(2E,4E,6Z,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohexen-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenoic acid | 1962-15-8

• 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,6Z,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohexen-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenoic acid
• 英文别名: trans-8'-apo-β-caroten-8'-oic acid；8'-apo-β-caroten-8'-oic acid；β-apo-8'-carotenoic acid；8'-Apo-β-carotin-8'-saeure
• CAS: 1962-15-8
• 化学式: C₃₀H₄₀O₂
• 分子量: 432.646
• InChiKey: MREKHRDVEZGVPJ-JZCOZIFWSA-N

物化性质

• 熔点：
  189-191 °C
• 沸点：
  609.8±24.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.61
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2E,4E,6Z,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohexen-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenoic acid 在 吡啶 、 草酰氯 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 O¹-(8'-apo-β-apo-caroten-8'-oyl)-O²-[6-(methylselanyl)hexanoyl]glycerol
  参考文献：
  名称：

  Synthesis of a triantioxidant compound: combination of β-apo-8′-carotenoic acid, selenacapryloic acid and trolox in a triglyceride

  摘要：

  Carotenoids, vitamin-E and selenium show similar or complementary physiological properties and protect against a variety of pathological processes. Mixtures of these antioxidants are found in nutritional supplements and are used to prevent several diseases. The synthetic connection of carotenoids, vitamin-E and selenium may increase the chemopreventive activity of the individual compounds. A carotenoic acid, a selena fatty acid and the vitamin-E derivative trolox were successively esterified with glycerol to 1-(beta -apo-8'carotenoyl)-2-(7-selenaoctanoyl)-3-(6-hydroxy-2,5,7,8--tetramethylchroman-2-acyl)-glycerol. This triantioxidant compound revealed, in the DPPH (1,1-diphenyl-2-picrylhydrazyl) test, an additive effect, consisting of the radical quenching activity of the carotenoid and trolox. The DPPH test was not sensitive for the Se moiety in the triantioxidant compound. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00164-5
• 作为产物：
  描述：

  methyl 15,15'-didehydro-8'-apo-β-carotenoate 在 喹啉 、 Lindlar's catalyst 、 Petroleum ether 作用下， 生成 (2E,4E,6Z,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohexen-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenoic acid
  参考文献：
  名称：

  Testing the requirements of stages of physical activity among adults: The comparative effectiveness of stage-matched, mismatched, standard care, and control interventions

  摘要：

  We tested the comparative efficacy of 4 interventions to increase the physical activity behavior of college personnel randomly assigned to one condition (N = 196, 74% female, M age = 43.4 years) for 16 weeks. Stage-matched and mismatched interventions were developed based on the stages of change from the Transtheoretical Model and were contrasted with standard care (action-oriented) and control interventions to test the requirements of a true stage behavior Repeated measures of multivariate analyses of covariance indicated that the stage-matched and standard care interventions resulted in greater levels of both total and lifestyle physical activity compared with the mismatched and control interventions. The results supported the requirements of a stage behavior as defined by Weinstein, Rothman, and Sutton (1) and the superiority of the stage-matched intervention versus the mismatched intervention. However, the standard care intervention performed as well as the matched intervention, suggesting the need for further investigation. The results are discussed with respect to the high proportion of individuals in the action-oriented stages and previous research findings in the smoking literature.

  DOI：

  10.1207/s15324796abm2403_03

文献信息

• Optically Active Oligomer Units in Aggregates of a Highly Unsaturated, Optically Inactive Carotenoid Phospholipid
  作者：Bente Jeanette Foss、Hans-Richard Sliwka、Vassilia Partali、Christian Köpsel、Bernhard Mayer、Hans-Dieter Martin、Ferenc Zsila、Zsolt Bikadi、Miklos Simonyi

  DOI：10.1002/chem.200401191

  日期：2005.7.4

  Enantiomers of glycerophospholipids show low or no optical activity. Accordingly, optical activity was not observed with the R enantiomer of a highly unsaturated carotenoyl lysophospholipid in solution. In spite of this, strong Cotton effects are detected in water. The amphiphilic carotenoid-phospholipid monomers associate to form aggregates, whose optical activity is attributed to oligomeric entities.

