17-乙炔基-17-羟基雌甾-1,3,5(10)-三烯-3-基吡喃己醛糖苷酸 | 60134-76-1

• 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
• 中文名称: 17-乙炔基-17-羟基雌甾-1,3,5(10)-三烯-3-基吡喃己醛糖苷酸
• 中文别名: 乙炔基雌二醇-3-葡糖苷酸
• 英文名称: [3H]-Ethinylestradiol glucuronide
• 英文别名: Ethinylestradiol glucuronide；(17β-hydroxy-17α-ethynyl-1,3,5[10]-estratrien-3-yl) β-D-glucopyranosiduronic acid；ethynylestradiol-3-glucuronide；Ethynylestradiol-3-o-glucuronide；(2S,3S,4S,5R,6S)-6-[[(8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 60134-76-1
• 化学式: C₂₆H₃₂O₈
• 分子量: 472.535
• InChiKey: DYBBEZHAELJFKW-IWTIIAAJSA-N

物化性质

• 熔点：
  161-163°C
• 沸点：
  705.8±60.0 °C(Predicted)
• 密度：
  1.44±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)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  炔雌醇 在 吡啶 、 sodium hydroxide 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 97.0h， 生成 17-乙炔基-17-羟基雌甾-1,3,5(10)-三烯-3-基吡喃己醛糖苷酸
  参考文献：
  名称：

  Synthesis of β-Glucuronides of Estradiol, Ethynylestradiol and Estrone

  摘要：

  Improved syntheses for the 3-beta-D-glucuronides of the steroidal sex hormones 17 beta-estradiol, 17 alpha-ethynylestradiol and estrone are reported employing boron trifluoride diethyl etherate catalysis with tetraacetylated glucuronic acid or the corresponding imidate.

  DOI：

  10.1080/07328309908544025

文献信息

• Chromatographic patterns of urinary ethynyl estrogen metabolites in various populations
  作者：Mary C. Williams、Joseph W. Goldzieher

  DOI：10.1016/0039-128x(80)90001-x

  日期：1980.9

  Radioactive mestranol (ME) and/or ethynylestradiol (EE) were administered to women in Nigeria, Sri Lanka, and the USA, and the types and patterns of radioactive urinary conjugates examined by Sephadex LH-20 chromatography. There are no differences in the total excretion of urinary radioactivity over 3 days. Consistent geographic differences appear to be present in the proportion of 3-, 17-, and 3,17-glucuronides. If confirmed on larger population samples, these observations may indicate significant geographic differences in the hepatic metabolism of ethynyl estrogens. High performance liquid chromatographic patterns of the urinary aglycone metabolites of ME and EE were examined in a number of women. The separation was accomplished on a Chromegaprep Diol column with a gradient of isopropanol in heptane. Ethynyl estrogen metabolism shows considerable individual variation. EE is usually the principal compound escreted following ME or EE administration. Unmetabolized ME is present in the ME profiles. The profiles of EE and ME are similar, with EE demonstrating a more complex pattern. Oxidative metabolism occurs chiefly at positions 2, 6 and 16 and is fairly extensive in the USA subjects. The Sri Lankan women generally show less of the oxidative products and the Nigerian group display a notable lack of oxidative metabolism. There is no difference in the metabolic patterns of long-term oral contraceptive users vs. non-users. Using silver sulfoethylcellulose column chromatography, from 14.1 to 34.7% of the excreted radiolabeled aglycones are non-ethynyl (i.e., either D-homo or de-ethynylated estrogens).