2-oxiranylmethyl 2-ethyl-2,5-dimethylhexanoate | 253784-95-1

• 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-oxiranylmethyl 2-ethyl-2,5-dimethylhexanoate
• 英文别名: C₁₀GE；Neodecanoic acid, glycidyl ester；oxiran-2-ylmethyl 2-ethyl-2,5-dimethylhexanoate
• CAS: 253784-95-1
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: DHEHEJGXTUCSQF-UHFFFAOYSA-N

物化性质

• 沸点：
  286.9±13.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 2-oxiranylmethyl 2-ethyl-2,5-dimethylhexanoate 在 glutathione S-transferase 作用下， 以 二甲基亚砜 为溶剂， 生成 2-Ethyl-2,5-dimethyl-hexanoic acid 3-[(R)-2-((S)-4-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-2-hydroxy-propyl ester
  参考文献：
  名称：

  Metabolic inactivation of 2-oxiranylmethyl 2-ethyl2,5-dimethylhexanoate (C₁₀GE) in skin, lung and liver of human, rat and mouse

  摘要：

  1. The inactivation of 2-oxiranylmethyl 2-ethyl-2,5-dimethylhexanoate (C(10)GE), one of the most abundant isomers of the epoxy-resin Cardura(R) E-10 glycidyl ester, was studied in subcellular fractions of human, C3H mouse and F344 rat liver, lung and skin.2. C(10)GE is chemically very stable and resistant to aqueous hydrolysis, but it was rapidly metabolized in both cytosolic and microsomal fractions of all organs by epoxide hydrolase (EH)-catalysed hydrolysis of the epoxide moiety as well as carboxylesterase (CE)-catalysed hydrolysis of the ester bond. In cytosol the epoxide group was also effciently conjugated with glutathione, catalysed by glutathione S-transferase (GST), but this conjugation was much less important than hydrolysis in human as well as rodent samples. Although CE-catalysed hydrolysis of C(10)GE would theoretically give rise to the formation of glycidol, a directly acting mutagen, it is highly unlikely that any significant level of glycidol would occur in vivo since reported rates of inactivation of glycidol exceed the total rate of hydrolysis of C(10)GE.3. The overall rates of inactivation in vitro decreased in the following order: mouse, rat > human. Scaling of the data in vitro to clearances in vivo suggests that the detoxifying capacity in the rodents is similar and about an order of magnitude greater than in human. Nevertheless, the rate of inactivation is 2-3 orders of magnitude greater than for simple epoxides such as butadiene monoxide and about one order of magnitude higher than for the diglycidyl ether of bisphenol A (BADGE).4. The transdermal penetration and metabolism of [C-14]-C(10)GE was studied in fresh full-thickness mouse, and dermatomized human and rat skin. Of the total radioactivity applied on the skin, only 0.24+/-0.06 (SD), 1.8 +/- 0.2 and 6.8 +/- 0.6 % penetrated through human, mouse and rat skin respectively. The corresponding apparent skin permeability constants were 0.81, 6.42 and 26.4 x 10(-6) cm/h.5. During transdermal penetration, [C-14]-C(10)GE was extensively hydrolysed to the corresponding diol and the free acid. Only 0.01, 0.11 and 0.21 % of the applied dose was absorbed unchanged through the human, mouse and rat skin respectively.

  DOI：

  10.1080/004982599238065
• 作为产物：
  描述：

  2-甲基丁酸 在 sodium hydride 作用下， 以 正己烷 为溶剂， 反应 1.0h， 生成 2-oxiranylmethyl 2-ethyl-2,5-dimethylhexanoate
  参考文献：
  名称：

  Metabolic inactivation of 2-oxiranylmethyl 2-ethyl2,5-dimethylhexanoate (C₁₀GE) in skin, lung and liver of human, rat and mouse

