3-Methyl-2-oxobutanoic acid
Basic information
- CAS
759-05-7- Standard SMILES
CC(C)C(=O)C(=O)O- InChIKey
QHKABHOOEWYVLI-UHFFFAOYSA-N- Molecular formula
- C5H8O3
- Average molar mass
- 116.11 g/mol
- Monoisotopic mass
- 116.04734411
Overview
3-methyl-2-oxobutanoic acid is a 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid. It has a role as a Saccharomyces cerevisiae metabolite and a human metabolite. It is a branched-chain keto acid and a 2-oxo monocarboxylic acid. It is functionally related to a butyric acid. It is a conjugate acid of a 3-methyl-2-oxobutanoate. It is a tautomer of a 2-hydroxy-3-methyl-2-butenoic acid.
Names & identifiers
- Preferred name
- 3-Methyl-2-oxobutanoic acid
- IUPAC
- 3-methyl-2-oxobutanoic acid
- English name
- 3-Methyl-2-oxobutyric aciddiscontinued
- Molecular formula
- C5H8O3
- Molecular weight
- 116.12
Names & synonyms
3-Methyl-2-oxobutanoic acid759-05-73-Methyl-2-oxobutyric acidalpha-Ketoisovaleratealpha-ketovaline2-Oxo-3-methylbutanoic acidDimethylpyruvic acidButanoic acid, 3-methyl-2-oxo-2-ketovaline2-keto-3-methylbutyric acidIsopropylglyoxylic acid2-Oxo-3-methylbutyric acid
Show more names
2-Ketoisovaleric acid2-oxoisovaleric acida-Ketoisovaleric acidα-Keto-Valineα-Ketoisovaleric acidTalabostat Impurity 34ALPHA-KETOISOVALERICACID
alpha-Oxoisovaleric acidalpha-keto-valine2-Ketoisovaleratealpha-oxo-beta-methylbutyricacid34P71D50E0CHEBI:16530alpha-Oxo-beta-methylbutyric acidFEMA NO. 3869, ACID-
Database identifiers
- CAS
759-05-7- PubChem CID
- 49
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 115
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Branched fatty acids [FA0102]
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.115-1.120
Flavoring AgentsEU Flavoring substances
Solubility
Soluble in water
Soluble (in ethanol)
Boiling Point251 °C
Melting Point31.5 °C
Refractive Index1.436-1.446
Physical Description
Solid
Pale yellow liquid; fruity aroma
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
Danger
H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationButanoic acid, 3-methyl-2-oxo-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (33.3%)
Toxicology
Health EffectsChronically high levels of alpha-ketoisovaleric acid are associated with Maple Syrup Urine Disease.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- tsca
- TSCA listed
- hs_code
- 2918300090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
Tissue LocationsPlacenta
Cellular LocationsCytoplasm
Metabolite Pathways2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency
Uses & manufacturing
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationButanoic acid, 3-methyl-2-oxo-: ACTIVE
Applications
OccurrenceReported found in banana, bread, blue and provolone cheeses, asparagus, beer and cocoa
Upstream & downstream products
Upstream raw materials
Related reactions
1 records
Compound notes
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