2-oxoglutaric acid 5-ethyl ester | 20008-11-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-oxoglutaric acid 5-ethyl ester
• 英文别名: 5-ethoxy-2,5-diopentanoic acid；5-ethoxy-2,5-dioxovaleric acid；5-Ethoxy-2,5-dioxopentanoic acid；5-ethoxy-2,5-dioxopentanoic acid
• CAS: 20008-11-1
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: FKHRGABNNLLVAR-UHFFFAOYSA-N

物化性质

• 沸点：
  280.4±23.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-oxoglutaric acid 5-ethyl ester 在 citrate buffer 、 pyruvate decarboxylase 、 焦磷酸硫胺素 、 magnesium sulfate 作用下， 反应 24.0h， 以70%的产率得到4-氧代丁酸乙基酯
  参考文献：
  名称：

  Rationalizing the Origin of Solerone (5-Oxo-4-hexanolide):  Biomimetic Synthesis and Identification of Key Metabolites in Sherry Wine

  摘要：

  A biomimetic synthesis of solerone (5-oxo-4-hexanolide, 1) using both enzymatic and acid-catalyzed reactions was performed. Starting from L-glutamic acid 5-ethyl ester (2) enzymatic oxidative deamination followed by subsequent decarboxylation of the corresponding 2-oxoglutaric acid Ei-ethyl ester (3) led to ethyl 4-oxobutanoate (4). In the presence of pyruvate, 4 served as key substrate for a novel acyloin condensation catalyzed by pyruvate decarboxylase (EC 4.1.1.1) from Saccharomyces cerevisiae. Finally, the resulting ethyl 4-hydroxy-5-oxo-hexanoate (5) was easily converted into solerone (1) in the presence of acid. The acyloin condensation of 3 with acetaldehyde to ethyl 5-hydroxy-4-oxohexanoate (6) revealed an alternative route to solerone (1). Acid-catalyzed lactonization of 6 produced 4-oxo-5-hexanolide (7) as well as 5 and 1 via keto-enol tautomerization. Confirming the relevance of the proposed biogenetic pathway, the solerone precursors 2-6 as well as delta-lactone 7 were identified in sherry by GC/MS analysis for the first time.

  DOI：

  10.1021/jf960316j
• 作为产物：
  描述：

  L-谷氨酸5乙脂 在 disodium hydrogenphosphate 、 L-amino acid oxidase 、 camphor-10-sulfonic acid 、 catalase 作用下， 以68%的产率得到2-oxoglutaric acid 5-ethyl ester
  参考文献：
  名称：

  Rationalizing the Origin of Solerone (5-Oxo-4-hexanolide):  Biomimetic Synthesis and Identification of Key Metabolites in Sherry Wine

  摘要：

  A biomimetic synthesis of solerone (5-oxo-4-hexanolide, 1) using both enzymatic and acid-catalyzed reactions was performed. Starting from L-glutamic acid 5-ethyl ester (2) enzymatic oxidative deamination followed by subsequent decarboxylation of the corresponding 2-oxoglutaric acid Ei-ethyl ester (3) led to ethyl 4-oxobutanoate (4). In the presence of pyruvate, 4 served as key substrate for a novel acyloin condensation catalyzed by pyruvate decarboxylase (EC 4.1.1.1) from Saccharomyces cerevisiae. Finally, the resulting ethyl 4-hydroxy-5-oxo-hexanoate (5) was easily converted into solerone (1) in the presence of acid. The acyloin condensation of 3 with acetaldehyde to ethyl 5-hydroxy-4-oxohexanoate (6) revealed an alternative route to solerone (1). Acid-catalyzed lactonization of 6 produced 4-oxo-5-hexanolide (7) as well as 5 and 1 via keto-enol tautomerization. Confirming the relevance of the proposed biogenetic pathway, the solerone precursors 2-6 as well as delta-lactone 7 were identified in sherry by GC/MS analysis for the first time.

  DOI：

  10.1021/jf960316j

文献信息

• COMPOSITION FOR TREATING SULFUR MUSTARD TOXICITY AND METHODS OF USING SAME
  申请人：Varma Shambhu D.

  公开号：US20090048153A1

  公开（公告）日：2009-02-19

  One embodiment of the present invention provides a composition, comprising, in amounts effective to treat sulfur mustard or half sulfur mustard induced toxicity or skin damage: an agent that inhibits alkylation of —SH and >NH protein groups; an agent that reduces —SS— to SH; a scavenger of reactive oxygen species; a substrate that maintains tissue reduction-oxidation status; an agent that protects against invading inflammatory cells and associated oxidative stress; an antagonist of prostaglandin synthesis; and an agent that induces tissue regeneration. Methods of using the composition are also provided.

