(9R,10E,12Z)-9-羟基-10,12-十八碳二烯酸 | 15514-85-9

• 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: (9R,10E,12Z)-9-羟基-10,12-十八碳二烯酸
• 英文名称: (9R,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid
• 英文别名: (9R,10E,12Z)-9-hydroxyoctadecadienoic acid；(9R)-hydroxy-10E,12Z-octadecadienoic acid；9R-hydroxy-10E,12Z-octadecadienoic acid；9-hydroxy-10E,12Z-octadecadienoic acid；(9R)-hydroxylinoleic acid；(R)-dimorphecolic acid；(9R,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
• CAS: 15514-85-9；18104-44-4；73543-67-6；96745-45-8；98524-19-7；109281-79-0；115185-06-3；127911-30-2；127911-31-3；133397-72-5；133397-73-6；10075-11-3
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: NPDSHTNEKLQQIJ-WXUVIADPSA-N

物化性质

• 沸点：
  416.1±33.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：50 mg/ml； DMSO：50 mg/ml；乙醇：50 mg/ml； PBS pH 7.2：1 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为产物：
  描述：

  (R)-9-hydroxy-(10E,12Z)-10,12-octadecadienoic acid methyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以83%的产率得到(9R,10E,12Z)-9-羟基-10,12-十八碳二烯酸
  参考文献：
  名称：

  Lipase catalysed regio- and enantio-selective hydrolysis: molecular recognition phenomenon and synthesis of (R)-dimorphecolic acid

  摘要：

  已观察到在Candida cylindracea（E.C. 3.1.1.3）脂肪酶催化下水解（E）-9-醋酸氧基-11-溴十一烯酸的外消旋酯时发生分子识别，从中获得了光学活性的（R-（E）-9-醋酸氧基-11-溴十一烯酸[对映体过量（e.e.）> 99%]，该化合物用于合成（R）-二莫福酸。

  DOI：

  10.1039/c39910001197

文献信息

• Identification of an amino acid determinant of pH regiospecificity in a seed lipoxygenase from Momordica charantia
  作者：Ellen Hornung、Susan Kunze、Alena Liavonchanka、Grit Zimmermann、Diana Kühn、Kathrin Fritsche、Andreas Renz、Hartmut Kühn、Ivo Feussner

  DOI：10.1016/j.phytochem.2008.09.006

  日期：2008.11

  Lipoxygenases (LOX) form a heterogeneous family of lipid peroxidizing enzymes, which catalyze specific dioxygenation of polyunsaturated fatty acids. According to their positional specificity of linoleic acid oxygenation plant LOX have been classified into linoleate 9- and linoleate 13-LOX and recent reports identified a critical valine at the active site of 9-LOX. In contrast, more bulky phenylalanine or histidine residues were found at this position in 13-LOX. We have recently cloned a LOX-isoform from Momordica charantia and multiple amino acid alignments indicated the existence of a glutamine (Gln599) at the position were 13-LOX usually carry histidine or phenylalanine residues. Analyzing the pH-dependence of the positional specificity of linoleic acid oxygenation we observed that at pH-values higher than 7.5 this enzyme constitutes a linoleate 13-LOX whereas at lower pH, 9-H(P)ODE was the major reaction product. Site-directed mutagenesis of glutamine 599 to histidine (Gln599His) converted the enzyme to a pure 13-LOX. These data confirm previous observation suggesting that reaction specificity of certain LOX-isoforms is not an absolute enzyme property but may be impacted by reaction conditions such as pH of the reaction mixture. We extended this concept by identifying glutamine 599 as sequence determinant for such pH-dependence of the reaction specificity. Although the biological relevance for this alteration switch remains to be investigated it is of particular interest that it occurs at near physiological conditions in the pH-range between 7 and 8. (C) 2008 Elsevier Ltd. All rights reserved.
• Stereospecific production of 9R-hydroxy-10E,12Z-octadecadienoic acid from linoleic acid by recombinant Escherichia coli cells expressing 9R-lipoxygenase from Nostoc sp. SAG 25.82
  作者：Kyoung-Rok Kim、Min-Ho Seo、Jin-Byung Park、Deok-Kun Oh

