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alpha-naphthoflavone
4H-naphtho[1,2-b]pyran-4-one, 2-phenyl-

Supplier Sponsors

Name:2-phenylbenzo[h]chromen-4-one
CAS Number: 604-59-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:210-071-1
FDA UNII: FML65D8PY5
Nikkaji Web:J46.330B
Beilstein Number:0210862
MDL:MFCD00004985
XlogP3:4.80 (est)
Molecular Weight:272.30304000
Formula:C19 H12 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
a-NAPHTHOFLAVONE >98%
ExtraSynthese
For experimental / research use only.
7,8-Benzoflavone
Santa Cruz Biotechnology
For experimental / research use only.
a-Naphthoflavone 97%
Sigma-Aldrich: Aldrich
For experimental / research use only.
a-Naphthoflavone
TCI AMERICA
For experimental / research use only.
alpha-Naphthoflavone >98.0%(HPLC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):604-59-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11790
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-phenylbenzo[h]chromen-4-one
Chemidplus:0000604591
RTECS:QL6250000 for cas# 604-59-1
 
References:
 2-phenylbenzo[h]chromen-4-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:604-59-1
Pubchem (cid):11790
Pubchem (sid):134977279
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2932.99.7000
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
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
 

Articles:

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.
 
Notes:
inhibits p4501a1 and p4501a2; stimulates some activities of p4503a4.
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