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3-Thiopropionic acid is a versatile organosulfur compound with a carboxylic acid group and a thiol group, making it useful in both biological research and industrial applications.
In scientific research, 3-Thiopropionic acid serves as a crucial reagent in organic synthesis, enzyme inhibition studies, and as a capping agent for nanoparticles in various applications, including biosensors and biomedical labeling.
CAS Number: 107-96-0
EC Number: 203-537-0
IUPAC Name: 3-Sulfanylpropanoic acid
Chemical Formula: C3H6O2S
Other names: 3-MERCAPTOPROPIONIC ACID, 3-Mercaptopropanoic acid, 107-96-0, 3-Sulfanylpropanoic acid, 3-Thiopropionic acid, beta-Mercaptopropionic acid, 3-Thiopropanoic acid, Mercaptopropionic acid, Propanoic acid, 3-mercapto-, 3MPA, beta-Thiopropionic acid, Propionic acid, 3-mercapto-, 2-Mercaptoethanecarboxylic acid, Hydracrylic acid, 3-thio-, beta-Mercaptopropanoic acid, Thiohydracrylic acid, UNII-B03TJ3QU9M, NSC 437, 3-Thiolpropanoic acid, 3-thiohydracrylic acid, 3-Mercaptopropionicacid, 3-mercapto-propionic acid, MFCD00004897, .beta.-Thiopropionic acid, B03TJ3QU9M, .beta.-Mercaptopropionic acid, CHEMBL358697, CHEBI:44111, Propionic acid, 3-mercpato-, HSDB 5381, 3 Mercaptopropionic Acid, EINECS 203-537-0, BRN 0773807, AI3-26090, BMPA, ss--Thiopropionic acid, 3-mercaptopropanic acid, Sugammadex Impurity 60, betamercaptopropionic acid, 3-mercapto-propanoic acid, DSSTox_CID_6775, ss--Mercaptopropanoic acid, ss--Mercaptopropionic acid, EC 203-537-0, 3-Sulfanylpropanoic acid #, SCHEMBL7289, DSSTox_RID_78211, DSSTox_GSID_26775, .beta.-Mercaptopropanoic acid, 4-03-00-00726 (Beilstein Handbook Reference), 3-Mercaptopropanoic acid, 9CI, NSC437, 3-Mercaptopropionic acid, 98%, DTXSID8026775, NSC-437, 3-Mercaptopropionic acid, >=99%, AMY27767, BCP16636, STR01222, ZINC3860582, Tox21_200194, 7053AF, BDBM50121953, STL281859, Thiopropionic acid; 3-Thiopropanoic acid; beta-Mercaptopropionic acid, AKOS000121541, AC-4722, AT21041, MCULE-3211932163, SB66313, NCGC00248556-01, NCGC00257748-01, BP-21405, CAS-107-96-0, FT-0615955, FT-0658630, M0061, 3-Mercaptopropionic acid, >=99.0% (HPLC), Propanoic acid, 3-mercapto-, coco alkyl esters, 3-Dimethylamino-2-methylpropylchloridehydrochloride, A801785, J-512742, Q11751618, F2191-0215, 68307-97-1, hydracrylic acid, 3-thio-, 2-mercaptoethanecarboxylic acid, 3-mercaptopropanoic acid, beta-mercaptopropionic acid, 3-mercaptopropionicacid, propanoic acid, 3-mercapto-, propanoicacid, 3-mercapto-, propionic acid, 3-mercapto-, 3-sulfanylpropanoic acid, 3-thiohydracrylic acid, 3-thiolpropanoic acid, 3-thiopropanoic acid, 3-Thiopropionic acid, 3-Mercaptopropionic acid, 107-96-0 [RN], 203-537-0 [EINECS], 2-mercaptoethanecarboxylic acid, 3-mercaptopropanoic acid, 3-Sulfanylpropanoic acid [ACD/IUPAC Name], 3-Sulfanylpropansäure [German] [ACD/IUPAC Name], 3-Thiopropionic acid, 4-03-00-00726 [Beilstein], 773807 [Beilstein], Acide 3-sulfanylpropanoïque [French] [ACD/IUPAC Name], B03TJ3QU9M, Hydracrylic acid, 3-thio-, mercaptopropionic acid, MFCD00004897 [MDL number], Propanoic acid, 3-mercapto- [ACD/Index Name], SH2VQ [WLN], UF5270000, UNII-B03TJ3QU9M, β-Mercaptopropanoic acid, β-mercaptopropionic acid, β-Mercaptopropionic acid, β-thiopropionic acid, β-Thiopropionic acid, ??-mercaptopropionic acid, 203-537-0MFCD00004897, 3-Mercapto Propionic Acid, 3-Mercaptopropanic Acid, 3-mercaptopropanoate, 3-mercapto-propanoic acid, 3-Mercaptopropanoic acid, 9CI, 3-Mercaptopropionic acid-, 3-Mercapto-propionic acid, 3-Mercaptopropionic Acid (en), 3MPA, 3-MPA, 3-thiohydracrylic acid, 3-thiolpropanoic acid, 3-Thiopropanoic acid, Benzoic acid, 4-(aminomethyl)- (9CI), propionic acid, 3-mercapto-, propionic acid, mercapto-, ß-mercaptopropionic acid, STR01222, T5SJ B1 C1 DVQ E- AT5NJ [WLN], Thiohydracrylic acid, UNII:B03TJ3QU9M, β-Mercaptopropanoic acid, β-Mercaptopropionate, β-mercaptopropionic acid
3-Thiopropionic acid is utilized in industrial settings for its antioxidant properties to stabilize polymers and plastics, while also acting as a chelating agent for metal ions and an intermediate in the production of fine chemicals.
