title: 2,3-Erythro-dihydroxyhexacosanoic acid and homologs: isolation from yeast cerebrin phosphate and determination of their structures.
abstract: Homologs of methyl esters of very polar fatty acids were obtained by methanolysis of cerebrin phosphate isolated from baker's yeast. The major ester component was isolated by preparative gas-liquid chromatography and was found to be 2,3-dihydroxyhexacosanoic acid as deduced from the mass spectra of its trimethylsilyl ether and isopropylidene derivative, reaction with periodate, and comparison of its chromatographic behavior with that of synthetic erythro- and threo-dihydroxy acids. Its infrared spectrum supported the above conclusions. From their retention times by gas-liquid chromatography, the homologs were found to be saturated, unbranched 2,3-dihydroxy fatty acids with 24-27 carbon atoms. The synthesis of the new fatty acids, erythro- and threo-2,3-dihydroxyhexacosanoic acids, is also reported. A method for separating trans-2-hexacosenoic acid, a key intermediate of the above synthesis, and its isomer, trans-3-hexacosenoic acid, both formed by dehydrobromination of 2-bromohexacosanoic acid, is also described.
mesh_terms: D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D005227:Fatty Acids / Q000032:analysis* / Q000138:chemical synthesis / Q000302:isolation & purification; D006900:Hydroxylation; D007536:Isomerism; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D010504:Periodic Acid; D010743:Phospholipids / Q000032:analysis*; D012441:Saccharomyces cerevisiae; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
chemical_list: D005227:Fatty Acids; D010743:Phospholipids; D010504:Periodic Acid