1-oleoyl-3-palmitoyl-sn-glycerol | 36805-77-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-oleoyl-3-palmitoyl-sn-glycerol
• 英文别名: 3-hexadecanoyl-1-[(9Z)-octadec-9-enoyl]-sn-glycerol；1-Oleoyl-3-palmitoyl-sn-glycerol；[(2S)-3-hexadecanoyloxy-2-hydroxypropyl] (Z)-octadec-9-enoate
• CAS: 36805-77-3
• 化学式: C₃₇H₇₀O₅
• 分子量: 594.96
• InChiKey: NBBXPULYBQASLG-OZKTZCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  42
• 可旋转键数：
  35
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-oleoyl-3-palmitoyl-sn-glycerol 、 棕榈酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以0.758 g的产率得到1-oleoyl-2,3-dipalmitoyl-sn-glycerol
  参考文献：
  名称：

  环氧乙烷和甲硅烷氧基体系的区域选择性和立体选择性酰化是合成对映体纯的甘油单酯，甘油二酯和甘油三酯的新策略。

  摘要：

  三氟乙酸催化带有三氟乙酸酐（TFAA）的带有烯丙基酰基或烷基官能团的缩水甘油基衍生物的环氧乙烷环的开环，可有效进入构型均质的1（3）-酰基-或1（3）-O-烷基-sn -甘油。在这些关键中间体的末端位置选择性引入叔丁基二甲基甲硅烷基-（TBDMS）或三异丙基甲硅烷基-（TIPS）瞬态保护可确保1（3）-酰基-或1（3）-O-烷基-3（1）- O-TBDMS（或TIPS）-sn-甘油作为1,2（2,3）-二酰基-，1（3）-O-烷基-2-酰基-和1,3-二酰基-sn-的一般双功能前体甘油和三酯等排体。通过三氯乙酸酐（TCAA）在甲硅烷基化的合成子的中央碳原子上引入必要的酰基残基，并随后进行Et（3）N.3HF促进的，直接的三氯乙酰化作用穿过硅烷氧基体系 然后裂解三氯乙酰基，得到各自的1,2（2,3）-二酰基-或1（3）-O-烷基-2-酰基-sn-甘油。可选择地，反应序列包括：（i）三氯乙酰基片段连接在单甲硅烷基化甘油酯的立体C

  DOI：

  10.1039/b713246h
• 作为产物：
  描述：

  棕榈酸酐 在 吡啶 、 甲醇 、 三甲基溴硅烷 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 4.0h， 生成 1-oleoyl-3-palmitoyl-sn-glycerol
  参考文献：
  名称：

  Direct Acylation across a Silyloxy System of Glycerol with Carboxylic Acid Anhydrides: A Novel Strategy to the Prodrug Carrier Modules - 1,3-Diacyl-sn-glycerols

  摘要：

  通过三氯乙酰化1-酰基-3-O-叔丁基二甲基硅基-sn-甘油，随后利用四正丁基溴化铵（TBABr）-三甲基硅基溴化物（TMSBr）-羧酸酐（CAA）试剂体系直接将硅保护基团转化为酯功能性，构成了一种高效制备高收率手性纯1,3-二酰基-sn-甘油的方法。

  DOI：

  10.1055/s-2005-917084

文献信息

• NOVEL PHOSPHATIDYLALKANOLS AND COMPOSITIONS THEREOF
  申请人：PETHMARK AB

  公开号：US20160052946A1

  公开（公告）日：2016-02-25

  The present invention discloses a composition comprising a compound of formula I and a deuterated solvent. The deuterated solvent is miscible with water in any proportion at a temperature of 20 to 25° C. and comprises less than 5% residual 1 H-isotopes. The concentration of the compound of formula I may advantageously be determined by 1 H-QNMR. Methods of production of the composition and salts of compounds of formula I, as well as related analogs and novel reagents and intermediates for the production thereof, are also described.

  本发明揭示了一种包含式I化合物和氘化溶剂的组合物。氘化溶剂在20至25°C温度下与水可任意比例混合，并且含有少于5%的残留1H同位素。化合物式I的浓度可优选通过1H-QNMR确定。还描述了该组合物的生产方法、式I化合物的盐、以及相关类似物和新型试剂和中间体的生产方法。
• Chemoenzymatic Synthesis of ABC-Type Enantiostructured Triacylglycerols by the Use of the p-Methoxybenzyl Protective Group
  作者：Hafdis Haraldsdottir、Haraldur G. Gudmundsson、Kaisa M. Linderborg、Baoru Yang、Gudmundur G. Haraldsson

  DOI：10.3390/molecules29071633

  日期：——

  and (S)-solketals. The highly regioselective immobilized Candida antarctica lipase (CAL-B) played a crucial role in the regiocontrol of the synthesis. The synthesis also benefited from the use of the p-methoxybenzyl (PMB) ether protective group, which enabled the incorporation of two different unsaturated fatty acids into the glycerol skeleton. The total of six such TAGs were prepared, four constituting

