5β-孕烷-3Alpha,17Alpha,20Alpha-三醇 | 1098-45-9

• 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: 5β-孕烷-3Alpha,17Alpha,20Alpha-三醇
• 中文别名: 5β-孕烷-3α,17α,20α-三醇；孕三醇；5Beta-孕烷-3Alpha,17Alpha,20Alpha-三醇
• 英文名称: 5β-pregnane-3α,17α,20β-tetraol
• 英文别名: 5β-pregnane-3α,17α,20α-triol；5β-pregnane-3α,17α,20β-triol；5β-pregnan-3α,17α,20β-triol；(20S)-5β-pregnane-3α,17α,20-triol；pregnanetriol；PT；(3R,5R,8R,9S,10S,13S,14S,17R)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 1098-45-9
• 化学式: C₂₁H₃₆O₃
• 分子量: 336.515
• InChiKey: SCPADBBISMMJAW-UHHUKTEYSA-N

物化性质

• 熔点：
  254～255℃
• 沸点：
  469.9±10.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿/甲醇 (9:1)：50 mg/mL，澄清，无色

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 安全说明：
  S22,S24/25

反应信息

• 作为反应物：
  描述：

  5β-孕烷-3Alpha,17Alpha,20Alpha-三醇 在 lead(IV) acetate 、 溶剂黄146 作用下， 生成 还原胆烷醇酮
  参考文献：
  名称：

  Butler; Marrian, Journal of Biological Chemistry, 1937, vol. 119, p. 565,568

  摘要：

  DOI：
• 作为产物：
  描述：

  21-Brom-3α,17-dihydroxy-5β-pregnan-20-on 在 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5β-孕烷-3Alpha,17Alpha,20Alpha-三醇
  参考文献：
  名称：

  四对侧链环氧异构体在20位碳上的合成，这些分子衍生自5-beta-pregnan-3-alpha-ol。

  摘要：

  DOI：

  10.1021/jo01269a001

文献信息

• [EN] INHIBITING HYDROCARBON HYDRATE AGGLOMERATION<br/>[FR] INHIBITION DE L'AGGLOMÉRATION D'HYDRATES D'HYDROCARBURES
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2018218281A1

  公开（公告）日：2018-12-06

  A process for inhibiting the formation of gas hydrates in a hydrocarbon fluid comprising adding to the hydrocarbon fluid, a gas hydrate anti-agglomerate which is a biodegradable anti-agglomerant derived from a naturally occurring substance.

  一种抑制碳氢化合物流体中天然气水合物形成的方法包括向碳氢化合物流体中添加一种气体水合物抗凝聚剂，该抗凝聚剂是一种可生物降解的抗凝聚剂，来源于天然存在的物质。
• Diethylhydrogensilyl cyclic diethylsilylene derivatives in gas chromatography-mass spectrometry of hydroxylated steroids. II. Pregnanes with a hydroxylated 17.BETA.-side-chain.
  作者：MASATAKA ISHIBASHI、MASAHIRO ITOH、KOUWA YAMASHITA、HIROSHI MIYAZAKI、HISAO NAKATA

  DOI：10.1248/cpb.34.3298

  日期：——

  The gas chromatographic-mass spectrometric properties of diethylhydrogensilyl cyclic diethylsilylene derivatives of hydroxypregnanes were studied. Pregnanes with a sterically hindered 11β-hydroxyl group were smoothly silylated with a new silylating agent, N, O-bis(diethylhydrogensilyl)-trifluoroacetamide, under mild conditions. The mass spectra of these derivatives were characterized by the appearance of the intense molecular ion peak, which provides convenient and reliable confirmation of the molecular weight of these hydroxypregnanes. The most characteristic fragment ions were those at m/z 185 for 17, 20-diols and at m/z 287 for 17, 20, 21-triols, which were produced by cleavage at the C(13)-C(17) and C(15)-C(16) bonds with hydrogen atom transfer. This indicates that all of the major fragmentations are directed by the cyclic diethylsilylene group. Another fragmentation common to the spectra was the successive loss of diethylhydrogensilanol from the molecular ion. A remarkable difference in the appearance of peaks was observed between DEHS-DES derivatives of a 17α, 20α, 21-triol and its 20β-isomer. Structures are proposed for some of these fragment ions.

