beta-naphthoflavone
1H-naphtho[2, 1-b]pyran-1-one, 3-phenyl-
Identification
| Name | beta-naphthoflavone |
| CAS Number | 6051-87-2 |
| EINECS | 227-958-4 |
| FDA UNII | 1BT0256Y8O |
| Molecular Formula | C19 H12 O2 |
| Molecular Weight | 272.30304000 |
| MDL Number | MFCD00004986 |
| Nikkaji Number | J1.840F |
| Beilstein | 0018991 |
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 | intravenous-mouse LD50 180 mg/kg |
| 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', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03239']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for beta-naphthoflavone usage levels up to | not for fragrance use. |
| Recommendation for beta-naphthoflavone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
5,6-
benzoflavone
1H-
naphtho(2,1-b)pyran-1-one, 3-phenyl-
1H-
naphtho[2, 1-b]pyran-1-one, 3-phenyl-
b-
naphthoflavone
3-
phenyl-1H-benzo[f]chromen-1-one
3-
phenyl-1H-naphtho(2,1-b)pyran-1-one
3-
phenyl-1H-naphtho[2, 1-b]pyran-1-one
3-
phenyl-1H-naphtho[2,1-b]pyran-1-one
3-
phenyl-benzo[f]chromen-1-one
3-
phenylbenzo[f]chromen-1-one
PubMed:
Effect of dihydromyricetin on benzo[a]pyrene activation in rats.
PubMed:
Embryonic exposure of medaka (Oryzias latipes) to propylparaben: effects on early development and post-hatching growth.
PubMed:
Non-dioxin-like AhR ligands in a mouse peanut allergy model.
PubMed:
Impact of beta-naphthoflavone on genotoxicity of food-derived carcinogens.
PubMed:
Dynamics of BNF-induced in vivo ethoxyresorufin-O-deethylase (EROD) activity during embryonic development of medaka (Oryzias latipes).
PubMed:
Potent modification of inducible CYP1A1 expression by flavonoids.
PubMed:
Recombinant aryl hydrocarbon receptors for bioassay of aryl hydrocarbon receptor ligands in transgenic tobacco plants.
PubMed:
Induction of cytochromes P450 in small intestine by chemopreventive compounds.
PubMed:
Energy intake affects the biotransformation rate, scope for induction, and metabolite profile of benzo[a]pyrene in rainbow trout.
PubMed:
Inhibitory effects of a dietary phytochemical 3,3'-diindolylmethane on the phenobarbital-induced hepatic CYP mRNA expression and CYP-catalyzed reactions in female rats.
PubMed:
A noninvasive test of exposition to toxicants: quantitative analysis of cytochrome P4501A expression in fish scales.
PubMed:
Inducibility of UDP-glucuronosyltransferase 1As by beta-naphthoflavone in HepG2 cells.
PubMed:
Resveratrol affects CYP1A expression in rainbow trout hepatocytes.
PubMed:
The impact of glucuronidation on the bioactivation and DNA adduction of the cooked-food carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in vivo.
PubMed:
2,3,7,8-Tetrachlorodibenzo-p-dioxin induces suppressor of cytokine signaling 2 in murine B cells.
PubMed:
Blarina brevicauda as a biological monitor of polychlorinated biphenyls: evaluation of hepatic cytochrome P450 induction.
PubMed:
Human intestinal Caco-2 cells display active transport of benzo[a]pyrene metabolites.
PubMed:
Effects of lactic acid bacteria on the uptake and distribution of the food mutagen Trp-P-2 in mice.
PubMed:
Intestinal responses to xenobiotics.
PubMed:
Identification of multiple constitutive and inducible hepatic cytochrome P450 enzymes in market weight swine.
PubMed:
[In vitro study of the interference of certain food components with the metabolism of aflatoxin B1].
PubMed:
[In vivo studies of the inhbitory effect of various food components on aflatoxin B1 metabolism].
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:
DNA adducts of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in fetal tissues of patas monkeys after transplacental exposure.
PubMed:
Differential effects of dietary flavonoids on drug metabolizing and antioxidant enzymes in female rat.
PubMed:
Biotransformation and clearance of 3-(phenylamino)propane-1,2-diol, a compound present in samples related to toxic oil syndrome, in C57BL/6 and A/J mice.
PubMed:
An expressional system of human cytochrome P-450 CYP1A1 gene transcription.
PubMed:
In vitro inhibition of thyroid hormone sulfation by hydroxylated metabolites of halogenated aromatic hydrocarbons.
PubMed:
Characterization of flavonoids as monofunctional or bifunctional inducers of quinone reductase in murine hepatoma cell lines.
PubMed:
Induction of ethoxyresorufin O-deethylase (EROD) and endothelial activation of the heterocyclic amine Trp-P-1 in bird embryo hearts.
PubMed:
Inhibition of mouse and human CYP 1A- and 2E1-dependent substrate metabolism by the isoflavonoids genistein and equol.
PubMed:
Measuring the potency of pulp mill effluents for induction of hepatic mixed-function oxygenase activity in fish.
PubMed:
Major involvement of rabbit liver cytochrome P4501A in thiabendazole 5-hydroxylation.
PubMed:
Ahr locus phenotype in congenic mice influences hepatic and pulmonary DNA adduct levels of 2-amino-3-methylimidazo[4,5-f]quinoline in the absence of cytochrome P450 induction.
PubMed:
Effects of curcumin on cytochrome P450 and glutathione S-transferase activities in rat liver.
