(2,2-二甲基-1,3-二氧环烷-4-基)辛酸甲酯 | 115228-29-0

• 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: (2,2-二甲基-1,3-二氧环烷-4-基)辛酸甲酯
• 英文名称: (2,2-dimethyl-1,3-dioxolane-4-yl)methyl caprylate
• 英文别名: (2,2-dimethyl-1,3-dioxolan-4-yl)methyl octanoate；1-octanoyl-2,3-O-isopropylidene-rac-glycerol；(+/-)-2,2-dimethyl-4-octanoyloxymethyl-[1,3]dioxolane；(+/-)-2,2-Dimethyl-4-octanoyloxymethyl-[1,3]dioxolan；2,3-(Dimethylmethyldioxy)propyl-caprylat
• CAS: 115228-29-0
• 化学式: C₁₄H₂₆O₄
• 分子量: 258.358
• InChiKey: GLKYAJSVVULZFA-UHFFFAOYSA-N

物化性质

• 熔点：
  27.4 °C
• 沸点：
  318.3±22.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (2,2-二甲基-1,3-二氧环烷-4-基)辛酸甲酯 在 Pseudomonas fluorecens Amano AK lipase 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 (S)-(+)-1,2-异亚丙基甘油
  参考文献：
  名称：

  Kinetic resolution of (R,S)-1,2-isopropylidene glycerol (solketal) ester derivatives by lipases

  摘要：

  A study on the enantioselective hydrolysis of (R,S)-1,2-isopropylidene glycerol (4-hydroxymethyl-2,2dimethyl-1,3-dioxolane, solketal) octanoate catalyzed by different lipases was carried out. Among them, Pseudomonas sp. lipase proved to be the most effective. It was shown that the ester bearing the longer octanoyl acyl chain is a more suitable substrate for this lipase compared to the acetate counterpart. By properly combining enzyme load, temperature and reaction time, either the (S)-alcohol or the remaining ester could be obtained in moderate to high selectivities. Ethyl acetate was found to be the best solvent for the kinetic resolutions effected by such lipase but our results show that toluene may prove useful. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.12.008
• 作为产物：
  描述：

  辛酸 、 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 二氯甲烷 为溶剂， 以93%的产率得到(2,2-二甲基-1,3-二氧环烷-4-基)辛酸甲酯
  参考文献：
  名称：

  Tuatara，Sphenodon punctatus泄殖腔分泌物的组成。

  摘要：

  研究了at（Sphenodon punctatus）的泄殖腔分泌物的亲脂性含量。分泌物的CH2Cl2提取物的GC / EI-MS分析表明，三酰基甘油是腺体的主要成分。发现十二种主要的中链脂肪酸以不同的组合与甘油结合，形成复杂的混合物。这些酸通过酯交换反应和随后的天然样品衍生化来鉴定，其结构通过合成验证。天然甘油酯主要包含以下三种酸：辛酸（A），（E）-和（Z）-辛-4-烯酸（B和C，分别），（4E，6Z）-辛基-4,6 -二烯二酸（丁二酸; D），（R）-2,6-二甲基庚酸（E），（R）-2,6-二甲基庚-5-烯酸（F），（Z）-dec-4-烯酸（G ），（4Z，7Z）-癸-4,7-二烯酸（H），（R）-3,7-二甲基辛-6-烯酸（I），（R）-4，8-二甲基非-7-烯酸（J），（2R，6S）-2,6,10-三甲基十一烷基-9-烯酸（K）和（2R，5E）-2,6,10-三甲基十一烯-5,9

  DOI：

  10.1002/cbdv.200800265

文献信息

• Oxygenated biofuels: Synthesis of fatty acid solketal esters with a mixture of sulfonated silica and (Bu4N)(BF4) catalyst
  作者：Sandro L. Barbosa、Pamela C. Lima、Wallans T.P. dos Santos、Stanlei I. Klein、Giuliano C. Clososki、Franco J. Caires

  DOI：10.1016/j.catcom.2018.12.005

  日期：2019.2

  Amorphous SiO2-SO3H [1] with a small surface area and 1.32-mmol H+/g was used for the one-step preparation of solketal from glycerol and acetone; a 20%-w/w catalyst mixture (10% [1] and 10% (Bu4N)(BF4) was found to be very efficient for the synthesis of disolketal ether and of oxygenated biofuels fatty acids solketal esters (FASEs), by direct esterification of the caprylic, lauric, stearic, oleic and

