(2,2-dimethyl-1,3-dioxolane-4-yl)methyl caprate | 120294-04-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2,2-dimethyl-1,3-dioxolane-4-yl)methyl caprate
• 英文别名: decanoyl solketal；Decanoic acid, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester；(2,2-dimethyl-1,3-dioxolan-4-yl)methyl decanoate
• CAS: 120294-04-4
• 化学式: C₁₆H₃₀O₄
• 分子量: 286.412
• InChiKey: KRBSCYNTGIRIAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,2-dimethyl-1,3-dioxolane-4-yl)methyl caprate 生成 (R)-decanoyl solketal
  参考文献：
  名称：

  Resolution of Solketal by Enzymatic Hydrolysis of Its Decanoyl Ester

  摘要：

  (S) and (R)-solketal useful synthetic intermediates were prepared from the corresponding racemic decanoyl ester by an enantioselective hydrolysis mediated by porcine pancreas lipase in presence of acetonitrile.

  DOI：

  10.1080/00397919508015420
• 作为产物：
  描述：

  正癸酸 、 丙酮缩甘油 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以100%的产率得到(2,2-dimethyl-1,3-dioxolane-4-yl)methyl caprate
  参考文献：
  名称：

  New Synthetic Strategies Toward Pure Two-Component Triglycerides

  摘要：

  纯双组分甘油三酯是通过新的合成策略制备的，这些策略涉及甘油醛酸酯的酰基水解裂解。

  DOI：

  10.1055/s-1999-2936

文献信息

• Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids
  作者：Alaumy Joshi、Minhaj Shaikh、Shubham Singh、Abinaya Rajendran、Amol Mhetre、Siddhesh S. Kamat

  DOI：10.1074/jbc.ra118.005640

  日期：2018.11

  Polyneuropathy, hearing loss, ataxia, retinitis pigmentosa, and cataract (PHARC) is a rare genetic human neurological disorder caused by null mutations to the Abhd12 gene, which encodes the integral membrane serine hydrolase enzyme ABHD12. Although the role that ABHD12 plays in PHARC is understood, the thorough biochemical characterization of ABHD12 is lacking. Here, we report the facile synthesis of mono-1-(fatty)acyl-glycerol lipids of varying chain lengths and unsaturation and use this lipid substrate library to biochemically characterize recombinant mammalian ABHD12. The substrate profiling study for ABHD12 suggested that this enzyme requires glycosylation for optimal activity and that it has a strong preference for very-long-chain lipid substrates. We further validated this substrate profile against brain membrane lysates generated from WT and ABHD12 knockout mice. Finally, using cellular organelle fractionation and immunofluorescence assays, we show that mammalian ABHD12 is enriched on the endoplasmic reticulum membrane, where most of the very-long-chain fatty acids are biosynthesized in cells. Taken together, our findings provide a biochemical explanation for why very-long-chain lipids (such as lysophosphatidylserine lipids) accumulate in the brains of ABHD12 knockout mice, which is a murine model of PHARC.
• Study of the Effect of DATEM. 1. Influence of Fatty Acid Chain Length on Rheology and Baking
  作者：Peter Köhler、Werner Grosch

  DOI：10.1021/jf980891i

  日期：1999.5.1

  To answer the question of which fatty acid residue is the most effective, diacetyltartaric esters of monoglycerides (DATEMs) with fatty acids of chain lengths 6:0-20:0 were synthesized. The activity of synthesized DATEMs and commercial DATEM products was studied by means of rheological methods and a microscale baking test with 10 g of flour. Variation of the acyl residue from 6:0 to 22:0 showed that stearic acid (18:0) had the best effect on the baking activity of DATEM (loaf volume increased by 62%). DATEMs containing unsaturated fatty acids (18:1, 18:2) or DATEMs produced from diacylglycerols instead of monoacylglycerols showed a slight increase of the loaf volumes. A slight effect of DATEM on the rheology of dough was observed. However, much greater was the effect on the gluten isolated from doughs prepared with DATEM. The resistance of gluten to extension was increased after the addition of increasing amounts of DATEM (0.1-0.5%). Within the series of DATEMs derived from the homologous series of monoacylglycerols the product based on glycerol monostearate (18:0) showed a maximum increase of the gluten resistance.
• Lipase-mediated desymmetrization of glycerol with aromatic and aliphatic anhydrides
  作者：Daniela I. Batovska、Shuichirou Tsubota、Yasuo Kato、Yasuhisa Asano、Makoto Ubukata

  DOI：10.1016/j.tetasy.2004.09.033

  日期：2004.11

  Chirazyme L-2 (Candida antarctica) catalyzed esterification of glycerol with aromatic and aliphatic anhydrides in 1,4-dioxane is described. All the aromatic monoacylglycerols (MAGs) were produced as (R)-enantiomers, while aliphatic MAGs were obtained either as racemic mixtures or the (S)-enantiomers. The influence of substituted aromatic rings, chain length, and presence of a conjugated double bond in the acyl donor moiety on the enantiotopic selectivity as well as the efficiency of the enzyme was studied. (C) 2004 Elsevier Ltd. All rights reserved.
• New Synthetic Strategies Toward Pure Two-Component Triglycerides
  作者：Jean-Louis Gras、Jean-François Bonfanti

  DOI：10.1055/s-1999-2936

  日期：1999.11

  Pure two-component triglycerides were prepared following new synthetic strategies that involve the acylolytic cleavage of glycerol acetals.

  纯双组分甘油三酯是通过新的合成策略制备的，这些策略涉及甘油醛酸酯的酰基水解裂解。
• Resolution of Solketal by Enzymatic Hydrolysis of Its Decanoyl Ester
  作者：Anh Nga Phung、Jacques Braun、François Le Goffic

  DOI：10.1080/00397919508015420

  日期：1995.6

  (S) and (R)-solketal useful synthetic intermediates were prepared from the corresponding racemic decanoyl ester by an enantioselective hydrolysis mediated by porcine pancreas lipase in presence of acetonitrile.