  摘要：

  1. The inactivation of 2-oxiranylmethyl 2-ethyl-2,5-dimethylhexanoate (C(10)GE), one of the most abundant isomers of the epoxy-resin Cardura(R) E-10 glycidyl ester, was studied in subcellular fractions of human, C3H mouse and F344 rat liver, lung and skin.2. C(10)GE is chemically very stable and resistant to aqueous hydrolysis, but it was rapidly metabolized in both cytosolic and microsomal fractions of all organs by epoxide hydrolase (EH)-catalysed hydrolysis of the epoxide moiety as well as carboxylesterase (CE)-catalysed hydrolysis of the ester bond. In cytosol the epoxide group was also effciently conjugated with glutathione, catalysed by glutathione S-transferase (GST), but this conjugation was much less important than hydrolysis in human as well as rodent samples. Although CE-catalysed hydrolysis of C(10)GE would theoretically give rise to the formation of glycidol, a directly acting mutagen, it is highly unlikely that any significant level of glycidol would occur in vivo since reported rates of inactivation of glycidol exceed the total rate of hydrolysis of C(10)GE.3. The overall rates of inactivation in vitro decreased in the following order: mouse, rat > human. Scaling of the data in vitro to clearances in vivo suggests that the detoxifying capacity in the rodents is similar and about an order of magnitude greater than in human. Nevertheless, the rate of inactivation is 2-3 orders of magnitude greater than for simple epoxides such as butadiene monoxide and about one order of magnitude higher than for the diglycidyl ether of bisphenol A (BADGE).4. The transdermal penetration and metabolism of [C-14]-C(10)GE was studied in fresh full-thickness mouse, and dermatomized human and rat skin. Of the total radioactivity applied on the skin, only 0.24+/-0.06 (SD), 1.8 +/- 0.2 and 6.8 +/- 0.6 % penetrated through human, mouse and rat skin respectively. The corresponding apparent skin permeability constants were 0.81, 6.42 and 26.4 x 10(-6) cm/h.5. During transdermal penetration, [C-14]-C(10)GE was extensively hydrolysed to the corresponding diol and the free acid. Only 0.01, 0.11 and 0.21 % of the applied dose was absorbed unchanged through the human, mouse and rat skin respectively.

  DOI：

  10.1080/004982599238065

文献信息

• MULTI-AZIRIDINE COMPOUND
  申请人：DSM IP ASSETS B.V.

  公开号：US20210332031A1

  公开（公告）日：2021-10-28

  The present invention relates to a multi-aziridine compound having: a) from 2 to 6 of the following structural units (A): (A) whereby R′, R″, R 1 , R 2 , R 3 and R 4 are as defined herein m is an integer from 1 to 6; b) one or more linking chains wherein each one of these linking chains links two of the structural units A; and c) a molecular weight in the range from 600 Daltons to 5000 Daltons. The multi-aziridine compound can be used for example for crosslinking of for example carboxylic acid functional polymers dissolved and/or dispersed in an aqueous medium.

  本发明涉及一种多环氮丙烷化合物，其具有：a) 2至6个以下结构单元（A）：（A），其中R′、R″、R1、R2、R3和R4如本文所定义，m为1至6的整数；b) 一个或多个连接链，其中每个连接链连接两个结构单元A；以及c) 分子量在600道尔顿至5000道尔顿范围内。该多环氮丙烷化合物可用于例如交联溶解和/或分散在水性介质中的羧酸官能聚合物。
• TITANIUM-BASED CATALYST FOR VITRIMER RESINS OF EPOXY/ANHYDRIDE TYPE
  申请人：ARKEMA FRANCE

  公开号：US20170044307A1

  公开（公告）日：2017-02-16

  The present invention relates to a composition containing, besides a thermosetting resin of epoxy type and a hardener of anhydride type, at least one catalyst comprising an organometallic titanium complex. This composition enables the manufacture of vitrimer resins, that is to say resins that can be deformed in the thermoset state. It also relates to a kit for manufacturing this composition, an object obtained from this composition and a kit for manufacturing this object. Another subject of the invention relates to an organometallic titanium complex corresponding to the structure titanium bis(3-phenoxy-1,2-propane dioxide) (Ti(PPD) 2 ), and the use thereof as vitrimer effect catalyst in systems based on epoxy resin and on hardener of anhydride type.

  本发明涉及一种组合物，除了包含一种环氧型热固性树脂和一种酸酐型固化剂外，还包含至少一种催化剂，其中该催化剂包括一种有机金属钛络合物。该组合物使得可以制备玻璃转变树脂，即能在热固态下变形的树脂。此外，本发明还涉及一种用于制备该组合物的工具包、从该组合物获得的物体以及用于制造该物体的工具包。本发明的另一个主题涉及一种与结构钛双(3-苯氧基-1,2-丙二醇)（Ti(PPD)2）相对应的有机金属钛络合物，以及其作为基于环氧树脂和酸酐型固化剂体系中玻璃转变效应催化剂的用途。
• [EN] PROCESS FOR PREPARING GLYCIDYL ESTERS OF BRANCHED MONOCARBOXYLIC ACIDS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ESTERS GLYCIDYLIQUES D'ACIDES MONOCARBOXYLIQUES RAMIFIÉS
  申请人：MOMENTIVE SPECIALTY CHEMICALS RES BELGIUM SA

