(2S)-2-hydroxy-3-methylbutanoic acid

• ChemBase ID: 78196
• Molecular Formular: C5H10O3
• Molecular Mass: 118.1311
• Monoisotopic Mass: 118.06299418
• SMILES: O=C(O)[C@H](C(C)C)O
• Canonical SMILES: O[C@H](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)/t4-/m0/s1
• InChIKey: NGEWQZIDQIYUNV-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-hydroxy-3-methylbutanoic acid
• IUPAC Traditional name: α-hydroxyisovaleric acid; 2-hydroxyisopentanoic acid
• Synonyms: (S)-2-Hydroxy-3-methylbutyric acid; L-α-Hydroxyisovaleric acid; L-α-Hydroxyisovaleric acid; (S)-(+)-2-Hydroxy-3-methylbutyric acid; (2R)-2-Hydroxy-3-methylbutyric acid; D-alpha-Hydroxyisovaleric acid; (2R)-2-Hydroxy-3-methylbutanoic acid 97%; (S)-(+)-2-HYDROXY-3-METHYLBUTYRIC ACID; (2S)-(+)-2-Hydroxy-3-methylbutyric acid; L-alpha-Hydroxyisovaleric acid; (2S)-(+)-2-Hydroxy-3-methylbutanoic acid; (S)-(+)-2-羟基-3-甲基丁酸; L-α-羟基异戊酸; L-α-羟基异戊酸; (S)-(+)-2-羟基-3-甲基丁酸

Database IDs

• CAS Number: 17407-56-6; 17407-55-5
• MDL Number: MFCD00066442; MFCD00066443
• Beilstein Number: 1721140
• PubChem SID: 24863611; 162043007
• PubChem CID: 853180

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: 65-67 °C; 68-70 °C(lit.); 68-70°C
• Boiling Point: 124-125 °C/13 mmHg(lit.); 124-125°C/13mm
• Optical Rotation: [α]20/D +18±1°, c = 1% in chloroform; [α]20/D +19°, c = 1 in chloroform

Safety Information

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

Product Information

• Purity: ≥98.0% (T); 97%; 99%
• Grade: purum
• Optical Purity: ee: 99% (GLC)
• Linear Formula: (CH3)2CHCH(OH)CO2H
• Empirical Formula (Hill Notation): C5H10O3

DETAILS

Sigma Aldrich - 379093

Packaging
1, 5 g in glass bottle
Application
A useful chiral building block for peptide synthesis.1,2 Used in the preparation of the cytotoxic didemnin cyclopeptides and of the antineoplastic agent dolastatin 15.3,4