(2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid

• ChemBase ID: 169681
• Molecular Formular: C6H10O7
• Molecular Mass: 194.1394
• Monoisotopic Mass: 194.04265266
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1C(=O)O)O)O)O)O
• Canonical SMILES: OC1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6?/m0/s1
• InChIKey: AEMOLEFTQBMNLQ-AQKNRBDQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: D-glucopyranuronic acid
• Synonyms: D-(+)-Glucuronic Acid; Glucosiduronic Acid; Glucuronic Acid; D-Glucuronic Acid

Database IDs

• CAS Number: 6556-12-3
• PubChem SID: 162263813
• PubChem CID: 94715

CALCULATED PROPERTIES

• Acid pKa: 3.207791
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -4.8822365
• LogD (pH = 7.4): -6.0563807
• Log P: -2.6122646
• Molar Refractivity: 35.7908 cm^3
• Polarizability: 15.209947 Å^3
• Polar Surface Area: 127.45 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol; Water
• Apperance: White Solid
• Melting Point: 153-155°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G596850

D-Glucuronic acid is widely distributed in the plant and animal kingdoms. D-Glucuronic acid usually occurs in ‘’paired’’ form as a glycosidic combination with phenols, alcohols. Such glucuronides form in the liver to detoxify poisonous hydroxyl-containing

REFERENCES

• Levene, M., et al.: J. Biol. Chem., 92, 257 (1931)
• Miyamoto, I., et al.: Anal. Biochem., 115, 308 (1931)