7-hydroxyflavone
4H-1-benzopyran-4-one, 7-hydroxy-2-phenyl-
Identification
| Name | 7-hydroxyflavone |
| IUPAC | 7-hydroxy-2-phenylchromen-4-one |
| CAS Number | 6665-86-7 |
| EINECS | 229-705-3 |
| FDA UNII | ZE72458E4L |
| Molecular Formula | C15 H10 O3 |
| Molecular Weight | 238.24230000 |
| MDL Number | MFCD00006835 |
| Nikkaji Number | J46.306J |
| XlogP3 | 3.60 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 245.00 °C. @ 760.00 mm Hg |
| Boiling Point | 450.12 °C. @ 760.00 mm Hg (est) |
| Flash Point | 349.00 °F. TCC ( 176.30 °C. ) (est) |
| logP (o/w) | 3.620 |
| Soluble in | water, 84.55 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for 7-hydroxyflavone usage levels up to | not for fragrance use. |
| Recommendation for 7-hydroxyflavone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one, 7-hydroxy-2-phenyl-
flavone, 7-hydroxy-
7-
hydroxy flavone
7-
hydroxy-2-phenyl-4-benzopyrone
7-
hydroxy-2-phenyl-4H-chromen-4-one
7-
hydroxy-2-phenyl-chromen-4-one
7-
hydroxy-2-phenylchromen-4-one
7-
hydroxy-2-phenylchromone
7-
hydroxy-flavone
PubMed:
Analysis of the erythroid differentiation effect of flavonoid apigenin on K562 human chronic leukemia cells.
PubMed:
Effects of 6-Hydroxyflavone on Osteoblast Differentiation in MC3T3-E1 Cells.
PubMed:
7-hydroxyflavone revisited: spectral, acid-base properties, and interplay of the protolytic forms in the ground and excited states.
PubMed:
Inhibition of Enterovirus 71 replication by 7-hydroxyflavone and diisopropyl-flavon7-yl Phosphate.
PubMed:
Differences in the hydroxylation pattern of flavonoids alter their chemoprotective effect against direct- and indirect-acting mutagens.
PubMed:
Natural potential therapeutic agents of neurodegenerative diseases from the traditional herbal medicine Chinese dragon's blood.
PubMed:
Simultaneous quantitation of 5- and 7-hydroxyflavone antioxidants and their binding constants with BSA using dual chiral capillary electrophoresis (dCCE) and HPLC with fluorescent detection.
PubMed:
Urease inhibitory constituents from Daphne retusa.
PubMed:
Identification of a novel flavonoid glycoside sulfotransferase in Arabidopsis thaliana.
PubMed:
Evaluation of estrogenic potential of flavonoids using a recombinant yeast strain and MCF7/BUS cell proliferation assay.
PubMed:
Mutual regioselective inhibition of human UGT1A1-mediated glucuronidation of four flavonoids.
PubMed:
Identification and characterization of a novel kaempferol sulfotransferase from Arabidopsis thaliana.
PubMed:
Summation solute hydrogen bonding acidity values for hydroxyl substituted flavones determined by NMR spectroscopy.
PubMed:
Binding of diverse environmental chemicals with human cytochromes P450 2A13, 2A6, and 1B1 and enzyme inhibition.
PubMed:
Influences of glucose on the dietary hydroxyflavonoid-plasma protein interaction.
PubMed:
Structural and functional analysis of the natural JNK1 inhibitor quercetagetin.
PubMed:
Iron reduction potentiates hydroxyl radical formation only in flavonols.
PubMed:
Inhibitory effects and underlying mechanism of 7-hydroxyflavone phosphate ester in HeLa cells.
PubMed:
Mutagenicity of flavonoids assayed by bacterial reverse mutation (Ames) test.
PubMed:
Spectroscopic study of solvent effects on the electronic absorption spectra of flavone and 7-hydroxyflavone in neat and binary solvent mixtures.
PubMed:
Structure of flavonoids influences the degree inhibition of Benzo(a)pyrene - induced DNA damage and micronuclei in HepG2 cells.
PubMed:
Sulfation of selected mono-hydroxyflavones by sulfotransferases in vitro: a species and gender comparison.
PubMed:
Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives.
PubMed:
Comprehensive review of Clerodendrum phlomidis: a traditionally used bitter.
PubMed:
A comparative study of flavonoid analogues on streptozotocin-nicotinamide induced diabetic rats: quercetin as a potential antidiabetic agent acting via 11beta-hydroxysteroid dehydrogenase type 1 inhibition.
PubMed:
Structure-affinity relationship of flavones on binding to serum albumins: effect of hydroxyl groups on ring A.
