(1R,2S,3R)-1-{6-[(2S,3R)-2,3,4-trihydroxybutyl]pyrazin-2-yl}butane-1,2,3,4-tetrol

• ChemBase ID: 165948
• Molecular Formular: C12H20N2O7
• Molecular Mass: 304.2964
• Monoisotopic Mass: 304.12705099
• SMILES: c1ncc(nc1C[C@@H]([C@@H](CO)O)O)[C@H]([C@@H]([C@@H](CO)O)O)O
• Canonical SMILES: OC[C@H]([C@H](Cc1cncc(n1)[C@H]([C@@H]([C@@H](CO)O)O)O)O)O
• InChI: InChI=1S/C12H20N2O7/c15-4-9(18)8(17)1-6-2-13-3-7(14-6)11(20)12(21)10(19)5-16/h2-3,8-12,15-21H,1,4-5H2/t8-,9+,10+,11+,12+/m0/s1
• InChIKey: MBHUNOHYVYVNIP-VSSNEEPJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3R)-1-{6-[(2S,3R)-2,3,4-trihydroxybutyl]pyrazin-2-yl}butane-1,2,3,4-tetrol
• IUPAC Traditional name: (1R,2S,3R)-1-{6-[(2S,3R)-2,3,4-trihydroxybutyl]pyrazin-2-yl}butane-1,2,3,4-tetrol
• Synonyms: (1R,2S,3R)-1-[6-[(2S,3R)-2,3,4-Trihydroxybutyl]-2-pyrazinyl]-1,2,3,4-butanetetrol; 2-(D-arabino-1',2',3',4'-Tetrahydroxybutyl)-6-(D-erythro-2'',3'',4''-trihydroxybutyl)pyrazine; 2,6-Deoxyfructosazine

Database IDs

• CAS Number: 36806-15-2
• PubChem SID: 162260081
• PubChem CID: 18732279

CALCULATED PROPERTIES

• Acid pKa: 12.28346
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -4.5963306
• LogD (pH = 7.4): -4.596333
• Log P: -4.596328
• Molar Refractivity: 68.9186 cm^3
• Polarizability: 27.78488 Å^3
• Polar Surface Area: 167.39 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Brown Solid
• Melting Point: 124-127°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D235800

Contained in tobacco flavor additives.

REFERENCES

• Tsuchida, H., et al.: Agric. Biol. Chem., 40, 921 (1976)