3597-54-4Relevant articles and documents
5α-Androst-16-en-3α-ol β-D-glucuronide, precursor of 5α-androst-16-en-3α-ol in human sweat
Starkenmann, Christian,Mayenzet, Fabienne,Brauchli, Robert,Troccaz, Myriam
, p. 2197 - 2208 (2014/01/06)
5α-Androst-16-en-3α-ol (α-androstenol) is an important contributor to human axilla sweat odor. It is assumed that α-andostenol is excreted from the apocrine glands via a H2O-soluble conjugate, and this precursor was formally characterized in this study for the first time in human sweat. The possible H2O-soluble precursors, sulfate and glucuronide derivatives, were synthesized as analytical standards, i.e., α-androstenol, β-androstenol sulfates, 5α-androsta-5,16-dien- 3β-ol (β-androstadienol) sulfate, α-androstenol β-glucuronide, α-androstenol α-glucuronide, β-androstadienol β-glucuronide, and α-androstenol β-glucuronide furanose. The occurrence of α-androstenol β-glucuronide was established by ultra performance liquid chromatography (UPLC)/MS (heated electrospray ionization (HESI)) in negative-ion mode in pooled human sweat, containing eccrine and apocrine secretions and collected from 25 female and 24 male underarms. Its concentration was of 79 ng/ml in female secretions and 241 ng/ml in male secretions. The release of α-androstenol was observed after incubation of the sterile human sweat or α-androstenol β-glucuronide with a commercial glucuronidase enzyme, the urine-isolated bacteria Streptococcus agalactiae, and the skin bacteria Staphylococcus warneri DSM 20316, Staphylococcus haemolyticus DSM 20263, and Propionibacterium acnes ATCC 6919, reported to have β-glucuronidase activities. We demonstrated that if α- and β-androstenols and androstadienol sulfates were present in human sweat, their concentrations would be too low to be considered as potential precursors of malodors; therefore, the H2O-soluble precursor of α-androstenol in apocrine secretion should be a β-glucuronide. Copyright
Catalytic hydrogenation of halosteroidal derivatives by bipyridine or phenanthroline complexes of copper(II) in hydrazine aqueous media
Du, Huang-Chi,Liu, Kung-Cheng,Li, Wen-Shan
, p. 621 - 630 (2007/10/03)
We report two synthetic systems, Cu(Bpy)2+ and Cu(Phen) 2+, for catalytic hydrogenation of steroidal haloalkenes in the presence of hydrazine and air. These studies demonstrated that the selective hydrogenation is faster for the 1,10-phenanthroline-Cu(II) system because forming more stable copper complex are formed, leaving fewer free copper ions in solution. Evidence also supports that the catalytic power of Cu(II) ions can be tuned moderately through the addition of bidentate ligand, Bpy or Phen. Copyright Taylor & Francis Group, LLC.
PREPARATION OF UNLABELLED AND 3H>-LABELLED EPITESTOSTERONE AND ITS METABOLITES
Kasal, Alexander,Fuksova, Kveta,Pouzar, Vladimir
, p. 600 - 611 (2007/10/02)
Cold as well as 3H>-labelled substrates and metabolites IX-XI, XV, XVI, XX-XXII, XXIV, XXV and XXVIII were prepared by catalytic hydrogenation of epitestosterone (VIII) and Λ1-dehydroepitestosterone (XIII).The key step in the preparation of compound XXVIII was reaction of 3β-tosylates XXVI and XXX with potassium nitrite in dimethyl sulfoxide.
