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

• ChemBase ID: 155844
• Molecular Formular: C12H14O7
• Molecular Mass: 270.23536
• Monoisotopic Mass: 270.07395279
• SMILES: c1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](Oc2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H14O7/c13-7-8(14)10(11(16)17)19-12(9(7)15)18-6-4-2-1-3-5-6/h1-5,7-10,12-15H,(H,16,17)/t7-,8-,9+,10-,12+/m0/s1
• InChIKey: WVHAUDNUGBNUDZ-GOVZDWNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-phenoxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-phenoxyoxane-2-carboxylic acid
• Synonyms: Phenyl-β-D-glucopyranosiduronic acid; Phenyl-β-D-glucuronide; Phenyl β-D-Glucopyranosiduronic Acid; Phenyl β-D-Glucosiduronic Acid; Phenyl β-D-Glucuronide

Database IDs

• CAS Number: 17685-05-1
• EC Number: 241-666-4
• MDL Number: MFCD00057515
• Beilstein Number: 89117
• PubChem SID: 162249982
• PubChem CID: 87235

CALCULATED PROPERTIES

• Acid pKa: 3.3626032
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.4014032
• LogD (pH = 7.4): -3.690188
• Log P: -0.27811307
• Molar Refractivity: 60.0507 cm^3
• Polarizability: 24.593225 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 144-153°C
• Optical Rotation: [α]20/D -87±5°, c = 1% in H2O

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (HPLC)
• Impurities: ≤8% water
• Empirical Formula (Hill Notation): C12H14O7

DETAILS

Toronto Research Chemicals - P326500

A metabolite of Phenol.

REFERENCES

• Barr, W., et al.: J. Pharm. Sci., 59, 164 (1970)
• Sabourin, P., et al.: Toxicol. Appl. Pharmacol., 99, 421 (1970)
• Ballinger, L., et al.: J. Pharm. Pharmacol., 47, 949 (1970)
• Dunn, R., et al.: Drug Metab. Dispos., 26, 598 (1970)
• Mottino, A., et al.: J.