(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbaldehyde

• ChemBase ID: 91329
• Molecular Formular: C6H10O5
• Molecular Mass: 162.1406
• Monoisotopic Mass: 162.05282342
• SMILES: O[C@H]1[C@H](O)[C@@H](CO)O[C@@H]1C=O
• Canonical SMILES: OC[C@H]1O[C@@H]([C@H]([C@@H]1O)O)C=O
• InChI: InChI=1S/C6H10O5/c7-1-3-5(9)6(10)4(2-8)11-3/h1,3-6,8-10H,2H2/t3-,4-,5-,6-/m1/s1
• InChIKey: LKAPTZKZHMOIRE-KVTDHHQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbaldehyde
• IUPAC Traditional name: (2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbaldehyde
• Synonyms: 2,5-Anhydro-D-mannose; Chitose; D-2,5-Anhydromannose

Database IDs

• CAS Number: 495-75-0
• MDL Number: MFCD04039402
• PubChem SID: 162078033
• PubChem CID: 11116353

CALCULATED PROPERTIES

• Acid pKa: 12.179663
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.406657
• LogD (pH = 7.4): -2.4066641
• Log P: -2.406657
• Molar Refractivity: 33.8355 cm^3
• Polarizability: 13.910811 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Yellow to Orange Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A653240

This compound is a mixture of the acetal and aldehyde forms.

REFERENCES

• Zamani, A., et al.: J. Agric. Food Chem., 56, 8314 (2008)
• Nowicki, M., et al.: Bioorg. Med. Chem., 16, 5050 (2008)