[U-14C]-epichlorohydrin | 164534-15-0

• 英文名称: [U-14C]-epichlorohydrin
• 英文别名: 14C-epichlorohydrin；2-(chloro(114C)methyl)(2,3-14C2)oxirane
• CAS: 164534-15-0
• 化学式: C₃H₅ClO
• 分子量: 98.4921
• InChiKey: BRLQWZUYTZBJKN-FIXSIXJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5,3',5'-四甲基-4,4'-二羟基联苯 、 [U-14C]-epichlorohydrin 生成 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl [U-14C]diglycidyl ether
  参考文献：
  名称：

  Dermal penetration and metabolism of five glycidyl ethers in human, rat and mouse skin

  摘要：

  1. Glycidyl ethers (GE), an important class of industrial chemicals, are considered to be potentially mutagenic in vivo because some GE have been shown to be direct mutagens in short-term in vitro tests.2. The percutaneous penetration and metabolism of representatives of different classes of GE was studied in the fresh, full-thickness C3H mouse, and dermatomed human and Fisher 344 rat skin to determine the apparent permeability constants, lag times and metabolic profiles.3. Five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C(12)GE) and o-cresol (o-CGE), were synthesized by reaction of their alcohols with epichlorohydrin. Their radiolabelled analogues were synthesized with a C-14- label using [U-C-14]-epichlorohydrin.4. There was a large variation (four orders of magnitude) in percutaneous penetration between the five GE. In general, penetration through full-thickness mouse skin was higher than through dermatomed rat skin, whereas dermatomed human skin was the least permeable. The permeability increased in the order YX4000 < BADGE < C(12)GE < o-CGE < HDDGE.5. The relative skin permeability of the five GE could be explained for a significant part by the lipophilicity, expressed as log P-o/w, in combination with the molecular weight of the compounds. 6. During skin penetration, all GE were extensively metabolized to their corresponding (bis-)diols. Virtually no YX4000, and only very small amounts of C,,GE and BADGE, penetrated the skin unchanged, but significant amounts of HDDGE and o-CGE penetrated the skin unchanged. For o-CGE, but none of the other GE, the percentage of the applied dose that penetrated the skin unchanged increased over time.7. The large variation in response observed with the five selected GE indicates that GE should not be considered as a single class of compounds but rather on the basis of their individual properties.

  DOI：

  10.1080/004982500237488
• 作为产物：
  描述：

  14C-1,3-dichloro-2-propanol 在 sodium hydroxide 作用下， 以 乙醚 为溶剂， 反应 20.0h， 以100%的产率得到[U-14C]-epichlorohydrin
  参考文献：
  名称：

  Synthesis of 14C-labelled hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX), 2,4,6-trinitrotoluene (TNT), nitrocellulose (NC) and glycidylazide polymer (GAP) for use in assessing the biodegradation potential of these energetic compounds

  摘要：

  在受高能化合物污染的土壤生物修复研发项目的框架内，研究人员正在研究高能产品（如六亚甲基三硝胺（RDX）、三硝基甲苯（TNT）、硝化纤维素（NC）和缩水甘油叠氮聚合物（GAP））的生物降解。为了跟踪生物降解过程，必须使用放射性碳-14标记产品进行微环境测定。14C-RDX是通过根据Hale工艺对六亚甲基四胺（HMTA）进行硝化制备的。14C-环和甲基标记的TNT是根据Dorey和Carper程序合成的。14C-纤维素是由乙酰木糖杆菌从14C-葡萄糖合成的。14C-纤维素的硝化反应产生了14C-硝化纤维素。14C-缩水甘油叠氮聚合物是通过14C-环氧氯丙烷（ECH）的聚合和叠氮化合成的，而14C-环氧氯丙烷是由14C-甘油合成的。14C-甘油的氢氯化反应和所得14C-1,3-二氯-2-丙醇的环氧化反应产生了14C-环氧氯丙烷。本文描述了这些14C标记炸药的合成方法。

  DOI：

  10.1002/jlcr.2580360608

文献信息

• Metabolic inactivation of five glycidyl ethers in lung and liver of humans, rats and mice<i>in vitro</i>
  作者：P. J. Boogaard、K. P. De Kloe、J. Bierau、G. Kuiken、P. E. D. Borkulo、N. J. Van Sittert

  DOI：10.1080/004982500237497

  日期：2000.1

  1. Some glycidyl ethers (GE) have been shown to be direct mutagens in short-term in vitro tests and consequently GE are considered to be potentially mutagenic in vivo. However, GE may be metabolically inactivated in the body by two different enzymatic routes: conjugation of the epoxide moiety with the endogenous tripeptide glutathione (GSH) catalysed by glutathione S-transferase (GST) or hydrolysis of the epoxide moiety catalysed by epoxide hydrolase (EH).2. The metabolic inactivation of five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol(HDDGE) and the GE of 1-dodecanol (C(12)GE) and o-cresol (o-CGE), has been studied in subcellular fractions of human, C3H mouse and F344 rat liver and lung.3. All GE were chemically very. stable and resistant to aqueous hydrolysis, but were rapidly hydrolysed by EH in cytosolic and microsomal fractions of liver and lung. The aromatic GE were very good substrates for EH. In general, microsomal EH is more efficient than cytosolic EH in hydrolysis of GE, and human microsomes are more efficient than rodent microsomes.4. The more water-soluble GE, o-CGE and HDDGE, were good substrates for GST whereas the more lipophilic GE, YX4000 and C(12)GE, were poor substrates for GST. In general, rodents are more efficient in GSH conjugation of GE than humans.5. In general, the epoxide groups of YX4000 are the most and those of HDDGE the least efficiently inactivated of the five GE under study. For the other three GE no general trend was observed: the relative efficiency of inactivation varied with organ and species.6. The large variation in metabolism observed with five representative GE indicate that GE have variable individual properties and should not be considered as a single, homogenous class of compounds.