外消旋1-油酰基-2-棕榈酰甘油 | 3331-34-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 外消旋1-油酰基-2-棕榈酰甘油
• 中文别名: 1-油酰基-2-棕榈酰基-rac-甘油
• 英文名称: 1-oleoyl-2-palmitoylglycerol
• 英文别名: 1-oleoyl-2-palmitoyl-rac-glycerol；1-oleoyl-2-palmitoyl glyceride；1-Oleoyl-2-palmitoyl-rac-glycerin；(2-hexadecanoyloxy-3-hydroxypropyl) (Z)-octadec-9-enoate
• CAS: 3331-34-8
• 化学式: C₃₇H₇₀O₅
• 分子量: 594.96
• InChiKey: DOZKMFVMCATMEH-ZCXUNETKSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

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：

  烟酸 、 外消旋1-油酰基-2-棕榈酰甘油 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 Nicotinic acid 2-hexadecanoyloxy-3-((Z)-octadec-9-enoyloxy)-propyl ester
  参考文献：
  名称：

  Analysis of phospholipid molecular species by liquid chromatography — atmospheric pressure chemical ionisation mass spectrometry of diacylglycerol nicotinates

  摘要：

  A method using liquid chromatography - atmospheric pressure chemical ionisation mass spectrometry was evaluated for determining the molecular species composition of phospholipids (phosphatidylcholines from soybean. egg yolk and bovine liver) after conversion to diacylglycerol nicotinate derivatives. The structures could be deduced from pseudo-molecular ions ([MH-123](+)) and three pairs of monoacyl containing fragment ions. All molecular species in mixed peaks were readily identified and many minor components, earlier not encountered in the samples under investigation. were identified. Acyl chain regioisomers were readily distinguished by the ratio of the [MH RCHCO](+) ions. Molecular species differing only in the position of the double bonds in one polyunsaturated acyl chain were separated on the basis of retention times. A half quantitative estimation of the molecular species composition of complex samples was achieved by a combination of UV detection and, for mixed peaks, the areas of [MH-123](+) ions. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00130-x
• 作为产物：
  描述：

  三棕榈酸甘油酯 在 Difco bile salt No_.3 吡啶 、 pancreas lipase type II (EC 3.1.1.3) 、 Tris buffer 、 calcium chloride 作用下， 以 氯仿 、 水 为溶剂， 反应 72.75h， 生成 外消旋1-油酰基-2-棕榈酰甘油
  参考文献：
  名称：

  摘要：

  A host-recognizing kairomone responsible for the stinging behavior of the parasitic wasp, Dinarmus basalis, was studied. Fresh azuki beans coated with an acetone extract of the azuki beans, from which both emerged wasps and their host weevils were removed. elicited stinging behavior from female wasps. The kairomone is a mixture of saturated hydrocarbons and diacylglycerols, both of which art: required Fur activity. The kairomone is composed of normal and methyl-branched hydrocarbons with carbon numbers ranging from 25 to 35, most of which are known as the hydrocarbon constituents of an oviposition-marking pheromone of the host azuki bean weevils, Callosobruchus chinensis. This indicates that D. basalis utilizes the oviposition-marking pheromone of its host weevils as a host-recognizing kairomone.

  DOI：

  10.1023/a:1026425407150

文献信息

• Inflammation Modulatory Phorbol Esters from the Seeds of <i>Aquilaria malaccensis</i>
  作者：Vitthal D. Wagh、Michal Korinek、I-Wen Lo、Yu-Ming Hsu、Shu-Li Chen、Hsue-Yin Hsu、Tsong-Long Hwang、Yang-Chang Wu、Bing-Hung Chen、Yuan-Bin Cheng、Fang-Rong Chang

  DOI：10.1021/acs.jnatprod.6b01096

  日期：2017.5.26

  malaccensis is a valuable source of agarwood, which is used in herbal medicinal preparations. Phytochemical research on A. malaccensis seeds has led to the isolation of four new phorbol esters (1–4), two known phorbol esters (5, isolated from Nature for the first time, and 6), and two known glycerides (7 and 8). The structures of these isolates were elucidated by means of spectroscopic data interpretation

  马来沉香树是沉香的重要来源，沉香用于草药。上的植物化学研究A.芏种子已经导致的四个新的佛波醇酯（隔离1 - 4），两个已知的佛波醇酯（5，从自然界中分离的第一次，和6），以及两个公知的甘油酯（7和8）。这些分离物的结构通过光谱数据解释得以阐明。评价了分离物对人嗜中性粒细胞中弹性蛋白酶释放和超氧阴离子产生的炎症调节活性。有趣的是，佛波醇酯1，图5和图6显示了对人嗜中性粒细胞中的弹性蛋白酶释放的有效抑制活性，IC 50值分别为2.7、0.8和2.1μM。所有分离的佛波酯都对超氧阴离子的产生具有增强的活性。结果表明佛波醇酯可能在炎症过程中起双边调节作用。此外，评估了这些化合物对HepG2（肝癌），MDA-MB-231（乳腺癌）和A549（肺癌）癌细胞的细胞毒性，但所有化合物对所有使用的细胞系均无活性（IC 50 > 10μM ）。
• Pharmaceutical compositions having a modified vehicle
  申请人：——

  公开号：US20040170650A1

  公开（公告）日：2004-09-02

  A composition comprising: (a) one to three bioactive agents; and (b) a vehicle comprising; (i) a modified liquid carrier, and (ii) an unmodified liquid carrier wherein the ratio by volume of the modified liquid carrier to the unmodified liquid carrier is between 0.00001:99.99999 to less than 0.01:99.99, that provide the composition with predictable sustained-release properties and wherein immediately after manufacture of the composition, said composition can be administered to a host such that the one to three bioactive agents is released to the host on a sustained basis.

  一种组合物，包括 (a) 一至三种生物活性剂；和 (b) 一种载体，包括 (i) 改性液体载体，和 (ii) 未改性液体载体 其中，改性液体载体与未改性液体载体的体积比介于 0.00001:99.99999 至小于 0.01:99.99 之间，从而使该组合物具有可预测的持续释放特性，并且在制造该组合物后，可立即将所述组合物施用到宿主体内，从而使一至三种生物活性剂持续释放到宿主体内。
• 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.
• USE OF DIACYLOLYCEROLS FOR INCREASING THE MELANIN CONTENT IN MELANOCYTES
  申请人：TRUSTEES OF BOSTON UNIVERSITY

  公开号：EP0655907B1

  公开（公告）日：1999-04-28
• PROCESS FOR THE PRODCUTION OF GLYCERIDES WITH LIPASES
  申请人：NIPPON SUISAN KAISHA, LTD.

  公开号：EP1300470B1

  公开（公告）日：2010-09-15