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

• ChemBase ID: 153931
• Molecular Formular: C6H10O5
• Molecular Mass: 162.1406
• Monoisotopic Mass: 162.05282342
• SMILES: C1[C@@H]([C@H](OC(C1=O)O)CO)O
• Canonical SMILES: OC[C@H]1OC(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-OPAZFOKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)oxan-3-one
• IUPAC Traditional name: (5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)oxan-3-one
• Synonyms: 3-Deoxy-D-erythro-hexosulose; 3-Deoxyglucosone

Database IDs

• CAS Number: 4084-27-9
• PubChem SID: 162248070
• PubChem CID: 71311760

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

Safety Information

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

Product Information

• Purity: ≥75% (TLC)
• Empirical Formula (Hill Notation): C6H10O5

DETAILS

Sigma Aldrich - 75762

Application
3-Deoxyglucosone is used as a reference for the analysis and detection of glucose degradation products, glycating agents, generated by processes such as heat sterilization.