methyl (2S)-3-hydroxy-2-methylpropanoate

• ChemBase ID: 149316
• Molecular Formular: C5H10O3
• Molecular Mass: 118.1311
• Monoisotopic Mass: 118.06299418
• SMILES: C[C@@H](CO)C(=O)OC
• Canonical SMILES: C[C@H](C(=O)OC)CO
• InChI: InChI=1S/C5H10O3/c1-4(3-6)5(7)8-2/h4,6H,3H2,1-2H3/t4-/m0/s1
• InChIKey: ATCCIZURPPEVIZ-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-3-hydroxy-2-methylpropanoate
• IUPAC Traditional name: methyl (2S)-3-hydroxy-2-methylpropanoate
• Synonyms: (+)-Methyl (S)-3-hydroxy-2-methylpropionate; S-(+)-3-Hydroxy-2-methylpropionic acid methyl ester; (+)-Methyl L-β-hydroxyisobutyrate; (S)-3-Hydroxyisobutyric acid methyl ester; (S)-3-Hydroxy-2-methylpropionic acid methyl ester; (+)-Methyl L-β-hydroxyisobutyrate; (S)-(+)-3-Hydroxy-2-methylpropionic acid methyl ester; Methyl (S)-(+)-3-hydroxy-2-methylpropionate; (S)-Methyl 3-hydroxy-2-Methylpropanoate; 3-Hydroxy-2-methylpropanoic Acid; β-Hydroxyisobutyric Acid; 2-(Hydroxymethyl)propionic Acid; 2-Methyl-3-hydroxypropanoic Acid; 2-Methyl-3-hydroxypropionic Acid; DL-3-Hydroxyisobutyric Acid; rac 3-Hydroxyisobutyric Acid; (+)-甲基(S)-3-羟基-2-甲基丙酸酯; S-(+)-3-羟基-2-甲基丙酸甲酯; (+)-甲基L-β-羟基异丁酸酯; (+)-甲基L-β-羟基异丁酸酯; (S)-(+)-3-羟基-2-异丁酸甲酯; (S)-(+)-3-羟基-2-甲基丙酸甲酯

Database IDs

• CAS Number: 80657-57-4; 2068-83-9
• MDL Number: MFCD00064520
• Beilstein Number: 1720830
• PubChem SID: 24856356; 24879377; 162243484
• PubChem CID: 10192563

CALCULATED PROPERTIES

• Acid pKa: 15.242007
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.11470069
• LogD (pH = 7.4): -0.1147007
• Log P: -0.11470069
• Molar Refractivity: 28.3889 cm^3
• Polarizability: 11.390625 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Liquid
• Boiling Point: 74 °C/10 mmHg(lit.); 74°C/10mm; 74-76 °C/12 mmHg(lit.)
• Flash Point: 176 °F; 80 °C; 81°C(178°F)
• Density: 1.066 g/mL at 20 °C(lit.); 1.07; 1.071 g/mL at 25 °C(lit.)
• Refractive Index: 1.4250; n20/D 1.425; n20/D 1.425(lit.)
• Optical Rotation: [α]19/D +26°, c = 4 in methanol; [α]20/D +26±1°, c = 2% in methanol; +27 (c=4 in methanol)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37-60
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335-H227
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: ≥95.0% (sum of enantiomers, GC); 98%; 99%
• Grade: purum
• Optical Purity: ee: 99% (GLC)
• Linear Formula: HOCH2CH(CH3)CO2CH3
• Empirical Formula (Hill Notation): C5H10O3

DETAILS

Sigma Aldrich - 270121

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 55412

Other Notes
Stable derivative of (S)-3-hydroxy-2-methyl-propionic acid. The free acid is described to be an unstable compound 1; Chiral building block; preparation of protected chiral 2-methyl-1,3-propanediols and derivatives 2,3,4,5

Toronto Research Chemicals - H943555

A metabolite of 3-Hydroxyisobutyrate dehydrogenase.

REFERENCES

• Berg, P., et al.: Lancet, 2, 1423 (1982)
• Bixel, M., et al.: J. Neurochem., 65, 2450 (1982)
• Broer, S., et al.: J. Biol. Chem., 272, 30096 (1982)
• Charlton, M., et al.: J. Nutr., 136, 295S (1982)
• Zwingmann, C., et al.: Metab. Brain Dis., 22, 235 (1982)