Basic information
- CAS
600-22-6- Standard SMILES
COC(=O)C(C)=O- InChIKey
CWKLZLBVOJRSOM-UHFFFAOYSA-N- Molecular formula
- C4H6O3
- Average molar mass
- 102.09 g/mol
- Monoisotopic mass
- 102.03169405
Overview
Methyl pyruvate is a pyruvate ester resultinf grom the formal condensation of the carboxy group of pyruvic acid with the hydroxy group of methanol. It is a methyl ester and a pyruvate ester. It is functionally related to a pyruvic acid.
Names & identifiers
- Preferred name
- Methyl pyruvate
- IUPAC
- methyl 2-oxopropanoate
- English name
- Methyl pyruvate
- Molecular formula
- C4H6O3
- Molecular weight
- 102.09
Names & synonyms
METHYL PYRUVATE600-22-6Methyl 2-oxopropanoateMethyl 2-oxopropionatePyruvic acid, methyl esterPropanoic acid, 2-oxo-, methyl esterMethylglyoxylic acid methyl ester2-oxo-propionic acid methyl ester3KJM65G5XLNSC-65430CHEBI:51850RefChem:818068
Show more names
PAMEMethyl acetoformateksbyPYR MEMethyl pyruyateMethylPyruvate>Methylpyruvate,96%
209-987-4MethylpyruvatePyruvic acid methyl estermethyl-PyruvateDTXSID9049326MFCD000087542-oxopropanoic acid methyl esterUNII-3KJM65G5XL
Database identifiers
- CAS
600-22-6- PubChem CID
- 11748
- DTXSID
DTXSID9049326- ChEMBL
CHEMBL3185405- ChEBI
CHEBI:51850- UNII
- 3KJM65G5XL
- EC Number
- 209-987-4
- Nikkaji
- J483I
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 95.1
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
Flavoring AgentsEU Flavoring substances
Physicochemical properties
- Melting point
- -22 °C · -22 °C
- Boiling point
- 134 · 134-137 °C (lit.)
- Density
- 1.13 g/mL · 1.13 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.404(lit.)
- FLAVIS Number
- 9.626 · 09.626 | Methyl 2-oxopropionate
- Flash point
- 103 °F · 103 °F
- storage temp.
- 2 · 2-8°C
- solubility
- 1.1 g/10 · ethanol: soluble1.1g/10 mL, clear, colorless to almost colorless
- form
- liquid
- color
- Yellow
- Water Solubility
- Soluble in chloroform, methanol, ether, alcohol. Slightly soluble in water.
- Merck
- 14 · 14,8021
- BRN
- 1361953 · 1361953
- InChI
- 1S/C4H6O3/c1-3(5)4(6)7-2/h1-2H3
- InChIKey
- CWKLZLBVOJRSOM-UHFFFAOYSA-N
- SMILES
- COC(=O)C(C)=O
- LogP
- -0.159 · -0.159 (est)
- CAS DataBase Reference
- 600 · 600-22-6(CAS DataBase Reference)
- FDA UNII
- 3 KJM65G5XL · 3KJM65G5XL
- NIST Chemistry Reference
- 2 · Propanoic acid, 2-oxo-, methyl ester(600-22-6)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Warning
- Hazard statements
- 226 · H226
- Precautionary statements
- 261 · P261
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xi,F
- Risk Statements
- 10 · 10
- Safety Statements
- 23 · 23-24/25-16
- RIDADR
- 3272 · UN 3272 3/PG 3
- WGK Germany
- 3 · 3
- F
- 10 · 10-21
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29183000 · 29183000
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 · Flam. Liq. 3
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Warning
H226 (92.3%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P319, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 52 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Propanoic acid, 2-oxo-, methyl ester
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 13-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18742
Propanoic acid, 2-oxo-, methyl ester: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesFlam. Liq. 3 (92.3%)
Safety data
- F
- 10-21
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- ridadr
- UN 3272 3/PG 3
- hs_code
- 29183000
- risk_code
- 10
- Signal word
- Warning
- Symbol(GHS)
- GHS02
- hazard_code
- Xi,F
- safety_code
- 23-24/25-16
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H226
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Flam. Liq. 3
- Precautionary statements
- P261
Chemistry & industry
Applications
UsesMethyl Pyruvate acts as a potent secretagogue used in the study of stimulus-secretion coupling. Also used in the preparation of quinoxalines as dual phoosphodiesterase 2/10 (PDE2/10) inhibitors. It increases free calcium ion concentration in the cytosol of pancreatic cells. It is used in the preparation of dimethyl 2,3-dimethylenebutanedioate.
UsesMethyl pyruvate may be used to investigate the adsorption and reactivity of methyl pyruvate on Pt{111}. It may be used in the preparation of dimethyl 2,3-dimethylenebutanedioate.
General DescriptionMethyl pyruvate is a pyruvic ester. Surface conditions during Pt/silica EUROPT-1 modified by cinchonidine catalyzed by enantioselective hydrogenation of methyl pyruvate to R-(+)-methyl lactate were investigated. Enantioselective hydrogenation of methyl pyruvate over finely dispersed polyvinylpyrrolidone-stabilized and the corresponding alumina-supported iridium clusters modified with cinchonidine was studied. The molecular orientation and conformation of methyl pyruvate on Ni(111) surface has been investigated in the temperature range 105-220K. Methyl pyruvate is reported to stimulate insulin secretion in vitro and in vivo.
Preparation methods
PreparationMethyl pyruvate has been prepared from the silver salt of pyruvic acid and methyl iodide; from the free acid, by the ethanol-vapor method without a catalyst, by azeotropic removal of the water produced by the reaction of methanol in the presence of p-toluenesulfonic acid (the present method), and by refluxing with methanol in ethylene dichloride using ethanesulfonic acid as a catalyst (73% yield). Pyruvic esters have also been prepared by the catalytic dehydrogenation of lactic acid esters and by the oxidation of ethyl lactate with potassium permanganate. DOI: 10.15227/orgsyn.024.0072
Upstream & downstream products
Upstream raw materials
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Additional notes
DefinitionChEBI: Methyl pyruvate is a pyruvate ester resultinf grom the formal condensation of the carboxy group of pyruvic acid with the hydroxy group of methanol. It is a pyruvate ester and a methyl ester. It derives from a pyruvic acid.
Related reactions
172 records
Compound notes
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