sitostanyl oleate | 108515-19-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: sitostanyl oleate
• 英文别名: sitostanyl-18:1；β-Sitostanol Oleate；[(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] (Z)-octadec-9-enoate
• CAS: 108515-19-1
• 化学式: C₄₇H₈₄O₂
• 分子量: 681.183
• InChiKey: OKCXVZHLTRBBOQ-CCTBPIBKSA-N

物化性质

• 沸点：
  687.3±34.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  18.2
• 重原子数：
  49
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  油酸甲酯 、 豆甾烷醇 在 Novozym 435 作用下， 80.0 ℃ 、4.0 kPa 条件下， 反应 48.0h， 生成 sitostanyl oleate
  参考文献：
  名称：

  Steryl and Stanyl Esters of Fatty Acids by Solvent-Free Esterification and Transesterification in Vacuo Using Lipases from Rhizomucor miehei, Candida antarctica, and Carica papaya

  摘要：

  Sitostanol has been converted in high to near-quantitative extent to the corresponding long-chain acyl esters via esterification with oleic acid or transesterification with methyl oleate or trioleoylglycerol using immobilized lipases from Rhizomucor miehei (Lipozyme IM) and Candida antarctica (lipase B, Novozym 435) as biocatalysts in vacuo (20-40 mbar) at 80 degreesC, whereas the conversion was markedly lower at 60 and 40 degreesC. Corresponding conversions observed with papaya (Carica papaya) latex lipase were generally lower. High conversion rates, observed in transesterification of sitostanol with methyl oleate at 80 degreesC using Lipozyme IM were retained even after 10 repeated uses of the biocatalyst. Saturated sterols such as sitostanol and 5 alpha -cholestan-3 beta -ol were the preferred substrates as compared to Delta (5)-unsaturated cholesterol in transesterification reactions with methyl oleate using Lipozyme IM. Transesterification of cholesterol with dimethyl 1,8-octanedioate using Lipozyme IM in vacuo yielded methylcholesteryl 1,8-octanedioate (75%) and dicholesteryl 1,8-octanedioate (5%). However, transesterification. of cholesterol with diethyl carbonate and that of oleyl alcohol with ethylcholesteryl carbonate, both catalyzed by Lipozyme IM, gave ethylcholesteryl carbonate and oleylcholesteryl carbonate, respectively, in low yield (20%). Moreover, cholesterol was transesterified with ethyl dihydrocinnamate using Lipozyme IM to give cholesteryl dihydro cinnamate in moderate yield (56%), whereas the corresponding reaction of lanosterol gave lanosteryl oleate in low yield (14%).

  DOI：

  10.1021/jf0107407

文献信息

• Preparation of sterol and stanol-esters
  申请人：McNeil-PPC, Inc.

  公开号：US05892068A1

  公开（公告）日：1999-04-06

  The present invention provides a method for the direct esterification of stanols and sterols with fatty acids to form stanol/sterol-esters. The method provides a synthetic route that is amenable to large scale production of the esters in high yields. A preferred embodiment employs a food grade process free of organic solvents or mineral acids.

  本发明提供了一种直接酯化甾醇和甾醇酯与脂肪酸形成甾醇/甾醇酯的方法。该方法提供了一种适用于高产量酯类合成的合成路线。首选实施方式采用食品级过程，不含有机溶剂或矿物酸。
• Preparation of sterol and stanol esters
  申请人：McNEIL-PPC, INC.

  公开号：EP0982315A2

  公开（公告）日：2000-03-01

  The present invention provides a method for the direct esterification of stanols and sterols with fatty acids to form stanol/sterol-esters. The method provides a synthetic route that is amenable to large scale production of the esters in high yields. A preferred embodiment employs a food grade process free of organic solvents or mineral acids.

  本发明提供了一种将甾醇和固醇与脂肪酸直接酯化形成甾醇/固醇酯的方法。该方法提供了一种可大规模高产率生产酯类的合成途径。一个优选的实施方案采用了不含有机溶剂或矿物酸的食品级工艺。
• [EN] STEROLS, ESTERS WITH FATTY ACIDS AND GLUCOSIDES OF SUCH STEROLS; A METHOD OF PREPARATION THEREOF; SPONTANEOUSLY DISPERSABLE AGENTS CONTAINING THESE COMPOUNDS; AND THE USE OF SUCH AGENTS TO TREAT TUMOURS
  申请人：MARIGEN S.A.

  公开号：WO1991001139A1

  公开（公告）日：1991-02-07

  (DE) Es werden antitumorale Sterole, deren Fettsäureester und Glucoside, Verfahren zu ihrer Herstellung, spontan dispergierbare Mittel mit diesen Sterolen, deren Fettsäureester und Glucoside, und ihre Verwendung zur Behandlung von Tumoren beschrieben.(EN) Described are sterols, their esters with fatty acids and their glucosides, a method of preparation thereof, spontaneously dispersable agents containing these sterols, their esters with fatty acids or their glucosides, and the use of such agents in the treatment of tumours.(FR) On décrit des stérols antitumoraux, leurs esters d'acides gras et leur glucosides, le procédé pour leur fabrication, les agents spontanément dispersibles avec ces stérols, leurs esters d'acides gras et leur glucosides, ainsi que leur utilisation pour le traitement des tumeurs.

  (中文)描述了具有脂肪酸酯和糖苷的抗肿瘤类固醇及其制备方法，具有脂肪酸酯或其糖苷的自溶药物及其制备方法以及用于肿瘤治疗的这些药物。
• US6184397
  申请人：——

  公开号：——

  公开（公告）日：——
• STEROLE, DEREN FETTSÄUREESTER UND GLUCOSIDE; VERFAHREN ZU IHRER HERSTELLUNG; SPONTAN DISPERGIERBARE MITTEL MIT DIESEN VERBINDUNGEN, SOWIE IHRE VERWENDUNG ZUR BEHANDLUNG VON TUMOREN
  申请人：MARIGEN S.A.

  公开号：EP0436682B1

  公开（公告）日：1994-01-19