title: Synthesis and labeling of isoflavone phytoestrogens, including daidzein and genistein.
abstract: The synthesis of the important diphenolic isoflavone type phytoestrogens starting from the corresponding unprotected phenols and arylacetic acids is discussed. The aryl rings may carry additional alkyl, methoxy, and/or halogeno groups. Intermediate polyhydroxy deoxybenzoins can also be isolated in good yield. Isotopically labeled isoflavone phytoestrogens were prepared for use as internal standards in ion exchange chromatography and GC-MS selected ion monitoring (SIM technique). Traditional methods rely on total synthesis using deuterated starting materials for the preparation of labeled isoflavonoid structures. We have used successfully an application where the H/D exchange is performed within the finished molecular framework, based on the exchange of aromatic protons that are  ortho or para to a phenolic OH group. By this method the deuterated products are available in an isotopic purity of 90% or higher.
authors.affiliation: Department of Chemistry, University of Helsinki, Finland.
authors.forename: K
authors.initials: K
authors.lastname: Wähälä
authors.forename: T
authors.initials: T
authors.lastname: Hase
authors.forename: H
authors.initials: H
authors.lastname: Adlercreutz
mesh_terms: D002852:Chromatography, Ion Exchange; D003903:Deuterium / Q000737:chemistry; D004968:Estrogens, Non-Steroidal / Q000138:chemical synthesis*; D019833:Genistein; D007529:Isoflavones / Q000138:chemical synthesis*; D013058:Mass Spectrometry / Q000379:methods; D048789:Phytoestrogens; D028321:Plant Preparations; D014269:Trifluoroacetic Acid / Q000737:chemistry
chemical_list: D004968:Estrogens, Non-Steroidal; D007529:Isoflavones; D048789:Phytoestrogens; D028321:Plant Preparations; C004742:daidzein; D003903:Deuterium; D019833:Genistein; D014269:Trifluoroacetic Acid