(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one

• ChemBase ID: 119253
• Molecular Formular: C5H8O5
• Molecular Mass: 148.11402
• Monoisotopic Mass: 148.03717336
• SMILES: C1(=O)[C@@H]([C@@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1OC(=O)[C@@H]([C@@H]1O)O
• InChI: InChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4-/m1/s1
• InChIKey: CUOKHACJLGPRHD-BXXZVTAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
• IUPAC Traditional name: D-ribosone
• Synonyms: (3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one; D-(+)-Ribono-1,4-lactone; D-(+)-Ribonic acid-γ-lactone; D(+)-Ribono-1,4-lactone; D-(+)-Ribonic γ-lactone; D-(+)-核糖酸-γ-内酯; D-(+)-核糖酸-1,4-内酯; D-(+)-核糖酸 γ-内酯

Database IDs

• CAS Number: 5336-08-3
• EC Number: 226-256-5
• MDL Number: MFCD00063241
• Beilstein Number: 82057
• PubChem SID: 24888146; 24888436; 24888147; 162107955
• PubChem CID: 111064

CALCULATED PROPERTIES

• Acid pKa: 11.633838
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.1149385
• LogD (pH = 7.4): -2.1149635
• Log P: -2.1149383
• Molar Refractivity: 28.8163 cm^3
• Polarizability: 12.117866 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear
• Melting Point: 80-86 °C; 82-86 °C; 85-87 °C(lit.)
• Optical Rotation: [α]20/D +18.0±0.5°, c = 5% in H2O; [α]20/D +18±1°, c = 5% in H2O; [α]24/D +18°, c = 1 in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (T); ≥99.0% (T); 97%
• Grade: puriss.; purum
• Empirical Formula (Hill Notation): C5H8O5
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 857297

Packaging
5 g in glass bottle
Application
Important building block for chiral acyclics, cyclopentenones, and oxabicyclic systems.1 Also employed in studies on nonlinear optical materials.2

Sigma Aldrich - 83820

Other Notes
Chiral building block1,2,3,4