(all-Z)-(eicosa-5,8,11,14-tetraenyloxy)acetic acid | 178178-33-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (all-Z)-(eicosa-5,8,11,14-tetraenyloxy)acetic acid
• 英文别名: 2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoxy]acetic acid
• CAS: 178178-33-1
• 化学式: C₂₂H₃₆O₃
• 分子量: 348.526
• InChiKey: CXTUOCLXSRCCAA-DOFZRALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  (all-Z)-(eicosa-5,8,11,14-tetraenyloxy)acetic acid 在 15-lipoxygenase sodium tetrahydroborate 、 氧气 作用下， 反应 2.0h， 生成 15'-(S)-hydroxy-(Z,Z,Z,E)-eicosa-5',8',11',13'-tetraenyloxyacetic acid
  参考文献：
  名称：

  多不饱和脂肪酸氢过氧化物和Perketal衍生物的合成作为潜在的抗疟剂

  摘要：

  通过15-脂氧合酶催化氧化制备β-氧杂取代的多不饱和脂肪酸的氢过氧化物衍生物，并合成了脂肪酸氢过氧化物的全酮衍生物。硬膜外皮比其母体脂肪酸氢过氧化物更稳定，但在体外抑制恶性疟原虫的生长中作为抗疟剂的活性较低。

  DOI：

  10.1016/s0040-4039(98)00747-3
• 作为产物：
  描述：

  arachidonyl alcohol 在 dirhodium tetraacetate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (all-Z)-(eicosa-5,8,11,14-tetraenyloxy)acetic acid
  参考文献：
  名称：

  Synthesis of Polyunsaturated β-Oxa Fatty Acids via Rhodium Mediated Carbenoid Insertion

  摘要：

  多不饱和β-氧脂肪酸1可以通过与叔丁基二氮乙酸酯3的铑(II)醋酸盐催化反应，从天然来源的多不饱和脂肪醇2中容易获得，随后进行酯裂解。

  DOI：

  10.1055/s-1997-1355

文献信息

• Oxidation of oxa and thia fatty acids and related compounds catalysed by 5- and 15-lipoxygenase
  作者：Christopher J. Easton、Thomas A. Robertson、Michael J. Pitt、Deborah A. Rathjen、Antonio Ferrante、Alfred Poulos

  DOI：10.1016/s0968-0896(00)00246-7

  日期：2001.2

  The modified fatty acids, (Z,Z,Z)-(octadeca-6,9,12-trienyloxy)acetic acid, (Z,Z,Z)-(octadeca-9,12,15-trienyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid, 3-[(all-Z)-(eicosa-5,8,11,14-tetraenylthio)]propionic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)succinic acid, N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]glycine and N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]aspartic acid, all react with soybean 15-lipoxygenase. The products were treated with triphenylphosphine to give alcohols, which were isolated using HPLC. Analysis of the alcohols using negative ion tandem electrospray mass spectrometry, and by comparison with compounds obtained by autoxidation of arachidonic acid, shows that each enzyme catalysed oxidation occurs at the omega -6 position of the substrate. In a similar fashion, it has been found that (Z,Z,Z)-(octadeca-6,9,12-trienyloxy)acetic acid, (Z,Z,Z)-(octadeca-9,12,15-trienyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid and N-[(all-Z)-(eicosa-5,8, 11.14-tetraenylthio)]propionic acid each undergoes regioselective oxidation at the carboxyl end of the polyene moiety on treatment with potato 5-lipoxygenase. Neither (all-Z)-(eicosa-5,8,11,14-tetraenylthio)succinic acid nor N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]aspartic acid reacts in the presence of this enzyme, while N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]glycine affords the C11' oxidation product. The alcohol derived from (Z,Z,Z)-(octadeca-6,9, 12-trienyloxy)acetic acid using the 15-lipoxygenase reacts at the C6' position with the 5-lipoxygenase. (C) 2001 Elsevier Science Ltd. All rights reserved.
• EP0869941A4
  申请人：——

  公开号：EP0869941A4

  公开（公告）日：1998-10-14
• MODIFIED POLYUNSATURATED FATTY ACIDS
  申请人：Peptech Limited

  公开号：EP0869941B1

  公开（公告）日：2001-12-12
• Therapeutic and carrier molecules
  申请人：Ferrante Antonio

  公开号：US20090215895A1

  公开（公告）日：2009-08-27

  The present invention relates generally to compounds comprising a hydrocarbon chain portion and more particular to compounds comprising chemical derivatizations of the hydrocarbon chain which are useful therapeutic and prophylactic molecules. The present invention further provides compounds where the hydrocarbon chain portion is a carrier molecule for functional groups, moieties or agents. The compounds of the present invention are particularly useful in the treatment and prophylaxis of a range of conditions including cancers, protein kinase c(PKC)- or NFkB-related- or -associated conditions, cardiovascular conditions, pain, inflammatory conditions, vascular or immunological conditions such as diabetes, neurological conditions and infection by a range of viruses or prokaryotic or eukaryotic organisms. The present invention further provides pharmaceutical compositions and methods of medical treatment.
• US6376688B1
  申请人：——

  公开号：US6376688B1

  公开（公告）日：2002-04-23