  本发明的一种实施例提供了一种组合物，包括以下成分，其有效量用于治疗硫芥或半硫芥诱导的毒性或皮肤损伤：抑制—SH和>NH蛋白质基团烷基化的药剂；将—SS—还原为SH的药剂；清除活性氧物种的清除剂；维持组织氧化还原状态的底物；保护免受侵入性炎症细胞和相关氧化应激的药剂；前列腺素合成的拮抗剂；以及诱导组织再生的药剂。还提供了使用该组合物的方法。
• METHOD OF PREPARING CREATINE ESTER SALTS AND USES THEREOF.
  申请人：Ferguson Chris

  公开号：US20080103202A1

  公开（公告）日：2008-05-01

  This invention discloses the method of preparation of creatine ester-salts. Creatine is an extremely popular ergogenic aid, and is found most often in the form of creatine monohydrate. Creatine monohydrate is poorly soluble in water however and while esters gain solubility, there functionality is greatly decreased. The material can be administered in a variety of ways including capsules, tablets, powdered beverages, bars, gels, liquids, liposomes or drinks.

  这项发明披露了肌酸酯盐的制备方法。肌酸是一种极受欢迎的增强运动表现的辅助剂，通常以肌酸单水合物的形式出现。然而，肌酸单水合物在水中溶解性较差，而酯类虽然增加了溶解性，但其功能性大大降低。该材料可以通过胶囊、片剂、粉末饮料、能量棒、凝胶、液体、脂质体或饮料等多种方式进行给药。
• 一种降血脂小分子化合物、中间体及各自制备方法
  申请人：天津迪尔斯化学科技有限公司

  公开号：CN105801405A

  公开（公告）日：2016-07-27

  本发明公开了一种降血脂小分子化合物制备方法，具体涉及通式(I)所示的一种降血脂小分子化合物、中间体及各自制备方法，主要用于治疗高胆固醇血症等代谢疾病及其他心血管危险因素的药物。
• Process for preparation of alpha-ketoglutaric acid
  申请人：Zhang Guoji

  公开号：US20120095261A1

  公开（公告）日：2012-04-19

  A process for preparation of α-ketoglutaric acid, which is adapted for preparing L-arginine α-ketoglutarate 1:1 and 2:1, comprising the steps of: (a) reacting methyl dichloroacetate and acrylic acid methyl ester with sodium methoxide to obtain dimethyl 2,2-dichloroglutarate; (b) reacting the dimethyl 2,2-dichloroglutarate from step (a) with hydroxide solution to obtain crude α-ketoglutaratic acid aqueous solution; (c) purifying the crude α-ketoglutaratic acid aqueous solution to obtain purified α-ketoglutaratic acid aqueous solution; and (d) adjusting a concentration of the purified α-ketoglutaratic acid aqueous solution by adding water, thereby a yield of the purified α-ketoglutaratic acid aqueous solution is approximately 75%. While avoiding the use of massive organic solvents, the process of the present invention has a remarkable high yield to realize mass production with low manufacturing cost and shortened production time.

  一种制备α-酮戊二酸的方法，适用于制备L-精氨酸α-酮戊二酸1:1和2:1，包括以下步骤：(a)将二氯乙酸甲酯和丙烯酸甲酯与甲氧基钠反应，得到二甲基2,2-二氯戊二酸酯；(b)将步骤(a)中得到的二甲基2,2-二氯戊二酸酯与氢氧化物溶液反应，得到粗α-酮戊二酸水溶液；(c)纯化粗α-酮戊二酸水溶液，得到纯化的α-酮戊二酸水溶液；(d)通过加水调节纯化的α-酮戊二酸水溶液的浓度，从而获得纯化的α-酮戊二酸水溶液的收率约为75%。本发明的方法避免了使用大量的有机溶剂，具有显著的高收率，能够实现低成本的大规模生产并缩短生产时间。
• Method of Preparing Creatine Ester Salts and Uses Thereof
  申请人：Ferguson Chris

  公开号：US20080254198A1

  公开（公告）日：2008-10-16

  This invention discloses the method of preparation of creatine ester-salts. Creatine is an extremely popular ergogenic aid, and is found most often in the form of creatine monohydrate. Creatine monohydrate is poorly soluble in water however and while esters gain solubility, there functionality is greatly decreased. The material can be administered in a variety of ways including capsules, tablets, powdered beverages, bars, gels, liquids, liposomes or drinks.

  这项发明揭示了肌酸酯盐的制备方法。肌酸是一种极其流行的增强运动能力的辅助剂，通常以单水合肌酸盐的形式出现。然而，单水合肌酸盐在水中的溶解度很差，而酯类虽然具有溶解性，但其功能大大降低。该物质可以通过多种方式进行给药，包括胶囊、片剂、粉状饮料、棒状食品、凝胶、液体、脂质体或饮料。