(2S,3S,4S,5R,6S)-6-[4-(2-carboxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 167567
• Molecular Formular: C16H20O10
• Molecular Mass: 372.324
• Monoisotopic Mass: 372.10564684
• SMILES: c1c(c(cc(c1)CCC(=O)O)OC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: COc1cc(CCC(=O)O)ccc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H20O10/c1-24-9-6-7(3-5-10(17)18)2-4-8(9)25-16-13(21)11(19)12(20)14(26-16)15(22)23/h2,4,6,11-14,16,19-21H,3,5H2,1H3,(H,17,18)(H,22,23)/t11-,12-,13+,14-,16+/m0/s1
• InChIKey: KYERCTIKYSSKPA-JHZZJYKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[4-(2-carboxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[4-(2-carboxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-(2-Carboxyethyl)-2-methoxyphenyl β-D-Glucopyranosiduronic Acid Lithium; Dihydroferulic Acid 4-O-Glucuronide Lithium; Dihydro Ferulic Acid 4-O-β-D-Glucuronide Dilithium Salt

Database IDs

• PubChem SID: 162261700
• PubChem CID: 190069

CALCULATED PROPERTIES

• Acid pKa: 3.0453503
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.446634
• LogD (pH = 7.4): -7.098687
• Log P: -0.35346738
• Molar Refractivity: 82.4225 cm^3
• Polarizability: 33.289215 Å^3
• Polar Surface Area: 162.98 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: >91°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D448910

A metabolite profiling of hydroxycinnamate derivative in plasma and urine after the ingestion of coffee by humans: identification of biomarkers of coffee consumption.

REFERENCES

• Buchanan, C., et al.: J. Sci. Food Agric., 71, 459 (1996)
• Andreasen, M., et al.: J. Agric. Food Chem., 49, 5679 (1996)
• Poquet, L., et al.: Drug Metab. Dispos., 36, 190 (1996)