alpha-naphthoflavone
4H-naphtho[1,2-b]pyran-4-one, 2-phenyl-
Identification
| Name | alpha-naphthoflavone |
| IUPAC | 2-phenylbenzo[h]chromen-4-one |
| CAS Number | 604-59-1 |
| EINECS | 210-071-1 |
| FDA UNII | FML65D8PY5 |
| Molecular Formula | C19 H12 O2 |
| Molecular Weight | 272.30304000 |
| MDL Number | MFCD00004985 |
| Nikkaji Number | J46.330B |
| Beilstein | 0210862 |
| XlogP3 | 4.80 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 460.94 °C. @ 760.00 mm Hg (est) |
| Flash Point | 420.00 °F. TCC ( 215.80 °C. ) (est) |
| logP (o/w) | 5.003 (est) |
| Soluble in | water, 1.772 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 | information only not used for fragrances or flavors |
| Recommendation for alpha-naphthoflavone usage levels up to | not for fragrance use. |
| Recommendation for alpha-naphthoflavone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
7,8-
benzoflavone
4H-
naphtho(1,2-b)pyran-4-one, 2-phenyl-
4H-
naphtho[1, 2-b]pyran-4-one, 2-phenyl-
4H-
naphtho[1,2-b]pyran-4-one, 2-phenyl-
a-
naphthoflavone
a-
naphthylflavone
2-
phenyl-4H-benzo[h]chromen-4-one
2-
phenyl-4H-naphtho(1,2-b)pyran-4-one
2-
phenyl-4H-naphtho[1,2-b]pyran-4-one
2-
phenyl-4H-naphthol(1,2-b)pyran-4-one
2-
phenyl-benzo[h]chromen-4-one
2-
phenylbenzo(h)chromen-4-one
2-
phenylbenzo[h]chromen-4-one
PubMed:
Effect of dihydromyricetin on benzo[a]pyrene activation in rats.
PubMed:
α-Naphthoflavone modulates inflammatory response in adipocytes-macrophages interaction through NFκB signaling.
PubMed:
Metabolism of chamaechromone in vitro with human liver microsomes and recombinant human drug-metabolizing enzymes.
PubMed:
Synergistic effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin and N-nitrosodiethylamine on cell malignant transformation.
PubMed:
α-Naphthoflavone inhibits 3T3-L1 pre-adipocytes differentiation via modulating p38MAPK signaling.
PubMed:
Hepatic cytochrome P450s attenuate the cytotoxicity induced by leflunomide and its active metabolite A77 1726 in primary cultured rat hepatocytes.
PubMed:
Inhibition of cytochrome P450 2A participating in coumarin 7-hydroxylation in pig liver microsomes.
PubMed:
In vitro biotransformation and investigation of metabolic enzymes possibly responsible for the metabolism of bisdesoxyolaquindox in the liver fractions of rats, chicken, and pigs.
PubMed:
Mutagenic activation and detoxification of benzo[a]pyrene in vitro by hepatic cytochrome P450 1A1 and phase II enzymes in three meat-producing animals.
PubMed:
Metabolites of galangin by 2,3,7,8-tetrachlorodibenzo-p-dioxin-inducible cytochrome P450 1A1 in human intestinal epithelial Caco-2 cells and their antagonistic activity toward aryl hydrocarbon receptor.
PubMed:
Validation of cytochrome P450 time-dependent inhibition assays: a two-time point IC50 shift approach facilitates kinact assay design.
PubMed:
EROD and MROD as Markers of Cytochrome P450 1A Activities in Hepatic Microsomes from Entire and Castrated Male Pigs.
PubMed:
A human intervention study with foods containing natural Ah-receptor agonists does not significantly show AhR-mediated effects as measured in blood cells and urine.
PubMed:
Human cytochrome p450 enzyme specificity for the bioactivation of estragole and related alkenylbenzenes.
PubMed:
Estrogen receptor alpha as a target for indole-3-carbinol.
PubMed:
alpha-Naphthoflavone, a potent antiplatelet flavonoid, is mediated through inhibition of phospholipase C activity and stimulation of cyclic GMP formation.
PubMed:
Intestinal metabolism of PAH: in vitro demonstration and study of its impact on PAH transfer through the intestinal epithelium.
