(5S)-2,5-dihydroxy-6-(hydroxymethyl)oxan-3-one

• ChemBase ID: 165964
• Molecular Formular: C6H10O5
• Molecular Mass: 162.1406
• Monoisotopic Mass: 162.05282342
• SMILES: [C@@H]1(CC(=O)C(OC1CO)O)O
• Canonical SMILES: OCC1OC(O)C(=O)C[C@@H]1O
• InChI: InChI=1S/C6H10O5/c7-2-5-3(8)1-4(9)6(10)11-5/h3,5-8,10H,1-2H2/t3-,5?,6?/m0/s1
• InChIKey: UHPMJDGOAZMIID-ORLPHIGFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-2,5-dihydroxy-6-(hydroxymethyl)oxan-3-one
• IUPAC Traditional name: (5S)-2,5-dihydroxy-6-(hydroxymethyl)oxan-3-one
• Synonyms: 3-Deoxy-D-erythro-hexulose; 2-Keto-3-deoxyglucose; D-3-Deoxyglucosone; 3-Deoxy-D-erythro-hexos-2-ulose; 3DG; 3-Deoxy-D-glucosone; 3-Deoxyglucosone

Database IDs

• CAS Number: 4084-27-9
• PubChem SID: 162260097
• PubChem CID: 71315480

CALCULATED PROPERTIES

• Acid pKa: 10.440278
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.6789145
• LogD (pH = 7.4): -1.6793048
• Log P: -1.6789095
• Molar Refractivity: 33.9119 cm^3
• Polarizability: 13.910811 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Warm Ethanol; Water
• Apperance: Amorphous Yellow Solid
• Melting Point: 73-75°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D239150

An intermediate in the Maillard reaction of proteins with glucose, which is metabolised to 3-Deoxyfructose. An intermediate in the formation of pyrraline, which might contribute to a pathological effect, such as carcinogenesis.

REFERENCES

• Kato, H. et al.: Agric. Biol. Chem., 51, 683 (1987)
• Hayase, F. et al.: J. Biol. Chem., 264, 3758 (1987)
• Kato, H. et al.: Biochimica et Biophysica Acta, 1035, 71 (1990)