  公开号：WO2010142396A1

  公开（公告）日：2010-12-16

  Accordingly, the invention relates to a process for the preparation of a glycidyl ester of a branched monocarboxylic acid by reacting an aliphatic monocarboxylic acid of the formula R1R2R3COOH, wherein R1, R2, and R3 each independently represent an alkyl radical of normal or branched structure containing from 1 to 20 carbon atoms and an epoxyalkyl halide containing from 3 to 13 carbon atoms in the presence of a catalyst, wherein a greater than stoichiometric amount of epoxyalkyl halide is reacted with the acid (e.g., preferably in the molar ratio of epoxyalkyl halide to acid that is in the range of from 1.02:1 to 1.50:1) to form an intermediate reaction product comprising a halohydrin, the epoxyalkyl halide is added to the acid with appropriate cooling of the reactants and/or the reaction mixture to keep the temperature of the reaction mixture below 80°C, whereupon the epoxyalkyl halide and the acid are reacted at a temperature below 80°C (preferably in the range of from 55 to 75°C) for a time sufficient to reduce the amount of acid to no more than 2 wt% but no less than 0.1 wt% calculated on the initial amount of acid, optionally removing any excess epoxyalkyl halide from the reaction product prior to the ring closure reaction, subjecting the reaction product to a ring closure reaction (DHC) and optionally to one or more after treatments (ADHC) for removal of any remaining halo functionality.

  因此，本发明涉及一种制备支链单羧酸的环氧丙酯的方法，通过在催化剂的存在下反应式R1R2R3COOH的脂肪族单羧酸，其中R1、R2和R3各自独立地表示含有1至20个碳原子的正常或支链结构的烷基基团，以及含有3至13个碳原子的环氧烷基卤化物，反应过量的环氧烷基卤化物与酸反应（例如，优选摩尔比范围为1.02:1至1.50:1的环氧烷基卤化物与酸的比例），形成包含卤水合物的中间反应产物，环氧烷基卤化物在适当冷却反应物和/或反应混合物的情况下加入酸中，以保持反应混合物的温度低于80°C，然后在低于80°C的温度下（优选范围为55至75°C）反应环氧烷基卤化物和酸的时间足以将酸的量减少到不超过初始酸量的2重量％但不少于0.1重量％，可在环合反应之前从反应产物中去除任何多余的环氧烷基卤化物，将反应产物进行环合反应（DHC）和可选地进行一种或多种后处理（ADHC），以去除任何剩余的卤功能。
• POLYESTER COMPOSITION, ITS PREPARATION METHOD, AND POLYESTER COMPOSITION FILM COMPRISING THE SAME
  申请人：Chang Chun Plastics Co., Ltd.

  公开号：EP4023697A1

  公开（公告）日：2022-07-06

  Provided are a polyester composition, its preparation method, and a polyester composition film comprising the same. The polyester composition comprises an aliphatic-aromatic copolyester modified with a monoepoxy compound. The acid value of the polyester composition is less than 25 meq KOH/kg. The polyester composition has great stability under conditions of high temperature and humidity. The polyester composition film made of the polyester composition has merits of few fish eyes and improved appearance, which is beneficial to product application.

  本文提供了一种聚酯组合物、其制备方法以及由其构成的聚酯组合物薄膜。该聚酯组合物包括用单环氧化合物改性的脂肪族-芳香族共聚聚酯。聚酯组合物的酸值小于 25 meq KOH/kg。该聚酯组合物在高温高湿条件下具有极高的稳定性。用该聚酯组合物制成的聚酯组合物薄膜具有鱼眼少、外观更好的优点，有利于产品应用。
• Titanium-based catalyst for vitrimer resins of epoxy/anhydride type
  申请人：ARKEMA FRANCE

  公开号：US10155842B2

  公开（公告）日：2018-12-18

  The present invention relates to a composition containing, besides a thermosetting resin of epoxy type and a hardener of anhydride type, at least one catalyst comprising an organometallic titanium complex. This composition enables the manufacture of vitrimer resins, that is to say resins that can be deformed in the thermoset state. It also relates to a kit for manufacturing this composition, an object obtained from this composition and a kit for manufacturing this object. Another subject of the invention relates to an organometallic titanium complex corresponding to the structure titanium bis(3-phenoxy-1,2-propane dioxide) (Ti(PPD)2), and the use thereof as vitrimer effect catalyst in systems based on epoxy resin and on hardener of anhydride type.

  本发明涉及一种组合物，除含有环氧类热固性树脂和酸酐类固化剂外，还含有至少一种由有机金属钛络合物组成的催化剂。这种组合物可以制造玻璃树脂，即可以在热固性状态下变形的树脂。本发明还涉及一种制造这种组合物的成套工具、一种由这种组合物制成的物体以及一种制造这种物体的成套工具。本发明的另一个主题涉及一种与双(3-苯氧基-1,2-丙烷二氧化钛)(Ti(PPD)2)结构相对应的有机金属钛络合物，以及将其用作基于环氧树脂和酸酐型固化剂的体系中的玻璃化效果催化剂。