3-mercaptopyruvic acid
pyruvic acid, mercapto- (6CI,7CI,8CI)
Identification
| Name | 3-mercaptopyruvic acid |
| CAS Number | 2464-23-5 |
| FDA UNII | 5Z1F5OW4YB |
| Molecular Formula | C3 H4 O3 S |
| Molecular Weight | 120.12748000 |
| Nikkaji Number | J72.997C |
| Beilstein | 1747058 |
Regulatory
| DG SANTE Food Flavourings | 12.136 3-mercapto-2-oxopropanoic acid |
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 97.00 °C. @ 760.00 mm Hg |
| Boiling Point | 253.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.028000 mmHg @ 25.00 °C. (est) |
| Flash Point | 196.00 °F. TCC ( 91.11 °C. ) |
| logP (o/w) | -0.834 (est) |
| Soluble in | alcohol |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for 3-mercaptopyruvic acid usage levels up to | not for fragrance use. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.24 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 160 (μg/person/day) |
| Threshold of Concern | 90 (μg/person/day) |
| Structure Class | III |
| Dairy products, excluding products of category 02.0 (01.0) | 0.40000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 0.20000 |
| Edible ices, including sherbet and sorbet (03.0) | 0.40000 |
| Processed fruit (04.1) | 0.30000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 0.40000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 0.20000 |
| Bakery wares (07.0) | 0.40000 |
| Meat and meat products, including poultry and game (08.0) | 0.10000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 0.10000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 0.20000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 0.40000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 0.20000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 0.40000 |
| Ready-to-eat savouries (15.0) | 1.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 0.20000 |
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Potential Uses
Natural Occurrence
Synonyms
3-
mercapto-2-oxopropanoic acid
propanoic acid, 3-mercapto-2-oxo-
propanoic acid, 3-mercapto-2-oxo- (9CI)
pyruvic acid, mercapto- (6CI,7CI,8CI)
2-oxo-3-
sulfanylpropanoic acid
PubMed:
A novel method for the analysis of 3-mercaptopyruvate using high-performance liquid chromatography with fluorescence detection.
PubMed:
Structure and kinetic analysis of H2S production by human mercaptopyruvate sulfurtransferase.
PubMed:
Oxidative stress suppresses the cellular bioenergetic effect of the 3-mercaptopyruvate sulfurtransferase/hydrogen sulfide pathway.
PubMed:
Cyanide antidotes for mass casualties: water-soluble salts of the dithiane (sulfanegen) from 3-mercaptopyruvate for intramuscular administration.
PubMed:
Intramitochondrial hydrogen sulfide production by 3-mercaptopyruvate sulfurtransferase maintains mitochondrial electron flow and supports cellular bioenergetics.
PubMed:
Cyanide toxicity in juvenile pigs and its reversal by a new prodrug, sulfanegen sodium.
PubMed:
Multiple hemodynamic effects of endogenous hydrogen sulfide on central nervous system in rats.
PubMed:
The combination of cobinamide and sulfanegen is highly effective in mouse models of cyanide poisoning.
PubMed:
Mercaptopyruvate inhibits tissue-nonspecific alkaline phosphatase and calcium pyrophosphate dihydrate crystal dissolution.
PubMed:
The mercaptopyruvate sulfurtransferase of Trichomonas vaginalis links cysteine catabolism to the production of thioredoxin persulfide.
PubMed:
Novel, orally effective cyanide antidotes.
PubMed:
The mercaptopyruvate pathway in cysteine catabolism: a physiologic role and related disease of the multifunctional 3-mercaptopyruvate sulfurtransferase.
PubMed:
Identification of putative sulfurtransferase genes in the extremophilic Acidithiobacillus ferrooxidans ATCC 23270 genome: structural and functional characterization of the proteins.
PubMed:
Properties of the Escherichia coli rhodanese-like protein SseA: contribution of the active-site residue Ser240 to sulfur donor recognition.
PubMed:
Study on the cytochrome P-450- and glutathione-dependent biotransformation of trichloroethylene in humans.
PubMed:
Effects of thyroxine on L-cysteine desulfuration in mouse liver.
PubMed:
Characterization of a sulfurtransferase from Arabidopsis thaliana.
PubMed:
The glutathione dependence of inorganic sulfate formation from L- or D-cysteine in isolated rat hepatocytes.
PubMed:
Glutathione-dependent bioactivation of haloalkenes.
PubMed:
Biomimetic dye affinity chromatography for the purification of bovine heart lactate dehydrogenase.
PubMed:
Cytosolic mercaptopyruvate sulfurtransferase is evolutionarily related to mitochondrial rhodanese. Striking similarity in active site amino acid sequence and the increase in the mercaptopyruvate sulfurtransferase activity of rhodanese by site-directed mutagenesis.
PubMed:
Electron paramagnetic resonance evidence for a cysteine-based radical in pyruvate formate-lyase inactivated with mercaptopyruvate.
PubMed:
Purification and characterization of 3-mercaptolactic acid S-conjugate oxidases.
PubMed:
Modifiers of mercaptopyruvate sulfurtransferase catalyzed conversion of cyanide to thiocyanate in vitro.
PubMed:
Alternative sulphur donors for detoxification of cyanide in the chicken.
PubMed:
Purification and characterization of 3-mercaptopyruvic acid S-conjugate reductases.
PubMed:
Formation of sulfate from L-cysteine in rat liver mitochondria.
PubMed:
Reduction of 3-mercaptopyruvate in rat liver is catalyzed by lactate dehydrogenase.
PubMed:
Modification of erythrocyte enzyme activities by persulfides and methanethiol: possible regulatory role.
PubMed:
3-Mercaptopyruvate, 3-mercaptolactate and mercaptoacetate.
PubMed:
Rat liver 4-hydroxy-2-ketoglutarate aldolase: purification and kinetic characterization.
PubMed:
The decarboxylation of 3-mercaptopyruvate to 2-mercaptoacetate.
PubMed:
Cyanide antagonism.
PubMed:
The inhibitory effect of L-cysteine and its derivatives on glycolysis in Ehrlich ascites tumour cells.
PubMed:
Ketomethylthiobutyric acid formation from methylthioadenosine: a diffusion assay.
PubMed:
Metabolism of 3-mercaptopyruvate in rat tissues.
PubMed:
Biosynthesis of S-(2-hydroxy-2-carboxyethylthio)-L-cysteine (3-mercaptolactate-cysteine disulfide) by the rat heart.
PubMed:
Reduction of beta-thiopyruvic acid by lactate dehydrogenase: a kinetic study.
PubMed:
On the chemistry and biochemistry of 3-mercaptopyruvic acid, the alpha-keto acid analog of cysteine.
PubMed:
3-mercaptolactate cysteine disulfiduria: biochemical studies on affected and unaffected members of a family.
PubMed:
3-Mercaptopyruvate sulfurtransferase.
PubMed:
[II. Tuberculostatic effect of isonicotinoylhydrazonopyruvic acid, isonicotinoylhydrazonoxalacetic acid, isonicotinoylhydrazono-3-mercaptopyruvic acid, isonicotinoylhydrazono-3-bromopyruvic acid, isonicotinoylhydrazono-2-oxoglutaric acid and isonicotinoylhydrazonolevulinic acid].