2-hydroxy-3-methylbutanoic acid

• ChemBase ID: 140125
• Molecular Formular: C5H10O3
• Molecular Mass: 118.1311
• Monoisotopic Mass: 118.06299418
• SMILES: CC(C)C(C(=O)O)O
• Canonical SMILES: OC(C(=O)O)C(C)C
• InChI: InChI=1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)
• InChIKey: NGEWQZIDQIYUNV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-3-methylbutanoic acid
• IUPAC Traditional name: 2-oxyisovaleric acid
• Synonyms: 2-Hydroxyisovaleric acid; 2-Hydroxy-3-methylbutyric acid; (±)-2-Hydroxy-3-methylbutyric acid; (±)-α-Hydroxyisovaleric acid; (±)-2-Hydroxyisopentanoic Acid; (±)-2-Hydroxyisovaleric Acid; (±)-α-Hydroxyisovaleric Acid; 2-Hydroxy-3-methylbutanoic Acid; 2-Oxyisovaleric Acid; 3-Methyl-2-hydroxybutyric Acid; DL-2-Hydroxy-3-methylbutanoic Acid; DL-2-Hydroxyisovaleric Acid; DL-α-Hydroxyisovaleric Acid; NSC 227884; α-Hydroxyisovaleric Acid; 2-Hydroxy-3-methylbutyric Acid; 2-羟基异戊酸; 2-羟基-3-甲基丁酸; (±)-2-羟基-3-甲基丁酸; (±)-α-羟基异戊酸

Database IDs

• CAS Number: 4026-18-0
• EC Number: 223-697-5
• MDL Number: MFCD00004242
• Beilstein Number: 1721138
• PubChem SID: 24853147; 24879405; 162234369
• PubChem CID: 99823

CALCULATED PROPERTIES

• Acid pKa: 4.138362
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.9615187
• LogD (pH = 7.4): -2.6587677
• Log P: 0.41566572
• Molar Refractivity: 27.8354 cm^3
• Polarizability: 11.1556 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 82-84 °C; 82-84°C; 86-87 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (T); 98%; 99%
• Linear Formula: (CH3)2CHCH(OH)CO2H; (CH3)2CHCH(OH)COOH

DETAILS

Sigma Aldrich - 219835

Packaging
1 g in glass bottle

Sigma Aldrich - 55450

包装
25 g in glass bottle

Toronto Research Chemicals - H946510

2-Hydroxy-3-methylbutyric Acid is a α-hydroxylated butyric acid derivative used as a marker in chemical diagnosis of organic aciduria and other inborn errors. 2-Hydroxy-3-methylbutyric Acid is also used as a metabolomic biomarkers in preeclampsia.

REFERENCES

• Nakagawa, K. et al.: J. Chrom. B Anal. Technol. Biomed. Life Sci., 878, 942 (2010)
• Kenny, L.C. et al.: Reprod. Sci., 15, 591 (2010)
• Garcia, A. et al.: Clin. Chem., 44, 1905 (2010)