all-trans-lutein 3-O-stearate

• 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: all-trans-lutein 3-O-stearate
• 英文别名: (3R,3'R,6'R)-β,ε-carotene-3,3'-diol 3-stearate；lutein-3-stearate；[(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-yl] octadecanoate
• 化学式: C₅₈H₉₀O₃
• 分子量: 835.351
• InChiKey: AGXQJWJFLPTKLG-WPUWGNEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20
• 重原子数：
  61
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  叶黄素 、 硬脂酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (3R,3'R,6'R)-β,ε-carotene-3,3'-diol 3'-stearate 、 all-trans-lutein 3-O-stearate 、 distearoyl-lutein
  参考文献：
  名称：

  Identification of Synthetic Regioisomeric Lutein Esters and Their Quantification in a Commercial Lutein Supplement

  摘要：

  Synthetic mixtures of 24 mono- and diesters of the asymmetric hydroxylated carotenoid lutein with lauric, myristic, palmitic, and stearic acids were analyzed by liquid chromatography-ultraviolet/visible spectroscopy (LC-UV-vis) and characterized by LC-mass spectrometry (MS) and nuclear magnetic resonance spectroscopy (NMR). These compounds were then used for identifying the composition of a commercial lutein supplement. This is the first report of chromatographic separation of mixed fatty acid lutein diesters. Preferential MS loss of fatty acids or water occurred initially at the 3'-hydroxy position in the epsilon-ionone ring and subsequently at the 3-hydroxy position in the beta-ionone ring. This selective fragmentation leads to facile assignment of the specific fatty acids to the appropriate regioisomeric ionone ring. A commercial lutein supplement contained low levels of two pairs of regioisomeric monoesters and nearly equal levels of three homogeneous diesters and five pairs of mixed diesters. Palmitic acid was the predominant fatty acid, with lower amounts of myristic, stearic, and lauric acids.

  DOI：

  10.1021/jf070357n

文献信息

• Highly regioselective enzymatic synthesis of lutein-3-monoesters
  作者：Jesus Armando Lujan-Montelongo、Humberto L. Mendoza-Figueroa、Carolina Silva-Cuevas、Anahí C. Sánchez-Chávez、Luis A. Polindara-García、Saray Oliveros-Cruz、Mario D. Torres-Cardona

  DOI：10.1016/j.tetlet.2018.10.006

  日期：2018.11

  approach for the regioselective synthesis of 3-O-acyl monoester lutein derivatives (β-ionone selectivity, up to 17:1), using a lipase (Novozyme 435, immobilized CALB), and vinyl carboxylates (vinyl propionate and stearate) as acyl donors. The regioselectivity arises from the highly stereoselective feature of CALB. This methodology addresses the long-standing problem of regioselective monoesterification

  叶黄素是一种富含脂肪酸的酯衍生物的形式，是一种富含万寿菊花的叶黄素类胡萝卜素（Tagetes spp。）。本文中，我们介绍了使用脂肪酶（Novozyme 435，固定的CALB）和羧酸乙烯酯（丙酸乙烯酯和丙酸乙烯酯）区域选择性合成3- O-酰基单酯叶黄素衍生物（β-紫罗兰酮选择性，高达17：1）的酶促方法。硬脂酸酯）作为酰基供体。区域选择性源自CALB的高度立体选择性。这种方法论解决了叶黄素区域选择性单酯化的长期存在的问题，这可能使与其他单酯叶黄素类胡萝卜素的新型半合成途径成为可能。
• Identification of Synthetic Regioisomeric Lutein Esters and Their Quantification in a Commercial Lutein Supplement
  作者：J. Christopher Young、El-Sayed M. Abdel-Aal、Iwona Rabalski、Barbara A. Blackwell

  DOI：10.1021/jf070357n

  日期：2007.6.1

  Synthetic mixtures of 24 mono- and diesters of the asymmetric hydroxylated carotenoid lutein with lauric, myristic, palmitic, and stearic acids were analyzed by liquid chromatography-ultraviolet/visible spectroscopy (LC-UV-vis) and characterized by LC-mass spectrometry (MS) and nuclear magnetic resonance spectroscopy (NMR). These compounds were then used for identifying the composition of a commercial lutein supplement. This is the first report of chromatographic separation of mixed fatty acid lutein diesters. Preferential MS loss of fatty acids or water occurred initially at the 3'-hydroxy position in the epsilon-ionone ring and subsequently at the 3-hydroxy position in the beta-ionone ring. This selective fragmentation leads to facile assignment of the specific fatty acids to the appropriate regioisomeric ionone ring. A commercial lutein supplement contained low levels of two pairs of regioisomeric monoesters and nearly equal levels of three homogeneous diesters and five pairs of mixed diesters. Palmitic acid was the predominant fatty acid, with lower amounts of myristic, stearic, and lauric acids.