  用甘油和丙酮一步法制备表面积较小，1.32 mmol H + / g的无定形SiO 2 -SO 3 H [1] 。发现20％-w / w的催化剂混合物（10％[1]和10％（Bu 4 N）（BF 4））对于合成二油基醚和含氧生物燃料，脂肪酸，油基酯（FASEs）非常有效。通过将辛酸，月桂酸，硬脂酸，油酸和亚油酸与邻苯二酚在回流的甲苯中以4：1的酸：己二醛比例直接酯化，还可以定量获得乙酸丁二酯。
• Synthesis of the Fatty Esters of Solketal and Glycerol-Formal: Biobased Specialty Chemicals
  作者：Alvise Perosa、Andrea Moraschini、Maurizio Selva、Marco Noè

  DOI：10.3390/molecules21020170

  日期：——

  The caprylic, lauric, palmitic and stearic esters of solketal and glycerol formal were synthesized with high selectivity and in good yields by a solvent-free acid catalyzed procedure. No acetal hydrolysis was observed, notwithstanding the acidic reaction conditions.

  通过无溶剂酸催化方法以高选择性和高产率合成了醇缩酮和甘油缩甲醛的辛酸酯、月桂酸酯、棕榈酸酯和硬脂酸酯。尽管存在酸性反应条件，但未观察到缩醛水解。
• An Esterase with Superior Activity and Enantioselectivity towards 1,2-<i>O</i>-Isopropylideneglycerol Esters Obtained by Protein Design
  作者：Luis F. Godinho、Carlos R. Reis、Ronald van Merkerk、Gerrit J. Poelarends、Wim J. Quax

  DOI：10.1002/adsc.201200211

  日期：2012.11.12

  selected as targets for mutagenesis, in order to enhance YbfF activity and enantioselectivity towards IPG esters. Random mutagenesis at positions 25, 124, 185 and 235 yielded several best YbfF variants with enhanced activity and enantioselectivity towards IPG esters. The best YbfF mutant, W235I, exhibited a 2-fold higher enantioselectivity than wild-type YbfF, with an E=38 for IPG butyrate and an E=77

  的大肠杆菌酯酶YbfF显示高朝1,2-活性ø -isopropylideneglycerol（IPG）丁酸酯和辛酸IPG，和更喜欢ř这些底物对映体，产生š超过IPG产物的对映体。为了提高该酶用于动力学拆分IPG的外消旋酯的潜力，非常需要提高活性和对映选择性。R的分子对接两种IPG酯的对映体都进入YbfF的活性位点，从而鉴定了近端的YbfF活性位点残基。选择四个残基（25、124、185和235）作为诱变目标，以增强YbfF活性和对IPG酯的对映选择性。在位置25、124、185和235处进行随机诱变产生了几种最佳的YbfF变体，具有增强的活性和对IPG酯的对映选择性。最好YbfF突变体，W235I，表现出2倍与更高的对映选择性比野生型YbfF，Ë用于IPG丁酸和= 38 È对于IPG辛酸酯＝ 77。分子对接实验进一步支持了实验显示的增强的对映选择性，并提供了该氨基酸取代对YbfF活性位点的
• pH-indicator based assay for selective enzymes
  申请人：ThermoGen, Inc.

  公开号：US20020177180A1

  公开（公告）日：2002-11-28

  Provided herein is a method for the quantitative screening of hydrolase for desired substrate activity using pH indicators which are sensitive to the release of protons from a chemical reaction in a reaction mixture. The method comprises selecting buffer and indicator conditions such that both have the same affinity for protons such that the relative amount of buffer protonated is proportional to the amount of indicator protonated as the pH of the reaction mixture shifts. A reaction mixture is then prepared comprising a buffer, indicator, hydrolase to be tested, and desired substrate to be tested, allowing the hydrolase to react with the substrate. The reaction is monitored by detection of change in color of the reaction mixture, determined by the affect of the reaction on the indicator.

  本文提供了一种利用 pH 指示剂定量筛选水解酶所需底物活性的方法，pH 指示剂对反应混合物中化学反应释放的质子敏感。该方法包括选择缓冲液和指示剂条件，使两者对质子具有相同的亲和力，从而使缓冲液质子化的相对量与指示剂质子化的量成比例，随着反应混合物 pH 值的变化而变化。然后制备由缓冲液、指示剂、待测水解酶和所需底物组成的反应混合物，让水解酶与底物发生反应。通过检测反应混合物的颜色变化来监测反应，颜色变化由反应对指示剂的影响决定。
• 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.