3-Thiopropionic acid contains both carboxylic acid and thiol groups.
3-Thiopropionic acid is a colorless oil and derived from the addition of hydrogen sulfide to acrylic acid.
3-Thiopropionic acid that is propanoic acid carrying a sulfanyl group at position 3.
3-Thiopropionic acid is an organic compound.
3-Thiopropionic acid exists as a colourless liquid that demonstrates solubility in both water and organic solvents.
As a sulfur-containing carboxylic acid and a derivative of propionic acid, 3-Mercaptopropionic acid serves as a crucial precursor for the synthesis of various organic compounds, making 3-Thiopropionic acid invaluable across scientific and industrial applications.
In scientific research, 3-Thiopropionic acid finds widespread usage as a reagent in organic synthesis and in the production of proteins and other biomolecules.
3-Thiopropionic acid also functions as a chelating agent, adept at binding metal ions within aqueous solutions, and plays a vital role as a stabilizing agent in polymer production.
3-Thiopropionic acid is an organosulfur compound with the formula HSCH2CH2CO2H.
3-Thiopropionic acid is a bifunctional molecule, containing both carboxylic acid and thiol groups.
3-Thiopropionic acid is a colorless oil.
3-Thiopropionic acid is derived from the addition of hydrogen sulfide to acrylic acid.
3-Thiopropionic acid is used as a self-assembled monolayer (SAM) with a thiol and carboxylic groups.
3-Thiopropionic acid has short carbon chains and is mainly used as a capping agent on a variety of nanoparticles.
3-Thiopropionic acid was introduced as a cheap new O-demethylating agent as exemplified by its application in the synthesis of antidepressant O-desmethylvenlafaxine from venlafaxine.
The application of 3-Thiopropionic acid allowed high conversion of venlafaxine to O-desmethylvenlafaxine and a facile workup, which enabled the isolation of the desired O-desmethylvenlafaxine with a high >99.8% chromatographic purity and 76% yield by a simple extractive workup followed by the precipitation.
3-Thiopropionic acid, also known as β-mercaptopropionic acid or 3-mercaptopropionic acid, is an organic compound with the molecular formula C₃H₆O₂S.
3-Thiopropionic acid features a three-carbon chain with a carboxylic acid group (-COOH) at one end and a thiol group (-SH) attached to the third carbon, giving 3-Thiopropionic acid both acidic and thiol properties.
This dual functionality makes 3-Thiopropionic acid a versatile compound in both biological and industrial applications.
In biological systems, 3-Thiopropionic acid is known for its ability to inhibit enzymes that rely on sulfhydryl groups, making it an important research tool in studying various biochemical pathways.
3-Thiopropionic acid's thiol group makes it a potential reducing agent, while the carboxyl group enables it to form esters and amides, making it useful in synthetic organic chemistry.
3-Thiopropionic acid is often utilized in the production of pharmaceuticals, agrochemicals, and various other fine chemicals.
3-Thiopropionic acid is also employed as an intermediate in the synthesis of polymers, resins, and coatings.
In industrial settings, 3-Thiopropionic acid is valued for its antioxidant properties, particularly in the stabilization of polymers and plastics.
However, 3-Thiopropionic acid's handling requires caution, as exposure can lead to irritation of the skin, eyes, and respiratory system.
Despite these hazards, its multifunctional nature makes 3-Thiopropionic acid a valuable compound in numerous fields, ranging from material science to biochemistry.
