视黄醇油酸酯 | 631-88-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 视黄醇油酸酯
• 英文名称: retinyl stearate
• 英文别名: retinyl oleate；O-Oleoyl-all-trans-retinol；9-(Octadecen-(9c)-oyloxy)-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraen-(1.3t.5t.7t)；O-Oleoyl-[7t.9t.11t.13t]retinol；Retinol oleate；[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] (Z)-octadec-9-enoate
• CAS: 631-88-9
• 化学式: C₃₈H₆₂O₂
• 分子量: 550.909
• InChiKey: FXKDHZXYYBPLHI-TUTABMRPSA-N

物化性质

• 沸点：
  631.6±34.0 °C(Predicted)
• 密度：
  0.923±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）
• LogP：
  14.932 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  13.7
• 重原子数：
  40
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 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 、 维生素 A 醋酸酯 在 novozyme 435 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 视黄醇油酸酯
  参考文献：
  名称：

  An LC/MS/MS method for stable isotope dilution studies of β-carotene bioavailability, bioconversion, and vitamin A status in humans

  摘要：

  Isotope dilution is currently the most accurate technique in humans to determine vitamin A status and bioavailability/bioconversion of provitamin A carotenoids such as beta-carotene. However, limits of MS detection, coupled with extensive isolation procedures, have hindered investigations of physiologically-relevant doses of stable isotopes in large intervention trials. Here, a sensitive liquid chromatography-tandem mass spectrometry (LC/MS/MS) analytical method was developed to study the plasma response from coadministered oral doses of 2 mg [C-13(10)]beta-carotene and 1 mg [C-13(10)]retinyl acetate in human subjects over a 2 week period. A reverse phase C-18 column and binary mobile phase solvent system separated beta-carotene, retinol, retinyl acetate, retinyl linoleate, retinyl palmitate/retinyl oleate, and retinyl stearate within a 7 min run time. Selected reaction monitoring of analytes was performed under atmospheric pressure chemical ionization in positive mode at m/z 537 -> 321 and m/z 269 -> 93 for respective [C-12]beta-carotene and [C-12]retinoids; m/z 547 -> 330 and m/z 274 -> 98 for [C-13(10)]beta-carotene and [C-13(5)] cleavage products; and m/z 279 -> 100 for metabolites of [C-13(10)]retinyl acetate. A single one-phase solvent extraction, with no saponification or purification steps, left retinyl esters intact for determination of intestinally-derived retinol in chylomicrons versus retinol from the liver bound to retinol binding protein. Coadministration of [C-13(10)]retinyl acetate with [C-13(10)]beta-carotene not only acts as a reference dose for inter-individual variations in absorption and chylomicron clearance rates, but also allows for simultaneous determination of an individual's vitamin A status.

  DOI：

  10.1194/jlr.d040204

文献信息

• Chroman derivatives as lipoxygenase inhibitors
  申请人：Zhang Wei

  公开号：US20060193797A1

  公开（公告）日：2006-08-31

  The present invention is concerned with certain novel derivatives of Formula I: wherein X and R 1 to R 10 are as described in the specification, and where either R 5 is OH, —NR d OR a or —NR d —NR b R c , or R 7 is —NR d OR a or —NR d —NR b R c , or C═R 7 R 8 is C═NOR a or C═N—NR b R c , which may be useful in the manufacture of pharmaceutical compositions for treating disorders mediated by lipoxygenases. They may also be useful in the manufacture of skin care and/or pharmaceutical compositions for the treatment of lipoxygenase mediated disorders.

  本发明涉及Formula I的某些新颖衍生物：其中X和R1至R10如规范中所述，其中R5为OH，—NRdORa或—NRd—NRbRc之一，或R7为—NRdORa或—NRd—NRbRc之一，或C═R7R8为C═NORa或C═N—NRbRc，这些可能在制造用于治疗通过脂氧合酶介导的疾病的药物组合物中有用。它们还可能在制造用于治疗脂氧合酶介导疾病的皮肤护理和/或药用组合物中有用。
• Preparation of retinyl esters
  申请人：Eastman Chemical Company

  公开号：US07566795B2

  公开（公告）日：2009-07-28

  Long-chain esters of retinol are prepared via a chemoenzymatic process from short-chain retinyl esters and an appropriate long-chain acid or ester in the presence of an enzyme. Use of various additives enhance the yield of the desired ester and facilitated its purification.

  长链视黄醇酯是通过在酶的存在下，从短链视黄醇酯和适当的长链酸或酯经化酶过程制备而成的。使用各种添加剂可以增加所需酯的产量，并促进其纯化。
• Cosmetic composition
  申请人：UNILEVER PLC

  公开号：EP0512814A1

  公开（公告）日：1992-11-11

  Topical compositions for preventing or at least reducing the damaging effects of ultra-violet light on skin comprise 1-hydroxycholecalciferol and/or 1,25 dihydroxycholecalciferol in combination with a sunscreen material and preferably also retinol and/or a derivative thereof. The compositions may also be used for promoting repair of photodamaged skin.

  用于预防或至少减少紫外线对皮肤的损害的局部组合物包括1-羟基胆钙化醇和/或1,25-二羟基胆钙化醇，与防晒材料结合，最好还包括视黄醇和/或其衍生物。该组合物还可用于促进光损伤皮肤的修复。
• Method of producing retinyl esters
  申请人：Bosley Anthony John

  公开号：US20060183184A1

  公开（公告）日：2006-08-17

  A method of producing a retinyl ester compound comprising subjecting a composition comprising retinyl or a retinyl ester and a fat or oil of animal or vegetable origins to enzyme catalysed trans-esterification in solvent free conditions to produce a retinyl ester.

  一种制备视黄醇酯类化合物的方法，包括将含有视黄醇或视黄醇酯和动物或植物源脂肪或油的组合物，在无溶剂条件下通过酶催化的转酯化反应来制备视黄醇酯。
• METHOD OF PRODUCING RETINYL ESTERS
  申请人：BOSLEY John Anthony

  公开号：US20090124694A1

  公开（公告）日：2009-05-14

  A method of producing a retinyl ester compound comprising subjecting a composition comprising retinyl or a retinyl ester and a fat or oil of animal or vegetable origins to enzyme catalysed trans-esterification in solvent free conditions to produce a retinyl ester.

  一种制备视黄醇酯化合物的方法，包括将含有视黄醇或视黄醇酯和动物或植物油脂的组合物，在无溶剂条件下进行酶催化酯交换反应，以制得视黄醇酯。