  研究了羟基孕烷的二乙基氢硅烷基环二乙基硅烷衍生物的气相色谱-质谱特性。在温和的条件下，用一种新的硅烷化剂 N, O-双（二乙基氢代苯甲酰）-三氟乙酰胺顺利地硅烷化了带有立体受阻的 11β- 羟基的孕烷。这些衍生物的质谱特征是出现了强烈的分子离子峰，这为确定这些羟基孕烷的分子量提供了方便可靠的依据。最有特征的碎片离子是 17、20-二醇的 m/z 185 和 17、20、21-三醇的 m/z 287，它们是通过氢原子转移裂解 C(13)-C(17) 和 C(15)-C(16) 键产生的。这表明所有主要碎片都是由环状二乙基硅基引导的。光谱中的另一个共同碎片是分子离子中的二乙基氢硅醇相继消失。在 17α、20α、21-三醇的 DEHS-DES 衍生物与其 20β 异构体之间，观察到峰值出现的明显差异。提出了其中一些碎片离子的结构。
• LC/MS/MS of Steroids Having Vicinal Diol as Electrospray-Active Boronates
  作者：Tatsuya Higashi、Katsumi Kawasaki、Nagisa Matsumoto、Shoujiro Ogawa、Kuniko Mitamura、Shigeo Ikegawa

  DOI：10.1248/cpb.c12-00979

  日期：——

  A derivatization procedure with (3-dimethylaminophenyl)dihydroxyborane (DAPB) was introduced to enhance the detectability of steroids having a vicinal diol in LC/electrospray ionization (ESI)-MS/MS. DAPB reacted with the vicinal diol on the steroids [4β-hydroxycholesterol (4-HCh), pregnanetriol (PT) and 20R,22R-dihydroxycholesterol] in pyridine at 50°C within 1 h. The resulting DAPB-derivatives were highly responsive in ESI-MS operating in the positive-ion mode and gave characteristic product ions during MS/MS, which enabled sensitive detection using a selected reaction monitoring mode; the detection responses of the DAPB-derivatives were increased by 20–160-fold over those of the intact steroids and the limits of detection were in the low femtomole or attomole range. The derivatization procedure was successfully applied to biological sample analysis; the derivatization followed by LC/ESI-MS/MS enabled the specific detection of trace amounts of 4-HCh in human plasma and PT in human urine with a small sample volume, simple pretreatment and short chromatographic run time.

  为了提高液相色谱/电喷雾离子化（ESI）-质谱/质谱中具有邻位二醇的类固醇的可检测性，我们引入了（3-二甲基氨基苯基）二羟基硼烷（DAPB）衍生化程序。DAPB 与类固醇[4β-羟基胆固醇 (4-HCh)、孕三醇 (PT) 和 20R,22R-二羟基胆固醇]的邻位二醇在 50°C 的吡啶中反应 1 小时。生成的 DAPB 衍生物在以正离子模式运行的 ESI-MS 中反应灵敏，并在 MS/MS 中给出了特征性的产物离子，因此可以使用选择反应监测模式进行灵敏检测；DAPB 衍生物的检测反应比完整类固醇的检测反应提高了 20-160 倍，检测限在低飞摩尔或阿托摩尔范围内。该衍生化程序被成功应用于生物样品分析；衍生化后采用 LC/ESI-MS/MS 方法可特异性检测人体血浆中的痕量 4-HCh 和人体尿液中的 PT，且样品量小、前处理简单、色谱运行时间短。
• 5β-Pregn-6-ene-3α,17,20-triols
  作者：George Cooley、Alexander E. Kellie

  DOI：10.1039/p19760000452

  日期：——

  5β-Pregn-6-ene-3α,17,20α-triol (I) and its 20β-isomer (II), have been prepared and reduced with hydrogen to the corresponding pregnanes.

  已经制备了5β-Pregn-6-ene-3α，17,20α-三醇（I）及其20β-异构体（II），并用氢还原成相应的孕烷。
• Cholesterol-lowering agents, secondary bile acid production inhibitors and foods and drinks
  申请人：Sawada Haruji

  公开号：US20050244426A1

  公开（公告）日：2005-11-03

  Secondary bile acid production inhibitors and cholesterol-lowering agents containing a yeast as the active ingredient.

  含有酵母作为活性成分的次级胆汁酸生产抑制剂和降低胆固醇药物。