O-palmitoyl-12-hydroxystearic acid | 1997286-65-3

• 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: O-palmitoyl-12-hydroxystearic acid
• 英文别名: 12-Pahsa；12-hexadecanoyloxyoctadecanoic acid
• CAS: 1997286-65-3
• 化学式: C₃₄H₆₆O₄
• 分子量: 538.896
• InChiKey: XXHBLSWAKHZVLN-UHFFFAOYSA-N

物化性质

• 沸点：
  614.3±28.0 °C(Predicted)
• 密度：
  0.916±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：20mg/mL； DMSO：15mg/mL；乙醇：20mg/mL；乙醇:PBS(pH 7.2) (1:1): 0.5 mg/ml
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  38
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  O-palmitoyl-12-hydroxystearic acid 在 吡啶 、 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 18.0h， 生成 PAHSA/18:1/18:1-d5-TG
  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：

  12-羟基硬脂酸 、 棕榈酸 在 Candida antarctica Lipase A 作用下， 以 甲苯 为溶剂， 以63.4 %的产率得到O-palmitoyl-12-hydroxystearic 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

• PHARMACEUTICAL COMPOSITIONS
  申请人：ZANDA Matteo

  公开号：US20110200581A1

  公开（公告）日：2011-08-18

  Synthesis natural tubulisine derivatives of formula (A) having a high cytotoxicity wherein: B is selected from CH 2 , CH 2 —CH 2 or CH 2 —CH 2 —CH 2 , D is an aromatic linker, X 1 is alkyl or alkenyl, X 2 is selected from the X 2a , substituted or non substituted, selected from: aryl, heteroaryl, arylalkyl, cycloalkylalkyl, heterocycloalkylalkyl, or heteroarylalkyl, X 2b : alkylene-O-alkyl, wherein alkylene is C 2 -C 10 , X 2c : CH 2 —O-alkyl, X 3 is selected from H, or together with X 4 forms the group ═O, X 4 is selected from H, halogen, OH, SH, alkyl, alkenyl, (OR 5 ) n —OR 6 , OC(O)R 7 , NR 6 R 7 , or together with X 4 forms the group ═O, R 5 is an alkylene, n is zero or an integer from 1 to 10, R 6 and R 7 , equal to or different from each other, have the following meanings: z1: H, alkyl, z2 substituted or non substituted: aryl, heteroaryl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, cycloalkylalkyl, heterocycloalkylalkyl, X 5 is z2, or has the meaning of z3=alkyl, alkenyl, X 6 is selected from NR 8 R 9 , OR 8 , NH—NR 8 R 9 , SR 8 , R 10 , wherein R 8 and R 9 , equal to or different from each other, have the same meanings of R 8 , R 10 has the same meanings as R 6 but excluding H, X 7 is z3 or H, X 8 is selected from z3, H, halogen, OH, SH, OCH 3 .

  合成具有高细胞毒性的具有以下结构的天然管状素衍生物（A）其中：B从CH2、CH2—CH2或CH2—CH2—CH2中选择，D是芳香连接体，X1是烷基或烯基，X2从X2a中选择，替代或未替代，从中选择：芳基、杂环芳基、芳基烷基、环烷基烷基、杂环烷基烷基或杂环芳基烷基，X2b：烷基氧烷基，其中烷基是C2-C10，X2c：CH2—氧烷基，X3从H中选择，或与X4一起形成═O基团，X4从H、卤素、羟基、硫基、烷基、烯基、（OR5）n—OR6、OC（O）R7、NR6R7中选择，或与X4一起形成═O基团，R5是烷基，n为零或1至10之间的整数，R6和R7，彼此相等或不同，具有以下含义：z1：H、烷基，z2替代或未替代：芳基、杂环芳基、环烷基、杂环烷基、芳基烷基、杂环芳基烷基、环烷基烷基、杂环烷基烷基，X5是z2，或具有z3=烷基、烯基的含义，X6从NR8R9、OR8、NH—NR8R9、SR8、R10中选择，其中R8和R9，彼此相等或不同，具有R8的相同含义，R10具有与R6相同但不包括H的含义，X7是z3或H，X8从z3、H、卤素、羟基、硫基、OCH3中选择。
• Tricyclic condensed pyrazole derivatives as CB1 inhibitors
  申请人：Neuroscienze Pharmaness S.C. A R.L.

