外消旋1-油酰基-3-棕榈酰甘油 | 3343-30-4

• 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-3-棕榈酰甘油
• 中文别名: 1-油酰基-3-棕榈酰基-rac-甘油
• 英文名称: 1-oleoyl-3-palmitoylglycerol
• 英文别名: (3-hexadecanoyloxy-2-hydroxypropyl) (Z)-octadec-9-enoate
• CAS: 3343-30-4
• 化学式: C₃₇H₇₀O₅
• 分子量: 594.96
• InChiKey: NBBXPULYBQASLG-ZCXUNETKSA-N

物化性质

• 熔点：
  39-41°C
• 沸点：
  655.5±25.0 °C(Predicted)
• 密度：
  0.932±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（少量溶解）、DMSO、乙酸乙酯（少量溶解）、甲醇（少量，加热）

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

安全信息

• 储存条件：
  -20°C，干燥，密封

反应信息

• 作为反应物：
  描述：

  外消旋1-油酰基-3-棕榈酰甘油 、 三甲基硅咪唑 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  二酸1,3-二酰基甘油的制备

  摘要：

  介绍了制备1,3-DAG的完整方法（包括合成，纯化和分析）。对于成功的综合项目，应考虑每个特定过程的优点和缺点，并应采取措施来弥补或平衡潜在的缺点。为此，我们描述了与以下相关的一些挑战：化学和酶催化的酰基甘油合成；重结晶和快速色谱法纯化部分酰基甘油；和DAG的薄层色谱（TLC）分离。对于这项工作，使用非酶法制备1-MAG中间体和随后的二酸1,3-DAG，而通过酶法制备单酸1,3-DAG。f。此外，DAG的TLC R f由两个主要因素决定：酰基链长度和位置异构性。有趣的是，虽然位置异构的作用众所周知，但酰基链长度在这些分离中的作用只是最近才被发现。

  DOI：

  10.1007/s11746-010-1625-7
• 作为产物：
  描述：

  甘油三油酸酯 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-3-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

• Therapeutic use of acyl glycerols and the nitrogen- and sulphur- containing analogues thereof
  申请人：Darteil Raphael

  公开号：US20060154984A1

  公开（公告）日：2006-07-13

  The invention relates to the use of acyl glycerols and the nitrogen- and sulfur-containing analogues thereof in the therapeutic field, particularly in human health. The inventive compounds have advantageous pharmacological properties and are particularly of use for the prevention or treatment of neurodegenerative diseases.

  这项发明涉及在治疗领域中使用酰基甘油及其氮和硫含量类似物，特别是在人类健康领域。这些创新化合物具有有益的药理特性，特别适用于预防或治疗神经退行性疾病。
• Therapeutic use of of acyglycerols and the nitrogen-and sulphur-containing analogues thereof
  申请人：Darteil Raphael

  公开号：US20060252827A1

  公开（公告）日：2006-11-09

  The invention relates to the use of acylglycerols and the nitrogen- and sulfur-containing analogues thereof in therapy, particularly for the treatment of cerebral ischemia. The invention further relates to methods for preparing said derivatives, novel compounds, in particular acylglycerols, the nitrogen- and sulfur-containing analogues thereof and methods for preparing same.

  这项发明涉及在治疗中使用酰基甘油和其氮和硫含量类似物，特别是用于治疗脑缺血。该发明还涉及制备这些衍生物的方法，新颖化合物，特别是酰基甘油，其氮和硫含量类似物以及制备它们的方法。
• Fatty acid compounds, preparation and uses thereof
  申请人：——

  公开号：US20040192908A1

  公开（公告）日：2004-09-30

  The invention concerns novel molecules, their preparation and their uses, in particular in the field of human and veterinary medicine and cosmetics. The inventive compounds are partly fatty acid derivatives and exhibit advantageous pharmacological and cosmetic properties. The invention also concerns various uses of said compounds, the pharmaceutical compositions containing them and methods for preparing them. The inventive compounds are useful in particular for preventing and/or treating dyslipidemiae, cardiovascular diseases, syndrome X, restenosis, diabetes, obesity, hypertension, certain cancers, dermatological diseases and in cosmetics, for fighting against skin aging and its effects notably against wrinkles and the like

  这项发明涉及新颖分子，它们的制备和用途，特别是在人类和兽医医学以及化妆品领域。这些创新化合物部分是脂肪酸衍生物，并具有有利的药理和化妆品特性。该发明还涉及所述化合物的各种用途，含有它们的药物组合物以及制备它们的方法。这些创新化合物特别适用于预防和/或治疗血脂异常、心血管疾病、X综合征、再狭窄、糖尿病、肥胖、高血压、某些癌症、皮肤病以及在化妆品中，用于对抗皮肤衰老及其影响，尤其是对抗皱纹等。
• Improved enzymatic synthesis route for highly purified diacid 1,3-diacylglycerols
  作者：Xiaosan Wang、Jianhui Xiao、Wanzhen Zou、Zhengyang Han、Qingzhe Jin、Xingguo Wang

  DOI：10.1016/j.procbio.2014.12.020

  日期：2015.3

  conditions for the synthesis of diacid 1,3-DAGs were evaluated. Under the selected conditions, the crude mixture contained 90.6% pure 1-oleoyl-3-palmitoylglycerol. After purification by two-step crystallization, pure 1-oleoyl-3-palmitoylglycerol was obtained with a yield of 83.6%. The main innovations were the use of enzymatic transesterification to obtain highly purified diacid 1,3-DAGs instead of using

  二酰基甘油（DAG）的营养价值和生物学功能引起了人们对其合成的广泛关注。在这项研究中，我们通过 1-单油酸甘油酯与作为酰基供体的脂肪酸乙烯基酯的酶促酯交换来改进二酸 1,3-DAG 的合成。首先，在 95% 乙醇中，以 Amberlyst 树脂为催化剂，通过 1,2-丙酮-3-油酰甘油的裂解制备 1-单油精，1,2-丙酮-3-油酰甘油是通过 1,2-丙酮甘油与油酸的酶促酯化反应合成的。其次，将纯化的 1-单油酸甘油酯与棕榈酸乙烯酯在脂肪酶存在下反应，得到 1-油酰-3-棕榈酰甘油。随后，评估了合成二酸 1,3-DAG 的反应条件。在选定的条件下，粗混合物含有 90.6% 纯度的 1-油酰-3-棕榈酰甘油。通过两步结晶纯化后，以83.6%的产率获得纯的1-油酰-3-棕榈酰甘油。主要创新是使用酶促酯交换来获得高度纯化的二酸 1,3-DAG，而不是使用化学合成，以及使用脂肪酸乙烯基酯作为酰基供体的不可逆反应而不是可逆反应。
• Discovery of FAHFA-Containing Triacylglycerols and Their Metabolic Regulation
  作者：Dan Tan、Meric Erikci Ertunc、Srihari Konduri、Justin Zhang、Antonio M. Pinto、Qian Chu、Barbara B. Kahn、Dionicio Siegel、Alan Saghatelian

  DOI：10.1021/jacs.9b00045

  日期：2019.6.5

  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.