17-环雌三醇 | 1228-72-4

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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-环雌三醇
• 中文别名: 雌三醇杂质E；17-雌二醇
• 英文名称: 17-epiestriol
• 英文别名: 16α,17α-estra-1,3,5(10)-triene-3,16,17-triol；estra-1,3,5(10)-trien-3,16α,17α-triol；16α,17α-estriol；estra-1,3,5(10)-triene-3,16α,17α-triol；Oestra-1,3,5(10)-trien-3,16α,17α-triol；(8R,9S,13S,14S,16R,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
• CAS: 1228-72-4
• 化学式: C₁₈H₂₄O₃
• mdl: MFCD00069500
• 分子量: 288.387
• InChiKey: PROQIPRRNZUXQM-PNVOZDDCSA-N

物化性质

• 熔点：
  239-241°C
• 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)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  17-环雌三醇 在 potassium carbonate 、 三乙胺 作用下， 以 正己烷 、 水 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  A novel GC-MS method in urinary estrogen analysis from postmenopausal women with osteoporosis

  摘要：

  Estrogen metabolites play important roles in the development of female-related disorders and homeostasis of the bone. To improve detectability, a validated gas chromatography-mass spectrometry (GC-MS) method was conducted with two-phase extractive ethoxycarbonlyation (EOC) and subsequent pentafluoropropionyl (PFP) derivatization was introduced. The resulting samples were separated through a high-temperature MXT-1 column within an 8 min run and were detected in the selected ion monitoring (SIM) mode. The optimized analytical conditions led to good separation with a symmetric peak shape for 19 estrogens as their EOC-PFP derivatives. The limit of quantification (LOQ) was from 0.02 to similar to 0.1 ng/ml for most estrogens analyzed, except for 2-hydroxyestriol (0.5 ng/ml). The devised method was found to be linear (r(2) > 0.995) in the range from the LOQ to 40 ng/ml, whereas the precision (% CV) and accuracy (% bias) ranged from 1.4 to 10.5% and from 91.4 to 108.5%, respectively. The good sensitivity and selectivity of this method even allowed quantification of the estrogen metabolites in urine samples obtained from the postmenopausal female patients with osteoporosis. The present technique can be useful for clinical diagnosis as well as to better understand the pathogenesis of estrogen-related disorders in low-level quantification.-Moon, J-Y., K. J. Kim, M. H. Moon, B. C. Chung, and M. H. Choi. A novel GC-MS method in urinary estrogen analysis from postmenopausal women with osteoporosis. J. Lipid Res. 2011. 52: 1595-1603.

  DOI：

  10.1194/jlr.d016113
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 四氧化锇 、 乙醚 作用下， 生成 17-环雌三醇
  参考文献：
  名称：

  Mapping land use/cover distribution on a mountainous tropical island using remote sensing and GIS

  摘要：

  The land use/cover distribution on Langkawi Island, Malaysia was mapped using remote sensing and a Geographic Information System (CIS). A Landsat Thematic Mapper (TM) satellite image taken in March 1995 was processed, geocorrected and analysed using IDRISI, raster-based GIS software. An unsupervised classification was performed based on spectral data from a composite image of the bands TM3, TM4 and TM5. Using this output, field data together with available secondary data consisting of topography, land use and soil maps were used to perform a maximum likelihood supervised classification. The overall accuracy of the output image was 90% and individual class accuracy ranged from 74% for rubber to 100% for paddy fields. The classified areas on the image were mainly confined to the mountainous and hilly regions on the island. A shaded relief map, simulating sunshine conditions, showed that the unclassified areas are located in the shadowed slopes, i.e. the slopes facing west. Consequently, the imagery was subdivided on the basis of slope aspect and a stratified classification was performed. As a result of this procedure, the overall accuracy increased to 92% and the individual class accuracy for the inland forest class increased by 9% to 90%. Using IDRISI, individual class areas as well as percentages were calculated The kappa coefficient for the classified image was 0.90. Qualitative analysis indicates that topography is the main control on the spatial distribution of land use/cover types on the island. As Langkawi Island has been developing rapidly over the last decade, successful planning will require reliable information about land use/cover distribution and change. This study illustrates that remote sensing and GIS techniques are capable of providing such information.