Applications of 3-Thiopropionic Acid:
3-Thiopropionic acid is used to produce hydrophilic SAMs, which are terminated with carboxylic acids and can be further functionalized to introduce more complex end groups such as enzymes for biosensor applications.
SAMs of 3-Thiopropionic acid are capped on ZnSe quantum dots for the electrochemical detection of dopamine.
3-Thiopropionic acid is used as a capping agent on CdTe quantum dot nanocrystals (QD NCs) for use as labeling materials in biomedical applications.
3-Thiopropionic acid can also be used to modify the surface of iron oxide nanoparticles (Fe2O3) in the extraction and preconcentration of Al3+ and Cr3+ ions from different biological samples.
3-Thiopropionic acid has a wide range of applications across various industries due to its unique chemical properties, particularly its thiol (-SH) and carboxyl (-COOH) groups.
Enzyme Inhibition:
3-Thiopropionic acid is used as a tool in biochemical research to inhibit enzymes that rely on sulfhydryl groups (thiol-containing enzymes), allowing the study of enzyme mechanisms and metabolic pathways.
Drug Development:
3-Thiopropionic acid's thiol group makes it useful in synthesizing compounds with potential therapeutic applications, such as antioxidants and enzyme modulators.
Polymer and Plastic Stabilization:
Antioxidant:
3-Thiopropionic acid acts as an antioxidant, helping to stabilize polymers and plastics by preventing oxidative degradation, thus improving the longevity and durability of these materials.
Polymer Additive:
3-Thiopropionic acid is used as an additive in the production of coatings, resins, and plasticizers, where it improves flexibility, thermal stability, and overall performance.
Agrochemicals:
3-Thiopropionic acid is employed in the synthesis of agrochemicals, including pesticides and herbicides, due to its ability to modify chemical structures, enhancing efficacy and stability in various environmental conditions.
Intermediate in Organic Synthesis:
3-Thiopropionic acid is used as a building block for the synthesis of more complex organic molecules.
3-Thiopropionic acid participates in esterification, amidation, and reduction reactions, making it a versatile intermediate in chemical manufacturing.
Corrosion Inhibitors:
3-Thiopropionic acid's thiol group allows it to bind to metal surfaces, forming a protective layer that inhibits corrosion, particularly in industrial processes involving metal parts and machinery.
Cosmetics:
In cosmetics, derivatives of 3-Thiopropionic acid are used in hair treatment formulations, particularly in perming and straightening products, where the thiol group helps to break and reform disulfide bonds in hair.
Resin and Coating Production:
3-Thiopropionic acid is used in the development of synthetic resins and coatings, providing increased resistance to environmental degradation and improving the mechanical properties of materials.
Uses of 3-Thiopropionic Acid:
3-Thiopropionic acid is widely used in food and beverage industries as a flavoring agent.
3-Thiopropionic acid is used in the production of PVC stabilizers, which are used as chain transfer agents in polymerizations.
3-Thiopropionic acid can be used as primary or secondary, color stabilizer in combination with phenolic antioxidant for polymers.
3-Thiopropionic acid and its derivatives are main materials for the synthesis of PVC-stabilizers and are used as chain transfer and cross-linking agents in polymerizations.
These compounds are also useful as ion exchange catalysts, coupling agents, and in UV-curable formulations.
3-Thiopropionic acid is a clear, near water-white liquid with strong odor used as a basic material in the production of PVC stabilizers.
3-Thiopropionic acid's unique reducing properties make it an ideal candidate for a wide variety of chemical reactions including addition, elimination, or cyclization reactions.
3-Thiopropionic acid's thiol-group (-SH) will react in the presence of bases, acids, ketone groups or organic halogens.
In the presence of alcohols or amines, the carboxylic group will react preferentially.
3-Thiopropionic acid is a compound suitable for amino acid analysis by means of OPA.
3-Thiopropionic acid is widely used in food and beverage industries as a flavoring agent.
3-Thiopropionic acid is used in the production of PVC stabilizers, which are used as chain transfer agents in polymerizations.
3-Thiopropionic acid can be used as primary or secondary, color stabilizer in combination with phenolic antioxidant for polymers.
3-Thiopropionic acid acts as a sulfide ion equivalent and is utilized in the preparation of diaryl sulfide from aryl iodide.
3-Thiopropionic acid is a versatile compound with a wide range of uses in various industries.
In pharmaceuticals, 3-Thiopropionic acid is employed as a biochemical tool to inhibit thiol-dependent enzymes, aiding in the study of metabolic pathways and enzyme functions.
