myristoylpalmitoyl-lutein

• 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: myristoylpalmitoyl-lutein
• 英文别名: all-trans-lutein 3'-O-palmitate-3-O-myristate；(3R,3'R,6'R)-lutein 3-myristate-3'-palmitate；[(1R,4R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-[(4R)-2,6,6-trimethyl-4-tetradecanoyloxycyclohexen-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-2-en-1-yl] hexadecanoate
• 化学式: C₇₀H₁₁₂O₄
• 分子量: 1017.66
• InChiKey: HQJUBCKVYCXDJM-HIEIUOFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.7
• 重原子数：
  74
• 可旋转键数：
  40
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙醇 、 all-trans-lutein 3'-O-myristate-3-O-palmitate 、 zeaxanthin myristate palmitate 、 酸浆果红素 、 堆心菊素 、 zeaxanthin dimyristate 、 (3R,3'R,6'R)-lutein dimyristate 、 myristoylpalmitoyl-lutein 在 盐酸 、 氢氧化钾 作用下， 以 正己烷 、 水 、 甲醇 为溶剂， 反应 21.0h， 生成 (3R,3'R,6'R)-lutein 3'-propyl ether 、 玉米黄质
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF ALPHA- AND BETA-CRYPTOXANTHIN
  [FR] PROCESSUS DE PREPARATION D'ALPHA ET DE BETA-CRYPTOXANTHINE

  摘要：

  本发明涉及一种将叶黄素和/或叶黄素酯转化为β-隐子黄质和α-隐子黄质的过程，适合作为膳食补充剂供人类消费，采用安全和环保的试剂。在第一合成步骤中，利用商业上可获得的叶黄素和/或叶黄素酯在少量酸的存在下转化为叶黄素的脱水产物混合物（脱水叶黄素）。然后，利用过渡元素群VIII在各种有机溶剂中，在氢气大气压下进行异质催化加氢，将所得的脱水叶黄素转化为β-隐子黄质（主要产物）和α-隐子黄质（次要产物）。本发明的一个新特点是在保持这些类胡萝卜素高度共轭多烯链完整的情况下，对脱水叶黄素进行区域选择性加氢。

  公开号：

  WO2005044769A1
• 作为产物：
  描述：

  叶黄素 、 肉豆蔻酸 、 棕榈酸 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 all-trans-lutein 3-O-palmitate 、 all-trans-lutein 3'-O-myristate-3-O-palmitate 、 all-trans-lutein 3-O-myristate 、 myristoylpalmitoyl-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

• [EN] PROCESS FOR THE PREPARATION OF ALPHA- AND BETA-CRYPTOXANTHIN<br/>[FR] PROCESSUS DE PREPARATION D'ALPHA ET DE BETA-CRYPTOXANTHINE
  申请人：UNIV MARYLAND

  公开号：WO2005044769A1

  公开（公告）日：2005-05-19

  The present invention relates to a process for converting lutein and/or lutein esters to β-cryptoxanthin and α-cryptoxanthin, suitable for human consumption as dietary supplements, by employing safe and environmentally friendly reagents. In the first synthetic step, commercially available lutein and/or lutein esters are transformed into a mixture of dehydration products of lutein (anhydroluteins) in the presence of a catalytic amount of an acid. The resulting anhydroluteins are then converted to β-cryptoxanthin (major product) and α-cryptoxanthin (minor product) by heterogeneous catalytic hydrogenation employing transition elements of group VIII in a variety of organic solvents under atmospheric pressure of hydrogen. A novel feature of this invention is the regioselective hydrogenation of anhydroluteins while the highly conjugated polyene chain of these carotenoids remains intact.

  本发明涉及一种将叶黄素和/或叶黄素酯转化为β-隐子黄质和α-隐子黄质的过程，适合作为膳食补充剂供人类消费，采用安全和环保的试剂。在第一合成步骤中，利用商业上可获得的叶黄素和/或叶黄素酯在少量酸的存在下转化为叶黄素的脱水产物混合物（脱水叶黄素）。然后，利用过渡元素群VIII在各种有机溶剂中，在氢气大气压下进行异质催化加氢，将所得的脱水叶黄素转化为β-隐子黄质（主要产物）和α-隐子黄质（次要产物）。本发明的一个新特点是在保持这些类胡萝卜素高度共轭多烯链完整的情况下，对脱水叶黄素进行区域选择性加氢。
• 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.