(2E,4E,6E)-3,7,11-trimethyldodeca-2,4,6,10-tetraenoic acid | 29448-60-0

• 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: (2E,4E,6E)-3,7,11-trimethyldodeca-2,4,6,10-tetraenoic acid
• 英文别名: (2E,4E,6E)-4,5-Didehydrofarnesylsaeure；apo-11-lycopenoic acid；3,7,11-trimethyl-dodeca-2,4,6,10-tetraenoic acid；3,7,11-Trimethyl-dodeca-2,4,6,10-tetraensaeure；(2E,4E,6E)-3,7,11-trimethyl-2,4,6,10-dodecatetraenoic acid；3,7,11-trimethyl-2,4,6,10-dodecatetraenoic acid
• CAS: 29448-60-0；70143-08-7；70143-09-8；81680-53-7；81485-29-2
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: SDZKOOLLRITKEF-VVAFVYIFSA-N

物化性质

• 沸点：
  393.2±21.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E,6E)-3,7,11-trimethyldodeca-2,4,6,10-tetraenoic acid 在 Lindlar's catalyst 喹啉 、 氢氧化钾 、 sodium methylate 、 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 19.0h， 生成 (3R,15Z)-rubixanthin
  参考文献：
  名称：

  Das Carotinoidspektrum der Hagebutten von Rosa pomifera：Nachweis von（5 Z）-Neurosporin; 合成von（3 R，15 Z）-泛黄嘌呤†

  摘要：

  蔷薇果臀部的类胡萝卜素：（5 Z）-神经孢菌素的发现；（3 R，15 Z）-黄嘌呤的合成

  DOI：

  10.1002/hlca.19830660211
• 作为产物：
  描述：

  (E)-3,7-二甲基-2,6-辛二烯醛 在 氢氧化钾 、 potassium methanolate 、 三乙胺 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 0.3h， 生成 (2E,4E,6E)-3,7,11-trimethyldodeca-2,4,6,10-tetraenoic acid
  参考文献：
  名称：

  A survey of mono- or bis-decarboxylation of β-methyl polyethylenic-malonic acids

  摘要：

  Diverse experimental conditions, leading to mono- or bis-decarboxylation of beta-methyl polyethylenic-malonic acids, were examined. A clean and easy bis-decarboxylation was reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01022-0

文献信息

• Novel Intramolecular Cyclisations Involving Ketene Radical Intermediates as an Approach to the Synthesis of Polyquinanes
  作者：Nicole M. Harrington-Frost、Gerald Pattenden

  DOI：10.1055/s-1999-2980

  日期：1999.12

  Treatment of the polyene selenyl ester 1 with Bu3SnH-AIBN leads to a concise synthesis of the diquinane 6 via a novel cyclisation involving a ketenyl radical intermediate. By contrast under the same radical initiating conditions the selenyl esters 2 and 10 produced cyclopentenone products, viz 9 and 11, and the allene substituted selenyl ester 16 led to the unusual cyclooctadienone 18.

  用 Bu3SnH-AIBN 处理多烯硒酯 1，可通过涉及酮基中间体的新颖环化反应，简便地合成二喹啉 6。相比之下，在相同的自由基引发条件下，硒酯 2 和 10 产生了环戊烯酮产物，即 9 和 11，而烯取代的硒酯 16 则产生了不常见的环辛二烯酮 18。
• Method for preparing polyprenyl compounds
  申请人：NIKKEN CHEMICALS CO., LTD.

  公开号：US20040242690A1

  公开（公告）日：2004-12-02

  A method for preparing a polyprenyl compound wherein an aldehyde represented by the following general formula [I]: 1 [wherein n represents an integer of from 0 to 3] and a Wittig reagent represented by the following general formula [II]: 2 [wherein each of R 1 and R 2 represents a group consisting of hydrocarbon] are reacted in a medium as a mixture of water and an organic solvent in the presence of a base, and further in the presence of a crown ether. Said method achieves an excellent selectivity and a high yield.

