α-Naphthoflavone
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α-Naphthoflavone
structure -
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CAS No:
604-59-1
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Formula:
C19H12O2
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Chemical Name:
α-Naphthoflavone
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Synonyms:
4H-Naphtho[1,2-b]pyran-4-one,2-phenyl-;7,8-Benzoflavone;2-Phenyl-4H-naphtho[1,2-b]pyran-4-one;α-Naphthoflavone;α-Naphthylflavone;Benzo[h]flavone;ANF;UCCF 023;NSC 407011;2-Phenyl-4H-benzo[h]chromen-4-one;2-Phenylbenzo[h]chromen-4-one
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CAS No:
Description
Alpha-Naphthoflavone is a synthetic flavonoid, acts as a potent and competitive aromatase inhibitor with an IC50 and a Ki of 0.5 and 0.2 μM, respectively[1].
Alpha-naphthoflavone is an extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14). It has a role as an EC 1.14.14.14 (aromatase) inhibitor, an aryl hydrocarbon receptor antagonist and an aryl hydrocarbon receptor agonist. It is an organic heterotricyclic compound, an extended flavonoid and a naphtho-gamma-pyrone.
α-Naphthoflavone Basic Attributes
272.3
272.30
210862
210-071-1
FML65D8PY5
407011
DTXSID2040650
2914399090
Characteristics
26.3
4.79
yellow Crystalline Powder or Crystals
1.3±0.1 g/cm3
167 °C
460.9±45.0 °C at 760 mmHg
215.8±22.3 °C
1.695
2-8°C
Safety Information
NONH for all modes of transport
3
68-34-11
24/25-36/37-45-36/37/39-26-16
QL6250000
Xi,Xn,C,F
Irritant
Stable. Incompatible with strong oxidizing agents.
α-Naphthoflavone Use and Manufacturing
Dissolve 2g of chalcone in 120ml of ethanol, heat to boiling, mix with hydrochloric acid and reflux for 24h. The residue was filtered while hot, and the filtrate was cooled and crystallized to obtain flavanone. Then the bromine-carbon disulfide solution is added to flavanone to generate benzoflavonoids.
The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that promotes the expression of phase I and II xenobiotic chemical metabolizing enzyme genes, including the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2. α-Naphthoflavone is a flavone that modulates xenobiotic metabolism at several points. It antagonizes AhR, blocking the expression of phase I and II genes at nanomolar concentrations, although it can agonize AhR at higher concentrations (10 μM). α-Naphthoflavone inhibits CYP19 (aromatase), CYP1A1, CYP1A2, and CYP1B1 (IC50s = 500, 60, 6, and 5 nM, respectively), whereas it activates CYP3A4 (Kd = 7.4 μM). Dietary α-naphthoflavone can contribute to carcinogenesis in the presence of synthetic estrogens.[Cayman Chemical]
4H-Naphtho[1,2-b]pyran-4-one, 2-phenyl-: INACTIVE
Computed Properties
Molecular Weight:272.3
XLogP3:4.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:272.083729621
Monoisotopic Mass:272.083729621
Topological Polar Surface Area:26.3
Heavy Atom Count:21
Complexity:433
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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