Basic information
- CAS
1460-34-0- Standard SMILES
CCC(C)C(=O)C(=O)O- InChIKey
JVQYSWDUAOAHFM-UHFFFAOYSA-N- Molecular formula
- C6H10O3
- Average molar mass
- 130.14 g/mol
- Monoisotopic mass
- 130.06299418
Overview
3-methyl-2-oxovaleric acid is a 2-oxo monocarboxylic acid that is valeric acid carrying oxo- and methyl substituents at C-2 and C-3, respectively. An alpha-keto acid analogue and metabolite of isoleucine in man, animals and bacteria. Used as a clinical marker for maple syrup urine disease (MSUD). It has a role as a human metabolite. It is a branched-chain keto acid and a 2-oxo monocarboxylic acid. It is functionally related to a valeric acid. It is a conjugate acid of a 3-methyl-2-oxovalerate.
Names & identifiers
- Preferred name
- alpha-Keto-beta-methylvaleric acid
- IUPAC
- 3-methyl-2-oxopentanoic acid
- English name
- 3-METHYL-2-OXOVALERIC ACID
- Molecular formula
- C6H10O3
- Molecular weight
- 130.14
Names & synonyms
3-Methyl-2-oxovaleric acid1460-34-0alpha-Keto-beta-methylvaleric acid2-OXO-3-METHYLVALERIC ACID2-Oxo-3-methylpentanoic acid3-Ethyl-3-methylpyruvic acid3-methyl-2-oxo-pentanoic acid2-oxo-3-methyl-n-valeric acid2-oxoisoleucine787T50HCIValpha-keto-beta-methyl-n-valeric acidCHEBI:35932
Show more names
3-METHYL-2-OXOPENTANOIC ACIDα-Keto-β-methylvaleric acidPentanoic acid, 3-methyl-2-oxo-3-METHYL-2-OXOVALERICMETHYLETHYLPYRUVIC ACID3-methyl-2-oxovalericaciα-Keto-3-methylvaleric acid
DTXSID508626702-keto-3-methylvaleric acidalpha-oxo-beta-methylvaleric acidalpha-oxo-beta-methyl-n-valeric acidKMVARefChem:503701DTXCID30203608FEMA NO. 3870, ACID-(A+-)-
Database identifiers
- CAS
1460-34-0、39748-49-7- PubChem CID
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 128
Experimental & physicochemical properties
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
Soluble in water
Soluble (in ethanol)
Boiling Point233 °C
Physical DescriptionWhite crystalline powder; slight fruity aroma
Collision Cross Section
127.1 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
127.3 Ų [M-H]-
Physicochemical properties
- Melting point
- 42 °C · 42°C
- Boiling point
- 84 °C · 84 °C / 18mmHg
- Density
- 1.087 · 1.087±0.06 g/cm3(Predicted)
- FEMA
- 3870 · 3870 | 3-METHYL-2-OXOPENTANOIC ACID
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
Warning
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Informationalpha-Keto-beta-methylvaleric acid: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesEye Irrit. 2A (100%)
Toxicology
Health EffectsChronically high levels of 3-methyl-2-oxovaleric acid are associated with Maple Syrup Urine Disease.
Toxicity Summary
3-Methyl-2-oxovaleric acid is produced from isoleucine by cytosolic branched chain aminotransferase 1, whereupon it is further degraded by branched chain keto acid dehydrogenase E1 to 2-methyl-1-hydroxybutyl-ThPP. It is used as a clinical marker for maple syrup urine disease (MSUD). MSUD is caused by a deficiency of the branched-chain -keto acid dehydrogenase complex resulting in an accumulation of branched-chain amino acids and the corresponding -keto-and -hydroxy acids in blood, urine and cerebrospinal fluid causing neurological damage and mental retardation.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
Chemistry & industry
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
Applications
Uses3-Methyl-2-oxovaleric acid is a degradation product from Isoleucine. 3-Methyl-2-oxovaleric acid is a biomarker of mustard airway diseases (MADs) and uric acid stone[1][2].
Suppliers80 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
河南赢创生物科技有限公司16650615803 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
上海迈瑞尔生化科技有限公司
Related reactions
1 records
Compound notes
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