(1-14C)亚油酸 | 3131-66-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (1-14C)亚油酸
• 英文名称: [1-14C]linoleic acid
• 英文别名: (1-14C)Linoleic acid；(9Z,12Z)-(114C)octadeca-9,12-dienoic acid
• CAS: 3131-66-6
• 化学式: C₁₈H₃₂O₂
• 分子量: 282.44
• InChiKey: OYHQOLUKZRVURQ-SLFAJGNUSA-N

物化性质

• 闪点：
  14 °C

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  F
• 安全说明：
  S16,S26,S36
• 危险类别码：
  R11,R36/37/38

反应信息

• 作为反应物：
  描述：

  (1-14C)亚油酸 在 Tris-HCl buffer 、 soybean lipoxygenase type I-B 、 氧气 作用下， 反应 0.33h， 以8%的产率得到[1-14C](9E,11E,13R,S)-13-hydroperoxy-9,11-octadecadienoic acid
  参考文献：
  名称：

  结构和pH值在环氧乙烷脂肪酸环化中的作用：对反应机理的影响。

  摘要：

  在pH 7.5下，亚麻或玉米的氧化烯合成酶与亚油酸的13-氢过氧化物和9-氢过氧化物的E，E-异构体（分别为E，E-13-和E，E-9-HPOD）一起孵育反式二取代的环戊烯酮的产率。在使用的条件下，（Z，E）-HPODs主要转化为α-酮醇，仅提供痕量的环戊烯酮。这些发现表明，将双键的几何形状从Z改变为E显着增加了18：2-丙二烯氧化物电环化所需的环戊二烯基阳离子中间体的形成速率，从而提高了环戊烯酮的收率。众所周知，将α-亚麻酸13-氢过氧化物（E，Z-13-HPOT）衍生的均烯丙基氧化烯（12,13-EOT）环化为cis-12-oxo-10，在低于中性的pH值下15-植物二烯酸被抑制，在pH 4.5上不能观察到。相反，在低pH条件下，偏向于衍生自（E，E）-13-HPOD的氧化烯（（9E）-12,13-EOD）的环化作用略微有利。pH值变化对12,13-EOT和（9E）-12,13-EOD

  DOI：

  10.1016/s0009-3084(02)00107-x

文献信息

• A non-canonical caleosin from<i>Arabidopsis</i>efficiently epoxidizes physiological unsaturated fatty acids with complete stereoselectivity
  作者：Elizabeth Blée、Martine Flenet、Benoît Boachon、Marie-Laure Fauconnier

  DOI：10.1111/j.1742-4658.2012.08757.x

  日期：2012.10

  In plants, epoxygenated fatty acids (EFAs) are constituents of oil seeds as well as defence molecules and components of biopolymers (cutin, suberin). While the pleiotropic biological activities of mammalian EFAs have been well documented, there is a paucity of information on the physiological relevance of plant EFAs and their biosynthesis. Potential candidates for EFA formation are caleosin‐type peroxygenases which catalyze the epoxidation of unsaturated fatty acids in the presence of hydroperoxides as co‐oxidants. However, the caleosins characterized so far, which are mostly localized in seeds, are poor epoxidases. In sharp contrast, quantitative RT‐PCR analysis revealed that PXG4, a class II caleosin gene, is expressed in roots, stems, leaves and flowers of Arabidopsis. Expressed in yeast, PXG4 encodes a calcium‐dependent membrane‐associated hemoprotein able to catalyze typical peroxygenase reactions. Moreover, we show here that purified recombinant PXG4 is an efficient fatty acid epoxygenase, catalyzing the oxidation of cis double bonds of unsaturated fatty acids. Physiological linoleic and linolenic acids proved to be the preferred substrates for PXG4; they are oxidized into the different positional isomers of the monoepoxides and into diepoxides. An important regioselectivity was observed; the C‐12,13 double bond of these unsaturated fatty acids being the least favored unsaturation epoxidized by PXG4, linolenic acid preferentially yielded the 9,10‐15,16‐diepoxide. Remarkably, PXG4 catalyzes exclusively the formation of (R),(S)‐epoxide enantiomers, which is the absolute stereochemistry of the epoxides found in planta. These findings pave the way for the study of the functional role of EFAs and caleosins in plants.
• Iio, Toshihiro; Yoden, Kazuaki; Tabata, Toshikazu, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 12, p. 5015 - 5019
  作者：Iio, Toshihiro、Yoden, Kazuaki、Tabata, Toshikazu

  DOI：——

  日期：——
• INTRALIPID-IODINE FOR IMAGING
  申请人：Eldor Joseph

  公开号：US20190008973A1

  公开（公告）日：2019-01-10

  The present invention relates to intralipid-iodine and intralipid-iodine compounds for use in imaging and therapy.
• US5276204A
  申请人：——

  公开号：US5276204A

  公开（公告）日：1994-01-04
• Role of structure and pH in cyclization of allene oxide fatty acids: Implications for the reaction mechanism
  作者：Alexander N Grechkin、Ivan R Chechetkin、Lucia S Mukhtarova、Mats Hamberg

  DOI：10.1016/s0009-3084(02)00107-x

  日期：2002.12

  electrocyclization of 18:2-allene oxides and thus the yield of cyclopentenones. The well-known cyclization of the homoallylic allene oxide (12,13-EOT) derived from alpha-linolenic acid 13-hydroperoxide (E,Z-13-HPOT) into cis-12-oxo-10,15-phytodienoic acid was suppressed at pH below neutral and was not observable at pH 4.5. In contrast, cyclization of the allene oxide ((9E)-12,13-EOD) derived from (E

  在pH 7.5下，亚麻或玉米的氧化烯合成酶与亚油酸的13-氢过氧化物和9-氢过氧化物的E，E-异构体（分别为E，E-13-和E，E-9-HPOD）一起孵育反式二取代的环戊烯酮的产率。在使用的条件下，（Z，E）-HPODs主要转化为α-酮醇，仅提供痕量的环戊烯酮。这些发现表明，将双键的几何形状从Z改变为E显着增加了18：2-丙二烯氧化物电环化所需的环戊二烯基阳离子中间体的形成速率，从而提高了环戊烯酮的收率。众所周知，将α-亚麻酸13-氢过氧化物（E，Z-13-HPOT）衍生的均烯丙基氧化烯（12,13-EOT）环化为cis-12-oxo-10，在低于中性的pH值下15-植物二烯酸被抑制，在pH 4.5上不能观察到。相反，在低pH条件下，偏向于衍生自（E，E）-13-HPOD的氧化烯（（9E）-12,13-EOD）的环化作用略微有利。pH值变化对12,13-EOT和（9E）-12,13-EOD