(7alpha,12alpha)-7,12-二羟基-3-氧代胆-4-烯-24-酸 | 13587-11-6

• 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: (7alpha,12alpha)-7,12-二羟基-3-氧代胆-4-烯-24-酸
• 英文名称: 7α,12α-dihydroxy-3-oxochol-4-en-24-oic acid
• 英文别名: 7alpha,12alpha-Dihydroxy-3-oxochol-4-en-24-oic Acid；(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]pentanoic acid
• CAS: 13587-11-6
• 化学式: C₂₄H₃₆O₅
• 分子量: 404.547
• InChiKey: ZZUMXQCSMJCDDC-DFQOQHGMSA-N

物化性质

• 熔点：
  231-233 °C
• 沸点：
  604.2±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (7alpha,12alpha)-7,12-二羟基-3-氧代胆-4-烯-24-酸 在 吡啶 、 4-二甲氨基吡啶 、 aluminum oxide 、 氢氧化钾 、 sodium tetrahydroborate 、 potassium chromate 、 氨 、 lithium 、 对甲苯磺酸 、 palladium dichloride 作用下， 以 吡啶 、 甲醇 、 水 、 溶剂黄146 、 苯 为溶剂， 反应 122.08h， 生成 别胆酸
  参考文献：
  名称：

  Potential Bile Acid Metabolites; 12¹. Synthesis of Stereoisomeric 3,7,12-Trihydroxy-5α-cholanic Acids and Related Compounds²

  摘要：

  DOI：

  10.1055/s-1986-31848
• 作为产物：
  描述：

  cholic acid triformate 在 chromium(VI) oxide 、 sodium hydroxide 、 硫酸 、 溴 、 lithium carbonate 、 lithium bromide 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.75h， 生成 (7alpha,12alpha)-7,12-二羟基-3-氧代胆-4-烯-24-酸
  参考文献：
  名称：

  Improved synthesis of 3-keto, 4-ene-3-keto, and 4,6-diene-3-keto bile acids

  摘要：

  Cholic and deoxycholic acids can be converted into 3-keto derivatives in 75-80% yield, by a four-step synthesis consisting of formylation, selective deformylation of the 3-formoxyl group, oxidation, then deformylation of the remaining formoxyl groups. The intermediate 3-keto formoxyl acids in this sequence were shown to be suitable starting compounds for the synthesis of 4-ene-3-keto acids, in 55-60% yield, via bromination, dehydrobromination, and deformylation. By extending the dehydrobromination reaction, the 7 alpha-formoxyl group of the intermediate 4-ene-3-keto-7 alpha,12 alpha-diformoxyl acid is also lost, hence providing a useful synthetic route to 4,6-diene-3-keto bile acids.

  DOI：

  10.1016/0039-128x(83)90087-9

文献信息

• The “triamino-analogue” of methyl allocholate; a rigid, functionalised scaffold for supramolecular chemistry
  作者：Khadga M. Bhattarai、Vicente del Amo、Germinal Magro、Adam L. Sisson、Jean-Baptiste Joos、Jonathan P. H. Charmant、Anob Kantacha、Anthony P. Davis

  DOI：10.1039/b602415g

  日期：——

  Cholic acid 1 has been converted into triamine 5 with the all-trans polycyclic allocholanoyl skeleton and co-directed, axial amino groups; the potential of this system as a scaffold is illustrated by conversion to a preorganised anion receptor.

