(3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-羟基-6-甲基-庚烷-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊烯并[a]菲-3,7-二醇 | 4725-24-0

• 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: (3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-羟基-6-甲基-庚烷-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊烯并[a]菲-3,7-二醇
• 英文名称: 7α,27-dihydroxycholesterol
• 英文别名: 7alpha,27-Dihydroxycholesterol；(3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
• CAS: 4725-24-0
• 化学式: C₂₇H₄₆O₃
• 分子量: 418.66
• InChiKey: RXMHNAKZMGJANZ-DTTSCKGMSA-N

物化性质

• 沸点：
  552.6±35.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-羟基-6-甲基-庚烷-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊烯并[a]菲-3,7-二醇 在 recombinant Brevibacterium cholesterol oxidase 作用下， 以 phosphate buffer 、 异丙醇 为溶剂， 反应 12.0h， 生成 7alpha,26-二羟基-4-胆甾烯-3-酮
  参考文献：
  名称：

  Analysis of derivatised steroids by matrix-assisted laser desorption/ionisation and post-source decay mass spectrometry

  摘要：

  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.

  DOI：

  10.1016/j.steroids.2005.08.002
• 作为产物：
  描述：

  Acetic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-6-acetoxy-1,5-dimethyl-hexyl)-7-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 在 甲醇 、 氢氧化钾 作用下， 反应 1.0h， 生成 (3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-羟基-6-甲基-庚烷-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊烯并[a]菲-3,7-二醇 、 7β,27-dihydroxycholesterol
  参考文献：
  名称：

  Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs

  摘要：

  In connection with studies of alternative pathways in bile acid biosynthesis, potential intermediates in a pathway starting with 27-hydroxylation of cholesterol have been prepared in natural and deuterated forms. Established methods were used to prepare 27-hydroxycholesterol and 3beta-hydroxy-5-cholestenoic acid. Clemmensen reduction of kryptogenin in unlabeled and deuterated solvents yielded 27-hydroxy-cholesterol and 16-oxo-5-cholestene-3beta,27-diol, which were separated by adsorption chromatography on Unisil. The labeled 27-hydroxycholesterol and 3beta-hydroxy-5-cholestenoic acid derived from it consisted of molecules with seven (50%), six (20%), and eight (20%) deuterium atoms, and unlabeled molecules were not detected. The acetates of 27-hydroxycholesterol and methyl 3beta-hydroxy-5-cholestenoate were 7alpha-hydroxylated in a copper-catalyzed reaction with tert-butylperbenzoate, and the products were purified by chromatography on Unisil. The 7beta-epimers were obtained as side products. Labeled 3beta,7alpha-dihydroxy-5-cholenoic acid was prepared in the same way from 3beta-hydroxy-5-[2,2,4,4,23-H-2(5)-cholenoic acid. The 3-oxo-DELTA4 analogs of the 3beta-hydroxy-DELTA5 compounds were prepared by oxidation with cholesterol oxidase. The labeled products had the same isotopic composition as the starting materials. Gas chromatographic retention indices and mass spectral characteristics of the trimethylsilyl ether derivatives of the neutral steroid and the methylated acids are given for all compounds.

  DOI：

  10.1016/0039-128x(93)90048-r

文献信息

• Liposomal formulation of nonglycosidic ceramides and uses thereof
  申请人：LUDWIG INSTITUTE FOR CANCER RESEARCH LTD.

  公开号：US10039715B2

  公开（公告）日：2018-08-07

  The invention provides liposomes containing nonglycosidic ceramides within their bilayers, and compositions thereof. These liposomes activate murine iNKT cells and induce dendritic cell (DC) maturation, both in vitro and in vivo at an efficacy that is comparable to their corresponding soluble nonglycosidic ceramides. Also provided are methods for treating diseases using the liposomes and compositions of the invention.

  本发明提供了在其双层内含有非糖苷类神经酰胺的脂质体及其组合物。这些脂质体可在体外和体内激活小鼠 iNKT 细胞并诱导树突状细胞（DC）成熟，其功效与相应的可溶性非糖苷神经酰胺相当。此外，还提供了使用本发明脂质体和组合物治疗疾病的方法。
• Compound and method for the treatment and diagnosis of neurodegenerative conditions
  申请人：SWANSEA UNIVERSITY

  公开号：US10226475B2

  公开（公告）日：2019-03-12

  A reagent selected from cholestenoic acid or an inhibitor of an enzyme in the cholestenoic acid biosynthetic or metabolic pathway for use in the treatment of neurodegenerative conditions. In particular, the reagent is a cholestenoic acid of a particular form, such as 3β,7α-dihydroxycholest-5-en-26-oic (3β,7α-diHCA), not previously associated with neural tissue or CSF. Pharmaceutical compositions, methods of treatment or prevention of neurodegenerative conditions as well as diagnostic methods and novel biomarkers form further aspects of the invention.

  一种选自胆烯酸或胆烯酸生物合成或代谢途径中酶的抑制剂的试剂，用于治疗神经退行性疾病。特别是，该试剂是一种特殊形式的胆甾烯酸，如 3β,7α-二羟基胆甾烯-5-烯-26-酸（3β,7α-diHCA），以前与神经组织或 CSF 无关。本发明还包括药物组合物、治疗或预防神经退行性疾病的方法以及诊断方法和新型生物标记物。
• CYTOSTATIC STEROLS
  申请人：MEDIVIR AB

  公开号：EP0906331A1

  公开（公告）日：1999-04-07
• ORGANIC COMPOUNDS
  申请人：Novartis AG

  公开号：EP2376532A2

  公开（公告）日：2011-10-19
• METHOD OF IDENTIFYING MODULATORS OF THE INTERACTION BETWEEN CERTAIN OXYSTEROLS AND EBI2
  申请人：Novartis AG

  公开号：EP2376532B1

  公开（公告）日：2014-01-22