(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[2-(4-hydroxyphenyl)propan-2-yl]phenoxy}oxane-2-carboxylic acid

• ChemBase ID: 136448
• Molecular Formular: C21H24O8
• Molecular Mass: 404.41046
• Monoisotopic Mass: 404.14711773
• SMILES: CC(C)(c1ccc(cc1)O)c1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O)O
• Canonical SMILES: Oc1ccc(cc1)C(c1ccc(cc1)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O)(C)C
• InChI: InChI=1S/C21H24O8/c1-21(2,11-3-7-13(22)8-4-11)12-5-9-14(10-6-12)28-20-17(25)15(23)16(24)18(29-20)19(26)27/h3-10,15-18,20,22-25H,1-2H3,(H,26,27)/t15-,16-,17+,18-,20+/m0/s1
• InChIKey: KHZOXXYQSBJDHB-HBWRTXEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[2-(4-hydroxyphenyl)propan-2-yl]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[2-(4-hydroxyphenyl)propan-2-yl]phenoxy}oxane-2-carboxylic acid
• Synonyms: Bisphenol A mono-β-D-glucuronide; 4-[1-(4-Hydroxyphenyl)-1-methylethyl]phenyl β-D-Glucopyranosiduronic Acid; Bisphenol A β-D-Glucuronide

Database IDs

• CAS Number: 267244-08-6
• MDL Number: MFCD19105632
• PubChem SID: 162230718
• PubChem CID: 71309820

CALCULATED PROPERTIES

• Acid pKa: 3.2542336
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.12902485
• LogD (pH = 7.4): -1.3391258
• Log P: 2.0971818
• Molar Refractivity: 111.2869 cm^3
• Polarizability: 40.123863 Å^3
• Polar Surface Area: 136.68 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Gray Solid
• Melting Point: 105-107°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3

Product Information

• Purity: 95% (CP)
• Mol. Weight: mol wt 404.41 by atom % calculation
• Empirical Formula (Hill Notation): C21H24O8

DETAILS

Sigma Aldrich - 738395

Packaging
This product may be available from bulk stock and can be packaged on demand. For information on pricing, availability and packaging, please contact Stable Isotopes Customer Service.

Toronto Research Chemicals - B519510

A metabolite of Bisphenol A.

REFERENCES

• Zalko, D., et al.: Drug Metab. Dispos., 26, 28 (1998)
• Matthews, J., et al.: Chem. Res. Toxico., 14, 149 (1998)
• Kinjo, J., et al.: Biol. Pharm. Bull., 27, 185 (1998)
• Murata, M., et al.: Biochemistry, 43, 2569 (1998)