2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

• ChemBase ID: 154660
• Molecular Formular: C21H20O11
• Molecular Mass: 448.3769
• Monoisotopic Mass: 448.10056146
• SMILES: c1cc(c(cc1c1cc(=O)c2c(cc(c(c2o1)[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)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)cc(c2c1oc(cc2=O)c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1
• InChIKey: PLAPMLGJVGLZOV-VPRICQMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
• IUPAC Traditional name: orientin
• Synonyms: 8-β-D-Glucopyranosyl-3′,4′,5,7-tetrahydroxyflavone; Luteolin 8-C-β-D-glucopyranoside; Luteolin-8-glucoside; Lutexin; Orientin

Database IDs

• CAS Number: 28608-75-5
• MDL Number: MFCD00017432
• PubChem SID: 162248798
• PubChem CID: 5281675

CALCULATED PROPERTIES

• Acid pKa: 6.198737
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -0.43280727
• LogD (pH = 7.4): -1.5572325
• Log P: -0.35419708
• Molar Refractivity: 108.0131 cm^3
• Polarizability: 41.436474 Å^3
• Polar Surface Area: 197.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 1 M NaOH: soluble1 mg/mL, clear, yellow-orange
• Apperance: yellow powder

Safety Information

• RTECS: DJ3009300
• German water hazard class: 0; 3

Product Information

• Purity: ≥95% (HPLC); ≥97% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C21H20O11

DETAILS

Sigma Aldrich - O9765

Biochem/physiol Actions
Flavonoid glycoside found in the acai tree and globe and passion flowers. Antiviral1, antimicrobial and antioxidant. Exhibits radioprotective activities2.

Sigma Aldrich - 55736

Biochem/physiol Actions
Flavonoid glycoside found in the acai tree and globe and passion flowers. Antiviral1, antimicrobial and antioxidant. Exhibits radioprotective activities2.