β-sitosterol linoleic acid ester

• 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: β-sitosterol linoleic acid ester
• 英文别名: β-sitosterol linoleate；β-sitosteryl linoleate；β-sitosteryl-linoleate；18:2 Sitosteryl ester；[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (9Z,12Z)-octadeca-9,12-dienoate
• 化学式: C₄₇H₈₀O₂
• 分子量: 677.151
• InChiKey: TXNOTJVZNDGTOR-DCBLFMKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  49
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (Z,Z)-9,12-十八烷二烯酸二聚物 、 植物甾醇 在 pseudomonas lipase 作用下， 以 水 为溶剂， 反应 24.0h， 以91.2%的产率得到β-sitosterol linoleic acid ester
  参考文献：
  名称：

  酶法合成多不饱和脂肪酸的甾醇酯

  摘要：

  AbstractSteryl esters of long‐chain fatty acids have water‐holding properties, and polyunsaturated fatty acids (PUFA) have various physiological functions. Because steryl ester of PUFA can be expected to have both features, we attempted to synthesize steryl esters of PUFA by enzymatic methods. Among lipases used, Pseudomonas lipase was the most effective for the synthesis of cholesteryl docosahexaenoate. When a mixture of cholesterol/docosahexaenoic acid (3:1, mol/mol), 30% water, and 3000 units/g of lipase was stirred at 40°C for 24 h, the esterification extent attained 89.5%. Under the same reaction conditions, cholesterol, cholestanol, and sitosterol were also esterified efficiently with docosahexaenoic, eicosapentaenoic, arachidonic, and γ‐linolenic acids.

  DOI：

  10.1007/s11746-999-0164-6

文献信息

• [EN] COATINGS FOR IMPLANTABLE MEDICAL DEVICES COMPRISING CHOLESTEROL<br/>[FR] REVÊTEMENTS POUR DISPOSITIFS MÉDICAUX IMPLANTABLES COMPRENANT DU CHOLESTÉROL
  申请人：MIV THERAPEUTICS INC

  公开号：WO2008077247A1

  公开（公告）日：2008-07-03

  [EN] Disclosed herein are solid film coatings for implantable medical devices comprising a solid film covering at least a portion of the device. The solid film comprises: at least one lipid selected from cholesterol and cholesterol derivatives, at least one additional solid lipid other than cholesterol and cholesterol derivatives, and a therapeutically effective amount of at least one pharmaceutically active agent. Also disclosed herein are methods of preparing film coatings and methods of treating diseases with the implantable devices.
  [FR] La présente invention concerne des revêtements en pellicule solide pour dispositifs médicaux implantables comprenant une pellicule solide recouvrant au moins une partie du dispositif. La pellicule solide comprend : au moins un lipide choisi parmi le cholestérol et des dérivés du cholestérol; au moins un lipide solide supplémentaire autre que le cholestérol et les dérivés du cholestérol; et une quantité thérapeutiquement efficace d'au moins un agent pharmaceutiquement actif. Cette invention concerne également des procédés de préparation de revêtements pelliculaires et des méthodes de traitement de maladies utilisant ces dispositifs implantables.
• Enzymatic synthesis of steryl esters of polyunsaturated fatty acids
  作者：Yuji Shimada、Yoshinori Hirota、Takashi Baba、Akio Sugihara、Shigeru Moriyama、Yoshio Tominaga、Tadamasa Terai

  DOI：10.1007/s11746-999-0164-6

  日期：1999.6

  AbstractSteryl esters of long‐chain fatty acids have water‐holding properties, and polyunsaturated fatty acids (PUFA) have various physiological functions. Because steryl ester of PUFA can be expected to have both features, we attempted to synthesize steryl esters of PUFA by enzymatic methods. Among lipases used, Pseudomonas lipase was the most effective for the synthesis of cholesteryl docosahexaenoate. When a mixture of cholesterol/docosahexaenoic acid (3:1, mol/mol), 30% water, and 3000 units/g of lipase was stirred at 40°C for 24 h, the esterification extent attained 89.5%. Under the same reaction conditions, cholesterol, cholestanol, and sitosterol were also esterified efficiently with docosahexaenoic, eicosapentaenoic, arachidonic, and γ‐linolenic acids.