12-(9Z-Octadecenoyloxy)-octadecanoic acid | 101901-73-9

• 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: 12-(9Z-Octadecenoyloxy)-octadecanoic acid
• 英文别名: 12-Oahsa；12-[(Z)-octadec-9-enoyl]oxyoctadecanoic acid
• CAS: 101901-73-9
• 化学式: C₃₆H₆₈O₄
• 分子量: 564.934
• InChiKey: OCHJVQODRYVDAA-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  40
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-(9Z-Octadecenoyloxy)-octadecanoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-hydroxy-3-((12-(oleoyloxy)octadecanoyl)oxy)propyl-1,1,2,3,3-d5 oleate
  参考文献：
  名称：

  Discovery of FAHFA-Containing Triacylglycerols and Their Metabolic Regulation

  摘要：

  FAHFAs are a class of bioactive lipids, which show great promise for treating diabetes and inflammatory diseases. Deciphering the metabolic pathways that regulate endogenous FAHFA levels is critical for developing diagnostic and therapeutic strategies. However, it remains unclear how FAHFAs are metabolized in cells or tissues. Here, we investigate whether FAHFAs can be incorporated into other lipid classes and identify a novel class of endogenous lipids, FAHFA-containing triacylglycerols (FAHFA-TGs), which contain a FAHFA group esterified to the glycerol backbone. Isotope-labeled FAHFAs are incorporated into FAHFA-TGs when added to differentiated adipocytes, which implies the existence of enzymes and metabolic pathways capable of synthesizing these lipids. Induction of lipolysis (i.e., triacylglycerol hydrolysis) in adipocytes is associated with marked increases in nonesterified FAHFA levels, demonstrating that FAHFA-TGs breakdown is a regulator of cellular FAHFA levels. To quantify FAHFA levels in FAHFA-TGs and determine their regioisomeric distributions, we developed a mild alkaline hydrolysis method that liberates FAHFAs from triacylglycerols for easier detection. FAHFA-TG concentrations are greater than 100-fold than that of nonesterified FAHFAs, indicating that FAHFA-TGs are a major reservoir of FAHFAs in cells and tissues. The discovery of FAHFA-TGs reveals a new branch of TG and FAHFA metabolism with potential roles in metabolic health and regulation of inflammation.

  DOI：

  10.1021/jacs.9b00045
• 作为产物：
  描述：

  油酸 、 12-羟基硬脂酸 在 Candida antarctica Lipase A 作用下， 以 甲苯 为溶剂， 以39.3 %的产率得到12-(9Z-Octadecenoyloxy)-octadecanoic acid
  参考文献：
  名称：

  用于合成含有结构多样化 FAHFA 的磷脂酰胆碱的化学酶级联策略

  摘要：

  羟基脂肪酸的脂肪酸酯（FAHFAs）是一类新发现的人类内源性复合脂质，在治疗糖尿病和炎症性疾病方面显示出巨大的前景，天然存在的浓度极低。这项工作报告了一种化学酶法，通过连续步骤全面合成含有 FAHFA 的磷脂：水合酶催化不饱和脂肪酸水合，生成结构多样的羟基脂肪酸 (HFA)，然后将这些 HFA 与脂肪酸选择性酯化由仲醇特异性南极假丝酵母脂肪酶 A (CALA) 介导，导致形成一系列不同的 FAHFA 类似物。最终合成是通过 FAHFA 与甘油磷脂酰胆碱基于碳二亚胺的偶联来完成的。确定每个步骤的最佳反应条件，并通过分子对接评估负责 FAHFA 生产过程中催化机制的 CALA 的底物亲和力。与多步繁琐的实验室化学合成相比，该路线依赖于天然结构单元和天然生物催化剂，显着简便、可扩展且选择性高，在构建更高FAHFA的每个步骤中均提供高产率（74–98 mol%） -PC系列（10/12/13-FAHFA）。开发的策略旨在增加天然存在的

  DOI：

  10.1021/acs.joc.3c02131

文献信息

• [EN] BILE ACIDS AND USE IN DISEASE TREATMENT<br/>[FR] ACIDES BILIAIRES ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES
  申请人：UNIV CALIFORNIA

  公开号：WO2020154397A1

  公开（公告）日：2020-07-30

  Compositions and methods of use for modulating bile acids, including phenylalanocholic acid, tyrosocholic acid and leucocholic acid, to treat diseases, such as inflammatory bowel disease. In embodiments, the invention provides pharmaceutical compositions that modulate levels of a bile acid conjugate in a subject. In embodiments, the invention provides pharmaceutical compositions that modulate levels of a bile acid conjugate in a particular organ or bodily region of the subject.

