2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

• ChemBase ID: 154661
• Molecular Formular: C21H20O11
• Molecular Mass: 448.3769
• Monoisotopic Mass: 448.10056146
• SMILES: c1cc(c(cc1c1cc(=O)c2c(o1)cc(c(c2O)[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]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(c(c1)O)O
• InChI: InChI=1S/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14-,17-,19+,20-,21+/m1/s1
• InChIKey: ODBRNZZJSYPIDI-VJXVFPJBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
• IUPAC Traditional name: isoorientin
• Synonyms: Homoorientin; Luteolin 6-C-β-D-glucoside; Luteolin 6-C-glucoside; Isoorientin

Database IDs

• CAS Number: 4261-42-1
• MDL Number: MFCD00017433
• PubChem SID: 162248799
• PubChem CID: 114776

CALCULATED PROPERTIES

• Acid pKa: 6.1966066
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -0.43317616
• LogD (pH = 7.4): -1.5662336
• Log P: -0.35419708
• Molar Refractivity: 108.0131 cm^3
• Polarizability: 41.436478 Å^3
• Polar Surface Area: 197.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: methanol: soluble5 mg/mL, clear, colorless to yellow
• Apperance: yellow powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C21H20O11

DETAILS

Sigma Aldrich - 02187

Biochem/physiol Actions
C-glycosyl flavone with anti-inflammatory, antimicrobial and antioxidant properties2. Induces antioxidant response through PI3K singaling.3
Luteolin, a common flavonoid, has been shown to inhibit secretion of ET-1 by porcine aortic endothelial cells at a 10 uM concentration. However, the luteolin glycoside compound, luteolin 6-C-glucoside, showed very weak inhibition of ET-1 release and inhibition only occurred at higher concentrations of luteolin 6-C-glucoside. 1

Sigma Aldrich - I1536

Biochem/physiol Actions
C-glycosyl flavone with anti-inflammatory, antimicrobial and antioxidant properties1. Induces antioxidant response through PI3K singaling.2