3-酮基-delta-4-胆烯酸甲酯 | 55319-79-4

• 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: 3-酮基-delta-4-胆烯酸甲酯
• 英文名称: 7-α,12-α-dihydroxycholin-4-ene-3-one carboxylic acid methyl ester
• 英文别名: 7α,12α-dihydroxy-3-oxo-chol-4-en-24-oic acid methyl ester；7α,12α-Dihydroxy-3-oxo-chol-4-en-24-saeure-methylester；Chol-4-en-24-oic acid, 7,12-dihydroxy-3-oxo-, methyl ester, (7alpha,12alpha)-；methyl (4R)-4-[(7R,8R,9S,10R,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 55319-79-4
• 化学式: C₂₅H₃₈O₅
• 分子量: 418.574
• InChiKey: CTGYXJXWCGIHQC-CWVITHCZSA-N

物化性质

• 熔点：
  178-179℃
• 沸点：
  558.0±50.0 °C(Predicted)
• 密度：
  1.17

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-酮基-delta-4-胆烯酸甲酯 在 水 、 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (7alpha,12alpha)-7,12-二羟基-3-氧代胆-4-烯-24-酸
  参考文献：
  名称：

  [EN] COMPETITIVE IMMUNOASSAY METHODS
  [FR] PROCÉDÉS DE DOSAGE IMMUNOLOGIQUE PAR COMPÉTITION

  摘要：

  本发明提供了检测、测量或定量生物样本中7α-羟基-4-胆甾烯-3-酮（7C4）水平的测定方法和试剂盒，所述生物样本来自于受试者，例如人类受试者。在某些实施方式中，人类受试者患有与胆酸吸收不良或不明原因腹泻相关的疾病。本发明还提供了特异性结合于7α-羟基-4-胆甾烯-3-酮（7C4）并且与7-酮胆固醇、7α-羟基胆固醇和三羟基胆甾酸中的一个或多个成员的交叉反应小于1％的分离抗体或抗体片段。

  公开号：

  WO2018011691A1
• 作为产物：
  描述：

  胆酸甲酯 在 镍 4-异丙基甲苯 作用下， 生成 3-酮基-delta-4-胆烯酸甲酯
  参考文献：
  名称：

  Bile acids. LII. The synthesis of 24-nor-5α-cholic acid and its 3β-isomer

  摘要：

  To aid in the identification of trihydroxy acidic metabolite(s) derived from beta-sitosterol, 3alpha,7alpha,12alpha-trihydroxy-24-nor-5beta-cholan-23-oic acid was prepared and its methyl ester was treated with Raney nickel in boiling p-cymene to provide methyl 3-oxo-7alpha,12alpha-dihydroxy-24-nor-5alpha-cholanate, 3-oxo-7alpha,12alpha-dihydroxy-24-nor-5beta-cholante and 3-oxo-7alpha,12alpha-dihydroxy-24-norchol-4-enoate. The latter compound was synthesized from the 3-oxo-5beta-derivative with SeO2 to provide a product with identical properties. Catalytic reduction of either saturated 3-oxo-derivative provided the appropriate 3,7,12-triols isomeric at C-3. Results from gas liquid and partition chromatography, mass spectrometry, and otherr physical properties of the acids, their methyl esters and other derivatives are compatible with the assigned structures.

  DOI：

  10.1016/0039-128x(76)90007-6

文献信息

• Bile acids. LXXIX. synthesis and reduction of 1,4-dien-3-ones of various bile acids
  作者：Mohammed N. Iqbal、William H. Elliott

  DOI：10.1016/0039-128x(89)90022-6

  日期：1989.3

  bile acids (IIa-d), their methyl esters (IIe-h), and their formylated derivatives (IIi-k) were synthesized and their reduction investigated by both catalytic and chemical methods as an alternative route to the synthesis of allo bile acids. Lithium-ammonia reduction proved to be the better method for the reduction of these 1,4-dien-3-ones producing the 3-keto- and 3 beta-hydroxy-allo bile acids (Vb-d)

  合成了各种胆汁酸 (IIa-d) 的 1,4-Dien-3-ones、它们的甲酯 (IIe-h) 和它们的甲酰化衍生物 (IIi-k)，并通过催化和化学方法研究了它们的还原情况，如合成别胆汁酸的另一种途径。锂-氨还原被证明是还原这些 1,4-二烯-3-酮的更好方法，产生 3-酮-和 3-β-羟基-别胆酸 (Vb-d) 和 (VIb-d)产率为 66-72%。
• Fujii, American Journal of Biochemistry, 1957, vol. 44, p. 383,385
  作者：Fujii

  DOI：——

  日期：——
• Eguchi, American Journal of Biochemistry, 1957, vol. 44, p. 81,82
  作者：Eguchi

  DOI：——

  日期：——
• Bile acids. LII. The synthesis of 24-nor-5α-cholic acid and its 3β-isomer
  作者：Yehuda Shalon、William H. Elliott

  DOI：10.1016/0039-128x(76)90007-6

  日期：1976.11

  To aid in the identification of trihydroxy acidic metabolite(s) derived from beta-sitosterol, 3alpha,7alpha,12alpha-trihydroxy-24-nor-5beta-cholan-23-oic acid was prepared and its methyl ester was treated with Raney nickel in boiling p-cymene to provide methyl 3-oxo-7alpha,12alpha-dihydroxy-24-nor-5alpha-cholanate, 3-oxo-7alpha,12alpha-dihydroxy-24-nor-5beta-cholante and 3-oxo-7alpha,12alpha-dihydroxy-24-norchol-4-enoate. The latter compound was synthesized from the 3-oxo-5beta-derivative with SeO2 to provide a product with identical properties. Catalytic reduction of either saturated 3-oxo-derivative provided the appropriate 3,7,12-triols isomeric at C-3. Results from gas liquid and partition chromatography, mass spectrometry, and otherr physical properties of the acids, their methyl esters and other derivatives are compatible with the assigned structures.
• [EN] COMPETITIVE IMMUNOASSAY METHODS<br/>[FR] PROCÉDÉS DE DOSAGE IMMUNOLOGIQUE PAR COMPÉTITION
  申请人：NESTEC SA

  公开号：WO2018011691A1

  公开（公告）日：2018-01-18

  The invention provides assay methods and kits for detecting, measuring or quantitating the level of 7α-hydroxy-4-cholesten-3-one (7C4) in a biological sample from a subject, such as a human subject. In some embodiments, the human subject has a condition associated with bile acid malabsorption or diarrhea of unknown origin. The invention also provides isolated antibodies or antibody fragment thereof that specifically binds to 7α- hydroxy-4-cholesten-3-one (7C4) and have less than 1% cross-reactivity to one or more members selected from the group consisting of 7-ketocholesterol, 7α-hydroxycholesterol, and trihydroxycholestanoic acid.

  本发明提供了检测、测量或定量生物样本中7α-羟基-4-胆甾烯-3-酮（7C4）水平的测定方法和试剂盒，所述生物样本来自于受试者，例如人类受试者。在某些实施方式中，人类受试者患有与胆酸吸收不良或不明原因腹泻相关的疾病。本发明还提供了特异性结合于7α-羟基-4-胆甾烯-3-酮（7C4）并且与7-酮胆固醇、7α-羟基胆固醇和三羟基胆甾酸中的一个或多个成员的交叉反应小于1％的分离抗体或抗体片段。