(3S)-3-hydroxy-4,4-dimethyloxolan-2-one

• ChemBase ID: 136863
• Molecular Formular: C6H10O3
• Molecular Mass: 130.1418
• Monoisotopic Mass: 130.06299418
• SMILES: CC1(COC(=O)[C@H]1O)C
• Canonical SMILES: O[C@@H]1C(=O)OCC1(C)C
• InChI: InChI=1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m1/s1
• InChIKey: SERHXTVXHNVDKA-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-hydroxy-4,4-dimethyloxolan-2-one
• IUPAC Traditional name: (3S)-3-hydroxy-4,4-dimethyloxolan-2-one
• Synonyms: (S)-(+)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone; (S)-(+)-β,β-Dimethyl-α-hydroxy-γ-butyrolactone; (S)-Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone; L-Pantolactone; (S)-(+)-Pantolactone; (S)-(+)-Pantolactone; (S)-(+)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone; (S)-(+)-α-羟基-β,β-二甲基-γ-丁内酯; (S)-(+)-β,β-二甲基-α-羟基-γ-丁内酯; (S)-二氢-3-羟基-4,4-二甲基-2(3H)-呋喃酮; L-泛内酯; (S)-(+)-泛解酸内酯

Database IDs

• CAS Number: 5405-40-3
• MDL Number: MFCD00216625
• Beilstein Number: 4659425
• PubChem SID: 162231130; 24867363; 24879243
• PubChem CID: 736053

CALCULATED PROPERTIES

• Acid pKa: 12.228233
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.17736644
• LogD (pH = 7.4): 0.17736007
• Log P: 0.17736652
• Molar Refractivity: 30.516 cm^3
• Polarizability: 12.506425 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 89-93 °C; 90-94 °C
• Boiling Point: 120-122 °C/15 mmHg(lit.)
• Optical Rotation: [α]20/D +51±2°, c = 3% in H2O; [α]20/D +53°, c = 2.4 in H2O; [α]22/D +50.0°, c = 0.5 in H2O

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41
• Safety Statements: 26-39
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (T); 97%; 99%
• Grade: puriss.
• Empirical Formula (Hill Notation): C6H10O3

DETAILS

Sigma Aldrich - 729698

Packaging
1 g in glass bottle

Sigma Aldrich - 437328

Application
Employed in the resolution of ketoprofen, a non-steroidal, anti-inflammatory drug.1