2,6-cyclolycopene-1,5-diol A

• 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: 2,6-cyclolycopene-1,5-diol A
• 英文别名: (1R,2S,3R)-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaenyl]-3-(2-hydroxypropan-2-yl)-1-methylcyclopentan-1-ol
• 化学式: C₄₀H₅₈O₂
• 分子量: 570.899
• InChiKey: VDFVQEJGOSCZNZ-YKWPPURLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  番茄红素 在 硫酸 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 20.0h， 以13 mg的产率得到1,5-epoxyiridanyl-lycopene
  参考文献：
  名称：

  1,5-Dihydroxyiridanyl-lycopene in Tomato Puree

  摘要：

  1,5-二羟基紫菀烯-番茄红素从番茄泥中分离出来。番茄红素与过氧化氢的氧化反应还生成了1,5-二羟基紫菀烯-番茄红素，此外还有番茄红素-1,2-环氧化物和1,5-环氧紫菀烯-番茄红素。提出了一种该二羟基化合物的反应路径。

  DOI：

  10.1271/bbb.61.549

文献信息

• Partial Synthesis and Structural Elucidation of the Oxidative Metabolites of Lycopene Identified in Tomato Paste, Tomato Juice, and Human Serum
  作者：Frederick Khachik、Andrea Steck、Urs A. Niggli、Hanspeter Pfander

  DOI：10.1021/jf980322a

  日期：1998.12.1

  Two oxidative metabolites of lycopene in tomato paste, tomato juice, and human serum have been prepared by partial synthesis from oxidation of lycopene with m-chloroperbenzoic acid (MCPBA) followed by acidic hydrolysis. Extensive H-1 and C-13 NMR spectroscopy studies of the purified products of these reactions have confirmed that the major oxidation products of lycopene (I) are lycopene 1,2-epoxide (II) and lycopene 5,6-epoxide (III) (tentative assignment). Several diepoxides of lycopene, namely, lycopene 1,2;5,6-diepoxide (IV), lycopene 1,2;5',6'-diepoxide (V), lycopene 5,6;5',6'-diepoxide (VI), and lycopene 1,2;1',2'-diepoxide (VII), which were formed as minor products, were tentatively identified. Whereas lycopene 1,2-epoxide was found to be fairly stable, lycopene 5,6-epoxide underwent cyclization to form a mixture of diastereomeric epoxides A (VIII, major) and B (IX, minor). The trivial names of 2,6-cyclolycopene-l,5-epoxides A (VIII) and B (IX) have been assigned to these compounds with a novel five-membered ring end-group. Hydrolysis of VIII and IX in dilute solutions of sulfuric acid gave an epimeric mixture of 2,6-cyclolycopene-1,5-diols A (X, major) and B (XI, minor). During chromatographic purification on n-silica gel, II and III partially cyclized to 1,16-didehydro-2,6-cyclolycopen-5-ol (XII) and epoxides VIII and IX partially converted to their respective diols, X and XI. In the course of isolation and purification, the oxidation products of lycopene with MCPBA were found to be extremely sensitive to chromatography on n-silica gel and underwent rearrangement to a number of cyclic epoxides and diols. Upon acid treatment of the mixture of lycopene epoxides, a bicyclic diepoxide of lycopene was formed, which was identified as lycopene 1,6;2,5-diepoxide (XIII). Diols X and XI have also been detected at low concentrations in tomato paste, tomato juice, and human serum. All synthetic compounds have been fully characterized by NMR, UV-vis, and MS.
• Proposed Mechanisms for the Formation of Synthetic and Naturally Occurring Metabolites of Lycopene in Tomato Products and Human Serum
  作者：Frederick Khachik、Hanspeter Pfander、Bruno Traber

  DOI：10.1021/jf9803233

  日期：1998.12.1

  Oxidation of lycopene (I) with m-chloroperbenzoic acid has been previously shown to yield lycopene 1,2-epoxide (II) and lycopene 5,6-epoxide (III) as major products and lycopene 1,2;5,6-diepoxide (IV), lycopene 1,2;5',6'-diepoxide (V), lycopene 5,6;5',6'-diepoxide (VI), and lycopene 1,2;1',2'-diepoxide (VII) as minor products. Similarly, the acid-catalyzed rearrangement products of these epoxides have been identified as 2,6-cyclolycopene-1,5-epoxide A (VIII) and B (IX), 2,6-cyclolycopene-1,5-diol A (X) and B (XI), 1,16-didehydro-2,6-cyclolycopen-5-ol (XII), and lycopene 1,6;2,5-diepoxide (MII). On the basis of the stereochemistry of the observed products (VIII-M), here, it is proposed that the acid-catalyzed rearrangement of lycopene 5,6-epoxide may be proceeded by S(N)1- and/or S(N)2-type mechanisms, whereas an SN2-type mechanism is preferred for the rearrangement of lycopene 1,2-epoxide. Details of the acid-catalyzed rearrangement of lycopene epoxides by S(N)1; and S(N)2-type reactions are presented. Although II and VII-XI are present in tomato products at low concentrations, only X and XI are found in human serum. Possible pathways leading to the formation of the synthetic compounds and the oxidative metabolites of lycopene in tomato products and human serum are discussed.
• 1,5-Dihydroxyiridanyl-lycopene in Tomato Puree
  作者：Tadashi Yokota、Hideo Etoh、Nobuo Ukai、Syunji Oshima、Hideki Sakamoto、Yukio Ishiguro

  DOI：10.1271/bbb.61.549

  日期：1997.1

  1,5-Dihydroxyiridanyl-lycopene was isolated from tomato puree. The oxidation of lycopene by hydrogen peroxide also afforded 1,5-dihydroxyiridanyl-lycopene, in addition to lycopene-1,2-epoxide and 1,5-epoxyiridanyl-lycopene. A reaction pathway for this dihydroxy compound is proposed.

  1,5-二羟基紫菀烯-番茄红素从番茄泥中分离出来。番茄红素与过氧化氢的氧化反应还生成了1,5-二羟基紫菀烯-番茄红素，此外还有番茄红素-1,2-环氧化物和1,5-环氧紫菀烯-番茄红素。提出了一种该二羟基化合物的反应路径。