3-Thiopropionic acid's antioxidant properties make it valuable in the polymer and plastic industries, where it stabilizes materials by preventing oxidative degradation, thereby extending the lifespan of products such as resins, coatings, and plastics.
Additionally, 3-Thiopropionic acid is used as an intermediate in the synthesis of fine chemicals, agrochemicals, and pharmaceuticals, due to its ability to participate in reactions involving both thiol and carboxyl groups.
In industrial settings, 3-Thiopropionic acid acts as a corrosion inhibitor by binding to metal surfaces, protecting machinery and components from rust.
3-Thiopropionic acid also finds applications in cosmetics, particularly in hair treatment products, where it helps to break and reform disulfide bonds, making it useful in processes like perming and hair straightening.
These diverse uses highlight 3-Thiopropionic acid's importance across multiple sectors, from material science to biochemistry.
Reactions and uses:
3-Thiopropionic acid is competitive inhibitor of glutamate decarboxylase, and therefore acts as a convulsant.
3-Thiopropionic acid has higher potency and faster onset of action compared to allylglycine.
3-Thiopropionic acid is used to prepare hydrophilic gold nanoparticles, exploiting the affinity of gold for sulfur ligands.
Benefits of 3-Thiopropionic Acid:
Versatility in Applications:
3-Thiopropionic acid is used in various industries including pharmaceuticals, polymers, agrochemicals, and cosmetics due to its multifunctional chemical structure.
Antioxidant Properties:
Acts as an antioxidant, protecting polymers, plastics, and resins from oxidative degradation, which extends their lifespan and improves their performance.
Enzyme Inhibition:
Useful in biochemical research as 3-Thiopropionic acid inhibits thiol-dependent enzymes, aiding in the study of metabolic processes and enzyme mechanisms.
Corrosion Inhibition:
Binds to metal surfaces, providing an effective barrier against corrosion, particularly in industrial applications.
Organic Synthesis Building Block:
A versatile intermediate in the synthesis of more complex molecules, aiding in the production of fine chemicals, pharmaceuticals, and agrochemicals.
Improved Flexibility in Polymers:
When used as a polymer additive, 3-Thiopropionic acid enhances the flexibility and durability of materials like resins and plastics.
Environmental Stability:
Improves the stability of agrochemical products like pesticides and herbicides, increasing their effectiveness in a variety of environmental conditions.
Cosmetic Applications:
Provides benefits in hair treatment products by helping to reform disulfide bonds in hair, aiding in straightening and perming.
Key Features of 3-Thiopropionic acid:
Dual Functional Groups:
Contains both a thiol (-SH) group and a carboxyl (-COOH) group, giving 3-Thiopropionic acid reactive capabilities in both acid- and thiol-mediated reactions.
Antioxidant Capabilities:
Exhibits strong antioxidant properties, particularly in polymer and plastic applications, where 3-Thiopropionic acid prevents degradation due to oxidation.
Redox Reactivity:
3-Thiopropionic acid's thiol group makes it an effective reducing agent, which can participate in various redox reactions in chemical synthesis and biochemical processes.
Metal Binding Capacity:
The thiol group allows 3-Thiopropionic acid to bind effectively to metals, providing protection against corrosion and oxidation.
Water Solubility:
3-Thiopropionic acid is soluble in water, making it easy to handle in aqueous reactions and solutions, important in both industrial and biological settings.
Intermediate in Chemical Synthesis:
Plays a key role as an intermediate in organic synthesis, particularly in the production of polymers, resins, and pharmaceutical products.
Thermal Stability:
Offers good thermal stability when used in industrial processes, ensuring reliable performance under high-temperature conditions.
Mild Irritant:
While 3-Thiopropionic acid requires careful handling due to potential skin and eye irritation, it is generally considered manageable in industrial and research environments when proper precautions are taken.
Production of 3-Thiopropionic Acid:
The production of 3-Thiopropionic acid typically involves several chemical processes.
One common method is through the reaction of acrylonitrile with hydrogen sulfide (H₂S).
This reaction forms a thiolated intermediate, which is then hydrolyzed to yield 3-Thiopropionic acid.
Another method involves the thiolation of propionic acid or 3-Thiopropionic acid's derivatives.
In this process, propionic acid is reacted with a thiolating agent, such as thiourea or hydrogen sulfide, under controlled conditions to introduce the thiol group (-SH) at the third carbon, converting 3-Thiopropionic acid into 3-Thiopropionic acid.
