2-羟基雌酚酮 | 362-06-1

• 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: 2-羟基雌酚酮
• 中文别名: 2-羟基雌激素酮；2-羟雌甾酮
• 英文名称: (+/-)-2,3-Dihydroxy-oestra-1,3,5(10)-trien-17-on
• 英文别名: 2-Hydroxyestrone；(8R,9S,13S,14S)-2,3-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 362-06-1
• 化学式: C₁₈H₂₂O₃
• mdl: MFCD00056414
• 分子量: 286.371
• InChiKey: SWINWPBPEKHUOD-JPVZDGGYSA-N

物化性质

• 熔点：
  199-201°C
• 沸点：
  481.3±45.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、乙醇（微溶）、甲醇（微溶）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.611
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

2-羟基雌酮的人类已知代谢物包括雌酮2-O-葡萄糖苷酸、2-甲氧基雌酮和3-O-甲氧基雌酮。

2-hydroxyestrone has known human metabolites that include Estrone 2-O-glucuronide, 2-Methoxyestrone, and 3-O-methoxyestrone.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  2-羟基雌酚酮 在 三乙胺 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  2-羟基雌酮的氧化转化。2,3-雌酮醌的稳定性和反应性及其与雌激素致癌性的关系。

  摘要：

  雌激素在啮齿动物和人类中的致癌性归因于细胞大分子的烷基化和/或氧化还原循环，活性自由基的产生以及DNA损伤。导致形成儿茶酚雌激素的雌二醇的代谢活化被认为是其遗传毒性作用的先决条件。4-羟基雌二醇，虽然不是2-羟基雌二醇，但是是仓鼠肿瘤的有效诱导剂。先前的研究表明3,4-雌酮醌可以进行氧化还原循环，并能够诱导MCF-7乳腺癌细胞中的单链DNA断裂，并且可以与各种亲核试剂（硫醇，咪唑，氨基，酚盐和乙酰氧基）制得迈克尔加成产物。这些结果支持3，4-邻苯二酚/醌雌激素可能与雌激素的致癌性有关。为了解释2-羟基雌激素降低的致癌性，研究了2,3-雌酮醌（2,3-EQ）与亲核试剂的反应。4-甲基咪唑与2,3-EQ的反应产生了复杂的产物混合物，导致形成儿茶酚，CO二聚产物和被确定为1-（4-甲基咪唑）-2的1,6-Michael加成产物-羟基雌酮。2,3-EQ在弱碱性条件下与酚酸乙酯或乙酸酯的反应生成了几

  DOI：

  10.1021/tx950205z
• 作为产物：
  描述：

  19-去甲-4-雄烯二酮 在 rat NADPH-P₄₅₀ reductase 、 human cytochrome P₄₅₀ 19A₁ , steroid aromatase 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 甲醇 、 aq. phosphate buffer 为溶剂， 反应 0.66h， 生成 2-羟基雌酚酮
  参考文献：
  名称：

  Oxidation of Dihydrotestosterone by Human Cytochromes P450 19A1 and 3A4

  摘要：

  Dihydrotestosterone is a more potent androgen than testosterone and plays an important role in endocrine function. We demonstrated that, like testosterone, dihydrotestosterone can be oxidized by human cytochrome P450 (P450) 19A1, the steroid aromatase. The products identified include the 19-hydroxy- and 19-oxo derivatives and the resulting Delta(1,10)-, Delta(5,10)-, and Delta(9,10)-dehydro 19-norsteroid products (loss of 19-methyl group). The overall catalytic efficiency of oxidation was similar to 10-fold higher than reported for 3 alpha-reduction by 3 alpha-hydroxysteroid dehydrogenase, the major enzyme known to deactivate dihydrotestosterone. These and other studies demonstrate the flexibility of P450 19A1 in removing the 1- and 2-hydrogens from 19-norsteroids, the 2-hydrogen from estrone, and (in this case) the 1-, 5 beta-, and 9 beta-hydrogens of dihydrotestosterone. Incubation of dihydrotestosterone with human liver microsomes and NADPH yielded the 18- and 19-hydroxy products plus the Delta(1,10)-dehydro 19-nor product identified in the P450 19A1 reaction. The 18- and 19-hydroxylation reactions were attributed to P450 3A4, and 18- and 19-hydroxydihydrotestosterone were identified in human plasma and urine samples. The change in the pucker of the A ring caused by reduction of the Delta(4,5) bond is remarkable in shifting the course of hydroxylation from the 6 beta-, 2 beta-, 1 beta-, and 15 beta-methylene carbons (testosterone) to the axial methyl groups (18, 19) in dihydrotestosterone and demonstrates the sensitivity of P450 3A4, even with its large active site, to small changes in substrate structure.

