EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

methyl pyruvate
propanoic acid, 2-oxo-, methyl ester

Supplier Sponsors

Name:methyl 2-oxopropanoate
CAS Number: 600-22-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:209-987-4
FDA UNII:3KJM65G5XL
Nikkaji Web:J483I
Beilstein Number:1361953
MDL:MFCD00008754
CoE Number:10848
XlogP:-0.10 (est)
Molecular Weight:102.08942000
Formula:C4 H6 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome 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
FLAVIS Number:09.626 (Old)
DG SANTE Food Flavourings:09.626 methyl 2-oxopropionate
 
Physical Properties:
Appearance:colorless clear liquid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:1.14500 to 1.15100 @ 25.00 °C.
Pounds per Gallon - (est).: 9.528 to 9.577
Refractive Index:1.40100 to 1.40700 @ 20.00 °C.
Boiling Point: 137.00 °C. @ 760.00 mm Hg
Vapor Pressure:7.704000 mmHg @ 25.00 °C. (est)
Flash Point: 103.00 °F. TCC ( 39.44 °C. )
logP (o/w): -0.159 (est)
Soluble in:
 alcohol
 water, slightly
 water, 7.568e+005 mg/L @ 25 °C (est)
Insoluble in:
 water
Similar Items:note
isoamyl pyruvate
ethyl pyruvate
(Z)-3-hexen-1-yl pyruvate
propyl pyruvate
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Methyl Pyruvate
Penta International
METHYL PYRUVATE
Santa Cruz Biotechnology
For experimental / research use only.
Methyl Pyruvate 98%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Methyl pyruvate 90%, technical grade
TCI AMERICA
For experimental / research use only.
Methyl Pyruvate >97.0%(GC)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 10 - Flammable.
R 38 - Irritating to skin.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
 
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 methyl pyruvate usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.024 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 3900 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
 
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): 7.0000035.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 5.0000025.00000
Edible ices, including sherbet and sorbet (03.0): 10.0000050.00000
Processed fruit (04.1): 7.0000035.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000050.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 10.0000050.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.0000010.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 5.0000025.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000050.00000
Ready-to-eat savouries (15.0): 20.00000100.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000
 
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):

Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 92 (FGE.92): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (68th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones evaluated by EFSA in FGE.10Rev1 (2009)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 10, Revision 2 (FGE.10Rev2): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 10, Revision 3 (FGE.10Rev3): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30
View page or View pdf

EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11748
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 3272
WGK Germany:3
methyl 2-oxopropanoate
Chemidplus:0000600226
 
References:
 methyl 2-oxopropanoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):11748
Pubchem (sid):134976377
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2918.30.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 arctic bramble fruit
Search Trop Picture
 celery
Search Trop Picture
 vanilla bean
Search Picture
 
Synonyms:
 methyl 2-oxopropanoate
 methyl 2-oxopropionate
 methyl glyoxylic acid methyl ester
 methylglyoxylic acid methyl ester
2-oxopropanoic acid methyl ester
2-oxo-propanoic acid methyl ester
 propanoic acid, 2-oxo-, methyl ester
2-oxo-propionic acid methyl ester
 pyruvic acid methyl ester
 pyruvic acid, methyl ester
 

Articles:

