2-arachidonyl-glycerol | 35474-99-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 2-arachidonyl-glycerol
• 英文别名: 1-arachidonoylglycerol；1-AG；2-arachidonoyl glycerol；1-Monoarachidin；Glyceryl arachidonate；2,3-dihydroxypropyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 35474-99-8
• 化学式: C₂₃H₃₈O₄
• 分子量: 378.552
• InChiKey: DCPCOKIYJYGMDN-DOFZRALJSA-N

物化性质

• 熔点：
  81.5 °C
• 沸点：
  508.6±50.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• LogP：
  6.286 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  oleoyl-CoA(4-) 、 2-arachidonyl-glycerol 生成 1-Arachidonoyl-2-oleoylglycerol 、 coenzyme A
  参考文献：
  名称：

  MGAT2, a Monoacylglycerol Acyltransferase Expressed in the Small Intestine

  摘要：

  Acyl CoA:monoacylglycerol acyltransferase (MGAT) catalyzes the synthesis of diacylglycerol, a precursor of triacylglycerol. In the intestine, MGAT plays a major role in the absorption of dietary fat by catalyzing the resynthesis of triacylglycerol in enterocytes. This resynthesis is required for the assembly of lipoproteins that transport absorbed fat to other tissues. Despite intense efforts, a gene encoding an intestinal MGAT has not been found. Previously, we identified a gene encoding MGAT1, which in mice is expressed in the stomach, kidney, adipose tissue, and liver but not in the intestine. We now report the identification of homologous genes in humans and mice encoding MGAT2. Expression of the MGAT2 cDNA in either insect or mammalian cells markedly increased MGAT activity in cell membranes. MGAT activity was proportional to the level of MGAT2 protein expressed, and the amount of diacylglycerol produced depended on the concentration of MGAT substrates (fatty acyl CoA or monoacylglycerol). In humans, the MGAT2 gene is highly expressed in the small intestine, liver, stomach, kidney, colon, and white adipose tissue; in mice, it is expressed predominantly in the small intestine. The discovery of the MGAT2 gene will facilitate studies to determine the functional role of MGAT2 in fat absorption in the intestine and to determine whether blocking MGAT activity in enterocytes is a feasible approach to inhibit fat absorption and treat obesity.

  DOI：

  10.1074/jbc.m301633200
• 作为产物：
  描述：

  花生四烯酸 在 草酰氯 、 B-氯-1,2-苯二酚硼烷 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 2-arachidonyl-glycerol
  参考文献：
  名称：

  大麻素受体的内源性配体2-花生四烯酰基甘油的简化化学和放射化学合成

  摘要：

  内源性大麻素已成为一类新型的脂质介体，在中枢神经系统和周围神经系统中起着多种作用。几项研究已确定2-花生四烯酰基甘油（2-AG）是大麻素受体的主要内源性激动剂。在此，报告了2-AG的化学合成及其tri标记衍生物的合成。这些未标记和放射性标记的化合物是揭示2-AG在各种细胞和组织中的某些代谢途径和生物活性的合适工具。

  DOI：

  10.1016/j.tetlet.2004.02.045

文献信息

• [EN] PROCESS FOR INCREASING THE STABILITY OF A COMPOSITION COMPRISING POLYUNSATURATED OMEGA-6 FATTY ACIDS<br/>[FR] PROCÉDÉ D'AUGMENTATION DE LA STABILITÉ D'UNE COMPOSITION COMPRENANT DES ACIDES GRAS OMÉGA-6 POLYINSATURÉS
  申请人：EVONIK DEGUSSA GMBH

  公开号：WO2016102316A1

  公开（公告）日：2016-06-30

  The present invention relates to processes for increasing the stability of compositions comprising polyunsaturated omega-6 fatty acids against oxidation. The processes comprise the following steps: (i) providing a starting composition comprising at least one polyunsaturated omega-6 fatty acid component; (ii) providing a lysine composition; (iii) admixing aqueous, aqueous-alcoholic or alcoholic solutions of starting composition and lysine composition, and subjecting resulting admixture to spray drying conditions subsequently, thus forming a solid product composition comprising at least one salt of a cation derived from lysine with an anion derived from a polyunsaturated omega-6 fatty acid; the product composition exhibiting a solvent content SC selected from the following: SC < 5 wt%, SC < 3 wt%, SC < 1 wt%, SC < 0.5 wt%. Compositions obtainable by such spray drying processes and use of such compositions for the manufacture of food, nutritional and pharmaceutical products are further comprised by the present invention.

  本发明涉及增加含有多不饱和ω-6脂肪酸的组合物抗氧化稳定性的过程。该过程包括以下步骤：(i)提供包含至少一种多不饱和ω-6脂肪酸成分的起始组合物；(ii)提供赖氨酸组合物；(iii)混合起始组合物和赖氨酸组合物的水、水醇或醇溶液，并随后将所得混合物暴露于喷雾干燥条件，从而形成包含至少一种来自赖氨酸阳离子和来自多不饱和ω-6脂肪酸阴离子的盐的固体产品组合物；所述产品组合物具有以下所选的溶剂含量SC：SC < 5 wt%，SC < 3 wt%，SC < 1 wt%，SC < 0.5 wt%。通过这种喷雾干燥过程获得的组合物以及利用这种组合物制造食品、营养和制药产品的方法也包含在本发明中。
• [EN] HEXAFLUOROISOPROPYL CARBAMATE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION<br/>[FR] DÉRIVÉS DE CARBAMATE D'HEXAFLUOROISOPROPYLE, LEUR PRÉPARATION ET LEUR APPLICATION THÉRAPEUTIQUE
  申请人：SANOFI SA

  公开号：WO2011151808A1

  公开（公告）日：2011-12-08

  The invention relates to hexafluoroisopropyl carbamate derivatives of general formula (I): wherein R, Z, A, m and n as defined in the description, in the form of the base or of an addition salt with an acid. The compounds can be used as inhibitors of the enzyme MGL (monoacyl glycerol lipase).

