[(8R,9S,13S,14S)-13-甲基-17-氧代-7,8,9,11,12,14,15,16-八氢-6H-环戊二烯并[a]菲-3-基]5-二甲基氨基萘-1-磺酸酯 | 30804-69-4

• 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: [(8R,9S,13S,14S)-13-甲基-17-氧代-7,8,9,11,12,14,15,16-八氢-6H-环戊二烯并[a]菲-3-基]5-二甲基氨基萘-1-磺酸酯
• 英文名称: estrone
• 英文别名: 3-Dansylestrone；[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] 5-(dimethylamino)naphthalene-1-sulfonate
• CAS: 30804-69-4
• 化学式: C₃₀H₃₃NO₄S
• 分子量: 503.662
• InChiKey: FUQSZFCTVMQWSY-KCUJWJGTSA-N

物化性质

• 沸点：
  667.4±55.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  雌酚酮 、 丹酰氯 在 碳酸氢钠 作用下， 反应 0.17h， 生成 [(8R,9S,13S,14S)-13-甲基-17-氧代-7,8,9,11,12,14,15,16-八氢-6H-环戊二烯并[a]菲-3-基]5-二甲基氨基萘-1-磺酸酯
  参考文献：
  名称：

  Characterizing the steroidal milieu in amniotic fluid of mid-gestation: A LC–MS/MS study

  摘要：

  Growth and development of an embryo or fetus during human pregnancy mainly depend on intact hormone biosynthesis and metabolism in maternal amniotic fluid (AF). We investigated the hormonal milieu in AF and developed a liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for the determination of 14 sulfated and 6 unconjugated steroids in AF. 65 A F samples (male: female = 35: 30) of mid-gestation ranging from 16th week of gestation to 25th week of gestation were analyzed. Reference data of 20 steroid levels in AF of healthy women were provided. 13 sulfated and 3 unconjugated steroids were for the first time quantified in AF by LC-MS/MS. Highest concentrations were found for pregnenolone sulfate (PregS: mean SD, 8.6 +/- 3.7 ng/mL), 17 alpha-hydroxypregnenolone sulfate (170HPregS: 4.9 +/- 2.0 ng/mL), epitestosterone sulfate (eTS: 7.3 +/- 3.6 ng/mL), 16 alpha-hydroxydehydroepiandrosterone sulfate (16OH-DHEAS: 21.5 +/- 10.7 ng/mL), androsterone sulfate (AnS: 9.2 +/- 7.4 ng/mL), estrone sulfate (E1S: 3.0 +/- 3.0 ng/mL), estriol 3-sulfate (E3S: 8.1 +/- 4.0 ng/mL) and estriol (E3: 1.2 +/- 0.4 ng/mL). Only testosterone (T) showed a significant sex difference (p <0.0001). Correlations between AF steroids mirrored the steroid metabolism of the feto-placental unit, and not only confirmed the classical steroid pathway, but also pointed to a sulfated steroid pathway.

  DOI：

  10.1016/j.jsbmb.2018.07.007

文献信息

• High-sensitivity determination of estrogens in fish plasma using chemical derivatization upstream UHPLC–MSMS
  作者：Ugo Bussy、Yu-Wen Chung-Davidson、Tyler J. Buchinger、Ke Li、Weiming Li

  DOI：10.1016/j.steroids.2017.04.003

  日期：2017.7

  This article describes the development and validation of a sensitive LC-MSMS method for determination of estrogen in fish plasma. Dansyl chloride derivatization of the phenol functional group in estrogen was used to enhance the response to atmospheric pressure ionization leading to improve the sensitivity. Individual C-13 internal standards were selected after comparison with deuterated standards. Liquid-liquid extraction (ethyl acetate or methyl tert-butyl ether) and protein precipitation (acetonitrile, methanol or acetone) were compared for the extraction and clean-up of estrogens from fish plasma. Ethyl acetate was selected as the best alternative with recovery ranging from 61 to 96% and matrix effect ranging from 88 to 106%. Limits of quantification ranged from 0.5 to 1 pg/mL showing a gain in sensitivity of 10,000 times over electrospray ionization of underivatized estrogens. Accuracy and precision were validated over three consecutive days and the method was applied to measure estrogen in sea lamprey (Petromyzon marinus) and lake trout (Salvelinus namaycush) plasma. Estrone and estriol were detected in fish below 1 ng/mL in plasma, justifying the need of a highly sensitive LC-MSMS quantification method.
• CARTONI, GIAMPAOLO;COCCIOLI, FRANCO;CAMILLI, LUCIA, ANN. CHIM., 80,(1990) N-10, C. 453-460
  作者：CARTONI, GIAMPAOLO、COCCIOLI, FRANCO、CAMILLI, LUCIA

  DOI：——

  日期：——