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3-mercaptopyruvic acid
pyruvic acid, mercapto- (6CI,7CI,8CI)

Supplier Sponsors

CAS Number: 2464-23-5Picture of molecule3D/inchi
FDA UNII: 5Z1F5OW4YB
Nikkaji Web:J72.997C
Beilstein Number:1747058
Molecular Weight:120.12748000
Formula:C3 H4 O3 S
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
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
 water
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.400002.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.200001.00000
Edible ices, including sherbet and sorbet (03.0): 0.400002.00000
Processed fruit (04.1): 0.300001.50000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 0.400002.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.200001.00000
Bakery wares (07.0): 0.400002.00000
Meat and meat products, including poultry and game (08.0): 0.100000.40000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.100000.40000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.200001.00000
Foodstuffs intended for particular nutritional uses (13.0): 0.400002.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.200001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 0.400002.00000
Ready-to-eat savouries (15.0): 1.000005.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.200001.00000
 
Safety References:
European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 8 (FGE.08)[1]: Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical group 20
View page or View pdf

Flavouring Group Evaluation 74 (FGE.74)[1]: Consideration of Simple Aliphatic Sulphides and Thiols evaluated by JECFA (61st meeting) Structurally related to Aliphatic and Alicyclic Mono-, Di-, Tri-, and Polysulphides with or without Additional Oxygenated Functional Groups from Chemical Group 20 evaluated by EFSA in FGE.08 (2008)
View page or View pdf

Flavouring Group Evaluation 8, Revision 1 (FGE.08Rev1): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30
View page or View pdf

Flavouring Group Evaluation 91 (FGE.91): Consideration of simple aliphatic and aromatic sulphides and thiols evaluated by JECFA (53rd and 68th meetings) structurally related to aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups evaluated by EFSA in FGE.08Rev1 (2009)
View page or View pdf

Flavouring Group Evaluation 08 Rev2 (FGE.08 Rev2): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 8, Revision 3 (FGE.08Rev3): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 08, Revision 4 (FGE.08Rev4): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 08, Revision 5 (FGE.08Rev5): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :98
National Institute of Allergy and Infectious Diseases:Data
2-oxo-3-sulfanylpropanoic acid
Chemidplus:0002464235
 
References:
 2-oxo-3-sulfanylpropanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):98
Pubchem (sid):135077811
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C00957
HMDB (The Human Metabolome Database):HMDB01368
FooDB:FDB021862
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
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
 

Articles:

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].
 
Notes:
3-Mercaptopyruvic acid is an intermediate in cysteine metabolism. (Wikipedia)
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