辅酶 M | 45127-11-5

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 辅酶 M
• 中文别名: 辅酶M；美司钠相关物质B
• 英文名称: dimesna
• 英文别名: 2,2'-Dithiodiethanesulfonic acid；2-(2-sulfoethyldisulfanyl)ethanesulfonic acid
• CAS: 45127-11-5
• 化学式: C₄H₁₀O₆S₄
• 分子量: 282.384
• InChiKey: BYUKOOOZTSTOOH-UHFFFAOYSA-N

物化性质

• 密度：
  1.769±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  176
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2930909090
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  辅酶 M 在 calcium hydroxide 作用下， 以 水 为溶剂， 以85%的产率得到calcium 2,2'-dithio-bis-ethane sulfonate
  参考文献：
  名称：

  Medicinal disulfide salts

  摘要：

  这项发明涉及新型药用二硫化物盐。这些化合物包括一个末端磺酸盐或膦酸盐基团，并具有许多用途，例如在与许多抗肿瘤药物一起使用时作为毒性减少剂。

  公开号：

  US20060063949A1
• 作为产物：
  描述：

  3,4-Dithia-1,6-hexan-disulfonyl-chlorid 在 水 作用下， 以 乙腈 为溶剂， 反应 120.0h， 以96%的产率得到辅酶 M
  参考文献：
  名称：

  Medicinal disulfide salts

  摘要：

  这项发明涉及新型药用二硫化物盐。这些化合物包括一个末端磺酸盐或膦酸盐基团，并具有许多用途，例如在与许多抗肿瘤药物一起使用时作为毒性减少剂。

  公开号：

  US20060063949A1

文献信息

• Alkaline decomposition of organic disulfides. II. Alternative pathways as determined by structure
  作者：James P. Danehy、Wood Eugene Hunter

  DOI：10.1021/jo01282a001

  日期：1967.7
• The reaction of <i>S</i>-nitrosothiols with thiols at high thiol concentration
  作者：Andrew P. Dicks、E. Li、Andrew P. Munro、Helen R. Swift、D. Lyn H. Williams

  DOI：10.1139/cjc-76-6-789

  日期：——

  Reactions of S-nitrosothiols (RSNO) with their corresponding thiols (RSH) present in a large excess (>20-fold) proceed readily to give the disulfide. Ammonia is formed together with some nitrite anion, and these constitute >90% of the "nitrogen" products. This is in marked contrast with the reaction at low thiol concentration, where nitric oxide is the major initial "nitrogen" product, which is rapidly converted in the presence of oxygen in water to nitrite anion. Also in marked contrast to the "low thiol concentration" reaction, the reaction at high thiol concentration is not affected by added Cu2+, nor by the metal-ion scavenger EDTA. Kinetically all reactions were excellent first-order processes, and the reactions were also strictly first order in thiol concentration. A large range of nitrosothiols were studied and the generality of the reaction established. Some reactions of RSNO with other thiols (R'SH) were examined and the results readily interpreted in terms of a prior rapid equilibrium transnitrosation. The pH dependence for the reaction of S-nitrosocysteine with cysteine clearly showed that the reactive species is the cysteine thiolate anion. The results are discussed along with those of two other recent reports of these reactions, in terms of thiolate attack initially at the nitroso nitrogen atom, and subsequently at sulfur atoms, eliminating RSSR and yielding hydroxylamine, which is rapidly reduced by thiolate ion to ammonia. The results are also discussed in connection with the release of NO from nitrosothiols and with the important biological consequences, both for the in vivo reactions of NO and for the potential of nitrosothiols as NO-releasing drugs for medical use.
• Fedoseyeva,V.N.; Petrun'kin,V.E., Soviet progress in chemistry, 1967, vol. 33, # 6, p. 57 - 58
  作者：Fedoseyeva,V.N.、Petrun'kin,V.E.

  DOI：——

  日期：——
• US6037336
  申请人：——

  公开号：——

  公开（公告）日：——
• Notes- The Synthesis of 2-Mercaptoethanesulfonamide
  作者：Henry Lemaire、Martin Rieger

  DOI：10.1021/jo01063a631

  日期：1961.4