17beta-(Acetyloxy)estra-1,5(10)-diene-3,4-dione | 144082-87-1

• 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
• 英文名称: 17beta-(Acetyloxy)estra-1,5(10)-diene-3,4-dione
• 英文别名: [(8R,9S,13S,14S,17S)-13-methyl-3,4-dioxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 144082-87-1
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: UPVDUXQHUURQJD-XQRBHQRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  17beta-雌二醇 17-乙酸酯 在 polystyrene-bound iodoxybenzoic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 17beta-(Acetyloxy)estra-1,5(10)-diene-3,4-dione 、 Estra-1(10),4-diene-2,3-dione, 17-(acetyloxy)-, (17beta)-
  参考文献：
  名称：

  Assay of labile estrogen o-quinones, potent carcinogenic molecular species, by high performance liquid chromatography–electrospray ionization tandem mass spectrometry with phenazine derivatization

  摘要：

  A sensitive and selective assay method for labile estrogen o-quinones, estrone (E-1)-2,3-quinone (Q), E-1-3,4-Q, estrachol (E-2)-2,3-Q and E-2-3,4-Q based on the use of phenazine (Phz) derivatization with o-phenylenediamine and high performance liquid chromatography-electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) was described The Phz derivatives of four estrogen o-quinones were purified by solid phase extraction and analyzed by HPLC-ESI-MS/MS The protonated molecule was observed as a base peak for all Phz derivatives in their ESI-mass spectra (positive mode) In multiple reaction monitoring, the transition from [M+H](+) to m/z 231 was chosen for quantification Calibration curves for the o-quinones were obtained using standard catechol estrogens after sodium metaperiodate treatment and Phz derivatization Using this method, these four estrogen o-quinones were analyzed with the limit of quantification of 5 ng/ml in acetonitrile (MeCN)-blank matrix (1 4, v/v), respectively, on a basis of the weight of catechol estrogens Assay accuracy and precision for four estrogen o-quinones were 896-113 0% and 3 1-12.6% (5, 125 and 2000 ng/ml in MeCN-blank matrix) Applications of this method enabled to determine the catalytic activities on hydroxylation and subsequent oxidation of E-1 and E2 of Mushroom tyrosinase and rat liver microsomal fraction It was confirmed by this method that tyrosinase exhibited 2- and 4-hydroxylation and further oxidation activities for catechols in the ring-A of estrogens. Whereas rat liver microsomal fraction possessed only 2- and 4-hydroxylation activities, and further oxidation activity for catechol estrogens was low (C) 2010 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.jsbmb.2010.02.016

文献信息

• Assay of labile estrogen o-quinones, potent carcinogenic molecular species, by high performance liquid chromatography–electrospray ionization tandem mass spectrometry with phenazine derivatization
  作者：Kouwa Yamashita、Akina Masuda、Yuka Hoshino、Sachiko Komatsu、Mitsuteru Numazawa

  DOI：10.1016/j.jsbmb.2010.02.016

  日期：2010.4

  A sensitive and selective assay method for labile estrogen o-quinones, estrone (E-1)-2,3-quinone (Q), E-1-3,4-Q, estrachol (E-2)-2,3-Q and E-2-3,4-Q based on the use of phenazine (Phz) derivatization with o-phenylenediamine and high performance liquid chromatography-electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) was described The Phz derivatives of four estrogen o-quinones were purified by solid phase extraction and analyzed by HPLC-ESI-MS/MS The protonated molecule was observed as a base peak for all Phz derivatives in their ESI-mass spectra (positive mode) In multiple reaction monitoring, the transition from [M+H](+) to m/z 231 was chosen for quantification Calibration curves for the o-quinones were obtained using standard catechol estrogens after sodium metaperiodate treatment and Phz derivatization Using this method, these four estrogen o-quinones were analyzed with the limit of quantification of 5 ng/ml in acetonitrile (MeCN)-blank matrix (1 4, v/v), respectively, on a basis of the weight of catechol estrogens Assay accuracy and precision for four estrogen o-quinones were 896-113 0% and 3 1-12.6% (5, 125 and 2000 ng/ml in MeCN-blank matrix) Applications of this method enabled to determine the catalytic activities on hydroxylation and subsequent oxidation of E-1 and E2 of Mushroom tyrosinase and rat liver microsomal fraction It was confirmed by this method that tyrosinase exhibited 2- and 4-hydroxylation and further oxidation activities for catechols in the ring-A of estrogens. Whereas rat liver microsomal fraction possessed only 2- and 4-hydroxylation activities, and further oxidation activity for catechol estrogens was low (C) 2010 Elsevier Ltd All rights reserved.