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H4530

Sigma-Aldrich

7-Hydroxyflavone

≥98%

Synonym(s):

7-Hydroxy-2-phenyl-4H-1-benzopyran-4-one, NSC 94258

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About This Item

Empirical Formula (Hill Notation):
C15H10O3
CAS Number:
6665-86-7
Molecular Weight:
238.24
EC Number:
229-705-3
MDL number:
MFCD00006835
UNSPSC Code:
12352100
PubChem Substance ID:
57654239
NACRES:
NA.22

Assay

≥98%

mp

245-247 °C (lit.)

SMILES string

Oc1ccc2C(=O)C=C(Oc2c1)c3ccccc3

InChI

1S/C15H10O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-9,16H

InChI key

MQGPSCMMNJKMHQ-UHFFFAOYSA-N

Gene Information

mouse ... Hexa(15211)
rat ... Ar(24208) , Gabra2(29706)

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Application

Reactant:
  • Acting as a biologically valuable acceptor in O-glycosidation reactions
  • Involved in synthesis of fully phosphorylated flavones for use as pancreatic cholesterol esterase inhibitors
  • For O-methylation with di-Me carbonate
  • Linked by a polymethylene chain for synthesis of α1-adrenoceptor antagonists
  • Involved in Baylis-Hillman reactions
  • Involved in phase-transfer catalyzed glucosylation for synthesis of glucosylated flavonoids

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Osamu Kagami et al.
Journal of bioscience and bioengineering, 106(2), 121-127 (2008-09-23)
A central part (amino-acid position 268-397 of 458 amino-acid residues) of the biphenyl dioxygenase large (alpha) subunit, BphA1, from Pseudomonas pseudoalcaligenes strain KF707 was exchanged with the corresponding part of BphA1 from another biphenyl-degrading bacterium, Pseudomonas putida strain KF715, to
Jianbo Xiao et al.
Molecular nutrition & food research, 54 Suppl 2, S253-S260 (2010-03-23)
Four flavones (flavone, 7-hydroxyflavone, chrysin, and baicalein) sharing the same B- and C-ring structure but a different numbers of hydroxyl groups on the A-ring were studied for their affinities for BSA and HSA. The hydroxylation on ring A of flavones
Nga Ta et al.
The Journal of steroid biochemistry and molecular biology, 107(1-2), 127-129 (2007-07-13)
Previous studies have shown chrysin, 7-hydroxyflavone and 7,4'-dihydroxyflavone to be the most potent flavonoid inhibitors of aromatase. However, very poor oral bioavailability is a major limitation for the successful use of dietary flavonoids as chemopreventive agents. We have recently shown
Wimal Herath et al.
Chemical & pharmaceutical bulletin, 54(3), 320-324 (2006-03-02)
Fermentation of 3-hydroxyflavone (1) with Beauveria bassiana (ATCC 13144) yielded 3,4'-dihdroxyflavone (3), flavone 3-O-beta-D-4-O-methylglucopyranoside (4) and two minor metabolites. 7-Hydroxyflavone (2) was transformed by Nocardia species (NRRL 5646) to 7-methoxyflavone (5) whilst Aspergillus alliaceus (ATCC 10060) converted it to 4',7-dihydroxyflavone
Sudip Chaudhuri et al.
Biophysical chemistry, 139(1), 29-36 (2008-11-04)
Steady state and time resolved fluorescence spectroscopy have been used to probe microenvironments of the therapeutically active intrinsically fluorescent flavonoid, 7-hydroxyflavone (7-HF), in model membranes consisting of multilamellar phosphatidylcholine liposomes. Additionally, the antioxidant effects of 7-HF against lipid peroxidation have
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