1,3-dibutyroyl-2-oleoylglycerol

• 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: 1,3-dibutyroyl-2-oleoylglycerol
• 英文别名: 1,3-dibutyryl-2-oleoylglycerol；(Z)-2-(oleoyloxy)propane-1,3-diyl dibutyrate；9Z-octadecenoic acid, 2-(1-oxobutoxy)-1-[(1-oxobutoxy)methyl]ethyl ester；1,3-di(butanoyloxy)propan-2-yl (Z)-octadec-9-enoate
• 化学式: C₂₉H₅₂O₆
• 分子量: 496.728
• InChiKey: KRXPSEOQLIRGLX-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  35
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-dibutyroyl-2-oleoylglycerol 在 Rhizomucor miehei lipase 、 乙醇 作用下， 反应 24.0h， 以83%的产率得到2-十八烯酸单甘油酯
  参考文献：
  名称：

  Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols

  摘要：

  The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2 h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24 h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.101
• 作为产物：
  描述：

  正丁酸乙烯酯 在 4-二甲氨基吡啶 、 Candida antarctica lipase 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 1,3-dibutyroyl-2-oleoylglycerol
  参考文献：
  名称：

  Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols

  摘要：

  The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2 h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24 h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.101

文献信息

• Acidolysis between Triolein and Short-Chain Fatty Acid by Lipase in Organic Solvents
  作者：Wakako TSUZUKI

  DOI：10.1271/bbb.69.1256

  日期：2005.1

  Ten kinds of lipases were examined as biocatalysts for the incorporation of short-chain fatty acids (acetic, propionic, and butyric acids) into triolein in order to produce one kind of reduced-calorie structured lipids. Trans-esterification (acidolysis) was successfully done in n-hexane by several microbial lipases. Among them, lipase from Aspergillus oryzae was used to investigate the effects of incubation time, substrate molar ratio, and water content on acidolysis. Finally, more than 80% of triolein was incorporated by butyric acid (molar ratio of triolein to butyric acid, 1:10) in the dried n-hexane at 52 °C for 72 h. More than 90% of the products was monosubstituent, which was esterified with this short chain fatty acid at the 1-position of the glycerol moiety of triolein. These results suggest that A. oryzae lipase would be a powerful biocatalyst for the synthesis of low caloric oil, such as triacylglycerol containing a mixture of long- and short-chain aliphatic acids.

  研究了十种脂肪酶作为生物催化剂将短链脂肪酸（乙酸、丙酸和丁酸）掺入三烯酚，以生产一种热量降低的结构脂。几种微生物脂肪酶成功地在正己烷中完成了反酯化（酸解）。其中，利用黑曲霉的脂肪酶研究了培养时间、底物摩尔比和含水量对酸解的影响。结果表明，在 52 °C、72 h 的干燥正己烷中，80% 以上的三油酸被丁酸（三油酸与丁酸的摩尔比为 1:10）结合，90% 以上的产物为单取代基，在三油酸甘油分子的 1 位与这种短链脂肪酸酯化。这些结果表明，A. oryzae 脂肪酶是合成低热量油类（如含有长链和短链脂肪酸混合物的三酰甘油）的一种强有力的生物催化剂。
• DIETARY BUTYRATE
  申请人：SOCIETE DES PRODUITS NESTLE S.A.

  公开号：US20210038554A1

  公开（公告）日：2021-02-11

  Use of a compound having the formula (1), (2), (3), or (4) or combinations thereof, for providing a source of butyrate with improved organoleptic properties wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently a long chain fatty acid having between 16 and 20 carbons.

  使用化学式(1)，(2)，(3)或(4)或它们的组合，提供一种具有改善的感官特性的丁酸源，其中R1，R2，R3，R4，R5和R6分别是具有16到20个碳的长链脂肪酸。
• First Total Synthesis of 1,3-Diacetyl- and -Dibutyroyl-2-oleoylglycerol, Previously Isolated From Natural Products
  作者：J. Guillon、B. Lelong、M. Robba

  DOI：10.1211/146080899128734884

  日期：1999.5.1
• DIETARY BUTYRATE AND ITS USES
  申请人：SOCIETE DES PRODUITS NESTLE S.A.

  公开号：US20220195331A1

  公开（公告）日：2022-06-23

  1. Use of a compound having the formula (1) (2) (3) or (4) or combinations thereof, for providing a source of butyrate C with improved organoleptic properties wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently a long chain fatty acid having between 16 and 20 carbons for use in weight management
• Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols
  作者：Kyle M. Whitten、Alexandros Makriyannis、Subramanian K. Vadivel

  DOI：10.1016/j.tet.2012.04.101

  日期：2012.7

  The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2 h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24 h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved. (c) 2012 Elsevier Ltd. All rights reserved.