(+-)-Methionine
Basic information
- CAS
26062-47-5- Standard SMILES
CSCCC(N)C(=O)O- InChIKey
FFEARJCKVFRZRR-UHFFFAOYSA-N- Molecular formula
- C5H11NO2S
- Average molar mass
- 149.21 g/mol
- Monoisotopic mass
- 149.05104977
Overview
Methionine is a sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4. It has a role as a Saccharomyces cerevisiae metabolite, a plant metabolite, an Escherichia coli metabolite, a Daphnia magna metabolite and an algal metabolite. It is a sulfur-containing amino acid and an alpha-amino acid. It is functionally related to a butyric acid. It is a conjugate base of a methioninium. It is a conjugate acid of a methioninate. It is a tautomer of a methionine zwitterion.
Names & identifiers
- Preferred name
- (+-)-Methionine
- IUPAC
- 2-amino-4-methylsulfanylbutanoic acid
- English name
- Poly-L-methionine
- Molecular formula
- C5H11NO2S
- Molecular weight
- 149.21
Names & synonyms
DL-METHIONINE59-51-8RacemethionineAcimetionLobamineUrimeth(+-)-MethionineDL-MethioninumMethionine, DL-2-amino-4-methylsulfanylbutanoic acidFEMA No. 3301Methionine, amorphous
Show more names
Nsc118113Poly(Met)polymethioninePoly-L-methioninePOLY-L-METHIONINE USP/EP/BP2-amino-4-methylsulfanylbutanoicaci
2-amino-4-(methylsulfanyl)butanoic acidMethionine DL-DL-2-Amino-4-(methylthio)-butyric acidDTXSID9020821NSC-924173JWT2K6T3DTXCID50821CHEBI:16811
Database identifiers
- CAS
26062-47-5、33807-07-7、348-67-4、59-51-8、63-68-3- PubChem CID
- 876
- DTXSID
DTXSID9020821- ChEMBL
CHEMBL274119- ChEBI
CHEBI:16811- UNII
Properties
Computed structural properties
- XLogP
- -1.9
- Topological polar surface area
- 88.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 97
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Amino Acids and Derivatives
CosmeticsAntistatic; Skin conditioning; Hair conditioning
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, NUTRIENT SUPPLEMENT -> FDA Substance added to food
DensityRelative density (water = 1): 1.3
Flavoring AgentsEU Flavoring substances
Solubility
32.7 mg/mL at 25 °C
Solubility in water, g/100ml at 20 °C: 4.8
Soluble in water; Insoluble in ether
Soluble (in ethanol)
Boiling Point300.00 to 301.00 °C. @ 760.00 mm Hg
Decomposition281 °C
Melting Point281 °C
Physical Description
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 99% (197 of 199) of all reports.
Not Classified
Aggregated GHS information provided per 199 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: DL-Methionine
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Methionine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methionine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Methionine: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - DL-Methionine: Human health tier I assessment
Fire HazardsGives off irritating or toxic fumes (or gases) in a fire.
Hazards Summary
Causes pigmented or nucleated red blood cells, changes in leukocyte counts, and changes in liver, bladder, and spleen weights in repeated-dose oral studies of rats; [RTECS] No listed effects of short-term or long-term exposure; [ICSC] Safe when used as a flavoring agent in food; [JECFA] May cause irritation; [Sigma-Aldrich MSDS]
EPA Safer ChemicalChemical: DL-Methionine
Chemical DangersDecomposes on heating. This produces toxic fumes of sulfur oxides and nitrous oxides.
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesAn essential amino acid; Used therapeutically as an antidote for acetaminophen poisoning and a urinary acidifier; [Merck Index] Used as a flavoring agent and nutritional supplement; [FDA]
U.S. Production2021: 246,400 lb
Industry UsesNot Known or Reasonably Ascertainable
Use Classification
EPA Safer Chemical Functional Use Classes -> Enzymes and Enzyme Stabilizers
Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Cosmetics -> Antistatic; Skin conditioning; Hair conditioning
General Manufacturing Information
Not Known or Reasonably Ascertainable
Methionine: ACTIVE
Additional notes
DefinitionChEBI: Methionine is a sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4. It has a role as an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is an alpha-amino acid and a sulfur-containing amino acid. It is functionally related to a butyric acid. It is a conjugate base of a methioninium. It is a conjugate acid of a methioninate. It is a tautomer of a methionine zwitterion.
Related reactions
88 records
Compound notes
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