10-hydroperoxy-trans-8-cis-12-octadecadienoic acid | 90540-32-2

• 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: 10-hydroperoxy-trans-8-cis-12-octadecadienoic acid
• 英文别名: 10-Hydroperoxyoctadeca-8,12-dienoic acid；10-hydroperoxy-8,12-octadecadienoic acid；linoleic acid 10-hydroperoxide；10-Hpode；(8E,12Z)-10-hydroperoxyoctadeca-8,12-dienoic acid
• CAS: 90540-32-2
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: YONQBPOWOZLKHS-UEAALKJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-hydroperoxy-trans-8-cis-12-octadecadienoic acid 在 iron(II) sulfate 吡啶 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  10-Hydroperoxy-8,12-octadecadienoic acid. A diagnostic probe of alkoxyl radical generation in metal-hydroperoxide reactions

  摘要：

  DOI：

  10.1021/ja00243a048
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 tetrakis(p-sulfonatophenyl)porphyrin 、 氧气 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (10E,12Z)-9-氢过氧基十八碳-10,12-二烯酸 、 (9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoic acid 、 10-hydroperoxy-trans-8-cis-12-octadecadienoic acid 、 12-hydroperoxy-cis-9-trans-13-octadecadienoic acid
  参考文献：
  名称：

  Regioselectivities and stereoselectivities of singlet oxygen generated by cyclodextrin-sandwiched porphyrin sensitization. Lipoxygenase-like activity

  摘要：

  DOI：

  10.1021/ja00007a087

文献信息

• Mechanism of Lipid Peroxidation Photosensitized by Tiaprofenic Acid: Product Studies Using Linoleic Acid and 1,4-Cyclohexadienes as Model Substrates¶
  作者：Abdelouahid Samadi、Luis A. Martínez、Miguel A. Miranda、Isabel M. Morera

  DOI：10.1562/0031-8655(2001)073<0359:molppb>2.0.co;2

  日期：——

  A careful study of the linoleic acid hydroperoxide (LOOH) profile obtained upon peroxidation of linoleic acid (LA) photosensitized by tiaprofenic acid (TPA) and analogous ketones has been undertaken to distinguish between type-I and type-II photoperoxidation mechanisms. 1,4-Cyclohexadiene and 1,2-dimethylcyclohexa-2,5 -dienecarboxylic acid (CHDCA) have also been used as models for LA since they also have double allylic systems, Co-irradiation of LA with TPA and decarboxytiaprofenic acid (DTPA) in acetonitrile and micellar media produced significant amounts of conjugated dienic LOOH, The cis,trans to trans,trans ratio depended on the irradiation time; thus, this parameter is an ambiguous tool for mechanistic assignment. An interesting finding was the decrease of the LOOH level after long irradiation times in mixtures photooxidized by DTPA, which is attributed to quenching of the DTPA triplet by the generated dienic LOOH, High-performance liquid chromatography analyses confirmed that the main pathway operating in photodynamic lipid peroxidation sensitized by (D)TPA is a type-I mechanism. However, product studies using CHDCA have clearly shown that a type-II mechanism is also operating and might contribute to the overall photooxidation process in a significant way.
• Homolytic and heterolytic scission of organic hydroperoxides by (meso-tetraphenylporphinato)iron(III) and its relation to olefin epoxidation
  作者：Regine Labeque、Lawrence J. Marnett

  DOI：10.1021/ja00199a022

  日期：1989.8
• Production of 2-octenyl radicals from the iron(III).cntdot.bleomycin-mediated fragmentation of 10-hydroperoxy-8,12-octadecadienoic acid
  作者：Anand Natrajan、Sidney M. Hecht

  DOI：10.1021/jo00018a002

  日期：1991.8

  The Fe(III).BLM-mediated fragmentation of 10-hydroperoxy-8,12-octadecadienoic acid was demonstrated unambiguously to occur via homolytic O-O bond scission.
• NATRAJAN, ANAND;HECHT, SIDNEY M., J. ORG. CHEM., 56,(1991) N8, C. 5239-5241
  作者：NATRAJAN, ANAND、HECHT, SIDNEY M.

  DOI：——

  日期：——
• Regioselectivities and stereoselectivities of singlet oxygen generated by cyclodextrin-sandwiched porphyrin sensitization. Lipoxygenase-like activity
  作者：Yasuhisa Kuroda、Takashi Sera、Hisanobu Ogoshi

  DOI：10.1021/ja00007a087

  日期：1991.3