These processes require careful control of temperature, pressure, and reaction times to ensure high yields and minimize unwanted byproducts.
Purification steps such as distillation or recrystallization are then used to obtain the final product in a pure form.
3-Thiopropionic acid is produced on an industrial scale for use in applications ranging from the stabilization of polymers and resins to pharmaceutical and agrochemical manufacturing.
The production process is typically optimized for cost-efficiency and scalability, ensuring a steady supply for various industries.
Reactions of 3-Thiopropionic Acid:
3-Thiopropionic acid participates in several important chemical reactions due to the presence of both its thiol (-SH) and carboxyl (-COOH) functional groups.
Here are some key reactions:
Oxidation of Thiol Group:
The thiol group in 3-Thiopropionic acid can undergo oxidation to form disulfides.
For example:
2R−SH→R−S−S−R+2H+
This reaction is important in crosslinking processes, especially in biological systems and polymer chemistry, where disulfide bonds stabilize structures.
Esterification of Carboxyl Group:
The carboxyl group (-COOH) can react with alcohols in the presence of an acid catalyst to form esters:
R−COOH+R′−OH→R−COOR′+H2O
This reaction is utilized in the production of esters, which are valuable as solvents, plasticizers, and in chemical synthesis.
Amidation:
The carboxyl group of 3-Thiopropionic acid can react with amines to form amides:
R−COOH+NH 2R′→R−CONHR′+H2O
This is useful in pharmaceutical synthesis for creating bioactive compounds.
Michael Addition:
3-Thiopropionic acid can undergo Michael addition with electron-deficient alkenes, where the thiol group acts as a nucleophile:
R−SH+CH2=CHCOOR′→R−S−CH2−CH2−COOR′
This reaction is significant in organic synthesis, allowing the addition of sulfur-containing groups to α,β-unsaturated carbonyl compounds.
Decarboxylation:
The carboxyl group can be removed through decarboxylation, particularly under high temperatures, resulting in the formation of thiols:
R−CH 2−CH 2−COOH→R−CH 2−SH+CO2
This reaction is relevant in processes where the thiol is required without the carboxyl group.
Reaction with Metal Ions:
The thiol group in 3-Thiopropionic acid has a high affinity for metal ions, forming complexes with metals such as copper, zinc, and mercury.
This reaction is critical in corrosion inhibition, where the acid forms a protective film on metal surfaces:
2R−SH+Cu2+→(R−S)2−Cu+2H+
Polymerization:
3-Thiopropionic acid can act as a chain-transfer agent in radical polymerizations, modifying polymer structure and properties by incorporating sulfur atoms into the polymer backbone.
History of 3-Thiopropionic Acid:
The history of 3-Thiopropionic acid's discovery and development is rooted in the broader study of thiols and carboxylic acids, two important classes of organic compounds.
Thiols were first identified in the 19th century, with scientists exploring their sulfur-containing structures and reactivity, which led to the discovery of numerous thiol derivatives.
3-Thiopropionic acid, also known as β-mercaptopropionic acid, likely emerged from this period of research, as organic chemists were investigating ways to modify propionic acid by introducing functional groups like thiols (-SH).
By the 20th century, 3-Thiopropionic acid became of particular interest due to its potential applications in organic synthesis and industrial processes.
3-Thiopropionic acid's ability to form esters and amides, along with the unique properties of the thiol group, made it valuable for producing fine chemicals, pharmaceuticals, and polymers.
In the latter half of the 20th century, researchers identified 3-Thiopropionic acid's utility in enzyme inhibition and biochemical pathways, sparking its use in both academic research and industrial settings.
Natural Occurrence of 3-Thiopropionic Acid:
While 3-Thiopropionic acid is primarily synthesized for industrial and laboratory use, it can also occur naturally in trace amounts.
In biological systems, thiol-containing compounds like cysteine, glutathione, and other sulfur-based molecules play crucial roles in cellular metabolism, and 3-Thiopropionic acid is part of this broad group of thiol compounds.
In microorganisms like bacteria, 3-Thiopropionic acid and its derivatives can be produced through metabolic pathways that involve sulfur compounds.
Additionally, thiol-containing acids similar to 3-Thiopropionic acid are involved in biochemical detoxification processes, where they help neutralize reactive oxygen species and protect cells from oxidative stress.
Although 3-Thiopropionic acid itself is not a major metabolite, it shares functional similarities with naturally occurring thiol compounds in the biosphere.
Overall, 3-Thiopropionic acid has a history grounded in the study of thiols and has been synthesized for industrial applications, though small amounts can naturally form in biological systems.
