(Z)-10-oxooctadec-12-enoic acid | 103521-29-5

• 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: (Z)-10-oxooctadec-12-enoic acid
• 英文别名: 10-keto-12(Z)-octadecenoic acid；10-oxo-cis-12-octadecenoic acid；10-oxo-12(Z)-octadecenoic acid；KetoA；10-keto-12Z-octadecenoic acid
• CAS: 103521-29-5
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: IEQLMTRAAYQDSD-FLIBITNWSA-N

物化性质

• 沸点：
  447.4±28.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：10 mg/ml，DMSO：5 mg/ml，乙醇：5 mg/ml，PBS (pH 7.2)：不溶解

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• 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

制备方法与用途

10-氧代-12(Z)-十八碳烯酸是亚油酸的代谢产物，也是瞬时受体电位香草素1（TRPV1）的激活剂，能够选择性地提高表达TRPV1的HEK293细胞中的钙水平。

反应信息

• 作为反应物：
  描述：

  (Z)-10-oxooctadec-12-enoic acid 在 trametes sp. Ha-1 laccase 、 1-羟基苯并三唑 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 生成 癸二酸
  参考文献：
  名称：

  通过漆酶催化的氧化裂解从新型不饱和脂肪酸生产二羧酸。

  摘要：

  由于全球变暖和石油储备的枯竭，建立可再生的生物燃料和化学产品是可取的。癸二酸（癸二酸）是6,10尼龙的材料，是由蓖麻油酸（一种碳中性材料）生产的，但由于能源需求，该工艺不环保。漆酶催化脂肪酸的氧化裂解被用于生产二羧酸，使用参与植物乳杆菌中不饱和脂肪酸饱和代谢的羟基和羰基脂肪酸。具有一个在碳-碳双键附近的官能团的羟基或氧代脂肪酸被漆酶裂解在碳-碳双键，羟基或羰基上，并转化为二羧酸。8小时后，由1.生成0.58 mM的癸二酸。6 mM的10-氧代-顺式-12，顺式-15-十八碳二烯酸（αKetoA），转化率为35％（mol / mol）。这种漆酶催化的酶促工艺是一种从生物质衍生的脂肪酸生产二羧酸的有前途的方法。

  DOI：

  10.1080/09168451.2016.1200457
• 作为产物：
  描述：

  (S)-10-hydroxy-cis-12-octadecenoic acid 在 conjugated linoleic acid dehydrogenase 、 nicotinamide adenine dinucleotide 、 bovine serum albumin 作用下， 以 aq. buffer 为溶剂， 反应 0.25h， 生成 (Z)-10-oxooctadec-12-enoic acid
  参考文献：
  名称：

  Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a

  摘要：

  Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. The enzyme preferentially catalyzed NADH-dependent hydrogenation of oxo fatty acids over NAD(+)-dependent dehydrogenation of hydroxy fatty acids. In the dehydrogenation reaction, fatty acids with an internal hydroxy group such as 10-hydroxy-cis-12-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, and 13-hydroxy-cis-9-octadecenoic acid served as better substrates than those with alpha- or beta-hydroxy groups such as 3-hydroxyoctadecanoic acid or 2-hydroxyeicosanoic acid. The apparent Km value for 10-hydroxy-cis-12-octadecenoic acid (HYA) was estimated to be 38 mu M with a k(cat) of 7.6 x 10(-3) s(-1). The apparent K-m value for 10-oxo-cis-12-octadecenoic acid (KetoA) was estimated to be 1.8 mu M with a k(cat) of 5.7 x 10(-1) s(-1). In the hydrogenation reaction of KetoA, both (R)- and (S)-HYA were generated, indicating that the enzyme has low stereoselectivity. This is the first report of a dehydrogenase with a preference for fatty acids with an internal hydroxy group. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.03.020

文献信息

• Conversion of linoleic acid to 10‐hydroxy‐12(Z)‐octadecenoic acid by<i>Flavobacterium</i> sp. (NRRL B‐14859)
  作者：Ching T. Hou

  DOI：10.1007/bf02542264

  日期：1994.9

  A new microbial isolate,Flavobacterium sp. strain DS5, converts linoleic acid into 10‐hydroxy‐12(Z)‐octadecenoic acid (10‐HOA) with 55% yield. The product was characterized by gas chromatography (GC), GC/mass spectrometry, nuclear magnetic resonance and Fourier transform infrared spectroscopy. The specific optical rotation of 10‐HOA is [α]_D²⁴=−5.58 (methanol). The optimum time, pH and temperature for the production of 10‐HOA were 36h, 7.5 and 20–35°C, respectively. The enzyme(s) that converts linoleic acid to 10‐HOA is soluble and located intracellulary in strain DS5. Two minor products, 10‐methoxy‐12‐octade‐cenoic acid and 10‐keto‐12‐octadecenoic acid, were also identified. 10‐HOA was further metabolized by strain DS5. Among the unsaturated fatty acids studied, the order of reactivity for the DS5 enzyme(s) is oleic>palmitoleic> linoleic>linolenic>γ‐linolenic>myristoleic acid.

