24,25-methylene cholesterol

• 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
• 英文名称: 24,25-methylene cholesterol
• 英文别名: 24,25-methylenecholest-5-en-3 β-ol；(24RS)-24,25-Methano-cholest-5-en-3β-ol；24,25-Methylencholest-5-en-3β-ol；24,25-Methylenecholest-5-en-3beta-ol；(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-(2,2-dimethylcyclopropyl)butan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 化学式: C₂₈H₄₆O
• 分子量: 398.673
• InChiKey: RPIBVLMTWVBKKJ-RNRZRVCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  methyl 3-acetoxy-23a-homo-5-cholen-24-oate 在 sodium hydroxide 、 苄基三乙基氯化铵 、 lithium 、 溶剂黄146 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 24,25-methylene cholesterol
  参考文献：
  名称：

  甾族环丙烷的合成

  摘要：

  22,23-亚甲基stigma-5-en-3β-ol（IX），24,25-亚甲基胆甾-5-en-3β-ol（VII）和24,25-亚甲基-lanost-8-en-3β-ol（ XI）是通过用二氯卡宾处理豆甾醇，去甾醇和羊毛甾醇并还原形成的加合物（VIII）来合成的。用一种新颖的方法由3β-乙酰氧基-5--5-24酸（I）合成乙酸去十八烷基酯（V），主要步骤是重氮酮（II）的制备，其光化学Wolff重排成甲酯（III），（III）与甲基碘化镁的格氏反应和产物的脱水。

  DOI：

  10.1039/p19720002423

文献信息

• Sterols with Cyclopropane-Containing Side Chains: Synthesis and Acid Isomerization
  作者：Claudio Tarchini、Michel Rohmer、Carl Djerassi

  DOI：10.1002/hlca.19790620431

  日期：1979.6.8

  To test the eventual involvement of sterols with a cyclopropane containing side chain in bio-methylation processes, 24,25-methanocholest-5-en-3β-ol (5) and 24,25-methano-26-methylcholest-5-en-3β-ol (6) were synthesized. Together with the naturally occurring cyclopropane petrosterol (1), they were submitted to acid isomerization to provide chemical models for some of their potential metabolites.

  为了测试固醇与含环丙烷的侧链在生物甲基化过程中的最终参与情况，使用24,25-methanocholest-5-en-3β-ol（5）和24,25-methano-26-methylcholest-5-en-合成了3β-ol（6）。将它们与天然存在的环丙烷石油甾醇（1）一起进行酸异构化，以提供其某些潜在代谢物的化学模型。
• PROCESS FOR PREPARING FAT OR OIL CONTAINING UNSATURATED FATTY ACID
  申请人：SUNTORY LIMITED

  公开号：EP0957173A1

  公开（公告）日：1999-11-17

  A process for production of unsaturated fatty acid-containing oils which is characterized by culturing a microorganism belonging to the genus Mortierella subgenus Mortierella in a medium containing a nitrogen source derived from soybean, and collecting the unsaturated fatty acid-containing oil from the cultured product. The oils are obtained with a low 24,25-methylenecholest-5-en-3β-ol content.

  一种生产含不饱和脂肪酸油的工艺，其特征是在含有从大豆中提取的氮源的培养基中培养属于莫氏菌亚属的微生物，并从培养产物中收集含不饱和脂肪酸的油。获得的油中 24,25-亚甲基胆甾-5-烯-3β-醇含量较低。
• Process for producing unsaturated fatty acid-containing oils
  申请人：SUNTORY LIMITED

  公开号：EP1454990A1

  公开（公告）日：2004-09-08

  A process for production of unsaturated fatty acid-containing oils which is characterized by culturing a microorganism belonging to the genus Mortierella subgenus Mortierella in a medium containing a nitrogen source derived from soybean, and collecting the unsaturated fatty acid-containing oil from the cultured product. The oils are obtained with a low 24,25-methylenecholest-5-en-3β-ol content.

  一种含不饱和脂肪酸油的生产工艺，其特征在于在含有从大豆中提取的氮源的培养基中培养属于莫氏菌亚属的微生物，并从培养产物中收集含不饱和脂肪酸油。获得的油中 24,25-亚甲基胆甾-5-烯-3β-醇含量较低。
• Edible oil containing arachidonic acid and foods containing the same
  申请人：SUNTORY LIMITED

  公开号：EP1894472A1

  公开（公告）日：2008-03-05

  Edible oil containing arachidonic acid obtained from microorganisms belonging to the subgenus Mortierella of the genus Mortierella and being capable of producing arachidonic acid are provided. The oil contain little unsaponifiable matters and, above all, the smallest possible amount of sterol with cyclopropane structure which have not been recognized as food components, and are suitable for the production of foods, in particular, infant formula. Arachidonic acid-containing edible oil originating in microorganisms containing not more than 0.8% by weight, preferably not more than 0.6% by weight of unsaponifiable matters and 20% by weight or more of arachidonic acid. Further, these edible oil contain not more than 0.3% by weight, preferably not more than 0.15% by weight of 24,25-methylenecholest-5-en-3β-ol. The microorganisms are those belonging to the subgenus Mortierella of the genus Mortierella and being capable of producing arachidonic acid. These microorganisms belong to the species alpina of the genus Mortierella. Foods including the arachidonic acid-containing edible oil. Formula for premature infants, formula for infants, foods for infants, and foods for pregnant women and nursing mothers, including the arachidonic acid-containing edible oil.

  本发明提供了含有花生四烯酸的食用油，这种食用油是从属于莫氏菌属莫氏菌亚属并能产生花生四烯酸的微生物中获得的。这种油含有少量的不皂化物，尤其是含有尽可能少的具有环丙烷结构的甾醇，这些甾醇尚未被认定为食品成分，适用于生产食品，尤其是婴儿配方食品。 源自微生物的含花生四烯酸食用油，其不皂化物含量不超过 0.8%（按重量计），最好不超过 0.6%（按重量计），花生四烯酸含量不超过 20%（按重量计）。此外，这些食用油还含有不超过 0.3%（按重量计），最好不超过 0.15%（按重量计）的 24,25-亚甲基胆甾-5-烯-3β-醇。这些微生物属于莫氏菌属的莫氏菌亚属，能够产生花生四烯酸。这些微生物属于莫氏菌属的 alpina 种。含花生四烯酸食用油的食品。早产儿配方奶粉、婴儿配方奶粉、婴儿食品以及孕妇和哺乳期妇女食品，包括含花生四烯酸的食用油。
• EP0956774A4
  申请人：——

  公开号：EP0956774A4

  公开（公告）日：2000-03-01