(2E,4E,6E)-methyl 8-hydroxy-2,6-dimethylocta-2,4,6-trienoate | 1036759-73-5

• 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)-methyl 8-hydroxy-2,6-dimethylocta-2,4,6-trienoate
• 英文别名: 8-hydroxy-2,6-dimethylocta-2,4,6-trienoic acid methyl ester；methyl (2E,4E,6E)-8-hydroxy-2,6-dimethylocta-2,4,6-trienoate
• CAS: 1036759-73-5
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: JVTMKMNCIMKMCY-YHMDTEOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,4E,6E)-methyl 8-hydroxy-2,6-dimethylocta-2,4,6-trienoate 、 三苯基膦氢溴酸盐 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis of α-tocohexaenol (α-T6) a fluorescent, oxidatively sensitive polyene analogue of α-tocopherol

  摘要：

  A polyunsaturated analogue of alpha-tocopherol was synthesized that is both fluorescent and sensitive to peroxidative chemistry that occurs in phospholipid membranes. alpha-Tocohexaenol 1, [(S)-2,5,7,8-tetramethyl-2-((1E/Z,3E,5E,7E,9E)-4,8,12-trimethyltrideca-1,3,5,7,9,11-hexaenyl)chroman-6-ol, alpha-T6] was prepared by condensing a known triene fragment triphenyl-(2,6-dimethyl-octa-2,4,6-trienoic acid methyl ester)-phosphonium bromide with a protected chromanol aldehyde, (2S)-6-{[tert-butyl(dimethyl) silyl]oxy}-2,5,7,8-tetra-methyl-3,4-dihydro-2H-chromene-2-carbaldehyde. The full side chain was then completed with isopentyl(tri-n-butyl) phosphonium bromide to give 1. The geometry of the C1' - C2' alkene appears to be Z (cis) although the coupling constants of the olefinic protons are intermediate between values normally assigned to E and Z-isomers. In ethanol, alpha-T6 has a maximum absorption at 368 nm with an absorption coefficient of 45,000 M-1 cm(-1), and displays a maximum fluorescence emission at 523 nm. The susceptibility of alpha-T6 to peroxidative chemistry was dependent on the concentration of azo-initiators of lipid oxidation in acetonitrile solution as well as in phospholipid vesicles. A loss of fluorescence at 520 nm was observed when alpha-T6 ( vesicles or alpha-T6-lipid mixtures) was exposed to peroxidative conditions, and this loss mirrored the production of conjugated dienes and trienes during the peroxidation of bulk phospholipids. Addition of natural alpha-tocopherol during the AMVN induced oxidation of 4 mu M alpha-T6 and 0.5 mg/ml soybean PC induced a characteristic lag phase, after which the fluorescence of alpha-T6 began to lessen. Thus, alpha-T6 may be a useful reporter not only of tocopherol location in cells, but also of the extent of peroxidative events. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.051
• 作为产物：
  描述：

  8-(tert-butyldimethylsilanyloxy)-2,6-dimethylocta-2,4,6-trienoic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (2E,4E,6E)-methyl 8-hydroxy-2,6-dimethylocta-2,4,6-trienoate
  参考文献：
  名称：

  Synthesis of α-tocohexaenol (α-T6) a fluorescent, oxidatively sensitive polyene analogue of α-tocopherol