PubMed:
The model Ah-receptor agonist beta-naphthoflavone inhibits aflatoxin B1-DNA binding in vivo in rainbow trout at dietary levels that do not induce CYP1A enzymes.
PubMed:
Induction of hepatic CYP1A by indole-3-carbinol in protection against aflatoxin B1 hepatocarcinogenesis in rainbow trout.
PubMed:
DNA adducts of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in colon, bladder, and kidney of congenic mice differing in Ah responsiveness and N-acetyltransferase genotype.
PubMed:
Effects of enzyme induction on the distribution of the food carcinogen 2-amino-3,8-dimethyl-imidazo[4,5-ss]-quinoxaline (MeIQx) in Ah-receptor- responsive- and Ah-receptor-non-responsive mice.
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:
Regulation of hepatic cytochrome P4501A by indole-3-carbinol: transient induction with continuous feeding in rainbow trout.
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:
Indole-3-carbinol induces a rat liver glutathione transferase subunit (Yc2) with high activity toward aflatoxin B1 exo-epoxide. Association with reduced levels of hepatic aflatoxin-DNA adducts in vivo.
PubMed:
Indole-3-carbinol and beta-naphthoflavone induction of aflatoxin B1 metabolism and cytochromes P-450 associated with bioactivation and detoxication of aflatoxin B1 in the rat.
PubMed:
Metabolic activation of the food mutagen Trp-P-1 in endothelial cells of heart and kidney in cytochrome P450-induced mice.
PubMed:
Hepa-1 enzyme induction assay as an in vitro indicator of the CYP1A1-inducing potencies of laboratory rodent diets in vivo.
PubMed:
Effects of capsaicin on liver microsomal metabolism of the tobacco-specific nitrosamine NNK.
PubMed:
Cytochrome P450 induction and metabolism of alkoxyresorufins, ethylmorphine and testosterone in cultured hepatocytes from goats, sheep and cattle.
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:
Effects of D-limonene on hepatic microsomal monooxygenase activity and paracetamol-induced glutathione depletion in mouse.
PubMed:
Induction of cytochrome P-450-dependent enzyme activities in cultured rat liver slices.
PubMed:
Tissue distribution of the food mutagen MeIQx in control and BNF-treated mice.
PubMed:
Acute renal toxicity of thiabendazole (TBZ) in ICR mice.
PubMed:
[Mixed-function oxidase induction as a test for the biological monitoring of water: limitations and prospects].
PubMed:
Covalent binding of food carcinogens MeIQx, MeIQ and IQ to DNA and protein in microsomal incubations and isolated rat hepatocytes.
PubMed:
Effects of reserpine and L-cysteine and glutathione depletion on 2-bromoethylamine hydrobromide-induced tubular necrosis in Swiss ICR mice.
PubMed:
Chemoprotective and hepatic enzyme induction properties of indole and indenoindole antioxidants in rats.
PubMed:
Hepatotoxicity of eugenol in mice depleted of glutathione by treatment with DL-buthionine sulfoximine.
PubMed:
Effects of the food mutagens MeIQx and PhIP on the expression of cytochrome P450IA proteins in various tissues of male and female rats.
PubMed:
The contribution of N-oxidation to the metabolism of the food-borne carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in rat hepatocytes.
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:
Studies of cytotoxicity and metabolic competence with the rat intestinal cell line IEC-17.
PubMed:
Mechanisms of anti-carcinogenesis by indole-3-carbinol. Studies of enzyme induction, electrophile-scavenging, and inhibition of aflatoxin B1 activation.
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:
The metabolism of 4,8-DiMeIQx in conventional and germ-free rats.
PubMed:
Metaplastic pancreatic cells in liver tumors induced by diethylnitrosamine.
PubMed:
Modulation of diethylnitrosamine-induced hepatocarcinogenesis and O6-ethylguanine formation in rainbow trout by indole-3-carbinol, beta-naphthoflavone, and Aroclor 1254.
PubMed:
Comparative effect of dietary butylated hydroxyanisole and beta-naphthoflavone on aflatoxin B1 metabolism, DNA adduct formation, and carcinogenesis in rainbow trout.
PubMed:
Specificity of rabbit cytochrome P-450 isozymes involved in the metabolic activation of the food derived mutagen 2-amino-3-methylimidazo[4,5-f] quinoline.
PubMed:
Epoxide-metabolizing enzymes in mammary gland and liver from BALB/c mice and effects of inducers on enzyme activity.
PubMed:
The significance of glutathione conjugation for aflatoxin B1 metabolism in rainbow trout and coho salmon.
PubMed:
Alterations in hepatic microsomal protein levels in rainbow trout fed cyclopropenoid fatty acids analyzed by two-dimensional gel electrophoresis.
PubMed:
A model system for studying covalent binding of food carcinogens MeIQx, MeIQ and IQ to DNA and protein.
PubMed:
B-naphthoflavone induction and its effect on hepatic phospholipid metabolism in rainbow trout (Salmo gairdneri).
PubMed:
Influences of dietary restriction and age on liver enzyme activities and lipid peroxidation in mice.
PubMed:
In vitro metabolism of teratogens by differentiating rat embryo cells.
PubMed:
Mutagens in cooked foods--metabolism and genetic toxicity.
PubMed:
Identification and mutagenicity of aflatoxicol-M1 produced by metabolism of aflatoxin B1 and aflatoxicol by liver fractions from rainbow trout (Salmo gairdneri) fed beta-naphthoflavone.
PubMed:
Mutagenicity of structurally related aromatic amines in the Salmonella/mammalian microsome test with various S-9 fractions.