyanate, 8, 356-357). A practical synthesis of the methyl ester of (S)-5-HETE (1) from arachidonic acid involves chromatographic separation of the diastereomeric urethanes prepared" from the isocyanate derived from dehydroabietylamine (hydrogen chloride and phosgene).1 Urethanes from other chiral amines are less useful. The urethanes are cleaved with triethylamine and trichlorosilane to give the corresponding pure enantiomeric esters, which can be hydrolyzed by base. 

Beltramo et al. 1997). Arachidonamide and arachidonic acid esters (methyl, ethyl, propyl) do not show significant affinity for CBi (Sheskin et al. 1997), while cyclization of the head group into an oxazoline ring diminishes affinity (Lin et al. 1998). 

Abbreviations SUNTGA, high arachidonic acid oil DHASCO, high docosahexaenoic acid single cell oil FA, fatty acids TAG, triacyl-glycerol EE, ethyl ester. 

Hydroxy-esters.—Ethyl 5-3-hydroxybutanoate is obtained in 87% optical purity by the reduction of ethyl acetoacetate with Bakers yeast. " Two independent chiral synthesis of the leukotriene intermediates (46), R = CHO and R = CH2OH, have appeared. An effective large-scale conversion of arachidonic acid into 5-hydroxy-6-fran5-8,ll,14-cis-eicosatetraenoicacid (5)HETE, including its resolution, is also reported by Corey and Hashimoto. ... 

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