  公开号：EP2223914A1

  公开（公告）日：2010-09-01

  Condensed tricyclic compounds having a condensed structure containing one phenyl and one pyrazole ring linked with each other by a central ring rcomprising from five to eight atoms, having affinity for the CB1 and/or CB2 receptors, with central nervous system and/or peripheral activity, of formula (I) : wherein the various substituents are as defined in the description. The compounds show affinity for the CB1 and/or CB2 cannabinoidergic receptors.

  具有紧凑结构的三环化合物，其中包含一个苯环和一个吡唑环，通过一个含有五至八个原子的中心环相互连接，具有对CB1和/或CB2受体的亲和力，具有中枢神经系统和/或外周活性，化学式为(I)：其中各种取代基如描述中定义。这些化合物显示对CB1和/或CB2大麻素受体的亲和力。
• PHARMACEUTICAL COMPOUNDS
  申请人：LAZZARI Paolo

  公开号：US20100215741A1

  公开（公告）日：2010-08-26

  Condensed tricyclic compounds having a condensed structure containing one phenyl and one pyrazole ring linked with each other by a central ring comprising from five to eight atoms, having affinity for the CB1 and/or CB2 receptors, with central nervous system and/or peripheral activity, of formula (I): wherein the various substituents are as defined in the description. The compounds show affinity for the CB1 and/or CB2 cannabinoidergic receptors.

  具有紧凑结构的三环化合物，包含一个苯环和一个吡唑环，通过一个由五至八个原子组成的中心环相互连接，在CB1和/或CB2受体上具有亲和力，具有中枢神经系统和/或外周活性，化学式（I）如下：其中各种取代基如描述中所定义。这些化合物对CB1和/或CB2类大麻素受体具有亲和力。
• Pharmaceutical compounds
  申请人：Neuroscienze Pharmaness S.C. A R.L.

  公开号：EP2230243A1

  公开（公告）日：2010-09-22

  Condensed tricyclic pyrazole compounds having affinity for the CB1 and/or CB2 cannabinoidergic receptors, with activity both on the peripheral and central nervous system, of formula (I) : wherein: A represents a group selected from -(CH2)t-, -(CH2)r-O-(CH2)s- and -(CH2)r-S(O)p-(CH2)s- B is an heteroaryl, R is a group selected from heteroaryl, heteroarylalkyl, aryl, arylalkyl, arylalkenyl or bivalent aliphatic chain, R' is a group selected from the following: R'1: a substituent bearing a keto group of formula -C(O)-(Z')v-Z" R'2: a substituent having an hydroxylic function of formula -CH(OH)-(Z')v-Z", R'3: an amide substituent of formula -C(O)-NH-(Z')v-T'.

  具有对CB1和/或CB2大麻素受体亲和力的紧凑三环吡唑化合物，对外周和中枢神经系统均具有活性，其化学式为(I)：其中：A代表从-(CH2)t-, -(CH2)r-O-(CH2)s-和-(CH2)r-S(O)p-(CH2)s-B中选择的基团，B是杂芳基，R是从杂芳基、杂芳烷基、芳基、芳基烷基、芳基烯基或二价脂肪链中选择的基团，R'是从以下选择的基团：R'1：具有化学式-C(O)-(Z')v-Z"的酮基团的取代基，R'2：具有化学式-CH(OH)-(Z')v-Z"的羟基功能的取代基，R'3：具有化学式-C(O)-NH-(Z')v-T'的酰胺取代基。
• A Bi‐Enzymatic Cascade Pathway towards Optically Pure FAHFAs**
  作者：Yan Zhang、Bekir Engin Eser、Zheng Guo

  DOI：10.1002/cbic.202100070

  日期：2021.6.15

  Full enzymatic synthesis of FAHFAs: Various hydroxy fatty acids with different −OH positions can be synthesized from renewable fatty acids by wild-type and engineered fatty acid hydratases, which can be cascaded with lipase to prepare value-added FAHFAs with potential medical value.

  FAHFA 的全酶法合成：可以通过野生型和工程化脂肪酸水合酶从可再生脂肪酸合成具有不同 -OH 位置的各种羟基脂肪酸，这些水合酶可以与脂肪酶级联以制备具有潜在医疗价值的增值 FAHFA。