PubMed:
Protection by quercetin against cooking oil fumes-induced DNA damage in human lung adenocarcinoma CL-3 cells: role of COX-2.
PubMed:
Induction of cytochrome P4501A1 by autoclavable culture medium change in HepG2 cells.
PubMed:
Human intestinal Caco-2 cells display active transport of benzo[a]pyrene metabolites.
PubMed:
Differential response of cultured human umbilical vein and artery endothelial cells to Ah receptor agonist treatment: CYP-dependent activation of food and environmental mutagens.
PubMed:
Antioxidant protection against PCB-mediated endothelial cell activation.
PubMed:
Inhibition of mouse and human CYP 1A- and 2E1-dependent substrate metabolism by the isoflavonoids genistein and equol.
PubMed:
The role of xenobiotic metabolizing enzymes in arylamine toxicity and carcinogenesis: functional and localization studies.
PubMed:
Carbaryl induces CYP1A1 gene expression in HepG2 and HaCaT cells but is not a ligand of the human hepatic Ah receptor.
PubMed:
Metabolism of the aryl hydrocarbon receptor agonist 3,3',4,4'-tetrachlorobiphenyl by the marine fish scup (Stenotomus chrysops) in vivo and in vitro.
PubMed:
Metabolism of 2-amino-alpha-carboline. A food-borne heterocyclic amine mutagen and carcinogen by human and rodent liver microsomes and by human cytochrome P4501A2.
PubMed:
The metabolism and DNA binding of the cooked-food mutagen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in precision-cut rat liver slices.
PubMed:
Inhibition of in vitro aflatoxin B1-DNA binding in rainbow trout by CYP1A inhibitors: alpha-naphthoflavone, beta-naphthoflavone and trout CYP1A1 peptide antibody.
PubMed:
Metabolic activation of the food mutagen 3-amino-1,4-dimethyl-5H-pyrido-[4,3-b]indole (Trp-P-1) in endothelial cells of cytochrome P-450-induced mice.
PubMed:
Metabolic activation of the food mutagen Trp-P-1 in endothelial cells of heart and kidney in cytochrome P450-induced mice.
PubMed:
The role of sulfation and/or acetylation in the metabolism of the cooked-food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Salmonella typhimurium and isolated rat hepatocytes.
PubMed:
Flavonoid inhibition of aromatase enzyme activity in human preadipocytes.
PubMed:
Cytochrome P450 forms in the rodent lung involved in the metabolic activation of food-derived heterocyclic amines.
PubMed:
Metabolism of food-derived heterocyclic amines in human and rabbit tissues by P4503A proteins in the presence of flavonoids.
PubMed:
Covalent binding of food carcinogens MeIQx, MeIQ and IQ to DNA and protein in microsomal incubations and isolated rat hepatocytes.
PubMed:
Cytochrome P4501A2 constitutively expressed from transduced DNA mediates metabolic activation and DNA-adduct formation of aromatic amine carcinogens in NIH 3T3 cells.
PubMed:
Metabolism of 2-acetylaminofluorene and benzo(a)pyrene and activation of food-derived heterocyclic amine mutagens by human cytochromes P-450.
PubMed:
Differential rates of metabolic activation and detoxication of the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by different cytochrome P450 enzymes.
PubMed:
4-(2-amino-1-methylimidazo[4,5-b]pyrid-6-yl)phenyl sulfate--a major metabolite of the food mutagen 2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine (PhIP) in the rat.
PubMed:
Genotoxicity of the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP): formation of 2-hydroxamino-PhIP, a directly acting genotoxic metabolite.
PubMed:
Activation of the food-derived mutagen 2-amino-3-methylimidazo[4, 5-f]quinoline by human-liver microsomes.
PubMed:
Modulation of the mutagenic effects of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) in bacteria with rat-liver 9000 x g supernatant or monolayers of rat hepatocytes as an activation system.
PubMed:
Correlation of placental microsomal activities with protein detected by antibodies to rabbit cytochrome P-450 isozyme 6 in preparations from humans exposed to polychlorinated biphenyls, quaterphenyls, and dibenzofurans.
PubMed:
Effects of dietary constituents on the metabolism of chemical carcinogens.