PubMed:l-cysteine reversibly inhibits glucose-induced biphasic insulin secretion and ATP production by inactivating PKM2.
PubMed:Extended reaction scope of thiamine diphosphate dependent cyclohexane-1,2-dione hydrolase: from C-C bond cleavage to C-C bond ligation.
PubMed:Acuticoccus yangtzensis gen. nov., sp. nov., a novel member in the family Rhodobacteraceae, isolated from the surface water of the Yangtze Estuary.
PubMed:Methyl pyruvate rescues mitochondrial damage caused by SIGMAR1 mutation related to amyotrophic lateral sclerosis.
PubMed:T-type Ca2+ channel blocker, KYS05090 induces autophagy and apoptosis in A549 cells through inhibiting glucose uptake.
PubMed:Oxidative damage to mitochondria at the nodes of Ranvier precedes axon degeneration in ex vivo transected axons.
PubMed:Tetrandrine blocks autophagic flux and induces apoptosis via energetic impairment in cancer cells.
PubMed:Kinetic characterization of recombinant Bacillus coagulans FDP-activated l-lactate dehydrogenase expressed in Escherichia coli and its substrate specificity.
PubMed:Products and mechanism of the reactions of OH radicals and Cl atoms with methyl methacrylate (CH2═C(CH3)C(O)OCH3) in the presence of NOx.
PubMed:3-Methyl pyruvate enhances radiosensitivity through increasing mitochondria-derived reactive oxygen species in tumor cell lines.
PubMed:Glucose-stimulated single pancreatic islets sustain increased cytosolic ATP levels during initial Ca2+ influx and subsequent Ca2+ oscillations.
PubMed:Stereospecific synthesis of a twinned alanine ester.
PubMed:Thiazolidinediones are acute, specific inhibitors of the mitochondrial pyruvate carrier.
PubMed:Detection and characterization of impurities in commercial products with Fourier transform microwave spectroscopy.
PubMed:Synthesis of cytochrome C oxidase 2: a p53-dependent metabolic regulator that promotes respiratory function and protects glioma and colon cancer cells from hypoxia-induced cell death.
PubMed:Dual inhibition of tumor energy pathway by 2-deoxyglucose and metformin is effective against a broad spectrum of preclinical cancer models.
PubMed:Supplementation of pyruvate prevents palmitate-induced impairment of glucose uptake in C2 myotubes.
PubMed:Atmospheric chemistry of two biodiesel model compounds: methyl propionate and ethyl acetate.
PubMed:Ethyl pyruvate preserves IGF-I sensitivity toward mTOR substrates and protein synthesis in C2C12 myotubes.
PubMed:Troglitazone regulates anaplerosis via a pull/push affect on glutamate dehydrogenase mediated glutamate deamination in kidney-derived epithelial cells; implications for the Warburg effect.
PubMed:A general approach to anionic acid-labile surfactants with tunable properties.
PubMed:Glycolytic flux occurs in Drosophila melanogaster recovering from camptothecin treatment.
PubMed:Kinetics and products of gas-phase reactions of ozone with methyl methacrylate, methyl acrylate, and ethyl acrylate.
PubMed:AGI-1067, a novel antioxidant and anti-inflammatory agent, enhances insulin release and protects mouse islets.
PubMed:Dual role of poly(ADP-ribose) glycohydrolase in the regulation of cell death in oxidatively stressed A549 cells.
PubMed:Mitochondrial dysfunction contributes to impaired insulin secretion in INS-1 cells with dominant-negative mutations of HNF-1alpha and in HNF-1alpha-deficient islets.
PubMed:Starvation in the midst of plenty: making sense of ceramide-induced autophagy by analysing nutrient transporter expression.
PubMed:Ceramide starves cells to death by downregulating nutrient transporter proteins.
PubMed:C1-symmetric oxazolinyl sulfoximines as ligands in copper-catalyzed asymmetric mukaiyama aldol reactions.
PubMed:Keto-enol driven assembly of methyl pyruvate on Pt(111).
PubMed:Genistein-induced apoptosis and autophagocytosis in ovarian cancer cells.
PubMed:Rhythm of the beta-cell oscillator is not governed by a single regulator: multiple systems contribute to oscillatory behavior.
PubMed:(E)-Methyl 2-[(4-nitro-phen-yl)-hydrazono]-propanoate.
PubMed:Evidence for C-H...O=C bonding in coadsorbed aromatic-carbonyl systems on Pt(111).
PubMed:Dioxiranes generated in situ from pyruvates and oxone as environmentally friendly oxidizing agents for disinfection.
PubMed:Substrate effects on oscillations in metabolism, calcium and secretion in single mouse islets of Langerhans.
PubMed:The glucose dependence of Akt-transformed cells can be reversed by pharmacologic activation of fatty acid beta-oxidation.