PubMed:
Use of glucuronidation fingerprinting to describe and predict mono- and dihydroxyflavone metabolism by recombinant UGT isoforms and human intestinal and liver microsomes.
PubMed:
Metabolism and pharmacokinetics of 3,3',4',7-tetrahydroxyflavone (fisetin), 5-hydroxyflavone, and 7-hydroxyflavone and antihemolysis effects of fisetin and its serum metabolites.
PubMed:
Mechanism of CYP2C9 inhibition by flavones and flavonols.
PubMed:
Ground and excited state proton transfer and antioxidant activity of 7-hydroxyflavone in model membranes: absorption and fluorescence spectroscopic studies.
PubMed:
Intestinal first-pass glucuronidation activities of selected dihydroxyflavones.
PubMed:
Protein engineering on biphenyl dioxygenase for conferring activity to convert 7-hydroxyflavone and 5,7-dihydroxyflavone (chrysin).
PubMed:
Inhibition of fatty acid amide hydrolase by kaempferol and related naturally occurring flavonoids.
PubMed:
Empirically predicted 13C NMR chemical shifts for 8-hydroxyflavone starting from 7,8,4'-trihydroxyflavone and from 7,8-dihydroxyflavone.
PubMed:
[Effects of flavonoids with different structures on proliferation of leukemia cell line HL-60].
PubMed:
Interaction of 7-hydroxyflavone with human serum albumin: a spectroscopic study.
PubMed:
A novel approach to the synthesis of 6-amino-7-hydroxy-flavone.
PubMed:
Antimetastatic potentials of flavones on oral cancer cell via an inhibition of matrix-degrading proteases.
PubMed:
Aromatase inhibition by bioavailable methylated flavones.
PubMed:
Characterization of a potent and selective small-molecule inhibitor of the PIM1 kinase.
PubMed:
Design, synthesis, and antiproliferative and CDK2-cyclin a inhibitory activity of novel flavopiridol analogues.
PubMed:
Phytoestrogens as inhibitors of the human progesterone metabolizing enzyme AKR1C1.
PubMed:
Methylated flavonoids have greatly improved intestinal absorption and metabolic stability.
PubMed:
[Study on the non-covalent interaction of 7-hydroxy flavone and its phosphate with DNA by fluorescence method].
PubMed:
Effect of different flavonoids on collagen synthesis in human fibroblasts.
PubMed:
Microbial metabolism. Part 6. Metabolites of 3- and 7-hydroxyflavones.
PubMed:
Characterization of polyphenols from plant materials through their silylation and 29Si NMR spectroscopy-line assignment through 29Si, 13C spin-spin couplings.
PubMed:
Anti-inflammatory inhibition of endothelial cell adhesion molecule expression by flavone derivatives.
PubMed:
Vasorelaxing effects of flavonoids: investigation on the possible involvement of potassium channels.
PubMed:
Induction and inhibition of aromatase (CYP19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells.
PubMed:
The inhibitory effects of flavonoids and antiestrogens on the Glut1 glucose transporter in human erythrocytes.
PubMed:
Manganese-based complexes of radical scavengers as neuroprotective agents.
PubMed:
7-OH-flavone is sulfated in the human liver and duodenum, whereas 5-OH-flavone and 3-OH-flavone are potent inhibitors of SULT1A1 activity and 7-OH-flavone sulfation rate.
PubMed:
Effect of simple phenolic compounds on azoxymethane-induced aberrant crypt foci in rat colon.
PubMed:
Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements.
PubMed:
Evaluation of 7-hydroxy-flavones as inhibitors of oestrone and oestradiol biosynthesis.
PubMed:
No evidence for the in vivo activity of aromatase-inhibiting flavonoids.
PubMed:
Inhibitors of human and rat testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD) as potential agents for prostatic cancer.
PubMed:
Role of ATP sensitive potassium channel on 7-hydroxy flavone induced antinociception and possible association with changes in glycaemic status.
PubMed:
Effects of flavonoids on the growth and cell cycle of cancer cells.
PubMed:
Aromatase and 17beta-hydroxysteroid dehydrogenase inhibition by flavonoids.
PubMed:
Comparative inhibition of human cytochromes P450 1A1 and 1A2 by flavonoids.
PubMed:
Effects of flavonoids on aromatase activity, an in vitro study.
PubMed:
A chalcone glycoside from Clerodendron phlomidis.
PubMed:
Biochemical studies of a new class of alcohol dehydrogenase inhibitors from Radix puerariae.
PubMed:
Aromatase inhibition by flavonoids.
PubMed:
Flavone mutagenicity in Salmonella typhimurium: dependence on the pKM101 plasmid and excision-repair deficiency.