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

Überblick

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.

Namen und Bezeichner

Bevorzugter Name: 4-Methyl-2-oxovaleric acid
IUPAC: 4-methyl-2-oxopentanoic acid
Lokaler Name: 4-Methyl-2-oxovaleriansure
Englischer Name: 4-Methyl-2-oxovaleric acid
Summenformel: C6H10O3
Molmasse: 130.14

Namen und Synonyme

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

Weitere Namen anzeigen

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

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 0,9
Polarare Oberfläche (TPSA): 54,4 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 3
Schwere Atome: 9
Formalladung: 0
Komplexität: 126

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

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

Density1.053-1.058

Flavoring AgentsEU Flavoring substances

Solubility · 3 Einträge

32 mg/mL

Soluble in water

Soluble (in ethanol)

Boiling Point251 °C

Physikochemische Eigenschaften

Schmelzpunkt: 8 · 8-10 °C
Siedepunkt: 82 · 82-83 °C11 mm Hg(lit.)
Dichte: 1.055 g/mL · 1.055 g/mL at 20 °C(lit.)
Brechungsindex: 20 · n20/D 1.431
FEMA: 3871 · 3871 | 4-METHYL-2-OXOPENTANOIC ACID
storage temp.: 2 · 2-8°C
Löslichkeit: 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml
pka: 2.65 · 2.65±0.54(Predicted)
Aggregatzustand: clear liquid
Farbe: Colorless to Yellow
Geruch (Odor): fruity
Geruchsart: fruity
Wasserlöslichkeit: 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 Datenbank: 816 · 816-66-0(CAS DataBase Reference)
NIST chemische Informationen: 4 · 4-Methyl-2-oxovaleric acid(816-66-0)
EPA chemische Informationen: .alpha.-Ketoisocaproic acid (816-66-0)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

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%)

Toxikologische Informationen

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).

Sicherheitsdaten

F: 3-9-13
wgk: 3
tsca: TSCA listed
ridadr: UN 3265 8/PG 3
hs_code: 2918.30.9000
risk_code: 34
hazard_code: C
safety_code: 26-36/37/39-45
hazard_class: 8
packing_group: III
Speicherklasse: 8A - Combustible corrosive hazardous materials
Hazard Classifications: Skin Corr. 1B

Chemie und Industrie

Pharmakologische Informationen

Tissue LocationsNeuron

Cellular LocationsCytoplasm

Metabolite Pathways2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency

Verwendung und Herstellung

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 Einträge

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

Anwendungen

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

Verwenden4-Methyl-2-oxovaleric acid is an intermediate in the metabolism of leucine and also used as flavoring agents.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

L-Leucin

Nachgelagerte Produkte

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

Anbieter50 Anbieter

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]

Ergänzende Hinweise

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.