(5S)-5-(hydroxymethyl)oxolan-2-one

• ChemBase ID: 147377
• Molecular Formular: C5H8O3
• Molecular Mass: 116.11522
• Monoisotopic Mass: 116.04734412
• SMILES: C1CC(=O)O[C@@H]1CO
• Canonical SMILES: OC[C@@H]1CCC(=O)O1
• InChI: InChI=1S/C5H8O3/c6-3-4-1-2-5(7)8-4/h4,6H,1-3H2/t4-/m0/s1
• InChIKey: NSISJFFVIMQBRN-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-5-(hydroxymethyl)oxolan-2-one
• IUPAC Traditional name: (5S)-5-(hydroxymethyl)oxolan-2-one
• Synonyms: (S)-γ-Hydroxymethyl-γ-butyrolactone; (S)-4,5-Dihydro-5-hydroxymethyl-2(3H)-furanone; (S)-5-Hydroxymethyl-2-oxotetrahydrofuran; (S)-(+)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone; (S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one; (S)-γ-羟甲基-γ-丁内酯; (S)-4,5-二氢-5-羟甲基-2(3H)-呋喃酮; (S)-5-羟甲基-2-氧代四氢呋喃; (S)-5-羟甲基二氢呋喃-2-酮

Database IDs

• CAS Number: 32780-06-6
• MDL Number: MFCD00066224
• Beilstein Number: 1680284
• PubChem SID: 24861633; 162241565
• PubChem CID: 2733813

CALCULATED PROPERTIES

• Acid pKa: 14.652552
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.48078364
• LogD (pH = 7.4): -0.48078367
• Log P: -0.48078364
• Molar Refractivity: 26.2706 cm^3
• Polarizability: 10.689573 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 110-115 °C/0.2 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 1.237 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.471(lit.)
• Optical Rotation: [α]20/D +56°, c = 3 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 97%
• Optical Purity: ee: 98% (GLC)
• Empirical Formula (Hill Notation): C5H8O3

DETAILS

Sigma Aldrich - 348902

Packaging
1 g in glass bottle
Application
Versatile chiral synthon used in the synthesis of natural and unnatural products.1,2,3 Used as a chiral synthon for mevinic acids which are LDL cholesterol lowering agents.2,4