7-羟基胆甾-4-烯-3-酮 | 25876-54-4

• 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: 7-羟基胆甾-4-烯-3-酮
• 英文名称: 7β-hydroxycholest-4-en-3-one
• 英文别名: Δ⁴-7β-hydroxycholesterol；cholesta-6β-hydroxy-4-en-3-one；7β-Hydroxy-cholest-4-en-3-on；7beta-Hydroxycholest-4-en-3-one；(7S,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 25876-54-4
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: IOIZWEJGGCZDOL-BXLWXSRCSA-N

物化性质

• 熔点：
  175-180°C
• 溶解度：
  氯仿（微溶）、甲醇（微溶、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-羟基胆甾-4-烯-3-酮 在 氢氧化钾 、 blue tetrazolium chloride 作用下， 以 乙醇 为溶剂， 以77%的产率得到cholest-4-ene-3,6,7-trione
  参考文献：
  名称：

  Jasiczak, Jan, Journal of the Chemical Society. Perkin transactions I, 1988, p. 2687 - 2692

  摘要：

  DOI：
• 作为产物：
  描述：

  3β-hydroxycholest-5-en-7β-yl benzoate 在 吡啶 、 chromium(VI) oxide 作用下， 生成 7-羟基胆甾-4-烯-3-酮
  参考文献：
  名称：

  Illy; Martin Panizo, Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica, 1956, vol. 52, p. 571,578

  摘要：

  DOI：

文献信息

• Meiosis regulating compounds
  申请人：——

  公开号：US20020183283A1

  公开（公告）日：2002-12-05

  Certain novel sterol derivatives can be used for regulating the meiosis in oocytes and in male germ cells.

  某些新型甾醇衍生物可以用于调节卵母细胞和雄性生殖细胞中的减数分裂。
• Greenhalgh et al., Journal of the Chemical Society, 1952, p. 2380,2382
  作者：Greenhalgh et al.

  DOI：——

  日期：——
• Analysis of derivatised steroids by matrix-assisted laser desorption/ionisation and post-source decay mass spectrometry
  作者：Muhammad Atif Khan、Yuqin Wang、Sibylle Heidelberger、Gunvor Alvelius、Suya Liu、Jan Sjövall、William J. Griffiths

  DOI：10.1016/j.steroids.2005.08.002

  日期：2006.1

  Neutral steroids are difficult to analyse using desorption ionisation methods coupled with mass spectrometry (MS). However, steroids with an unhindered ketone group can readily be derivatised with the Girard P (GP) reagent to give GP hydrazones. Steroid GP hydrazones contain a quaternary nitrogen atom and are readily desorbed in the matrix-assisted laser desorption/ionisation (MALDI) process, giving an improvement in sensitivity of two orders of magnitude. Steroids without a ketone group, but with a 3 beta-hydroxy-Delta(5) function, can be readily converted to 3-OXO-Delta(4) steroids and subsequently derivatised to GP hydrazones for MALDI analysis. In addition to giving strong [M](+) ions upon MALDI, steroid GP hydrazones give informative post-source decay (PSD) spectra. By using the accurate mass of the precursor-ion measured by MALDI-MS, in combination with the structural information encoded in its PSD spectrum, steroid structures can readily be determined. (c) 2005 Elsevier Inc. All rights reserved.
• Cholesterol conversion to δ4 -cholestenone by cholesterol oxidase in polyphasic systems : extension to the selective oxidation of 7β-hydroxycholesterol
  作者：Kang Min Lee、Jean-François Biellmann

  DOI：10.1016/s0040-4020(01)85893-2

  日期：1988.1

  The preparative use of cholesterol oxidase has been extended to polyphasic systems. The enzyme is active in microemulsions with the organic phase composed of mixtures of cyclohexane and chloroform. The kinetic data for oxidation of 7.alpha.- and 7.beta.-hydroxycholesterol in microemulsion with the enzyme from Streptomyces are similar to those of cholesterol. The cholesterol oxidase is active in the two phase system aqueous buffer - butyl acetate and the preparative enzymic conversion of 7.beta.-hydroxycholesterol to .DELTA.4-7.beta.-hydroxycholestenone was performed in this medium. The enzymic conversion of cholesterol to .DELTA.4-cholestenone was also performed in two liquid-solid systems, in buffer with cholesterol adsorbed on silica gel and in organic medium with cholesterol oxidase and catalase entrapped in Chromosorb.
• A convenient synthesis of 7α-hydroxycholest-4-en-3-one by the hydroxypropyl-β-cyclodextrin-facilitated cholesterol oxidase oxidation of 3β,7α-cholest-5-ene-3,7-diol
  作者：D Alexander

  DOI：10.1016/0039-128x(95)93851-o

  日期：1995.3

  The initial biosynthetic conversions of cholesterol to the bile acids involve sequential 7 alpha-hydroxylation (catalyzed by cholesterol 7 alpha-hydroxylase) followed by C-3 oxidation and concomittant double bond migration (to a Delta(4)-configuration, catalyzed by 3 beta-Delta(5)-C-27-steroid oxidoreductase) to provide 7 alpha-hydroxycholest-4-en-3-one. A straightforward, and economical, preparation (on a 0.1 g scale) of this pivotal biosynthetic intermediate has been devised. Reduction of 3 beta-(benzoyloxy)-cholest-5-en-7-one with LiB(sec-butyl)(3)H provided a 4:1 mixture, respectively, of the 7 alpha- and 7 beta-hydroxy diastereomers, which were separated chromatographically. Solvolytic removal of the C-3 benzoyl group gave 3 beta,7 alpha-cholest-5-ene-3,7-diol. A suspension of the 1:1 (nu/nu) complex (formed by mutual dissolution in MeOH, followed by evaporation of the solvent) of this diol with hydroxypropyl-beta-cyclodextrin, at a concentration of 1 mg mL(-1) (in neutral phosphate bl(buffer), was converted by Brevibacterium sp cholesterol oxidase (0.25 U mg(-1) of substrate) and catalase (70 U mg(-1) of substrate, to recover O-2 from the H2O2 produced by the enzymatic oxidation) to a suspension of 7 alpha-hydroxycholest-4-en-3-one and the hydroxypropyl-beta-cyclodextrin. The yield for the enzymatic conversion was in excess of 90%. A much poorer and less reproducible yield (<20%) was seen in the absence of the hydroxypropyl-beta-cyclodextrin. Routine extraction of this aqueous suspension, and chromatographic purification (85:15 CHCl3/acetone nu/nu on silica) of the residue, gave pure 7 alpha-hydroxycholest-4-en-3-one in 68% isolated yield. This route is a significant improvement, in terms of reaction scale and convenience, over the previous procedures for the preparation of this steroid.