  该报告展示了 ABC 型对映纯结构三酰甘油 (TAG) 的首次不对称合成，其呈现三种不同的脂肪酸，其中两种是不饱和的。不饱和脂肪酸包括单不饱和油酸(C18:1n-9)和多不饱和亚油酸(C18:2n-6)。这是通过从 (R)-和 (S)-solketals 开始的六步化学酶方法完成的。高度区域选择性固定化南极假丝酵母脂肪酶（CAL-B）在合成的区域控制中发挥着至关重要的作用。该合成还得益于对甲氧基苯甲基（PMB）醚保护基的使用，这使得两种不同的不饱和脂肪酸能够并入甘油骨架中。总共制备了六个这样的TAG，其中四个在sn-1和sn-2位置构成不饱和脂肪酸，在甘油主链的剩余sn-3位置构成饱和脂肪酸。在剩下的两个 TAG 中，不同的不饱和脂肪酸容纳在 sn-1 和 sn-3 末端位置，而饱和脂肪酸则位于 sn-2 位置。迫切需要对映体纯 TAG 作为脂肪和油中完整 TAG 的对映特异性分析的标准。
• Studies on the Substrate and Stereo/Regioselectivity of Adipose Triglyceride Lipase, Hormone-sensitive Lipase, and Diacylglycerol-O-acyltransferases
  作者：Thomas O. Eichmann、Manju Kumari、Joel T. Haas、Robert V. Farese、Robert Zimmermann、Achim Lass、Rudolf Zechner

  DOI：10.1074/jbc.m112.400416

  日期：2012.11

  Adipose triglyceride lipase (ATGL) is rate-limiting for the initial step of triacylglycerol (TAG) hydrolysis, generating diacylglycerol (DAG) and fatty acids. DAG exists in three stereochemical isoforms. Here we show that ATGL exhibits a strong preference for the hydrolysis of long-chain fatty acid esters at the sn-2 position of the glycerol backbone. The selectivity of ATGL broadens to the sn-1 position upon stimulation of the enzyme by its co-activator CGI-58. sn-1,3 DAG is the preferred substrate for the consecutive hydrolysis by hormone-sensitive lipase. Interestingly, diacylglycerol-O-acyltransferase 2, present at the endoplasmic reticulum and on lipid droplets, preferentially esterifies sn-1,3 DAG. This suggests that ATGL and diacylglycerol-O-acyltransferase 2 act coordinately in the hydrolysis/re-esterification cycle of TAGs on lipid droplets. Because ATGL preferentially generates sn-1,3 and sn-2,3, it suggests that TAG-derived DAG cannot directly enter phospholipid synthesis or activate protein kinase C without prior isomerization.
• The acylation of lipophilic alcohols by lysosomal phospholipase A2
  作者：Akira Abe、Miki Hiraoka、James A. Shayman

  DOI：10.1194/jlr.m700277-jlr200

  日期：2007.10

  A novel lysosomal phospholipase A(2) (LPLA2) with specificity toward phosphatidylethanolamine and phosphatidylcholine was previously purified and cloned. LPLA2 transfers sn-1 or sn-2 acyl groups of phospholipids to the C1 hydroxyl of the short-chain ceramide N-acetylsphingosine (NAS) under acidic conditions. The common features of lipophilic alcohols serving as acceptor molecules in the transacylase reaction were examined. 1-O-Hexadecyl-2-acetyl-sn-glycerol (HAG) was acylated by LPLA2 similar to NAS. HAG competed with NAS and inhibited NAS acylation. The transacylation of 1-O-hexadecylglycerol (HG), 1-O-palmityl-2-O-methyl-sn-glycerol (PMG), and monoacylglycerols was also investigated. HG, PMG, 1- or 3-palmitoyl-sn-glycerol, and 2-palmitoylglycerol were converted to 1,3-alkylacylglycerol, 1,2-dialkyl-3-acylglycerol, 1,3-diacylglycerol, and 1,2- or 2,3-diacylglycerol, respectively. HG and monoacylglycerol inhibited the acylation of NAS by the enzyme with IC50 values of 35 and 45 mu M, respectively. Additionally, the enzyme acylated glycerol to produce 1- or 3-acyl-sn-glycerol but not 2- acylglycerol. Therefore, the preferred acceptor molecules for LPLA2 are primary alcohols with one long carbon chain and one small nonpolar residue linked to the C2 position of ethanol. The enzyme acylated other natural lipophilic alcohols, including anandamide and oleoylethanolamide. Thus, LPLA2 may function to remodel acyl groups and modulate the biological and pharmacological activities of some lipophilic alcohols.
• US9499572B2
  申请人：——

  公开号：US9499572B2

  公开（公告）日：2016-11-22