9-顺式-番茄红素 | 64727-64-6

• 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
• 中文名称: 9-顺式-番茄红素
• 英文名称: (9Z)-lycopene
• 英文别名: 9-cis-lycopene；(6E,8E,10E,12E,14E,16E,18E,20E,22Z,24E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
• CAS: 64727-64-6
• 化学式: C₄₀H₅₆
• 分子量: 536.885
• InChiKey: OAIJSZIZWZSQBC-CBEQXLMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-顺式-番茄红素 以 乙酸乙酯 为溶剂， 生成 番茄红素
  参考文献：
  名称：

  Stable and bioavailable compositions of isomers of carotenoids for skin and hair

  摘要：

  本发明涉及一种通过在溶剂中长时间加热番茄、番茄部分、其衍生物或番茄提取物来制备富含顺式番茄红素（z-异构体）的稳定组合物的方法。

  公开号：

  US20080038391A1
• 作为产物：
  描述：

  番茄红素 生成 9-顺式-番茄红素
  参考文献：
  名称：

  Effects of various factors of ultrasonic treatment on the extraction yield of all-trans-lycopene from red grapefruit (Citrus paradise Macf.)

  摘要：

  The effects of various factors, including the extraction time, temperature, solvent/material ratio, the ultrasonic intensity and duty cycle of ultrasonic irradiation on the extraction yield of all-trans-lycopene from red grapefruit by ultrasound-assisted extraction (UAE) were investigated. In comparison with conventional solvent extraction (CSE), UAE showed a pronounced greater extraction yield and reduced extraction time effectively with a peak value at 30 min. The extraction yield was significantly influenced by temperature and the optimum condition was 30 degrees C. The extraction yield increased with increasing of solvent/material ratio until equilibrium was arrived at the optimal ratio of 3:1 (mL/g). The extraction yield increased first and then decreased with an increase in ultrasonic intensity. The extraction yield of UAE increased with the increase of duty cycle, whereas pulsed ultrasound with proper intervals was more efficient than continuous ultrasonication. The degradation via isomerisation of all-trans-lycopene under ultrasonic treatment was also observed with the formation of 9,13'-di-cis-, 9,13-di-cis-, 15-cis-, 13-cis- and 9-cis-lycopene isomers which were tentatively identified by HPLC-PAD. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2013.01.006

文献信息

• Expeditious and Practical Synthesis of Lycopene
  作者：Eunho Choi、Jung Eun Yeo、Sangho Koo

  DOI：10.1002/adsc.200700484

  日期：2008.2.22

  Our lycopene synthesis highlights the expeditious assembly of the carbon skeleton by the use of a readily available ten-carbon unit, geraniol, rather than the original natural five-carbon building block, isopentenyl pyrophosphate. Furthermore, four oxidation steps by the enzyme desaturases to produce the conjugated carbon-carbon double bonds of lycopene are merged into one-pot double elimination reactions

  我们的番茄红素合成突出显示了碳骨架的快速组装，方法是使用容易获得的十碳单元香叶醇，而不是原始的天然五碳结构单元异戊烯基焦磷酸酯。此外，在我们的合成中，通过酶去饱和酶进行的四个氧化步骤以生成番茄红素的共轭碳-碳双键被合并为一锅双消除反应。这些通过七步顺序完成了从香叶醇高效合成全-（E）-番茄红素的过程，总收率为51％。
• Plant Carotene Cis-Trans Isomerase CRTISO
  作者：Qiuju Yu、Sandro Ghisla、Joseph Hirschberg、Varda Mann、Peter Beyer

  DOI：10.1074/jbc.m110.208017

  日期：2011.3

  regional specificity and the kinetics of the isomerization reaction were investigated in vitro using purified enzyme and biphasic liposome-based systems carrying specific cis-configured lycopene species as substrates. The reaction proceeded from cis to trans, recognizing half-sides of the symmetrical prolycopene and was accompanied by one trans-to-cis isomerization step specific for the C(5)-C(6) double

  胡萝卜素顺反异构酶 CRTISO 是在蓝藻中进化并在植物中普遍存在的胡萝卜素去饱和途径的组成部分，其中形成了称为原番茄红素的四顺式番茄红素种类。CRTISO 是细菌胡萝卜素去饱和酶 CRTI 的进化后代，催化顺式到反式异构化反应，导致全反式番茄红素，这是随后番茄红素环化形成全反式-α/β-胡萝卜素的底物。CRTISO 和 CRTI 在 N 末端共享一个二核苷酸结合基序。在这里，我们报告该站点被 CRTISO 中的 FAD 占用。这种辅因子的还原形式催化不涉及净氧化还原变化的反应。使用 C(1)-和 C(5)-deaza-FAD 获得的结果表明与 II 型异戊烯基二磷酸：二甲基烯丙基二磷酸异构酶 (IDI-2) 的机制相似。CRTISO，与番茄红素环化酶 CRTY 和 IDI-2 一起，因此代表了类异戊二烯代谢中属于非氧化还原酶类的第三种酶，其活性取决于还原的黄素。使用纯化的酶和基于双相脂质
• [EN] COMPOSITIONS CONTAINING CIS-ISOMERS OF A CAROTENOID COMPOUND AND PROCESS<br/>[FR] COMPOSITIONS CONTENANT DES ISOMERES CIS D'UN COMPOSE CAROTENOIDE
  申请人：NESTEC SA

  公开号：WO2005075575A1

  公开（公告）日：2005-08-18

  The present invention relates to a primary composition that includes at least one carotenoid-containing extract, concentrate or oleoresin enriched in cis-isomers of the carotenoid compound, and process of forming the same. It also relates to an oral composition that contains the primary composition in a foodstuff, in a food supplement, in a cosmetic preparation or in a pharmaceutical preparation.

  本发明涉及一种主要组成物，其中包括至少一种富含类胡萝卜素化合物顺式异构体的提取物、浓缩物或油脂浸出物，以及形成该组成物的过程。它还涉及一种口服组成物，其中包含该主要组成物在食品、食品补充剂、化妆品准备或药物准备中。
• Highly efficient trans–cis isomerization of lycopene catalyzed by iodine-doped TiO₂nanoparticles
  作者：Qingrui Sun、Cheng Yang、Jing Li、Waleed Aboshora、Husnain Raza、Lianfu Zhang

  DOI：10.1039/c5ra24074c

  日期：——

  Highly efficienttrans–cisisomerization of lycopene was achieved in the presence of a novel iodine-doped titanium dioxide (I-TiO₂) catalyst.

  在一种新型碘掺杂的二氧化钛（I-TiO₂）催化剂的存在下，番茄红素的trans–cis异构化反应实现了高效转化。
• A Highly Efficient Chain-Extension Process in the Systematic Syntheses of Carotenoid Natural Products This work was supported by the RRC program of MOST and KOSEF.
  作者：Minkoo Ji、Hojin Choi、Minsoo Park、Minyong Kee、Young Cheol Jeong、Sangho Koo

  DOI：10.1002/1521-3773(20011001)40:19<3627::aid-anie3627>3.0.co;2-e

  日期：2001.10.1