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

• ChemBase ID: 155947
• Molecular Formular: C21H20O10
• Molecular Mass: 432.3775
• Monoisotopic Mass: 432.10564684
• SMILES: c1cc(ccc1c1cc(=O)c2c(o1)cc(c(c2O)[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)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(cc1)O
• InChI: InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21+/m1/s1
• InChIKey: MYXNWGACZJSMBT-VJXVFPJBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
• IUPAC Traditional name: isovitexin
• Synonyms: Saponaretin; Isovitexin

Database IDs

• CAS Number: 38953-85-4
• MDL Number: MFCD00076044
• Beilstein Number: 66651
• PubChem SID: 162250085; 24850713
• PubChem CID: 162350

CALCULATED PROPERTIES

• Acid pKa: 6.1376967
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -0.14036272
• LogD (pH = 7.4): -1.4485534
• Log P: -0.050631773
• Molar Refractivity: 106.0322 cm^3
• Polarizability: 40.765347 Å^3
• Polar Surface Area: 177.14 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Yellow powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (HPLC); 96.0
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C21H20O10

DETAILS

Sigma Aldrich - 17804

Biochem/physiol Actions
Phytochemical found in medicinal herbs. Antioxidant.
Application
Isovitexin can be used to study biochemicals found in plants and nutrition. Isovitexin has been used in a study to assess collagenase inhibitors from Viola yedoensis. Isovitexin has also been used in a study to investigate the inhibitory activity of Gentiana lutea extracts on the enzyme myeloperoxidase (MPO), as well as the antioxidant activity of these extracts and their correlation with the total polyphenol content.

Sigma Aldrich - 67135

Biochem/physiol Actions
Phytochemical found in medicinal herbs. Antioxidant.