  DOI：10.1016/j.molcatb.2014.03.009

  日期：2014.6

  One of the most significant properties of lipoxygenase (LOX) as a biocatalyst is its stereo-selective oxygenation. In this study, the stereo-specific production of 9R-hydroxy-10E,12Z-octadecadienoic acid (9R-HODE) from linoleic acid was achieved using whole recombinant Escherichia coli cells expressing LOX from Nostoc sp. SAG 25.82. The optimal conditions for the production of 9R-HODE were pH 7.5, 25 degrees C, 40 gl(-1) cells, 15 gl(-1) linoleic acid, 2% (v/v) methanol, 1 working volume/oxygen volume/min (vvm) oxygenation rate, and 250 rpm agitation speed in 500 ml-baffled flask containing a working volume of 50 ml. Under these optimized conditions, whole recombinant cells expressing 9R-LOX protein produced 14.3 gl(-1) 9R-HODE for 1 h, with a conversion yield of 95% (w/w) and a productivity of 14.3 gl(-1) h(-1). The oxygen supply method significantly influenced stereo- and regio-selectivity of the oxygenation of linoleic acid. Among the oxygen supply methods tested, oxygenation (1 vvm) with agitation (250 rpm) resulted in the highest 9R/13S-HODE ratio of the products at 96:4. This is the first application using whole recombinant cells harboring R-specific LOX for the stereo-selective production of an R-specific hydroxy fatty acid. (C) 2014 Elsevier B.V. All rights reserved.
• METHOD OF NEUTRALISING ORGANOBORONATES WITH ACIDS
  申请人：Russel Vincent Patric

  公开号：US20100022646A1

  公开（公告）日：2010-01-28

  The use of specified compounds for the manufacture of a medicament for therapeutically neutralising an organoboronate drug. The specified compounds are typically hydroxy fatty acids or hydroperoxy fatty acids, for example 9(S)-HODE, 8(S)-HETRE or 8(S)-HEPE, or their salts or prodrugs. The organoboronate drug may be TRI 50c or a salt or prodrug thereof. Also disclosed are intravenous formulations containing the specified compounds.
• [EN] NEUTRALISING AGENTS FOR BORONIC ACID DRUGS<br/>[FR] AGENTS NEUTRALISANTS POUR MÉDICAMENTS DE TYPE ACIDES BORONIQUES
  申请人：TRIGEN LTD

  公开号：WO2006059083A1

  公开（公告）日：2006-06-08

  [EN] The use of specified compounds for the manufacture of a medicament for therapeutically neutralising an organoboronate drug. The specified compounds are typically hydroxy fatty acids or hydroperoxy fatty acids, for example 9(S)-HODE, 8(S)-HETRE or 8(S)-HEPE, or their salts or prodrugs. The organoboronate drug may be TRI 50c or a salt or prodrug thereof. Also disclosed are intravenous formulations containing the specified compounds.
  [FR] La présente invention décrit l'emploi de composés précis pour la fabrication d'un médicament employé dans la neutralisation thérapeutique d'un médicament de type organoboronate. Les composés spécifiés sont typiquement des acides gras hydroxylés ou des acides gras hydroperoxydes, par exemple 9(S)-HODE, 8(S)-HETRE ou 8(S)-HEPE, leurs sels ou leurs prodrogues. Le médicament de type organoboronate peut être le TRI 50c ou un sel ou une prodrogue de cette substance. La présente invention décrit également des formules pour administration intraveineuse contenant lesdits composés.
• Lipase catalysed regio- and enantio-selective hydrolysis: molecular recognition phenomenon and synthesis of (R)-dimorphecolic acid
  作者：U. T. Bhalerao、L. Dasaradhi、P. Neelakantan、N. W. Fadnavis

  DOI：10.1039/c39910001197

  日期：——

  Molecular recognition has been observed in hydrolysis of racemic esters of (E)-9-acetoxy-11-bromoundec-10-enoic acid by a lipase of Candida cylindracea(E.C. 3.1.1.3) where optically active (R-(E)-9-acetoxy-11-bromoundec-10-enoic acid [enantiomeric excess (e.e.) > 99%] was obtained which was used in synthesis of (R)-dimorphecolic acid.

  已观察到在Candida cylindracea（E.C. 3.1.1.3）脂肪酶催化下水解（E）-9-醋酸氧基-11-溴十一烯酸的外消旋酯时发生分子识别，从中获得了光学活性的（R-（E）-9-醋酸氧基-11-溴十一烯酸[对映体过量（e.e.）> 99%]，该化合物用于合成（R）-二莫福酸。