sodium 4-methyl-2-oxopentanoate

• ChemBase ID: 140835
• Molecular Formular: C6H9NaO3
• Molecular Mass: 152.12363
• Monoisotopic Mass: 152.04493843
• SMILES: CC(C)CC(=O)C(=O)[O-].[Na+]
• Canonical SMILES: CC(CC(=O)C(=O)[O-])C.[Na+]
• InChI: InChI=1S/C6H10O3.Na/c1-4(2)3-5(7)6(8)9;/h4H,3H2,1-2H3,(H,8,9);/q;+1/p-1
• InChIKey: IXFAZKRLPPMQEO-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 4-methyl-2-oxopentanoate
• IUPAC Traditional name: sodium α-ketoisocaproate
• Synonyms: 2-Ketoisocaproic Acid Sodium Salt; 2-Oxo-4-methylpentanoic Acid Sodium Salt; Sodium 2-Ketoisocaproate; Sodium 4-methyl-2-oxopentanoate; Sodium α-Keto-isocaproate; Sodium α-Ketoisocaproate; Sodium α-oxoisocaproate; 4-Methyl-2-oxovaleric Acid Sodium Salt; Sodium 4-methyl-2-oxovalerate; α-Ketoisocaproic acid sodium salt; 4-Methyl-2-oxopentanoic acid sodium salt; 4-Methyl-2-oxovaleric acid sodium salt; Ketoleucine sodium salt; Sodium 4-methyl-2-oxovalerate; 4-Methyl-2-oxopentanoic acid sodium salt; 4-甲基-2-氧代戊酸钠盐; α-酮异己酸 钠盐; 4-Methyl-2-oxovaleric acid 钠盐; 4-甲基-2-氧代戊酸 钠盐; 4-甲基-2-氧代戊酸钠盐; 酮亮氨酸 钠盐; 4-甲基-2-氧代戊酸 钠盐

Database IDs

• CAS Number: 4502-00-5
• EC Number: 224-816-3
• MDL Number: MFCD00064193
• Beilstein Number: 4239297
• PubChem SID: 162235073; 24896196
• PubChem CID: 4137900
• FEMA ID: 3871

CALCULATED PROPERTIES

• Acid pKa: 3.5280511
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.4667107
• LogD (pH = 7.4): -1.8688251
• Log P: 1.4979975
• Molar Refractivity: 42.6033 cm^3
• Polarizability: 12.32327 Å^3
• Polar Surface Area: 57.2 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 275 °C (dec.)(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC); 97%; 98%
• Impurities: ≤12% water
• Linear Formula: (CH3)2CHCH2COCOONa

DETAILS

Sigma Aldrich - K0629

Packaging
1, 5 g in poly bottle

Sigma Aldrich - 499137

Application
Condensation with α-amino ketones and subsequent cyclization provides pyrazinones.1,2
Packaging
1, 10 g in glass bottle

Sigma Aldrich - W387101

Packaging
25 g in poly bottle

Toronto Research Chemicals - M326425

4-Methyl-2-oxovaleric Acid is an α-ketomonocarboxylic acid that triggers insulin release by acting upon receptor sites which differ from those occupied by amino acids. 4-Methyl-2-oxovaleric Acid is an intermediate in the metabolism of Leucine.

REFERENCES

• Panten, U. et al.: Naun.-Schmied. Arch. Pharmacol., 291, 405 (1975)
• Vague, P. et al.: Diab. Metab., 1, 185 (1975)
• Francois, G. et al.: Lancet, 1, 858 (1975)