HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methyl-2-oxovaleric acid
KETOLEUCINE · 4-METHYL-2-OXOPENTANOIC ACID · ALPHA KETOISOCAPROATE · ALPHA-KETOISOCAPROIC ACID · 2-keto-isocaproate · 2-OXOISOCAPROIC ACID · 2-Oxo-4-methylpentanoic acid · ALPHA-KETOLEUCINE
Identifiers & Physical Properties
| CAS No. | 816-66-0 |
|---|---|
| Molecular formula | C6H10O3 |
| Average molar mass | 130.14 g/mol |
| Monoisotopic mass | 130.06299418 g/mol |
| SMILES | CC(C)CC(=O)C(=O)O |
| InChIKey | BKAJNAXTPSGJCU-UHFFFAOYSA-N |
| PubChem CID | 70 |
| ChEMBL | CHEMBL445647 |
| ChEBI | CHEBI:48430 |
| EC No. | 212-435-5 |
| DTXSID | DTXSID6061157 |
Chemical & Physical Properties
| XLogP | 0.9 |
|---|---|
| Topological polar surface area | 54.4 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 3 |
| Heavy atoms | 9 |
| Formal charge | 0 |
| Complexity | 126 |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Density | 1.053-1.0581.055 g/mL at 20 °C(lit.) |
| Flavoring agents | EU Flavoring substances |
| Solubility | 32 mg/mLSoluble in waterSoluble (in ethanol)DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlSoluble in water. |
| Boiling point | 251 °C82-83 °C11 mm Hg(lit.) |
| Melting point | 8 - 10 °C8-10 °C |
| Refractive index | 1.432-1.442n20/D 1.431 |
| Physical Description | LiquidPale yellow liquidfruity aroma |
| FEMA | 3871 | 4-METHYL-2-OXOPENTANOIC ACID |
| FLAVIS Number | 08.052 | 4-Methyl-2-oxovaleric acid |
| Storage conditions | 2-8°C |
| pKa (acidity coefficient) | 2.65±0.54(Predicted) |
| Physical state | clear liquid |
| Color | Colorless to Yellow |
| Odor | fruity |
| Odor type | fruity |
| JECFA Number | 633 |
| BRN | 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 (partition coefficient) | 0.17 |
| CAS DataBase Reference | 816-66-0(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | 4-METHYL-2-OXOPENTANOIC ACID |
| FDA UNII | 4GUJ8AH400 |
| NIST Chemistry Reference | 4-Methyl-2-oxovaleric acid(816-66-0) |
| EPA Substance Registry System | .alpha.-Ketoisocaproic acid (816-66-0) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS05 |
| Signal word | Danger |
| GHS hazard statements | H314 |
| GHS precautionary statements | P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Hazard symbols | C |
| Risk statements (R) | 34 |
| Safety statements (S) | 26-36/37/39-45 |
| UN transport number | UN 3265 8/PG 3 |
| Water hazard class (WGK) | 3 |
| F | 3-9-13 |
| TSCA inventory status | TSCA listed |
| Customs code | 2918.30.9000 |
| Hazard class | 8Skin Corr. 1B |
| Packing group | III |
| Storage class | 8A - Combustible corrosive hazardous materials |
Safety & Regulations
| GHS classification | DangerH314 (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. |
|---|---|
| Regulatory information | Pentanoic acid, 4-methyl-2-oxo-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Corr. 1C (100%) |
| Health effects | Chronically high levels of keto-leucine are associated with Maple Syrup Urine Disease. |
| Toxicity summary | Ketoleucine is a metabolite that accumulates in Maple Syrup Urine Disease (MSUD) and shown to compromise brain energy metabolism by blocking the respiratory chain. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| F | 3-9-13 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 3265 8/PG 3 |
| Customs code | 2918.30.9000 |
| Risk statements (R) | 34 |
| Signal word | Danger |
| GHS pictogram | GHS05 |
| Hazard symbols | C |
| Safety statements (S) | 26-36/37/39-45 |
| Hazard class | 8Skin Corr. 1B |
| Storage class | 8A - Combustible corrosive hazardous materials |
| Packing group | III |
| GHS hazard statements | H314 |
| GHS precautionary statements | P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405 |
Applications & Uses
Occurrence
Reported found in banana, asparagus, cheese, white wine, cocoa, blue cheese and provolone cheese.
Uses
4-Methyl-2-oxovaleric acid is an intermediate in the metabolism of leucine and also used as flavoring agents.