13-顺式维生素A棕榈酸酯 | 26771-20-0

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 13-顺式维生素A棕榈酸酯
• 英文名称: 9-Palmitoyloxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraen-(1.3t.5t.7c)
• 英文别名: O-Palmitoyl-[7t,9t,11t,13c]retinol；13-cis-Vitamin A palmitate；[(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] hexadecanoate
• CAS: 26771-20-0
• 化学式: C₃₆H₆₀O₂
• 分子量: 524.871
• InChiKey: VYGQUTWHTHXGQB-ILAPVCSWSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  38
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

制备方法与用途

生物活性

13-cis-Vitamin A palmitate (13-cis-Retinyl palmitate) 是玉米片中维生素 A 棕榈酸酯形成的 13-顺式异构体。13-cis-Vitamin A palmitate 的生物活性为全反式维生素 A 棕榈酸酯的 75％，全反式维生素 A 棕榈酸酯是维生素 A 最具生物活性的形式。

靶点

Human Endogenous Metabolite

体外研究

Of the total vitamin A palmitate content, 5% is the 13-cis and less than 1% is the 9-cis with 94% being all-trans.

反应信息

• 作为产物：
  描述：

  吡啶 、 13-顺式视黄醇 、 棕榈酰氯 在 1,2-二氯乙烷 作用下， 生成 13-顺式维生素A棕榈酸酯
  参考文献：
  名称：

  新维生素A

  摘要：

  DOI：

  10.1021/ja01193a037

文献信息

• The triacylglycerol synthesis enzyme DGAT1 also catalyzes the synthesis of diacylglycerols, waxes, and retinyl esters
  作者：Chi-Liang Eric Yen、Mara Monetti、Betty J. Burri、Robert V. Farese

  DOI：10.1194/jlr.m500036-jlr200

  日期：2005.7

  The final step of triacylglycerol biosynthesis is catalyzed by acyl CoA:diacylglycerol acyltransferase (DGAT) enzymes. The two known DGATs, DGAT1 and DGAT2, are encoded by unrelated genes. Although both DGAT1 and DGAT2 knockout mice have reduced tissue triacylglycerol contents, they have disparate phenotypes, prompting us to investigate whether the two enzymes have unrecognized functional differences. We now report that DGAT1 exhibits additional acyltransferase activities in vitro, including those of acyl CoA: monoacylglycerol acyltransferase (MGAT), wax monoester and wax diester synthases, and acyl CoA: retinol acyltransferase (ARAT), which catalyze the synthesis of diacylglycerols, wax esters, and retinyl esters, respectively. These activities were demonstrated in in vitro assays with membranes from insect cells or homogenates from COS7 cells overexpressing DGAT1. Wax synthase and ARAT activities were also demonstrated in intact COS7 cells expressing DGAT1. Additionally, cells and tissues from DGAT1-deficient mice exhibited reduced ARAT activity, and the mice had increased levels of unesterified retinol in their livers on a high-retinol diet. Our findings indicate that DGAT1 can utilize a variety of acyl acceptors as substrates in vitro and suggest that these activities may be relevant to the in vivo functions of DGAT1. - Yen, C-L. E., M. Monetti, B. J. Burri, and R. V. Farese, Jr. The triacylglycerol synthesis enzyme DGAT1 also catalyzes the synthesis of diacylglycerols, waxes, and retinyl esters.