PubMed:Regioselectively nucleus and/or side-chain fluorinated 2-(Phenanthryl)propionic acids by an effective combination of radical and organometallic chemistry.
PubMed:P2Y purinergic potentiation of glucose-induced insulin secretion and pancreatic beta-cell metabolism.
PubMed:Overexpression of short heterodimer partner recovers impaired glucose-stimulated insulin secretion of pancreatic beta-cells overexpressing UCP2.
PubMed:Taurine increases glucose sensitivity of UCP2-overexpressing beta-cells by ameliorating mitochondrial metabolism.
PubMed:Quantitative NAD(P)H/flavoprotein autofluorescence imaging reveals metabolic mechanisms of pancreatic islet pyruvate response.
PubMed:Stereoselective generation of vicinal stereogenic quaternary centers by photocycloaddition of 5-methoxy oxazoles to alpha-keto esters: synthesis of erythro beta-hydroxy dimethyl aspartates.
PubMed:Adsorption states and modifier-substrate interactions on Pt(111) relevant to the enantioselective hydrogenation of alkyl pyruvates in the Orito reaction.
PubMed:Utility of historical vehicle-control data in the interpretation of the local lymph node assay.
PubMed:Monitoring carbonyl-amine reaction between pyruvic acid and alpha-amino alcohols by FTIR spectroscopy--a possible route to Amadori products.
PubMed:Dacrymenone and VM 3298-2--new antibiotics with antibacterial and antifungal activity.
PubMed:Observation of high enantioselectivity for the gas phase hydrogenation of methyl pyruvate using supported Pt catalysts pre-modified with cinchonidine.
PubMed:Studies with GIP/Ins cells indicate secretion by gut K cells is KATP channel independent.
PubMed:Aspects of enantioselective heterogeneous catalysis: structure and reactivity of (S)-(-)-1-(1-naphthyl)ethylamine on Pt[111].
PubMed:Methyl pyruvate stimulates pancreatic beta-cells by a direct effect on KATP channels, and not as a mitochondrial substrate.
PubMed:Novel insulin/GIP co-producing cell lines provide unexpected insights into Gut K-cell function in vivo.
PubMed:Potentiation and prolongation of the insulinotropic action of glucagon-like peptide 1 by methyl pyruvate or dimethyl ester of L-glutamic acid in a type 2 diabetes animal model.
PubMed:New methyl pyruvate thiosemicarbazones and their copper and zinc complexes: synthesis, characterization, X-ray structures and biological activity.
PubMed:Selective C-C bond activation of methyl pyruvate on Ni(111) to yield surface methoxycarbonyl.
PubMed:Potentiation by methyl pyruvate of GLP-1 insulinotropic action in normal rats.
PubMed:Methyl pyruvate initiates membrane depolarization and insulin release by metabolic factors other than ATP.
PubMed:Differential regulation of [Ca2+]i oscillations in mouse pancreatic islets by glucose, alpha-ketoisocaproic acid, glyceraldehyde and glycolytic intermediates.
PubMed:Energetic requirement of carbachol-induced Ca2+ signaling in single mouse beta-cells.
PubMed:Insulin secretion, inositol phosphate levels, and phospholipase C isozymes in rodent pancreatic islets.
PubMed:Use of a soluble tetrazolium compound to assay metabolic activation of intact beta cells.
PubMed:Epoxidation reactions of unsaturated fatty esters with potassium peroxomonosulfate.
PubMed:Mitochondrial activation directly triggers the exocytosis of insulin in permeabilized pancreatic beta-cells.
PubMed:Influence of pyruvic acid methyl ester on rat pancreatic islets. Effects on insulin secretion, phosphoinositide hydrolysis, and sensitization of the beta cell.
PubMed:Insulinotropic action of methyl pyruvate: enzymatic and metabolic aspects.
PubMed:Insulinotropic action of methyl pyruvate: secretory, cationic, and biosynthetic aspects.
PubMed:Effects of the methyl esters of pyruvate, succinate and glutamate on the secretory response to meglitinide analogues in rat pancreatic islets.
PubMed:Activation of stimulus-secretion coupling in pancreatic beta-cells by specific products of glucose metabolism. Evidence for privileged signaling by glycolysis.
PubMed:In vitro and in vivo insulinotropic action of methyl pyruvate.
PubMed:Synthesis of 5-aminopentyl 4,6-O-[(R)-1-carboxyethylidene]-beta-D-galactopyranoside and its use as a ligand for the affinity chromatography of human serum amyloid P . protein.
PubMed:Structural studies of the capsular polysaccharide of Klebsiella type 33.
PubMed:Polarographic determination of methyl methacrylate.
 
Notes:
None found
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