  该发明涉及一般式（I）的六氟异丙基氨甲酸酯衍生物，其中R、Z、A、m和n如描述中所定义，以盐基形式或与酸的加成盐形式存在。这些化合物可用作酶MGL（单酰基甘油脂酶）的抑制剂。
• Simultaneous determination of 2-arachidonoylglycerol, 1-arachidonoylglycerol and arachidonic acid in mouse brain tissue using liquid chromatography/tandem mass spectrometry
  作者：Mei-Yi Zhang、Ying Gao、Joan Btesh、Natasha Kagan、Edward Kerns、Tarek A. Samad、Pranab K. Chanda

  DOI：10.1002/jms.1701

  日期：2010.2

  Endocannabinoids (ECs), such as anandamide (AEA) and 2-arachidonoylglycerol (2-AG), modulate a number of physiological processes, including pain, appetite and emotional state. Levels of ECs are tightly controlled by enzymatic biosynthesis and degradation in vivo. However, there is limited knowledge about the enzymes that terminate signaling of the major brain EC, 2-AG. Identification and quantification of 2-AG, 1-AG and arachidonic acid (AA) is important for studying the enzymatic hydrolysis of 2-AG. We have developed a sensitive and specific quantification method for simultaneous determination of 2-AG, 1-AG and AA from mouse brain and adipose tissues by liquid chromatography/tandem mass spectrometry (LC/MS/MS) using a simple brain sample preparation method. The separations were carried out based on reversed phase chromatography. Optimization of electrospray ionization conditions established the limits of detection (S/N = 3) at 50, 25 and 65 fmol for 2-AG, 1-AG and AA, respectively. The methods were selective, precise (%R.S.D. < 10%) and sensitive over a range of 0.02–20, 0.01–10 and 0.05–50 ng/mg tissue for 2-AG, 1-AG and AA, respectively. The quantification method was validated with consideration of the matrix effects and the mass spectrometry (MS) responses of the analytes and the deuterium labeled internal standard (IS). The developed methods were applied to study the hydrolysis of 2-AG from mouse brain extracts containing membrane bound monoacylglycerol lipase (MAGL), and to measure the basal levels of 2-AG, 1-AG and AA in mouse brain and adipose tissues. Copyright © 2009 John Wiley & Sons, Ltd.

  内源性大麻素（ECs），如阿奈酰胺（AEA）和2-花生四烯酸甘油酯（2-AG），调节多种生理过程，包括疼痛、食欲和情绪状态。ECs的水平在体内通过酶的生物合成和降解被严格控制。然而，关于终止主要脑内EC（2-AG）信号传导的酶的知识仍然有限。鉴定和定量2-AG、1-AG和花生四烯酸（AA）对于研究2-AG的酶水解非常重要。我们开发了一种灵敏且特异的定量方法，通过液相色谱/串联质谱（LC/MS/MS）利用简单的脑样本制备方法，能够同时测定小鼠脑和脂肪组织中的2-AG、1-AG和AA。分离是基于反相色谱进行的。电喷雾离子化条件的优化确定了检测限（信噪比=3），2-AG、1-AG和AA的检测限分别为50、25和65 fmol。这些方法在2-AG、1-AG和AA的范围内具有选择性、精确性（相对标准偏差<10%）和灵敏性，分别为0.02–20、0.01–10和0.05–50 ng/mg组织。定量方法经过考虑基质效应和分析物及相对氘标记内部标准（IS）的质谱响应进行了验证。这些方法应用于研究小鼠脑提取物中含膜结合单酰基甘油脂肪酶（MAGL）的2-AG水解，并测定小鼠脑和脂肪组织中2-AG、1-AG和AA的基础水平。版权 © 2009 John Wiley & Sons, Ltd.
• [EN] ABHD6 ANTAGONISTS FOR PROMOTING BROWNING OF WHITE ADIPOSE TISSUE AND BROWN ADIPOSE TISSUE FUNCTIONALITY<br/>[FR] ANTAGONISTES ABHD6 FAVORISANT LE BRUNISSEMENT DES TISSUS ADIPEUX BLANCS ET FONCTIONNALITÉ DES TISSUS ADIPEUX BRUNS
  申请人：VAL CHUM LTD PARTNERSHIP

  公开号：WO2015127559A1

  公开（公告）日：2015-09-03

  The present disclosure relates to compounds of formula I : compositions containing same and methods for treating or preventing a condition associated with brown adipose tissue dysfunction in a subject and/or for converting white adipose tissue into beige/brite adipose tissue.

  本公开涉及式I的化合物：包含相同化合物的组合物，以及用于治疗或预防与棕色脂肪组织功能障碍有关的疾病状态的方法，以及将白色脂肪组织转化为褐色/亮褐色脂肪组织的方法。
• TRIAZOLOPYRIDINE CARBOXAMIDE DERIVATIVES AND TRIAZOLOPYRIMIDINE CARBOXAMIDE DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF
  申请人：EVEN Luc

  公开号：US20100041670A1

  公开（公告）日：2010-02-18

  The invention relates to the triazolopyridine carboxamide derivatives and triazolopyrimidine carboxamide derivatives of general formula (I): Wherein X, A, R 1 and R 2 are as defined herein. The invention further relates to preparation methods and therapeutic use thereof.

  本发明涉及通式(I)的三唑并吡啶羧酰胺衍生物和三唑并嘧啶羧酰胺衍生物，其中X，A，R1和R2如本文所定义。本发明还涉及其制备方法和治疗用途。