17β-hydroxyandrost-1,4-dien-3-one 17-O-glucuronide | 827019-65-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17β-hydroxyandrost-1,4-dien-3-one 17-O-glucuronide
• 英文别名: boldenone 17-O-glucuronide；(17beta)-3-Oxoandrosta-1,4-dien-17-yl beta-D-glucopyranosiduronic acid；(2S,3S,4S,5R,6R)-6-[[(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 827019-65-8
• 化学式: C₂₅H₃₄O₈
• 分子量: 462.54
• InChiKey: WTOYIEKXMIILRQ-HMAFJQTKSA-N

物化性质

• 沸点：
  681.2±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl (androsta-1,4-dien-17β-ol-3-one)-17-O-2,3,4-tri-O-acetyl-β-D-glucuronate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以97%的产率得到17β-hydroxyandrost-1,4-dien-3-one 17-O-glucuronide
  参考文献：
  名称：

  17α- and 17β-boldenone 17-glucuronides: Synthesis and complete characterization by 1H and 13C NMR

  摘要：

  Boldenone is an androgenic anabolic steroid intensively used for growth promoting purposes in animals destined for meat production and as a performance enhancer in athletics. Therefore its use is officially banned either in animals intended for consumption or in humans. Because most anabolic steroids are completely metabolized and usually no parent steroid is excreted, metabolite identification is crucial to detect the illegal use of anabolic steroids either in humans or in livestock. 17 alpha- and 17 beta-boldenone 17-glucuronides were synthesized, purified and characterized in order to provide Suitable standards for the identification and quantification of these metabolites. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.11.012

文献信息

• The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: improved practicality and broader scope
  作者：Paul Ma、Nicholas Kanizaj、Shu-Ann Chan、David L. Ollis、Malcolm D. McLeod

  DOI：10.1039/c4ob00984c

  日期：——

  Steroid glucuronides can be quickly and conveniently prepared on the milligram scale using theE. coliglucuronylsynthase enzyme followed by purification with solid-phase extraction.

  甾体葡萄糖苷酸可以通过使用大肠杆菌葡萄糖苷酸合酶酶快速、方便地在毫克级别上制备，随后通过固相萃取进行纯化。
• 17α- and 17β-boldenone 17-glucuronides: Synthesis and complete characterization by 1H and 13C NMR
  作者：Silvana Casati、Roberta Ottria、Pierangela Ciuffreda

  DOI：10.1016/j.steroids.2008.11.012

  日期：2009.2

  Boldenone is an androgenic anabolic steroid intensively used for growth promoting purposes in animals destined for meat production and as a performance enhancer in athletics. Therefore its use is officially banned either in animals intended for consumption or in humans. Because most anabolic steroids are completely metabolized and usually no parent steroid is excreted, metabolite identification is crucial to detect the illegal use of anabolic steroids either in humans or in livestock. 17 alpha- and 17 beta-boldenone 17-glucuronides were synthesized, purified and characterized in order to provide Suitable standards for the identification and quantification of these metabolites. (C) 2008 Elsevier Inc. All rights reserved.