(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 154807
• Molecular Formular: C21H22O11
• Molecular Mass: 450.39278
• Monoisotopic Mass: 450.11621152
• SMILES: c1cc(c(cc1[C@@H]1CC(=O)c2c(cc(cc2O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc3O[C@@H](CC(=O)c3c(c2)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H22O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-5,14,16,18-25,27-29H,6-7H2/t14-,16+,18+,19-,20+,21+/m0/s1
• InChIKey: RAFHNDRXYHOLSH-SFTVRKLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: (2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one
• Synonyms: (2S)-Eriodictyol 7-O-β-D-glucopyranoside; 3′,4′,5,7-Tetrahydroxyflavanone 7-β -D-glucopyranoside; Eriodictyol 7-O-glucoside; Miscanthoside; Eriodictyol 7-O-β-D-glucopyranoside; Pyracanthoside; Eriodictyol 7-O-glucoside

Database IDs

• CAS Number: 38965-51-4
• EC Number: 254-225-6
• Beilstein Number: 1336490
• PubChem SID: 162248945
• PubChem CID: 13254473

CALCULATED PROPERTIES

• H Donor: 7
• LogD (pH = 5.5): 0.26307824
• LogD (pH = 7.4): 0.2327259
• Log P: 0.26347464
• Molar Refractivity: 105.4151 cm^3
• Polarizability: 41.699123 Å^3
• Polar Surface Area: 186.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false
• Acid pKa: 8.536153
• H Acceptors: 11

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• German water hazard class: 3
• Safety Statements: 22-24/25
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C21H22O11

DETAILS

Sigma Aldrich - 19474

Biochem/physiol Actions
Flavonoid which exhibits antioxidant activities, potent free radical scavenger2.
General description
Eriodictyol 7-O-β-D-glucopyranoside was isolated from the methanolic extract of the leaves of Acer mono which are commonly used in Asian countries for the treatment of various illneβ. 1