单(2-乙基-5-羧基戊基)邻苯二甲酸酯 | 40809-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 单(2-乙基-5-羧基戊基)邻苯二甲酸酯
• 中文别名: RAC-单(2-乙基-5-羧基戊基)邻苯二甲酸酯
• 英文名称: mono(5-carboxy-2-ethylpentyl) 1,2-benzenedicarboxylate
• 英文别名: phthalic acid mono(5-carboxy-2-ethylpentyl)ester；mono-(2-ethyl-5-carboxypentyl) phthalate；mono(2-ethyl-5-carboxypentyl) phthalate；mono(5-carboxy-2-ethylpentyl) phthalate；mono(2-ethyl-5-carboxypentyl)phthalate；5-cx-MEHP；2-Ethyl-5-carboxypentyl phthalate；2-(5-carboxy-2-ethylpentoxy)carbonylbenzoic acid
• CAS: 40809-41-4
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: XFGRNAPKLGXDGF-UHFFFAOYSA-N

物化性质

• 沸点：
  516.1±35.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少量）、DMSO（可溶）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

制备方法与用途

生物活性方面，Mono(5-羧乙戊基) 甲基化酞酸酯（MECPP）是邻苯二甲酸二（2-乙基己基酯）（DEHP）的代谢产物。DEHP 是主要添加到硬质聚氯乙烯（PVC）中的一种增塑剂，它赋予材料柔韧性、耐温性、光学透明性以及强度和抗扭结性能。

反应信息

• 作为产物：
  描述：

  2-乙基-5-己烯-1-醇 在 吡啶 、 chromium(VI) oxide 、 硫酸 、 diborane(6) 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 6.0h， 生成 单(2-乙基-5-羧基戊基)邻苯二甲酸酯
  参考文献：
  名称：

  Synthesis of DEHP metabolites as biomarkers for GC–MS evaluation of phthalates as endocrine disrupters

  摘要：

  Phthalates are used primarily as plasticizers to make polyvinyl chloride (PVC) soft and flexible. In recent years the phthalate esters have attracted increasing attention as environmental and biomedical pollutants and, because of their toxicological characteristics. In particular, they are more and more recognized as endocrine disrupters. In this context, we describe herein an efficient synthetic pathway leading to a series of metabolites of di(2-ethylhexyl) phthalate (DEHP). Mono(2-ethylhexenyl) phthalate was used as starting material to obtain these products in good yield, large scale and GC-MS purity. The metabolites of DEHP were synthesized, for the first time, as biomarkers to verify their quantitative determination in human urine and serum by GC-MS analysis for studying the exposure to phthalates and establishing reference values. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.005

文献信息

• Convenient and High-Yielding Preparations of Mono(5-carboxy-2-ethylpentyl) Phthalate and its Ring-Deuterated Isomer – The “Third” Major Metabolite of Bis(2-ethylhexyl) Phthalate
  作者：Hans-Detlev Gilsing、Jürgen Angerer、Dietrich Prescher

  DOI：10.1007/s00706-004-0267-6

  日期：2005.5

  The synthesis of an oxidative major metabolite of bis(2-ethylhexyl) phthalate is described. The target molecule and its ring-deuterated isomer were obtained via acylation of the appropriate ω-hydroxy benzyl ester or the corresponding carboxylate with phthalic anhydride or phthalic anhydride-d4. All transformation steps proceed with high yields.

  描述了邻苯二甲酸二（2-乙基己基）酯的氧化性主要代谢产物的合成。通过将适当的ω-羟基苄基酯或相应的羧酸酯与邻苯二甲酸酐或邻苯二甲酸酐-d 4酰化，获得目标分子及其环氘代异构体。所有转化步骤均以高收率进行。
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  公开号：EP2764122B1

  公开（公告）日：2017-12-06
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  公开号：EP3365820A1

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  公开号：EP3430165A2

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  公开号：EP3482328A1

  公开（公告）日：2019-05-15