(5Z,8Z,12E,14Z)-(R)-11-Hydroxy-icosa-5,8,12,14-tetraenoic acid methyl ester | 79083-18-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5Z,8Z,12E,14Z)-(R)-11-Hydroxy-icosa-5,8,12,14-tetraenoic acid methyl ester
• 英文别名: methyl (5Z,8Z,11R,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate
• CAS: 79083-18-4
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: UXMIJODNYUZSNX-ZVOTYKBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  24.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5Z,8Z,12E,14Z)-(R)-11-Hydroxy-icosa-5,8,12,14-tetraenoic acid methyl ester 在 platinum(IV) oxide 氢气 作用下， 生成
  参考文献：
  名称：

  2,4-Decadienals are produced via (R)-11-HPITE from arachidonic acid in marine green alga Ulva conglobata

  摘要：

  Marine green alga Ulva conglobata was investigated for the biogeneration of oxygenated products from exogenously added arachidonic acid (ARA). A crude enzyme from the alga afforded the detectable amount of a hydroperoxyicosatetraenoic acid (HPITE), which was identified as (R)-11-HPITE by HPLC and GC-MS. Headspace-SPME method indicated that ARA was selectively used to form 2,4-decadienals. These results showed that 2,4-decadienals are produced via (R)-11-HPITE from ARA exclusively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00364-x
• 作为产物：
  描述：

  花生四烯酸 在 crude enzyme of Ulva conglobata 、 三苯基膦 作用下， 反应 0.51h， 生成 (5Z,8Z,12E,14Z)-(R)-11-Hydroxy-icosa-5,8,12,14-tetraenoic acid methyl ester
  参考文献：
  名称：

  2,4-Decadienals are produced via (R)-11-HPITE from arachidonic acid in marine green alga Ulva conglobata

  摘要：

  Marine green alga Ulva conglobata was investigated for the biogeneration of oxygenated products from exogenously added arachidonic acid (ARA). A crude enzyme from the alga afforded the detectable amount of a hydroperoxyicosatetraenoic acid (HPITE), which was identified as (R)-11-HPITE by HPLC and GC-MS. Headspace-SPME method indicated that ARA was selectively used to form 2,4-decadienals. These results showed that 2,4-decadienals are produced via (R)-11-HPITE from ARA exclusively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00364-x

文献信息

• The synthesis of 11<i>R</i>- and 11<i>S</i>-HETE and of 11-<i>R</i>,<i>S</i>-HPETE methyl esters
  作者：George Just、Corinne Luthe、Minh Tan Phan Viet

  DOI：10.1139/v83-132

  日期：1983.4.1

  Methyl 11R- and 11S-hydroxyeicosa-5Z,8Z,12E,14Z-tetraenoate (17R, 17S) (11-HETE) and the corresponding 11-hydroperoxide 19 (11-HPETE) have been prepared from readily available starting materials. The yields were approximately 25% for 11R,S-HETE, and 5% each for 11R- and 11S-HETE.Extensive 400 MHz ¹H nmr studies of 17 (nOe difference, 2D J-resolved) were undertaken to confirm the structure. Some conformational properties are discussed.

  甲基11R-和11S-羟基二十碳-5Z,8Z,12E,14Z-四烯酸酯（17R，17S）（11-HETE）及其对应的11-过氧化物19（11-HPETE）已从易得的起始原料制备。11R，S-HETE的产率约为25％，11R-和11S-HETE各为5％。对17进行了广泛的400MHz 1H nmr研究（nOe差异，2D J-resolved）以确认结构。讨论了一些构象性质。
• Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5S-HETE by native and aspirin-acetylated COX-2
  作者：Surafel Mulugeta、Takashi Suzuki、Noemi Tejera Hernandez、Markus Griesser、William E. Boeglin、Claus Schneider

  DOI：10.1194/jlr.m001719

  日期：2010.3

  Biosynthesis of the prostaglandin endoperoxide by the cyclooxygenase (COX) enzymes is accompanied by formation of a small amount of 11R-hydroxyeicosatetraenoic acid (HETE), 15R-HETE, and 15S-HETE as by-products. Acetylation of COX-2 by aspirin abrogates prostaglandin synthesis and triggers formation of 15R-HETE as the sole product of oxygenation of arachidonic acid. Here, we investigated the formation of by-products of the transformation of 5S-HETE by native COX-2 and by aspirin-acetylated COX-2 using HPLC-ultraviolet, GC-MS, and LC-MS analysis. 5S,15S- dihydroxy (di)HETE, 5S,15R-diHETE, and 5S,11R-diHETE were identified as by-products of native COX-2, in addition to the previously described di-endoperoxide (5S,15S-dihydroxy-9S,11R,8S,12S-diperoxy-6E,13E-eicosadienoic acid) as the major oxygenation product. 5S,15R-diHETE was the only product formed by aspirin-acetylated COX-2. Both 5,15-diHETE and 5,11-diHETE were detected in CT26 mouse colon carcinoma cells as well as in lipopolysaccharide-activated RAW264.7 cells incubated with 5S-HETE, and their formation was attenuated in the presence of the COX-2 specific inhibitor, NS-398. Aspirin-treated CT26 cells gave 5,15-diHETE as the most prominent product formed from 5S-HETE. 5S,15S-diHETE has been described as a product of the cross-over of 5-lipoxygenase (5-LOX) and 15-LOX activities in elicited rat mononuclear cells and human leukocytes, and our studies implicate crossover of the 5-LOX and COX-2 pathways as an additional bio-synthetic route.-Mulugeta, S., T. Suzuki, N. T. Hernandez, M. Griesser, W. E. Boeglin, and C. Schneider. Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5S-HETE by native and aspirin-acetylated COX-2. J. Lipid Res. 2010. 51: 575-585.
• Stereospecific total synthesis of 11(R)-HETE (2), lipoxygenation product of arachidonic acid via the prostaglandin pathway
  作者：E. J. Corey、Jahyo Kang

  DOI：10.1021/ja00405a071

  日期：1981.7
• A method for the systematic resolution of unbranched α-acetoxyalkyl- and aralkylaldehydes: synthesis of and -hete
  作者：George Just、Corinne Luthe、Pierre Potvin

  DOI：10.1016/s0040-4039(00)87322-0

  日期：1982.1
• 2,4-Decadienals are produced via (R)-11-HPITE from arachidonic acid in marine green alga Ulva conglobata
  作者：Yoshihiko Akakabe、Kenji Matsui、Tadahiko Kajiwara

  DOI：10.1016/s0968-0896(03)00364-x

  日期：2003.8

  Marine green alga Ulva conglobata was investigated for the biogeneration of oxygenated products from exogenously added arachidonic acid (ARA). A crude enzyme from the alga afforded the detectable amount of a hydroperoxyicosatetraenoic acid (HPITE), which was identified as (R)-11-HPITE by HPLC and GC-MS. Headspace-SPME method indicated that ARA was selectively used to form 2,4-decadienals. These results showed that 2,4-decadienals are produced via (R)-11-HPITE from ARA exclusively. (C) 2003 Elsevier Ltd. All rights reserved.