(3R,4R)-2,3,5,6-tetrahydroxy-4-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanoic acid; N-cyclohexylcyclohexanamine

• ChemBase ID: 163963
• Molecular Formular: C24H45NO12
• Molecular Mass: 539.6136
• Monoisotopic Mass: 539.29417589
• SMILES: C1CCCC(C1)NC1CCCCC1.O([C@@H]([C@@H](C(O)C(=O)O)O)C(O)CO)[C@@H]1OC([C@H]([C@@H](C1O)O)O)CO
• Canonical SMILES: C1CCC(CC1)NC1CCCCC1.OCC([C@H]([C@@H](C(C(=O)O)O)O)O[C@@H]1OC(CO)[C@H]([C@@H](C1O)O)O)O
• InChI: InChI=1S/C12H23N.C12H22O12/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12/h11-13H,1-10H2;3-10,12-20H,1-2H2,(H,21,22)/t;3?,4?,5-,6+,7-,8?,9?,10-,12+/m.1/s1
• InChIKey: NPOIXYCQKIAOPS-SJMKLXHFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-2,3,5,6-tetrahydroxy-4-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanoic acid; N-cyclohexylcyclohexanamine
• IUPAC Traditional name: (3R,4R)-2,3,5,6-tetrahydroxy-4-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexanoic acid; dicha
• Synonyms: 4-O-β-D-Glucopyranosyl-D-gluconic Acid Ammonium Salt; Ammonium Cellobionate; Cellobionic Acid Ammonium Salt

Database IDs

• PubChem SID: 162258098
• PubChem CID: 71314635

CALCULATED PROPERTIES

• Acid pKa: 3.2613704
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): -7.400029
• LogD (pH = 7.4): -8.614589
• Log P: -5.18058
• Molar Refractivity: 70.6843 cm^3
• Polarizability: 29.630531 Å^3
• Polar Surface Area: 217.6 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Off-White Solid
• Melting Point: >75°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C254850

Cellobionic acid is produced by ozonization of Cellobiose. Cellobionic acid was not a good substrate for β-Glucosidase. The lactonized carboxyl group inhibited the enzymic hydrolysis. This inhibitory effect of Cellobionic acid was removed by gluconolacton

REFERENCES

• Bonnet, M., et al.: Environ. Technol. Lett., 10, 577 (1989)
• DeLaat, J., et al.: Environ. Technol., 16, 1035 (1989)