(2E)-3-(4-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

• ChemBase ID: 163531
• Molecular Formular: C15H18O9
• Molecular Mass: 342.29802
• Monoisotopic Mass: 342.09508216
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)Oc1c(ccc(c1)/C=C/C(=O)O)O)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2cc(/C=C/C(=O)O)ccc2O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(24-10)23-9-5-7(1-3-8(9)17)2-4-11(18)19/h1-5,10,12-17,20-22H,6H2,(H,18,19)/b4-2+/t10-,12-,13+,14-,15-/m1/s1
• InChIKey: QOPSZFXPZWQLOG-VHCZEJTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-(4-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
• IUPAC Traditional name: caffeic acid 3-glucoside
• Synonyms: 3-[3-(β-D-Glucopyranosyloxy)-4-hydroxyphenyl]-2-propenoic Acid; 3-(β-D-Glucopyranosyloxy)-4-hydroxy-cinnamic Acid; 3-(β-D-Glucopyranosyloxy)-4-hydroxycinnamic Acid; Caffeic Acid 3-β-D-Glucoside

Database IDs

• CAS Number: 24959-81-7
• PubChem SID: 162257666
• PubChem CID: 5281759

CALCULATED PROPERTIES

• Acid pKa: 3.425659
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.8021502
• LogD (pH = 7.4): -4.1370096
• Log P: -0.7391125
• Molar Refractivity: 79.1661 cm^3
• Polarizability: 31.22343 Å^3
• Polar Surface Area: 156.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C080025

Found in the berries of wild potato species, believed to be an important biosynthetic intermediate. Studies have shown the ability of this compound to inhibit melanin formation when used as a component of topical skin creams.

REFERENCES

• Hanson, K., et al.: J. Biol. Chem., 238, 1105 (1963)
• Bernards, M., et al.: Phytochem., 30, 497 (1963)
• Lim, E., et al.: Biochem. J., 373, 987 (1963)