(2S,3S,4S,5R,6S)-6-[2,6-bis(propan-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177011
• Molecular Formular: C18H26O7
• Molecular Mass: 354.39484
• Monoisotopic Mass: 354.16785317
• SMILES: c1(c(c(ccc1)C(C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C(C)C
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2c(cccc2C(C)C)C(C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C18H26O7/c1-8(2)10-6-5-7-11(9(3)4)15(10)24-18-14(21)12(19)13(20)16(25-18)17(22)23/h5-9,12-14,16,18-21H,1-4H3,(H,22,23)/t12-,13-,14+,16-,18+/m0/s1
• InChIKey: JZSJIASBMOIIKI-RUKPJNHUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[2,6-bis(propan-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-(2,6-diisopropylphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2,6-Bis(1-methylethyl)phenyl β-D-Glucopyranosiduronic Acid; Propofol Glucuronide; Propofol β-D-Glucuronide

Database IDs

• CAS Number: 114991-26-3
• PubChem SID: 164232921
• PubChem CID: 71751823

CALCULATED PROPERTIES

• Acid pKa: 3.8001232
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.50982857
• LogD (pH = 7.4): -1.0504273
• Log P: 2.2119052
• Molar Refractivity: 88.4323 cm^3
• Polarizability: 35.378937 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 142-143°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P829780

Propofol β-D-Glucuronide is a metabolite of Propofol (P829750), an anesthetic used in veterinary medicine.

REFERENCES

• Fujiwara, R., et al.: Drug Metab. Dispos., 35, 747 (2007)
• Soars, M., et al.: J. Pharmacol. Toxicol. Methods, 47, 161 (2007)