  DOI：

  10.1080/01431160119220

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

  公开号：WO2021234003A1

  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法的化合物，以及利用这些化合物进行分析物分子的质谱测定方法。
• [EN] REAGENT FOR MASS SPECTROMETRY<br/>[FR] RÉACTIF POUR LA SPECTROMÉTRIE DE MASSE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2021234002A1

  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，以及利用这些化合物进行分析物分子的质谱测定方法。
• [EN] STEREOSELECTIVE REDUCTION OF ALPHA-HYDROXYKETONE<br/>[FR] RÉDUCTION STÉRÉOSÉLECTIVE DE L'ALPHA-HYDROXYCÉTONE
  申请人：RELIANCE LIFE SCIENCES PVT LTD

  公开号：WO2012032529A1

  公开（公告）日：2012-03-15

  The present invention provides methods for 1, 2-asymmetric reduction of other compounds wherein 1,2- trans diol is present. In particular the present invention discloses preparation of 17β-Estriol and its derivatives having substantially free of 17α-Estriol impurity using an achiral reductant sodium triacetoxy borohydride.

  本发明提供了一种方法，用于对存在1,2-反式二醇的其他化合物进行1,2-不对称还原。具体地，本发明揭示了使用无手性还原剂三乙酰氧基硼氢化钠制备17β-雌三醇及其衍生物的方法，这些衍生物基本上不含有17α-雌三醇杂质。
• Regiospecificity and Stereospecificity of Human UDP-Glucuronosyltransferases in the Glucuronidation of Estriol, 16-Epiestriol, 17-Epiestriol, and 13-Epiestradiol
  作者：Nina Sneitz、Mikko Vahermo、Johanna Mosorin、Liisa Laakkonen、Donald Poirier、Moshe Finel

  DOI：10.1124/dmd.112.049072

  日期：2013.3

  The glucuronidation of estriol, 16-epiestriol, and 17-epiestriol by the human UDP-glucuronosyltransferases (UGTs) of subfamilies 1A, 2A, and 2B was examined. UGT1A10 is highly active in the conjugation of the 3-OH in all these estriols, whereas UGT2B7 is the most active UGT toward one of the ring D hydroxyls, the 16-OH in estriol and 16-epiestriol, but the 17-OH in 17-epiestriol. Kinetic analyses indicated that the 17-OH configuration plays a major role in the affinity of UGT2B7 for estrogens. The glucuronidation of the different estriols by the human liver and intestine microsomes reflects the activity of UGT1A10 and UGT2B7 in combination with the tissues’ difference in UGT1A10 expression. The UGT1A10 mutant 1A10-F93G exhibited much higher V max values than UGT1A10 in estriol and 17-epiestriol glucuronidation, but a significantly lower value in 16-epiestriol glucuronidation. To this study on estriol glucuronidation we have added experiments with 13-epiestradiol, a synthetic estradiol in which the spatial arrangement of the methyl on C18 and the hydroxyl on C17 is significantly different than in other estrogens. In comparison with estradiol glucuronidation, the C13 configuration change decreases the turnover of UGTs that conjugate the 3-OH, but increases it in UGTs that primarily conjugate the 17-OH. Unexpectedly, UGT2B17 exhibited similar conjugation rates of both the 17-OH and 3-OH of 13-espiestradiol. The combined results reveal the strong preference of UGT1A10 for the 3-OH of physiologic estrogens and the equivalently strong preference of UGT2B7 and UGT2B17 for the hydroxyls on ring D of such steroid hormones.

  检查了亚家族 1A、2A 和 2B 的人 UDP-葡萄糖醛酸基转移酶 (UGT) 对雌三醇、16-表三醇和 17-表三醇的葡萄糖醛酸化。 UGT1A10 在所有这些雌三醇中的 3-OH 缀合中具有高度活性，而 UGT2B7 是对 D 环羟基之一（雌三醇和 16-表三醇中的 16-OH）最活跃的 UGT，但 17 中的 17-OH -表三醇。动力学分析表明，17-OH构型在UGT2B7与雌激素的亲和力中起主要作用。人肝和肠微粒体对不同雌三醇的葡萄糖醛酸化反映了UGT1A10和UGT2B7的活性以及组织中UGT1A10表达的差异。 UGT1A10突变体1A10-F93G在雌三醇和17-表三醇葡萄糖醛酸化中表现出比UGT1A10高得多的V max 值，但在16-表三醇葡萄糖醛酸化中表现出显着较低的值。在这项关于雌三醇葡萄糖醛酸化的研究中，我们添加了 13-表雌二醇的实验，这是一种合成雌二醇，其中 C18 上的甲基和 C17 上的羟基的空间排列与其他雌激素显着不同。与雌二醇葡萄糖醛酸化相比，C13构型变化降低了缀合3-OH的UGT的周转率，但增加了主要缀合17-OH的UGT的周转率。出乎意料的是，UGT2B17 表现出与 13-espiestradiol 的 17-OH 和 3-OH 相似的缀合率。综合结果揭示了UGT1A10对生理雌激素的3-OH的强烈偏好，以及UGT2B7和UGT2B17对此类类固醇激素的环D上的羟基的同样强烈的偏好。