  摘要 一种新的微生物分离物--黄杆菌 (Flavobacterium sp.) 菌株 DS5 能将亚油酸转化为 10-hydroxy-12(Z)-octadecenoic acid (10-HOA)，产率为 55%。该产物通过气相色谱、气相色谱/质谱、核磁共振和傅立叶变换红外光谱进行了表征。10-HOA 的比旋光度为 [α]D24=-5.58 （甲醇）。生产 10-HOA 的最佳时间、pH 值和温度分别为 36 小时、7.5 和 20-35°C。将亚油酸转化为 10-HOA 的酶是可溶性的，位于菌株 DS5 的细胞内。此外，还发现了两种次要产物，即 10-甲氧基-12-十八烯酸和 10-酮基-12-十八烯酸。菌株 DS5 对 10-HOA 进行了进一步代谢。在所研究的不饱和脂肪酸中，DS5 酶的反应性顺序为油酸>棕榈油酸>亚油酸>亚麻酸>γ-亚麻酸>肉豆蔻油酸。
• INTESTINAL TRACT-PROTECTING AGENT CONTAINING HYDROXYLATED FATTY ACID
  申请人：Kyoto University

  公开号：EP2959897A1

  公开（公告）日：2015-12-30

  The present invention provides an intestinal tract-protecting agent, an agent for the prophylaxis or improvement of a disease caused by damage in intestinal tract barrier function, which contains hydroxylated fatty acid, particularly hydroxylated unsaturated fatty acid, having a hydroxyl group at the 10-position and/or the 12-position, which is an intermediate of the metabolism of unsaturated fatty acid by lactobacillus.

  本发明提供了一种肠道保护剂，一种用于预防或改善因肠道屏障功能受损而引起的疾病的药物，它含有羟基化脂肪酸，特别是羟基化不饱和脂肪酸，在 10 位和/或 12 位具有羟基，它是乳酸杆菌代谢不饱和脂肪酸的中间产物。
• ANTI-INFLAMMATORY AGENT CONTAINING RARE FATTY ACID
  申请人：Kyoto University

  公开号：EP3097910A1

  公开（公告）日：2016-11-30

  The present invention provides an anti-inflammatory agent containing a rare fatty acid such as hydroxylated fatty acid, oxo fatty acid and the like, and further, food, pharmaceutical product and the like containing the anti-inflammatory agent.

  本发明提供了一种含有稀有脂肪酸（如羟化脂肪酸、氧代脂肪酸等）的消炎剂，以及含有该消炎剂的食品、药品等。
• METHOD FOR PRODUCING RARE FATTY ACID USING NOVEL ENZYME, AND NOVEL RARE FATTY ACID
  申请人：Kyoto University

  公开号：EP3098313A1

  公开（公告）日：2016-11-30

  The present invention provides production of hydroxylated fatty acid by a hydration reaction using a novel enzyme derived from lactobacillus and using fatty acid as a substrate, and further, a production method of oxo fatty acid by an enzyme reaction or chemical oxidation reaction using the hydroxylated fatty acid as a substrate. In addition, a valuable novel rare fatty acid obtained by such production method is also provided.

  本发明提供了一种以脂肪酸为底物，使用源自乳酸杆菌的新型酶，通过水合反应生产羟基化脂肪酸的方法，并进一步提供了一种以羟基化脂肪酸为底物，通过酶反应或化学氧化反应生产氧化脂肪酸的方法。此外，还提供了通过这种生产方法获得的有价值的新型稀有脂肪酸。
• Method for producing oxo fatty acid and rare fatty acid
  申请人：KYOTO UNIVERSITY

  公开号：US10294501B2

  公开（公告）日：2019-05-21

  The present invention provides a production method of oxo fatty acid, as well as rare fatty acids such as conjugated fatty acid, hydroxylated fatty acid, partially saturated fatty acid and the like, which uses 4 kinds of enzymes (fatty acid-hydratase, hydroxylated fatty acid-dehydrogenase, oxo fatty acid-isomerase, oxo fatty acid-enone reductase) derived from Lactobacillus plantarum including lactic acid bacteria and the like. Furthermore, the present invention also provides a more efficient production method of oxo fatty acid and the like, which partly uses a chemical oxidation reaction in combination.

  本发明提供了一种氧化脂肪酸以及共轭脂肪酸、羟基化脂肪酸、部分饱和脂肪酸等稀有脂肪酸的生产方法，该方法使用了从植物乳杆菌（包括乳酸菌等）中提取的 4 种酶（脂肪酸-水解酶、羟基化脂肪酸-脱氢酶、氧化脂肪酸-异构酶、氧化脂肪酸-烯酮还原酶）。此外，本发明还提供了一种更高效的氧化脂肪酸等的生产方法，该方法部分结合使用了化学氧化反应。