rac-2,3-dimercaptosuccinic acid | 27887-84-9

• 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: rac-2,3-dimercaptosuccinic acid
• 英文别名: 2,3-dimercaptosuccinic acid；racemic-2,3-dimercaptosuccinic acid；rac-DMSA；dl-Dimercaptosuccinic acid；racem. 2,3-dimercapto-succinic acid；rac.-2,3-Dimercapto-bernsteinsaeure；dl-2,3-Dimercaptobernsteinsaeure；(2R,3R)-2,3-bis(sulfanyl)butanedioic acid
• CAS: 27887-84-9；10008-75-0
• 化学式: C₄H₆O₄S₂
• 分子量: 182.221
• InChiKey: ACTRVOBWPAIOHC-LWMBPPNESA-N

物化性质

• 沸点：
  267.6±40.0 °C(Predicted)
• 密度：
  1.617±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.6
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 rac-2,3-dimercaptosuccinic acid 在 硫酸 作用下， 生成 meso-dimercaptosuccinic acid dimethylester
  参考文献：
  名称：

  Zur Kenntnis der2,3-Dimercapto-bernsteinsäuren

  摘要：

  描述了内消旋和外消旋-2,3-二巯基琥珀酸（IIIa和IIIb）的制备。它们的构型已经通过化学方法和通过分离IIIb的两种旋光异构体来确定。

  DOI：

  10.1002/hlca.19610440410
• 作为产物：
  描述：

  2,3-bis(acetylthio)succinic acid 在 sodium hydroxide 作用下， 反应 0.05h， 以75.4%的产率得到rac-2,3-dimercaptosuccinic acid
  参考文献：
  名称：

  Comparativein vivoLead Mobilization ofmeso- andrac-2,3-Dimercaptosuccinic Acids in Albino Wistar Rats

  摘要：

  Abstract: Comparison of the racemic and meso forms of 2,3‐dimercaptosuccinic acid (DMSA) in lead mobilization from lead‐loaded albino Wistar rats demonstrates that the racemic form is significantly more effective in reducing femur lead levels. After four oral doses at 0.5 mmol/kg, femur lead levels were reduced to 87% of control values by meso‐DMSA and to 50% of control levels by rac‐DMSA. Similarly, when the dose was increased to 1.0 mmol/kg, femur lead levels were reduced to 69% of control levels by meso‐DMSA and to 45% of control levels by rac‐DMSA. A similar pattern was found for renal lead levels. Brain lead concentrations were significantly lower in treated groups than in control groups, but no differences were found between rac‐ and meso‐DMSA. Rac‐DMSA is more soluble than meso‐DMSA in acetonitrile, ethyl acetate, and ethyl ether. The partition coefficient of rac‐DMSA in the n‐octanol/water system was found to be about 2.8. These results indicate that rac‐DMSA deserves further attention as a possible substitute for meso‐DMSA.

  DOI：

  10.1111/j.1600-0773.1997.tb00393.x

文献信息

• Oxotechnetium(V)bis(dithiolato) complexes
  作者：Hartmut Spies、Bernd Johannsen

  DOI：10.1016/s0020-1693(00)90099-9

  日期：1981.1

  Abstract A series of ten bis(dithiolato)oxotechnetate(V) complexes has been prepared using ligand exchange reaction. Starting from Tc(V) gluconate in aqueous or aqueous/ethanolic solution, complexes with saturated, olefinic and aromatic dithioles have been obtained. Mass, infrared, n.m.r., and UV-visible data of the resulting compounds are reported.

  摘要利用配体交换反应制备了十种双（二硫代）氧代tech酸酯（V）配合物。从水溶液或水溶液/乙醇溶液中的Tc（V）葡萄糖酸酯开始，已经获得了具有饱和，烯属和芳族二硫醇的配合物。报告了所得化合物的质量，红外，核磁共振和紫外可见数据。
• Comparative<i>in vivo</i>Lead Mobilization of<i>meso</i>- and<i>rac</i>-2,3-Dimercaptosuccinic Acids in Albino Wistar Rats
  作者：Mark M. Jones、Pramod K. Singh、Krista Kostial、Maja Blanuša、Martina Piasek、Nada Restek-Samarožija

  DOI：10.1111/j.1600-0773.1997.tb00393.x

  日期：1997.4

  Abstract: Comparison of the racemic and meso forms of 2,3‐dimercaptosuccinic acid (DMSA) in lead mobilization from lead‐loaded albino Wistar rats demonstrates that the racemic form is significantly more effective in reducing femur lead levels. After four oral doses at 0.5 mmol/kg, femur lead levels were reduced to 87% of control values by meso‐DMSA and to 50% of control levels by rac‐DMSA. Similarly, when the dose was increased to 1.0 mmol/kg, femur lead levels were reduced to 69% of control levels by meso‐DMSA and to 45% of control levels by rac‐DMSA. A similar pattern was found for renal lead levels. Brain lead concentrations were significantly lower in treated groups than in control groups, but no differences were found between rac‐ and meso‐DMSA. Rac‐DMSA is more soluble than meso‐DMSA in acetonitrile, ethyl acetate, and ethyl ether. The partition coefficient of rac‐DMSA in the n‐octanol/water system was found to be about 2.8. These results indicate that rac‐DMSA deserves further attention as a possible substitute for meso‐DMSA.
• Zur Kenntnis der 2,3-Dimercapto-bernsteinsäuren
  作者：M. Gerecke、E. A. H. Friedheim、A. Brossi

  DOI：10.1002/hlca.19610440410

  日期：——

  The preparation of meso- and rac.-2,3-dimercaptosuccinic acid (III a resp. III b) is described. Their configuration has been established by chemical methods and by isolating both optically active isomers of III b.

  描述了内消旋和外消旋-2,3-二巯基琥珀酸（IIIa和IIIb）的制备。它们的构型已经通过化学方法和通过分离IIIb的两种旋光异构体来确定。