5-Hydroxyfisetin

Names

[ CAS No. ]:
490-31-3

[ Name ]:
5-Hydroxyfisetin

[Synonym ]:
Robinetin
Norkanugin
3,7,3',4',5'-pentahydroxyflavonol
3,7,3',4',5'-pentahydroxyflavone
3,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
4H-1-Benzopyran-4-one, 3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-
3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
5-Hydroxyfisetin
EINECS 207-709-6
3,3',4',5',7-Pentahydroxyflavone

Biological Activity

[Description]:

Robinetin (3,3',4',5',7-Pentahydroxyflavone), a naturally occurring flavonoid with remarkable ‘two color’ intrinsic fluorescence properties, has antifungal, antiviral, antibacterial, antimutagenesis, and antioxidant activity. Robinetin also can inhibit lipid peroxidation and protein glycosylation[1][2][3][4][5].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Metabolic Enzyme/Protease >> HIV Integrase

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Robinetin (0.1-10 μM; 1 h) inhibits HIV integrase cleavage and integration in a dose-dependent manner[1]. Robinetin inhibits the DNA synthesis in Proteus vulgaris, and the RNA synthesis in S. aureus[2]. Robinetin (100-200 or 25 μM; 1 or 72 h) inhibits egg yolk phosphatidylcholine (EYPC) membrane lipid peroxidation and hemoglobin A (HbA) glycosylation with high efficiency[3]. Robinetin exhibits photo-induced excited-state intramolecular proton transfer resulting in ‘two color’ (in ‘blue-violet’ and ‘yellow-green’ regions) fluorescence characteristic of flavonols, the relative contributions between the two colors being strongly modulated by the local environment of the fluorophore[3].

[References]

[1]. Fesen MR, et, al. Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds. Biochem Pharmacol. 1994 Aug 3;48(3):595-608.

[2]. Cushnie TPT, et, al. Antimicrobial activity of flavonoids. Int J Antimicrob Agents. 2005 Nov;26(5):343-56.

[3]. Chaudhuri S, et, al. Binding of the bioflavonoid robinetin with model membranes and hemoglobin: Inhibition of lipid peroxidation and protein glycosylation. J Photochem Photobiol B. 2010 Jan 21;98(1):12-9.

[4]. Birt DF, et, al. Anti-mutagenesis and anti-promotion by apigenin, robinetin and indole-3-carbinol. Carcinogenesis. 1986 Jun;7(6):959-63.

[5]. Manrique-de-la-Cuba MF, et, al. Theoretical study of the antioxidant capacity of the flavonoids present in the Annona muricata (Soursop) leaves. J Mol Model. 2019 Jun 25;25(7):200.

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
669.9±55.0 °C at 760 mmHg

[ Melting Point ]:
326-328ºC

[ Molecular Formula ]:
C₁₅H₁₀O₇

[ Molecular Weight ]:
302.236

[ Flash Point ]:
258.6±25.0 °C

[ Exact Mass ]:
302.042664

[ PSA ]:
131.36000

[ LogP ]:
2.55

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.823

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LK8780000

CHEMICAL NAME :: Flavone, 3,3',4',5',7-pentahydroxy-

CAS REGISTRY NUMBER :: 490-31-3

BEILSTEIN REFERENCE NO. :: 0308905

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C15-H10-O7

MOLECULAR WEIGHT :: 302.25

WISWESSER LINE NOTATION :: T66 BO EVJ CR CQ DQ EQ& DQ IQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Microorganism - not otherwise specified

DOSE/DURATION :: 25 mg/L

REFERENCE :: PYTCAS Phytochemistry. An International Journal of Plant Biochemistry. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1961- Volume(issue)/page/year: 26,2231,1987

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
22-45

[ RIDADR ]:
UN 2811

[ HS Code ]:
2932999099

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%