methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[2-methoxy-4-(3-methoxy-3-oxopropyl)phenoxy]oxane-2-carboxylate

• ChemBase ID: 167566
• Molecular Formular: C24H30O13
• Molecular Mass: 526.4872
• Monoisotopic Mass: 526.16864102
• SMILES: c1c(c(cc(c1)CCC(=O)OC)OC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC
• Canonical SMILES: COC(=O)CCc1ccc(c(c1)OC)O[C@@H]1O[C@@H](C(=O)OC)[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C24H30O13/c1-12(25)33-19-20(34-13(2)26)22(35-14(3)27)24(37-21(19)23(29)32-6)36-16-9-7-15(11-17(16)30-4)8-10-18(28)31-5/h7,9,11,19-22,24H,8,10H2,1-6H3/t19-,20-,21-,22+,24+/m0/s1
• InChIKey: NDVWMFUEOAYSNQ-VZGLXOSZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[2-methoxy-4-(3-methoxy-3-oxopropyl)phenoxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[2-methoxy-4-(3-methoxy-3-oxopropyl)phenoxy]oxane-2-carboxylate
• Synonyms: 4-(2-Carboxyethyl Methyl Ester)-2-methoxyphenyl 2,3,4-Triacetyl-β-D-glucopyranosiduronic Acid Methyl Ester; Dihydro Ferulic Acid 4-O-β-D-Glucuronide Triacetate Dimethyl Ester

Database IDs

• PubChem SID: 162261699
• PubChem CID: 71316153

CALCULATED PROPERTIES

• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 1.2616969
• LogD (pH = 7.4): 1.2616969
• Log P: 1.2616969
• Molar Refractivity: 119.4152 cm^3
• Polarizability: 48.95484 Å^3
• Polar Surface Area: 159.19 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Light Yellow Semi Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D448905

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

REFERENCES

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