2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one

• ChemBase ID: 5430
• Molecular Formular: C15H10O6
• Molecular Mass: 286.2363
• Monoisotopic Mass: 286.04773804
• SMILES: c1cc2c(cc1O)oc(c(c2=O)O)c1ccc(c(c1)O)O
• Canonical SMILES: Oc1ccc2c(c1)oc(c(c2=O)O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H
• InChIKey: XHEFDIBZLJXQHF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one
• IUPAC Traditional name: 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one; viset
• Synonyms: 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one; Fustel; Viset; Fisetin; 3,3',4',7-Tetrahydroxyflavone; Fisetin; 3,7,3',4'-TETRAHYDROXYFLAVONE; Cotinin (not to be confused with Cotinine); 5-Desoxyquercetin; Superfustel; Fisetholz; Fietin; Fustet; Junger fustik; Fisetin; 3,3',4',7-Tetrahydroxyflavone; 3,3',4',7-四羟基黄酮

Database IDs

• CAS Number: 528-48-3
• EC Number: 208-434-4
• MDL Number: MFCD00006829
• Beilstein Number: 292829
• Merck Index: 144088
• PubChem SID: 99444266; 160968858
• PubChem CID: 5281614
• CHEBI ID: 42567
• CHEMBL: 31574
• Chemspider ID: 4444933
• DrugBank ID: DB07795
• KEGG ID: C10041
• Wikipedia Title: Fisetin

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.318016
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.748803
• LogD (pH = 7.4): 0.6970341
• Log P: 1.8098648
• Molar Refractivity: 74.8813 cm^3
• Polarizability: 27.759434 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.03
• LOG S: -3.28
• Solubility (Water): 1.51e-01 g/l

PROPERTIES

Physical Property

• Melting Point: 330 °C; 330°C dec.
• Density: 1.688 g/mL

Safety Information

• Storage Condition: -20°C
• RTECS: LK9250000
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Pharmacology Properties

• Mechanism of Action: Potent antioxidant

Product Information

• Purity: 97%
• Salt Data: Free Base
• Biological Source: Colouring matter obtained from Rhus spp., also in Trachylobium verrucosum, Anthyllis vulneraria, Butea frondosa, Gleditsia spp., Acacia spp. and others
• Application(s): Anti-carcinogenic; Anti-inflammatory

DETAILS

DrugBank - DB07795

Drug information: experimental

Selleck Chemicals - S2298

Research Area: Inflammation
Biological Activity:
Fisetin (Fustel) is a potent sirtuin activating compound (STAC) and an agent that modulates sirtuins. Fisetin (Fustel) is therefore a caloric restriction mimetic candidate, a compound that has been shown to be able to alleviate ageing effects in certain model organisms such as the yeast S. cerevisiae, the nematode C. elegans and the fruit fly Drosophila melanogaster. [1] Aside from its effects on ageing,various in vitro studies have shown fisetin (Fustel) to exert anti-inflammatory and anti-carcinogenic effects in different lines of culture cells. [2]

REFERENCES

• Lim do Y et al. Am J Physiol Gastrointest Liver Physiol. 2009 May;296(5):G1060-8.
• Jankowska, T. et al., Acta Chim. Hung., 1962, 33, 135
• Plant Flavonoids in Biology and Medicine, (eds. Cody, V. et al), A.R. Liss, N.Y., 1986
• Roengsumaran, S. et al., J. Sci. Res. (Bhopal, India), 2000, 25, 169-176