(4S,5S)-4,5,6-trihydroxy-2-oxohexanal

• ChemBase ID: 88054
• Molecular Formular: C6H10O5
• Molecular Mass: 162.1406
• Monoisotopic Mass: 162.05282342
• SMILES: O=CC(=O)C[C@@H]([C@H](CO)O)O
• Canonical SMILES: O[C@H]([C@H](CO)O)CC(=O)C=O
• InChI: InChI=1S/C6H10O5/c7-2-4(9)1-5(10)6(11)3-8/h2,5-6,8,10-11H,1,3H2/t5-,6-/m0/s1
• InChIKey: ZGCHLOWZNKRZSN-WDSKDSINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5S)-4,5,6-trihydroxy-2-oxohexanal
• IUPAC Traditional name: (4S,5S)-4,5,6-trihydroxy-2-oxohexanal
• Synonyms: 3-Deoxyglucosone; (4S,5R)-2-Oxo-4,5,6-trihydroxyhexan-1-one

Database IDs

• CAS Number: 4084-27-9
• MDL Number: MFCD01723101
• PubChem SID: 162075094
• PubChem CID: 71299531

CALCULATED PROPERTIES

• Acid pKa: 10.464561
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.6449594
• LogD (pH = 7.4): -1.6453286
• Log P: -1.6449547
• Molar Refractivity: 35.3777 cm^3
• Polarizability: 14.0075035 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: Irritant

DETAILS

Apollo Scientific Ltd - OR3915T

An intermediate in the Maillard reaction of proteins with glucose that is metabolised to 3-deoxyfructose. Also an intermediate in the formation of pyrraline, which may contribute carcinogenic potential.