  一种制备多异戊烯化合物的方法，其中以以下一般式【I】表示的醛：1【其中n表示0至3的整数】和以以下一般式【II】表示的威特格试剂：2【其中R1和R2各自表示由碳氢化合物组成的基团】在碱存在下，在水和有机溶剂的混合物中反应，并进一步在冠醚的存在下进行。该方法实现了优异的选择性和高收率。
• Antioxidant activity of (all-E)-lycopene and synthetic apo-lycopenoids in a chemical model of oxidative stress in the gastro-intestinal tract
  作者：Pascale Goupy、Eric Reynaud、Olivier Dangles、Catherine Caris-Veyrat

  DOI：10.1039/c1nj20437h

  日期：——

  Lycopene, the main pigment of tomato, is known to have protective effects on health. Its metabolites could also be involved in these effects. Potentially bioactive lycopene metabolites namely apo-10′-lycopenol, apo-10′-lycopenal, apo-14′-lycopenol, apo-14′-lycopenal, and apo-11-lycopenoids with alcohol, carboxylic acid, aldehyde and ethyl ester terminal groups were obtained by organic synthesis as (all-E) stereoisomers using HWE condensation reactions. The ability of (all-E)-lycopene and the synthesized apo-lycopenoids to inhibit lipid peroxidation was tested in a chemical model of postprandial oxidative stress in the gastric compartment. Oxidative stress was generated by metmyoglobin, the main form of dietary iron (from red meat), which is able to catalyse the peroxidation of linoleic acid under mildly acidic conditions. In this model, apo-6′-lycopenal and apo-8′-lycopenal were better inhibitors of lipid peroxidation than (all-E)-lycopene itself. For the apo-lycopenoids, a long unsaturated chain and a terminal carboxylic acid group both favour the antioxidant activity. The short-chain apo-lycopenoic acid, apo-14′-lycopenoic acid, was shown to behave like a hydrophilic antioxidant, i.e. by reducing hypervalent iron forms of metmyoglobin. Thus, besides the polyene chain length, the terminal group of the apo-lycopenoids is expected to deeply influence the lipophilic/hydrophilic balance of the molecule (and consequently its distribution between the aqueous and lipid phases) and its affinity for the heme cavity. It can thus be concluded that the polyene chain length and terminal group are two important parameters modulating the mechanism by which apo-lycopenoids express their antioxidant activity.

  众所周知，番茄的主要色素番茄红素具有保护健康的作用。番茄红素的代谢物也可能参与了这些作用。利用 HWE 缩合反应，通过有机合成获得了具有潜在生物活性的番茄红素代谢物，即具有醇、羧酸、醛和乙酯末端基团的 (all-E) 立体异构体 (apo-10′-lycopenol、apo-10′-lycopenal、apo-14′-lycopenol、apo-14′-lycopenal 和 apo-11-lycopenoids)。在胃区餐后氧化应激的化学模型中，测试了（全-E）-甘油三酯和合成的apo-lycopenoids抑制脂质过氧化的能力。氧化应激是由高铁血红蛋白产生的，高铁血红蛋白是食物中铁的主要形式（来自红肉），它能在弱酸性条件下催化亚油酸的过氧化反应。在该模型中，apo-6′-lycopenal 和 apo-8′-lycopenal 比 (all-E)-lycopene 本身更能抑制脂质过氧化。对于apo-lycopenoids来说，长的不饱和链和末端的羧酸基团都有利于其抗氧化活性。事实证明，短链的apo-lycopenoic acid（apo-14′-lycopenoic acid）具有亲水性抗氧化剂的作用，即减少高铁血红蛋白的高价铁形式。因此，除了多烯链的长度外，环甘氨酸的末端基团预计也会对分子的亲油/亲水平衡（从而影响其在水相和脂相之间的分布）及其对血红素腔的亲和力产生深远影响。因此可以得出结论，多烯链长度和末端基团是调节脂环素抗氧化活性机制的两个重要参数。
• Moroe et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 543
  作者：Moroe et al.

  DOI：——

  日期：——
• Pharmaceutical preparations comprising polyprenyl compounds, especially as anti-cancer agents, and pharmaceutical compositions for the prevention and treatment of cancer and skin diseases
  申请人：Eisai Co., Ltd.

  公开号：EP0059258B1

  公开（公告）日：1984-05-30