Microwave-assisted synthesis of deuterium labeled estrogen fatty acid esters.
Deuterated analogs of estrogen fatty acid esters are needed as internal standards for isotope dilution GC/MS analyses. We have developed a rapid and efficient synthesis for 2,4,16,16-D4-estrone palmitate, stearate, oleate, linoleate, and linolenate and the corresponding 2,4,16,16,17alpha-D5-estradiol fatty acid 17-mono and 3,17-diesters using analogous fatty acid chlorides or fatty acid anhydrides and 4-(dimethylamino)pyridine under microwave irradiation. Chemoselective hydrolysis of fatty acid diesters was carried out by KOH in t-BuOH.
Kiuru
Paula S
PS
Department of Chemistry, Organic Chemistry Laboratory, A. I. Virtasen Aukio 1, P.O. Box 55, University of Helsinki, FIN-00014 Helsinki, Finland.
Wähälä
Kristiina
K
D003903:Deuterium; D004952:Esters / Q000737:chemistry*; D004967:Estrogens / Q000737:chemistry*; D004970:Estrone / Q000138:chemical synthesis* / Q000737:chemistry*; D005227:Fatty Acids / Q000737:chemistry*; D013058:Mass Spectrometry; D008872:Microwaves
D004952:Esters; D004967:Estrogens; D005227:Fatty Acids; D004970:Estrone; D003903:Deuterium