  DOI：

  10.1074/jbc.m112.390047

文献信息

• [EN] IMIDAZOLIUM REAGENT FOR MASS SPECTROMETRY<br/>[FR] RÉACTIF D'IMIDAZOLIUM POUR SPECTROMÉTRIE DE MASSE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2021234004A1

  公开（公告）日：2021-11-25

  The present invention relates to compounds which are suitable to be used in mass spectrometry as well as methods of mass spectrometric determination of analyte molecules using said compounds.

  本发明涉及适用于质谱的化合物，以及利用该化合物进行分析物分子的质谱测定方法。
• Studies on dimethyl-tert-butylsilyl ethers of steroid.
  作者：HIROSHI HOSODA、KOUWA YAMASHITA、HIROMITSU SAGAE、TOSHIO NAMBARA

  DOI：10.1248/cpb.23.2118

  日期：——

  In order to obtain the more precise knowledge on the nature of the dimethyl-tert-butylsilyloxy linkage, several steroid silyl ethers were prepared. The rate of acid-catalyzed hydrolysis was determined with the typical steroid derivatives. Convenient syntheses of 3β-hydroxy-4-androsten-17-one have also been described.

  为了更精确地了解二甲基叔丁基硅氧键的性质，制备了几种类固醇硅醚。通过典型的类固醇衍生物测定了酸催化水解的速率。同时，还描述了3β-羟基-4-雄烯-17-酮的便捷合成方法。
• Methylation of Catechol Estrogen with Diazomethane
  作者：MASANORI TERANISHI、YOUICHI FUJII、MITSURU YAMAZAKI、SUSUMU MIYABO

  DOI：10.1248/cpb.31.3309

  日期：——

  Dynamic aspects of methylation of catechol estrogen with diazomethane were investigated by means of thin-layer chromatography. The methylation rate of the hydroxyl group at the C-3 position was almost the same as that of the C-2 hydroxyl group in the reaction of 2-hydroxyestrogen, and 2-3 times that of the C-4 hydroxyl group in the reaction of 4-hydroxyestrogen. In these experiments, the maximum yields of 2-methoxyestrone, 2-hydroxyestrone 3-methyl ether, 4-methoxyestrone and 4-hydroxyestrone 3-methyl ether were 32, 39, 13 and 70%, respectively. In addition, demethylation of catechol estrogen dimethyl ethers with boron tribromide and synthesis of 4-hydroxyestrone monomethyl ethers are described.

  通过薄层色谱法研究了二氮甲烷与邻苯二酚雌激素的甲基化反应的动态过程。在2-羟基雌激素反应中，C-3位置的羟基甲基化速率几乎与C-2羟基相同，而在4-羟基雌激素反应中，C-3羟基的甲基化速率是C-4羟基的2-3倍。在这些实验中，2-甲氧基雌酮、2-羟基雌酮3-甲基醚、4-甲氧基雌酮和4-羟基雌酮3-甲基醚的最高产率分别为32%、39%、13%和70%。此外，还描述了用三溴化硼脱除邻苯二酚雌激素二甲基醚的甲基化和4-羟基雌酮单甲基醚的合成。
• [EN] ESTRATRIENE DERIVATIVES<br/>[FR] DERIVES D'ESTRATRIENE
  申请人：CRYPTOPHARMA PTY LTD

  公开号：WO2004101595A1

  公开（公告）日：2004-11-25

  Compounds and methods for modulating mesenchymal cell function, for instance smooth muscle and fibroblast proliferation or cytokine expression, and for treating conditions associated with mesenchymal cell function, for instance airway hyperresponsiveness associated with asthma. The compounds also supress inflammation. The compounds are a class of estratriene derivates, and includes various derivatives of 2-methoxyestradiol comprising a group A, including a substituted aromatic substituent in the 2-, 6- or 17- position.

  调节间叶细胞功能的化合物和方法，例如平滑肌和成纤维细胞增殖或细胞因子表达，以及治疗与间叶细胞功能相关的疾病，例如与哮喘相关的气道高反应性。这些化合物还抑制炎症。这些化合物是一类雌三烯衍生物，包括各种2-甲氧基雌二醇衍生物，其中包括A组，包括在2-、6-或17-位置有取代芳香基团。
• [EN] REAGENT FOR MASS SPECTROMETRY<br/>[FR] RÉACTIF POUR SPECTROMÉTRIE DE MASSE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2020020849A1

  公开（公告）日：2020-01-30

  The present invention relates to reagents which are suitable to be used in mass spectrometry as well as methods of mass spectrometric determination of analyte molecules using said reagents.

  本发明涉及适用于质谱的试剂，以及利用所述试剂进行分析物分子的质谱测定方法。