  甘油磷脂的对映异构体显示低或没有光学活性。因此，溶液中的高度不饱和胡萝卜素溶血磷脂的R对映异构体没有观察到光学活性。尽管如此，在水中仍检测到强烈的棉花效应。两亲类胡萝卜素-磷脂单体缔合形成聚集体，其光学活性归因于低聚实体。这些小的螺旋组件不能独立存在。然而，计算出的八聚体代表了最简单的重复一级单元，该单元足以表达吸收特性和超分子光学活性。
• Carotinoid-Glycosylester 4. Mitteilung. Synthese von 8′-Apo-β-carotin-8′-säure-(β-<scp>D</scp>-glucosyl)ester und Vitamin-A-säure-(β-<scp>D</scp>-glucosyl)ester
  作者：Hanspeter Pfander、Manfred Läderach、Fritz Wittwer

  DOI：10.1002/hlca.19800630128

  日期：1980.1.23

  Carotenoid Glycosyl Esters Synthesis of β-D-Glucosyl 8′-Apo-β-carotene-8′-oate and β-D-Glucosyl Vitamin-A-oate (β-D-Glucosyl Retionate)

  类胡萝卜素糖基酯合成β-D-葡萄糖基8'-Apo-β-胡萝卜素-8'-oate和β-D-葡萄糖基维生素A-oate（β-D-葡萄糖基果酸酯）
• High-efficiency Energy Transfer from Carotenoids to a Phthalocyanine in an Artificial Photosynthetic Antenna¶
  作者：Ernesto Mariño-Ochoa、Rodrigo Palacios、Gerdenis Kodis、Alisdair N. Macpherson、Tomas Gillbro、Devens Gust、Thomas A. Moore、Ana L. Moore

  DOI：10.1562/0031-8655(2002)076<0116:heetfc>2.0.co;2

  日期：——

  Abstract Two carotenoid pigments have been linked as axial ligands to the central silicon atom of a phthalocyanine derivative, forming molecular triad 1. Laser flash studies on the femtosecond and picosecond time scales show that both the carotenoid S1 and S2 excited states act as donor states in 1, resulting in highly efficient singlet energy transfer from the carotenoids to the phthalocyanine. Triplet

  摘要 两种类胡萝卜素色素已作为轴向配体与酞菁衍生物的中心硅原子相连，形成分子三联体 1。飞秒和皮秒时间尺度上的激光闪光研究表明，类胡萝卜素 S1 和 S2 激发态均作为供体态1，导致从类胡萝卜素到酞菁的高效单线态能量转移。还观察到了相反方向的三重态能量转移。在极性溶剂中，从类胡萝卜素到酞菁激发单线态的有效电子转移产生电荷分离态，该态重新结合到基态 1。
• 10.1002/(sici)1521-3765(199801)4:1<113::aid-chem113<3.0.co;2-q
  作者：Larsen, Eva、Abendroth, Jan、Partali, Vassilia、Schulz, Bernhard、Sliwka, Hans-Richard、Quartey, Edward G. K.

  DOI：10.1002/(sici)1521-3765(199801)4:1<113::aid-chem113<3.0.co;2-q

  日期：——
• Light Harvesting and Photoprotective Functions of Carotenoids in Compact Artificial Photosynthetic Antenna Designs
  作者：Gerdenis Kodis、Christian Herrero、Rodrigo Palacios、Ernesto Mariño-Ochoa、Stephanie Gould、Linda de la Garza、Rienk van Grondelle、Devens Gust、Thomas A. Moore、Ana L. Moore、John T. M. Kennis

  DOI：10.1021/jp036139o

  日期：2004.1.1

  Artificial light-harvesting constructs were synthesized by covalently linking two carotenoids to the central silicon atom of a phthalocyanine (PC) derivative. Triad 1 binds two carotenoids having nine conjugated double bonds, whereas triad 2 binds two carotenoids having 10 carbon-carbon double bonds in conjugation. Fluorescence excitation experiments indicated that, in triad 1 dissolved in n-hexane, the carotenoid to PC singlet energy transfer efficiency is ca. 92%, whereas in triad 2, it is 30%. Results from ultrafast laser spectroscopy indicate that upon population of the optically allowed S-2, state of the carotenoid the optically forbidden states S-1, and S* are rapidly generated in both triad 1 and triad 2. In triad 1, S-2, S-1, and S* all contribute singlet electronic energy to PC. In triad 2, singlet electronic energy transfer to PC occurs primarily from the optically allowed S-2 state with little energy transfer to PC via the S-1 state, and there is no evidence for energy transfer via S*. Instead, in triad 2, we find a multiphased quenching of the PC singlet excited state on the picosecond and nanosecond time scales. Upon intersystem crossing from the singlet excited state of PC to the triplet state in triad 1, triplet-triplet energy transfer to either of the carotenoids takes place on a time scale significantly shorter than 5 ns. When dissolved in polar solvents, triads 1 and 2 exhibit light-induced electron transfer from either of the carotenoid moieties to the excited singlet PC species with a time constant of about 2 ps. Charge recombination to the singlet ground state occurs in 10 ps in triad 1 and 17 ps in triad 2.