4-Methyl-2-oxovaleric acid (HCID 70)

Overview

4-methyl-2-oxopentanoic acid is a 2-oxo monocarboxylic acid that is pentanoic acid (valeric acid) substituted with a keto group at C-2 and a methyl group at C-4. A metabolite that has been found to accumulate in maple syrup urine disease. It has a role as a human metabolite and an algal 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 4-methyl-2-oxopentanoate.

Names & identifiers

Preferred name: 4-Methyl-2-oxovaleric acid
IUPAC: 4-methyl-2-oxopentanoic acid
English name: 4-Methyl-2-oxovaleric acid
Molecular formula: C6H10O3
Molecular weight: 130.14

Names & synonyms

4-methyl-2-oxopentanoic acid816-66-04-Methyl-2-oxovaleric acidalpha-Ketoisocaproic acid2-OXO-4-METHYLPENTANOIC ACID2-Oxoisocaproate2-Oxoisocaproic acid4-methyl-2-oxopentanoatePentanoic acid, 4-methyl-2-oxo-alpha-oxoisocaproate2-Oxo-4-methylvaleric acid2-Oxoleucine

Show more names

KETOLEUCINEALPHA KETOISOCAPROATE2-keto-isocaproateALPHA-KETOLEUCINEMethyl-2-oxovalericIsopropylpyruvicacid

2-ketoisocaproate2-oxo-4-methylpentanoatealpha-keto-isocaproic acid2-keto-4-Methylvaleric acid4GUJ8AH400DTXSID6061157CHEBI:48430CHEBI:17865

Database identifiers

CAS: 816-66-0
PubChem CID: 70
DTXSID: DTXSID6061157
ChEMBL: CHEMBL445647
ChEBI: CHEBI:48430
UNII: 4GUJ8AH400
EC Number: 212-435-5
Nikkaji: J39.557I

Properties

Computed structural properties

XLogP: 0.9
Topological polar surface area: 54.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 9
Formal charge: 0
Complexity: 126

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Density1.053-1.058

Flavoring AgentsEU Flavoring substances

Solubility · 3 items

32 mg/mL

Soluble in water

Soluble (in ethanol)

Boiling Point251 °C

Physicochemical properties

Melting point: 8 · 8-10 °C
Boiling point: 82 · 82-83 °C11 mm Hg(lit.)
Density: 1.055 g/mL · 1.055 g/mL at 20 °C(lit.)
refractive index: 20 · n20/D 1.431
FEMA: 3871 · 3871 | 4-METHYL-2-OXOPENTANOIC ACID
FLAVIS Number: 8.052 · 08.052 | 4-Methyl-2-oxovaleric acid
storage temp.: 2 · 2-8°C
solubility: 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml
pka: 2.65 · 2.65±0.54(Predicted)
form: clear liquid
color: Colorless to Yellow
Odor: fruity
Odor Type: fruity
Water Solubility: Soluble in water.
JECFA Number: 633 · 633
BRN: 1701823 · 1701823
InChI: 1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
InChIKey: BKAJNAXTPSGJCU-UHFFFAOYSA-N
SMILES: CC(C)CC(=O)C(O)=O
LogP: 0.17 · 0.17
CAS DataBase Reference: 816 · 816-66-0(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS): 4 · 4-METHYL-2-OXOPENTANOIC ACID
FDA UNII: 4 GUJ8AH400 · 4GUJ8AH400
NIST Chemistry Reference: 4 · 4-Methyl-2-oxovaleric acid(816-66-0)
EPA Substance Registry System: .alpha.-Ketoisocaproic acid (816-66-0)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 314 · H314
Precautionary statements: 280 · P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes: C
Risk Statements: 34 · 34
Safety Statements: 26 · 26-36/37/39-45
RIDADR: 3265 · UN 3265 8/PG 3
WGK Germany: 3 · 3
F: 3 · 3-9-13
TSCA: TSCA listed
HS Code: 2918.3 · 2918.30.9000
HazardClass: 8 · 8
PackingGroup: III
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 1 B · Skin Corr. 1B

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 3 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationPentanoic acid, 4-methyl-2-oxo-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Corr. 1C (100%)

Toxicology

Health EffectsChronically high levels of keto-leucine are associated with Maple Syrup Urine Disease.

Toxicity SummaryKetoleucine is a metabolite that accumulates in Maple Syrup Urine Disease (MSUD) and shown to compromise brain energy metabolism by blocking the respiratory chain.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

F: 3-9-13
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
ridadr: UN 3265 8/PG 3
hs_code: 2918.30.9000
risk_code: 34
Signal word: Danger
Symbol(GHS): GHS05
hazard_code: C
safety_code: 26-36/37/39-45
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: III
Hazard statements: H314
Hazard Classifications: Skin Corr. 1B
Precautionary statements: P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405

Chemistry & industry

Pharmacology

Tissue LocationsNeuron

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 · 3 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing InformationPentanoic acid, 4-methyl-2-oxo-: ACTIVE

Applications

OccurrenceReported found in banana, asparagus, cheese, white wine, cocoa, blue cheese and provolone cheese.

Uses4-Methyl-2-oxovaleric acid is an intermediate in the metabolism of leucine and also used as flavoring agents.

Upstream & downstream products

Upstream raw materials

L-Leucine

Downstream products

4-Methyl-2-oxopentanoic acid methyl ester (R)-2-Hydroxy-4-methylpentanoic acid L-Leucic acid

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]

阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

Additional notes

DefinitionChEBI: A 2-oxo monocarboxylic acid that is pentanoic acid (valeric acid) substituted with a keto group at C-2 and a methyl group at C-4. A metabolite that has been found to accumulate in maple syrup urine disease.