(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexanal

• ChemBase ID: 154066
• Molecular Formular: C6H10O6
• Molecular Mass: 178.14
• Monoisotopic Mass: 178.04773804
• SMILES: C([C@H]([C@H]([C@@H](C(=O)C=O)O)O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H](C(=O)C=O)O)O)O
• InChI: InChI=1S/C6H10O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,4-6,8,10-12H,2H2/t4-,5-,6-/m1/s1
• InChIKey: DCNMIDLYWOTSGK-HSUXUTPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexanal
• IUPAC Traditional name: D-glucosone
• Synonyms: D-Glucosone; 2-Keto-D-glucose; D-Arabino-hexos-2-ulose; Fructosone; Mannosone; 2-Keto-D-Glucose

Database IDs

• CAS Number: 1854-25-7
• MDL Number: MFCD01863408
• PubChem SID: 162248205
• PubChem CID: 159630

CALCULATED PROPERTIES

• Acid pKa: 8.615541
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.3604457
• LogD (pH = 7.4): -2.3857594
• Log P: -2.3601131
• Molar Refractivity: 36.7159 cm^3
• Polarizability: 14.728035 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 118-120°C

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C6H10O6

DETAILS

Sigma Aldrich - 61793

Biochem/physiol Actions
2-Keto-D-glucose is the key intermediate of a secondary metabolic pathway leading to the antibiotic cortalcerone1.
Application
2-Keto-D-glucose (D-Glucosone) is a key intermediate of a secondary metabolic pathway leading to the antibiotic cortalcerone. D-Glucosone is a substrate that may be used to identify, differentiate and characterize hexokinase(s).

Toronto Research Chemicals - K191000

A useful synthetic intermediate