10-oxophytomonoenoic acid

• 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-oxophytomonoenoic acid
• 英文别名: 2-Oxo-5-pentyl-3-cyclopentene-1-octanoic acid；8-(2-oxo-5-pentylcyclopent-3-en-1-yl)octanoic acid
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: WKABMUFTMQMEAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (9S,10E,12Z)-9-(氢过氧基)-10,12-十八碳二烯酸 在 recombinant tomato allene oxide synthase 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.25h， 生成 10-oxophytomonoenoic acid
  参考文献：
  名称：

  Thermal conversions of fatty acid peroxides to cyclopentenones: A biomimetic model for allene oxide synthase pathway

  摘要：

  The trimethylsilyl (TMS) peroxides of linoleic acid 9(S)-hydroperoxide (TMS or Me esters) were subjected to gas chromatography-mass spectrometry (GC-MS) analyses. The cyclopentenones, trans- and cis-10-oxo-11-phytoenoic acid (10-oxo-PEA, Me or TMS esters) were first time detected as the products of TMS-peroxide thermal conversions. The major products were ketodienes, epoxyalcohols, hemiacetals and decadienals. For further study of thermal cyclopentenone formation, 9(S)- or 13(S)-hydroperoxides of linoleic acid (Me esters) were sealed in ampoules and heated at 230 degrees C for 15 or 30 min. The products were separated by HPLC. The cyclopentenone fractions were collected and analyzed by GC-MS. Trans-10-oxo-PEA (Me) and 10-oxo-9(13)-PEA (Me) were formed during the thermal conversion of 9-hydroperoxide (Me ester). Similarly, the cyclopentenones trans-12-oxo-PEA (Me) and 12-oxo-9(13)-PEA (Me) were detected after the heating of 13-hydroperoxide (Me ester). Thermal formation of cyclopentenones can be considered as a biomimetic model of AOS pathway, providing new insights into the mechanisms of allene oxide formation and cyclization. (C) 2013 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2013.08.005

文献信息

• Replacement of two amino acids of 9 R -dioxygenase-allene oxide synthase of Aspergillus niger inverts the chirality of the hydroperoxide and the allene oxide
  作者：Linda Sooman、Anneli Wennman、Mats Hamberg、Inga Hoffmann、Ernst H. Oliw

  DOI：10.1016/j.bbalip.2015.11.009

  日期：2016.2

  amino acids for the stereospecificity. Recombinant EHA25900 oxidized 18:2n-6 sequentially to 9R-hydroperoxy-10(E),12(Z)-octadecadienoic acid (9R-HPODE) and to a 9R(10)-allene oxide. 9S- and 9R-DOX-AOS catalyze abstraction of the pro-R hydrogen at C-11, but the direction of oxygen insertion differs. A comparison between twelve 9-DOX domains of 9S- and 9R-DOX-AOS revealed conserved amino acid differences

  黑曲霉的基因组编码一个融合蛋白（EHA25900），该序列可以与尖孢镰刀菌的9S-双加氧酶（DOX）-氧化烯合酶（AOS），镰刀菌和炭疽菌复合物的同系物和与曲霉菌的同源物具有超过62％的序列同一性，包括曲霉菌的（DOX）-9R-AOS。目的是表征EHA25900的酶促活性，并鉴定立体特异性的关键氨基酸。重组EHA25900依次将18：2n-6氧化为9R-氢过氧-10（E），12（Z）-十八碳二烯酸（9R-HPODE）和9R（10）-丙二烯氧化物。9S-和9R-DOX-AOS催化C-11上pro-R氢的提取，但是氧的插入方向不同。比较9S-和9R-DOX-AOS的12个9-DOX域，可以发现保守的氨基酸差异，这可能有助于产品的手性。9R-DOX-AOS（黑曲霉）的Gly616Ile替代增加了9S-HPODE和9S（10）-丙二烯氧化物的生物合成，而Phe627Leu替代导致9S-HPODE和
• BENZENE POLYCARBOXYLIC ACID COMPOUNDS AND THEIR USE AS DRUG
  申请人：RDInnovation ApS

  公开号：EP2831151B1

  公开（公告）日：2016-12-14
• Benzene Polycarboxylic Acid Compounds and Their Use as Drug
  申请人：RDInnovation ApS

  公开号：US20160017104A1

  公开（公告）日：2016-01-21

  The present invention relates to new benzene polycarboxylic acids compound, which is prepared by alkaline oxidation of hydrolyzed lignin. The present invention also relates to the use of the new benzene polycarboxylic acids compound as part of a composite substance, where the composite substance is prepared by complexing or encapsulating the new benzene polycarboxylic acid compounds with a metal cation. The present invention also relates to a method for preparing the new benzene polycarboxylic acids compound and for its use in cosmetic, nutraceutical and pharmaceutical compositions.
• US9644074B2
  申请人：——

  公开号：US9644074B2

  公开（公告）日：2017-05-09
• [EN] BENZENE POLYCARBOXYLIC ACID COMPOUNDS AND THEIR USE AS DRUG<br/>[FR] COMPOSÉS ACIDES BENZÈNE POLYCARBOXYLIQUES ET LEUR UTILISATION COMME MÉDICAMENT
  申请人：RDINNOVATION APS

  公开号：WO2013143549A1

  公开（公告）日：2013-10-03

  The present invention relates to new benzene polycarboxylic acids compound, which is prepared by alkaline oxidation of hydrolyzed lignin. The present invention also relates to the use of the new benzene polycarboxylic acids compound as part of a composite substance, where the composite substance is prepared by complexing or encapsulating the new benzene polycarboxylic acid compounds with a metal cation. The present invention also relates to a method for preparing the new benzene polycarboxylic acids compound and for its use in cosmetic, nutraceutical and pharmaceutical compositions.