  胆酸1已被转化为三胺5，具有全反式多环异胆酰基骨架和共同定向的轴向氨基基团；该体系的潜在支架作用通过转化为预组织的阴离子受体得到了展示。
• Biotransformations of Bile Acids with Bacteria from Cayambe Slaughterhouse (Ecuador): Synthesis of Bendigoles
  作者：Stefania Costa、Maria Elena Maldonado Rodriguez、Irene Rugiero、Morena De Bastiani、Alessandro Medici、Elena Tamburini、Paola Pedrini

  DOI：10.1002/cbdv.201500300

  日期：2016.8

  The biotransformations of cholic acid (1a), deoxycholic acid (1b), and hyodeoxycholic acid (1c) to bendigoles and other metabolites with bacteria isolated from the rural slaughterhouse of Cayambe (Pichincha Province, Ecuador) were reported. The more active strains were characterized, and belong to the genera Pseudomonas and Rhodococcus. Various biotransformation products were obtained depending on

  据报道，胆酸 (1a)、脱氧胆酸 (1b) 和猪脱氧胆酸 (1c) 被从卡扬贝农村屠宰场（厄瓜多尔皮钦查省）分离出的细菌转化为苯菌灵和其他代谢物。更活跃的菌株被表征，属于假单胞菌属和红球菌属。根据细菌和底物获得各种生物转化产物。胆酸 (1a) 与 P. mendocina ECS10、3,12-dioxo-4-ene 衍生物 4a 一起提供了 3-oxo 和 3-oxo-4-ene 衍生物 2a 和 3a（分别为 45% 和 45%）（ 60%) 与 Rh。erythropolis ECS25 和 9,10-secosteroid 6 (15%) 与 Rh。红城 ECS12。Bendigole F (5a) 以 20% 的比例用 P. fragi ECS22 获得。脱氧胆酸 (1b) 与 P. prosekii ECS1 和 Rh 生成 3-氧代衍生物 2b。erythropolis ECS25（分别为
• [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。
• The synthesis of taurine-conjugated bile acids and bile acid sulfates labeled with 14C or 3H in the taurine moiety
  作者：Jie Zhang、William J. Griffiths、Jan Sjövall

  DOI：10.1002/(sici)1099-1344(199702)39:2<159::aid-jlcr954>3.0.co;2-w

  日期：1997.2
• Bile acid transformations by Alcaligenes recti
  作者：Ipsita Mazumder、Shashi B. Mahato

  DOI：10.1016/0039-128x(93)90057-t

  日期：1993.2

  Metabolism of cholic acid, chenodeoxycholic acid, ursodeoxycholic acid, and deoxycholic acid by the grown cells of the bacterium Alcaligenes recti suspended in water was studied. Each isolated metabolite was characterized by the application of various spectroscopic methods. Cholic acid, chenodeoxycholic acid, ursodeoxycholic acid, and deoxycholic acid yielded methylated derivatives 3alpha-methoxy-7alpha, 12alpha-dihydroxy-5beta-cholanoic acid, 3alpha-methoxy-7alpha-hydroxy-5beta-cholanoic acid, 3alpha-methoxy-7beta-hydroxy-5beta-cholanoic acid, and 3alpha-methoxy-12alpha-hydroxy-5beta-cholanoic acid, respectively. In addition, cholic acid furnished 7alpha,12alpha-dihydroxy-3-oxochol-4-en-24-oic acid; chenodeoxycholic acid gave 7alpha-hydroxy-3-oxo-5beta-cholanoic acid and 7alpha-hydroxy-3-oxochol-4-en-24-oic acid while ursodeoxycholic acid yielded 7beta-hydroxy-3-oxochol-4-en-24-oic acid and 3-oxochola-4,6-dien-24-oic acid. The formation of various metabolites showed that two competitive enzymic reactions, i.e., selective methylation of the 3alpha-hydroxy group and dehydrogenation in the A/B rings, were operative. The methylation process was found to be enzymic involving an S-adenosyl-L-methionine (AdoMet)-dependent methyl transferase, and this reaction appeared to be inhibitory to the process of degradation of the ring system. In the other reaction sequence, degradation of the ring system was initiated by dehydrogenation of the 3alpha-hydroxy group. A 7beta-dehydratase activity producing the DELTA6 double bond was also noticeable in the metabolism of ursodeoxycholic acid.