17β-hydroxy-17α-methyl-2,3-seco-5α-androstane-2,3-dioic acid | 21529-08-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 17β-hydroxy-17α-methyl-2,3-seco-5α-androstane-2,3-dioic acid
• 英文别名: 2-[(3S,3aS,5aS,6S,7S,9aR,9bS)-6-(carboxymethyl)-3-hydroxy-3,3a,6-trimethyl-1,2,4,5,5a,7,8,9,9a,9b-decahydrocyclopenta[a]naphthalen-7-yl]acetic acid
• CAS: 21529-08-8
• 化学式: C₂₀H₃₂O₅
• 分子量: 352.471
• InChiKey: GLMFZHFDUVUNOC-IVEVATEUSA-N

物化性质

• 熔点：
  255-257 °C
• 沸点：
  535.163±15.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.153±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  羟甲烯龙 在 potassium permanganate 、 sodium periodate 、 potassium carbonate 作用下， 反应 3.0h， 以32%的产率得到17β-hydroxy-17α-methyl-2,3-seco-5α-androstane-2,3-dioic acid
  参考文献：
  名称：

  Studies on anabolic steroids. 10. Synthesis and identification of acidic urinary metabolites of oxymetholone in a human11Part 9 of this paper is in press (itSteroids vol 57, 1992).

  摘要：

  Two major unconjugated acidic metabolites of oxymetholone (17-beta-hydroxy-2-hydroxymethylene-17-alpha-methyl-5-alpha-androstan-3-one, 1), namely, 17-beta-hydroxy-17-alpha-methyl-2,3-seco-5-alpha-androstane-2,3-dioic acid (2) and 3-alpha,17-beta-dihydroxy-17-alpha-methyl-5-alpha-androstane-2-beta-carboxylic acid (6a), were detected by gas chromatography/mass spectrometry in urine samples collected after oral administration of 1 to a human volunteer. Reference steroid 2 was synthesized and identified. The identification of urinary metabolite 6a was based on the synthesis of its stereoisomers and the isomerization of the methyl ester 6b to its 2-epimer, 3-alpha,17-beta-dihydroxy-17-alpha-methyl-5-alpha-androstane-2-alpha-carboxylic acid methyl ester (9b). The mechanisms accounting for the formation of these acidic metabolites are discussed.

  DOI：

  10.1016/0039-128x(92)90100-n