  调节胆汁酸，包括苯丙氨胆酸、酪氨酸胆酸和亮氨酸胆酸等的使用组合物和方法，用于治疗炎症性肠病等疾病。在实施例中，本发明提供了调节受试者体内胆汁酸共轭物水平的药物组合物。在实施例中，本发明提供了调节受试者特定器官或身体区域内胆汁酸共轭物水平的药物组合物。
• [EN] NEW NON-IONIC SURFACTANTS FOR SOLUBILIZING POORLY SOLUBLE MOLECULES<br/>[FR] NOUVEAUX TENSIOACTIFS NON IONIQUES DESTINES A SOLUBILISER DES MOLECULES FAIBLEMENT SOLUBLES
  申请人：ASTRAZENECA AB

  公开号：WO2004089869A1

  公开（公告）日：2004-10-21

  New non-ionic surfactants in the form of polyoxyalkylene glycol hydroxy fatty acid derivatives or monoalkylated polyoxyalkylene glycol hydroxy fatty acid derivatives having a polyoxyalkylene / alkyl polyoxyalkylene chain with a chain-length of 25 - 455 repeating units and a specified substituent on the hydroxy position of the specified hydroxy fatty acid, according to the general formula (I) CH3 - (CH2)x - CH - (CH2)y - CO - [-O - R3 - ]z - O - R1 R2 - O (I); wherein for example R1 is methyl, R2 is optionally substituted C14 - C22 acyl, alkyl, or alkenyl, R3 is ethylene, x is 2-12, y is 7-17, (x + y) is 3-19 and z is 25-57; advantageously prepared by involving an enzymatic process, formulations comprising them, their use as solubilizers and a process involving a hydrolytic enzyme for preparing them.

  新的非离子表面活性剂以聚氧烷基乙二醇羟基脂肪酸衍生物或单烷基化聚氧烷基乙二醇羟基脂肪酸衍生物的形式存在，具有聚氧烷基/烷基聚氧烷基链，链长为25-455个重复单元，并且在指定的羟基脂肪酸的羟基位置上具有特定的取代基，根据通式（I）CH3 -（CH2）x - CH -（ ）y - CO - [-O - R3 -]z - O - R1 R2 - O（I）；例如，其中R1为甲基，R2为可选的取代的C14 - C22酰基、烷基或烯基，R3为乙烯基，x为2-12，y为7-17，（x + y）为3-19，z为25-57；通过涉及酶过程有利地制备，包含它们的配方，它们作为溶剂的用途以及涉及水解酶制备它们的过程。
• Non-ionic surfactants for solubilizing poorly solubule molecules
  申请人：von Corswant Christian

  公开号：US20060287542A1

  公开（公告）日：2006-12-21

  New non-ionic surfactants in the form of polyoxyalkylene glycol hydroxy fatty acid derivatives or monoalkylated polyoxyalkylene glycol hydroxy fatty acid derivatives having a polyoxyalkylene / alkyl polyoxyalkylene chain with a chain-length of 25-455 repeating units and a specified substituent on the hydroxy position of the specified hydroxy fatty acid, according to the general formula (I) CH 3 —(CH 2 ) x —CH—(CH 2 ) y —CO—[—O—R 3 —] z —O—R 1 R 2 —O (I); wherein for example R 1 is methyl, R 2 is optionally substituted C 14 —C 22 acyl, alkyl, or alkenyl, R 3 is ethylene, x is 2-12, y is 7-17, (x+y) is 3-19 and z is 25-57; advantageously prepared by involving an enzymatic process, formulations comprising them, their use as solubilizers and a process involving a hydrolytic enzyme for preparing them.

  新的非离子表面活性剂采用聚氧烷基乙二醇羟基脂肪酸衍生物或单烷基化聚氧烷基乙二醇羟基脂肪酸衍生物形式，具有聚氧烷基/烷基聚氧烷基链，链长为25-455个重复单元，并且在指定羟基脂肪酸的羟基位置上具有指定的取代基，按照通式(I) CH3—(CH2)x—CH—( )y—CO—[—O—R3—]z—O—R1R2—O (I)；其中，例如R1为甲基，R2为可选取代的C14-C22酰基，烷基或烯基，R3为乙烯，x为2-12，y为7-17，(x+y)为3-19，z为25-57；通过涉及酶法的方法优选制备，包含它们的配方，它们作为溶解剂的用途以及涉及水解酶制备它们的方法。
• EP1615874A1
  申请人：——

  公开号：EP1615874A1

  公开（公告）日：2006-01-18
• NEW NON-IONIC SURFACTANTS FOR SOLUBILIZING POORLY SOLUBLE MOLECULES
  申请人：AstraZeneca AB

  公开号：EP1615874B1

  公开（公告）日：2013-12-25