  摘要：

  A polyunsaturated analogue of alpha-tocopherol was synthesized that is both fluorescent and sensitive to peroxidative chemistry that occurs in phospholipid membranes. alpha-Tocohexaenol 1, [(S)-2,5,7,8-tetramethyl-2-((1E/Z,3E,5E,7E,9E)-4,8,12-trimethyltrideca-1,3,5,7,9,11-hexaenyl)chroman-6-ol, alpha-T6] was prepared by condensing a known triene fragment triphenyl-(2,6-dimethyl-octa-2,4,6-trienoic acid methyl ester)-phosphonium bromide with a protected chromanol aldehyde, (2S)-6-{[tert-butyl(dimethyl) silyl]oxy}-2,5,7,8-tetra-methyl-3,4-dihydro-2H-chromene-2-carbaldehyde. The full side chain was then completed with isopentyl(tri-n-butyl) phosphonium bromide to give 1. The geometry of the C1' - C2' alkene appears to be Z (cis) although the coupling constants of the olefinic protons are intermediate between values normally assigned to E and Z-isomers. In ethanol, alpha-T6 has a maximum absorption at 368 nm with an absorption coefficient of 45,000 M-1 cm(-1), and displays a maximum fluorescence emission at 523 nm. The susceptibility of alpha-T6 to peroxidative chemistry was dependent on the concentration of azo-initiators of lipid oxidation in acetonitrile solution as well as in phospholipid vesicles. A loss of fluorescence at 520 nm was observed when alpha-T6 ( vesicles or alpha-T6-lipid mixtures) was exposed to peroxidative conditions, and this loss mirrored the production of conjugated dienes and trienes during the peroxidation of bulk phospholipids. Addition of natural alpha-tocopherol during the AMVN induced oxidation of 4 mu M alpha-T6 and 0.5 mg/ml soybean PC induced a characteristic lag phase, after which the fluorescence of alpha-T6 began to lessen. Thus, alpha-T6 may be a useful reporter not only of tocopherol location in cells, but also of the extent of peroxidative events. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.051

文献信息

• Practical synthesis of 1,5-dimethyl substituted conjugated polyenes from geranyl acetate
  作者：Yu-Jun Zhao、Teck-Peng Loh

  DOI：10.1016/j.tet.2008.03.094

  日期：2008.5

  A protocol to synthesize 1,5-dimethyl substituted conjugated polyenes via dehydrogenation of geranyl acetate was established. C-5 unit elongation to multi- 1,5-dimethyl substituted conjugated polyenes was also achieved via Horner-Wadsworth-Emmons olefination in good yields and good selectivities. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of α-tocohexaenol (α-T6) a fluorescent, oxidatively sensitive polyene analogue of α-tocopherol
  作者：Yongsheng Wang、Candace Panagabko、Jeffrey Atkinson

  DOI：10.1016/j.bmc.2009.11.051

  日期：2010.1

  A polyunsaturated analogue of alpha-tocopherol was synthesized that is both fluorescent and sensitive to peroxidative chemistry that occurs in phospholipid membranes. alpha-Tocohexaenol 1, [(S)-2,5,7,8-tetramethyl-2-((1E/Z,3E,5E,7E,9E)-4,8,12-trimethyltrideca-1,3,5,7,9,11-hexaenyl)chroman-6-ol, alpha-T6] was prepared by condensing a known triene fragment triphenyl-(2,6-dimethyl-octa-2,4,6-trienoic acid methyl ester)-phosphonium bromide with a protected chromanol aldehyde, (2S)-6-[tert-butyl(dimethyl) silyl]oxy}-2,5,7,8-tetra-methyl-3,4-dihydro-2H-chromene-2-carbaldehyde. The full side chain was then completed with isopentyl(tri-n-butyl) phosphonium bromide to give 1. The geometry of the C1' - C2' alkene appears to be Z (cis) although the coupling constants of the olefinic protons are intermediate between values normally assigned to E and Z-isomers. In ethanol, alpha-T6 has a maximum absorption at 368 nm with an absorption coefficient of 45,000 M-1 cm(-1), and displays a maximum fluorescence emission at 523 nm. The susceptibility of alpha-T6 to peroxidative chemistry was dependent on the concentration of azo-initiators of lipid oxidation in acetonitrile solution as well as in phospholipid vesicles. A loss of fluorescence at 520 nm was observed when alpha-T6 ( vesicles or alpha-T6-lipid mixtures) was exposed to peroxidative conditions, and this loss mirrored the production of conjugated dienes and trienes during the peroxidation of bulk phospholipids. Addition of natural alpha-tocopherol during the AMVN induced oxidation of 4 mu M alpha-T6 and 0.5 mg/ml soybean PC induced a characteristic lag phase, after which the fluorescence of alpha-T6 began to lessen. Thus, alpha-T6 may be a useful reporter not only of tocopherol location in cells, but also of the extent of peroxidative events. (C) 2009 Elsevier Ltd. All rights reserved.