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Thiomalic acid

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Identification
Molecular formula
C4H6O4S2
CAS number
70-49-5
IUPAC name
2,3-bis(sulfanyl)butanedioic acid
State
State

At room temperature, thiomalic acid is in a solid state. It is generally stable but should be kept in a tightly closed container and stored in a cool, dry location to maintain its integrity and prevent any degradation or reaction with moisture or air.

Melting point (Celsius)
85.00
Melting point (Kelvin)
358.15
Boiling point (Celsius)
219.30
Boiling point (Kelvin)
492.45
General information
Molecular weight
152.19g/mol
Molar mass
152.1900g/mol
Density
2.0480g/cm3
Appearence

Thiomalic acid appears as a white or off-white crystalline solid. It can also be found in a powdered form. The compound has a characteristic odor, often described as similar to that of sour milk or thiol-related substances due to the presence of sulfhydryl groups.

Comment on solubility

Solubility of 2,3-bis(sulfanyl)butanedioic acid

The solubility of 2,3-bis(sulfanyl)butanedioic acid, often referred to as a thio-acid due to the presence of sulfanyl (-SH) groups, plays a significant role in its chemical behavior and potential applications. Solubility in water and organic solvents can greatly influence its usability in both biochemical and industrial processes.

Key factors that affect the solubility of this compound include:

  • Hydrogen bonding: The -SH groups can engage in hydrogen bonding with water molecules, which may enhance solubility in aqueous solutions.
  • Polarity: The overall polarity of the molecule, dictated by the carboxylic acid groups and the sulfanyl groups, affects how well it interacts with solvents.
  • pH levels: As a dicarboxylic acid, the solubility can also depend on the pH of the solution, where deprotonation at higher pH can lead to increased solubility.

In general, it is expected that 2,3-bis(sulfanyl)butanedioic acid may exhibit moderate solubility in water, but its precise solubility will depend on the specific conditions. As a result, conducting solubility studies under various environmental conditions would provide a clearer understanding of its behavior in different matrices.

In conclusion, while the presence of functional groups suggests potentially interesting solubility characteristics, empirical data would be necessary to draw definitive conclusions about its solubility profile.

Interesting facts

Interesting Facts about 2,3-bis(sulfanyl)butanedioic acid

2,3-bis(sulfanyl)butanedioic acid, commonly known as a dithiol-derivative of succinic acid, presents a fascinating subject for study in the field of organic and medicinal chemistry. Here are some engaging insights:

  • Structure and Functionality: This compound features two sulfanyl (thiol) groups attached to a butanedioic acid backbone, enhancing its reactivity and making it an essential building block in various biochemical applications.
  • Biological Relevance: Dithiols are known for playing critical roles in maintaining the structural integrity of proteins through disulfide bridge formation, crucial for proper protein folding and function.
  • Chemical Reactions: The presence of thiol groups in this compound promotes a variety of reactions, such as nucleophilic substitutions and redox reactions, making it valuable in synthetic organic chemistry.
  • Potential Applications: Research indicates potential applications of this compound in drug design, particularly in the development of new antimicrobial agents or as a component in targeted drug delivery systems.
  • Research Interest: There is growing interest in its use as a ligand in coordination chemistry, where it might form complexes with transition metals, thereby influencing catalysis and materials science.

As a versatile compound, 2,3-bis(sulfanyl)butanedioic acid serves as a reminder of the interconnected nature of chemical compounds, their structures, and their implications in real-world applications. Its significance in ongoing research showcases the endless possibilities within the realm of chemistry.

Synonyms
2,3-Dimercaptosuccinic acid
Dimercaptosuccinic acid
2418-14-6
Suximer
2,3-bis(sulfanyl)butanedioic acid
Butanedioic acid, 2,3-dimercapto-
2,3-Dimercaptobutanedioic acid
DMSA
EINECS 219-334-5
UNII-4S9JU7XF01
NSC 259951
BRN 1725149
2,3-disulfanylbutanedioic acid
MLS001076671
DTXSID10859324
3-03-00-01033 (Beilstein Handbook Reference)
SMR000499575
Dimercatposuccinic acid
2,3-Dimercaptobutanedioic Acid; DMSA
NSC16866
Succinic acid, 2,3-dimercapto-
Dimercaptosuccinic acid;DMSA
2,3-Dimercapto-Succinic Acid
MFCD00004859
2,3Dimercaptosuccinic acid
cid_9354
Succinic acid,3-dimercapto-
SCHEMBL14942
2,3Dimercaptobutanedioic acid
MLS001332563
MLS001332564
CHEMBL28721
meso-2,3-Dithiosuccinic acid
Succinic acid, 2,3dimercapto
Butanedioic acid,3-dimercapto-
2,3-Disulfanylsuccinic acid #
4S9JU7XF01
BDBM60868
Butanedioic acid, 2,3dimercapto
DTXCID00209339
meso 2,3-dimercaptosuccinic acid
alpha,beta Dimercaptosuccinic acid
NSC259951
MPI DMSA kidney reagent (Salt/Mix)
AKOS006228463
.alpha.,.beta.-Dimercaptosuccinic acid
DB14089
NSC-259951
DIMERCAPTOSUCCINIC ACID [WHO-DD]
FD164695
LS-12987
NCI60_001347
NS00006623
NS00108481
EN300-7185614
Q56604713