alpha-Naphthoflavone

Names
IUPAC name

Benzo[7,8]flavone

Preferred IUPAC name

2-Phenyl-4H-naphtho[1,2-b]pyran-4-one

Other names

7,8-Benzoflavone, ANF,2-phenylbenzo[h]chromen-4-one

Identifiers

CAS Number

* 604-59-1 N

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:76995 Y

ChEMBL |

* ChEMBL283196 Y

ChemSpider |

* 11297 Y

DrugBank |

* DB07453 Y

EC Number |

* 210-071-1

PubChem CID

* 11790

UNII |

* FML65D8PY5

CompTox Dashboard (EPA)

* DTXSID2040650

InChI

* InChI=1S/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H Y

Key: VFMMPHCGEFXGIP-UHFFFAOYSA-N Y

* InChI=1/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H

Key: VFMMPHCGEFXGIP-UHFFFAOYAW

SMILES

* O=C\1c4c(O/C(=C/1)c2ccccc2)c3ccccc3cc4

Properties

Chemical formula

| C19H12O2
Molar mass | 272.303 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

alpha-Naphthoflavone, also known as 7,8-benzoflavone and 2-phenyl-benzo(h)chromen-4-one, is a synthetic[1][2] flavone derivative. It can be prepared from 2-naphthol and cinnamaldehyde.[3]

alpha-Naphthoflavone is a potent inhibitor of the enzyme aromatase, the enzyme that converts testosterone to estrogen.[1][2] alpha-Naphthoflavone has been shown to cause abnormal testicular development in young chickens.[4]

## See also

* beta-Naphthoflavone
* C19H12O2

## References

1. ↑ 1.0 1.1 Campbell, Deborah R.; Kurzer, Mindy S. (1993). "Flavonoid inhibition of aromatase enzyme activity in human preadipocytes". Journal of Steroid Biochemistry and Molecular Biology 46 (3): 381–388. doi:10.1016/0960-0760(93)90228-O. PMID 9831487.
2. ↑ 2.0 2.1 Kellis JT Jr; Vickery LE (1984). "Inhibition of human estrogen synthetase (aromatase) by flavones". Science 225 (4666): 1032–1034. doi:10.1126/science.6474163. PMID 6474163. Bibcode: 1984Sci...225.1032K.
3. ↑ Harvey, Ronald G.; Hahn, Jung Tai; Bukowska, Maria; Jackson, Henry (1990). "A new chromone and flavone synthesis and its utilization for the synthesis of potentially antitumorigenic polycyclic chromones and flavones". The Journal of Organic Chemistry 55 (25): 6161. doi:10.1021/jo00312a023.
4. ↑ Trefil, P.; Micakova, A.; Stiborova, M.; Poplstein, M.; Brillard, J.P.; Hodek, P. (2004). "Effects of alpha-naphthoflavone on body growth and gonad development in chickens (Gallus domesticus)". Czech Journal of Animal Science - UZPI 49 (6): 231–238. doi:10.17221/4305-CJAS.

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*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency