(3S)-3-hydroxyoxolan-2-one

• ChemBase ID: 147871
• Molecular Formular: C4H6O3
• Molecular Mass: 102.08864
• Monoisotopic Mass: 102.03169405
• SMILES: C1COC(=O)[C@H]1O
• Canonical SMILES: O=C1OCC[C@@H]1O
• InChI: InChI=1S/C4H6O3/c5-3-1-2-7-4(3)6/h3,5H,1-2H2/t3-/m0/s1
• InChIKey: FWIBCWKHNZBDLS-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-hydroxyoxolan-2-one
• IUPAC Traditional name: (3S)-3-hydroxyoxolan-2-one
• Synonyms: (S)-(-)-α-Hydroxy-γ-butyrolactone; 2,4-Dihydroxybutyric Acid Lactone; (S)-2-Hydroxybutyrolactone; (S)-(-)-α-Hydroxy-γ-butyrolactone; (3S)-3-Hydroxydihydrofuran-2(3H)-one; (S)-3-Hydroxydihydrofuran-2(3H)-one; (S)-(-)-α-羟基-γ-丁内酯

Database IDs

• CAS Number: 52079-23-9
• MDL Number: MFCD00211245
• PubChem SID: 162242053; 24868109
• PubChem CID: 357853

CALCULATED PROPERTIES

• Acid pKa: 12.630941
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.79430866
• LogD (pH = 7.4): -0.79431117
• Log P: -0.7943086
• Molar Refractivity: 21.7567 cm^3
• Polarizability: 8.881667 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether; Ethyl Acetate; Methanol
• Apperance: Colourless Liquid
• Boiling Point: 133 °C/10 mmHg(lit.)
• Flash Point: >113 °C; >235.4 °F
• Density: 1.309 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.467(lit.)
• Optical Rotation: [α]23/D -68°, c = 1.15 in chloroform

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 95+%; 97%
• Optical Purity: ee: 96% (GLC)
• Empirical Formula (Hill Notation): C4H6O3

DETAILS

Sigma Aldrich - 444235

Packaging
5 g in glass bottle
Application
Used to prepare the polyether antibiotic monensin,1 functionalized D-ring side chains of vitamin D analogs,2 and pesticides.3