Flavone

Names
IUPAC name

Flavone[1]

Systematic IUPAC name

2-Phenyl-4H-1-benzopyran-4-one
2-Phenyl-4H-chromen-4-one

Identifiers

CAS Number

* 525-82-6 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 157598
ChEBI |

* CHEBI:42491

ChEMBL |

* ChEMBL275638

ChemSpider |

* 10230

DrugBank |

* DB07776

ECHA InfoCard | 100.007.623
EC Number |

* 208-383-8

Gmelin Reference

| 1224858

IUPHAR/BPS

* 409

KEGG |

* C15608

PubChem CID

* 10680

RTECS number |

* DJ3100630

UNII |

* S2V45N7G3B

CompTox Dashboard (EPA)

* DTXSID2022048

InChI

* InChI=1S/C15H10O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H

Key: VHBFFQKBGNRLFZ-UHFFFAOYSA-N

SMILES

* C1=CC=C(C=C1)C2=CC(=O)C3=CC=CC=C3O2

Properties

Chemical formula

| C15H10O2
Molar mass | 222.243 g·mol−1
Appearance  | white solid
Melting point | 96–97 °C (205–207 °F; 369–370 K)

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

Infobox references

Chemical compound

Flavone is an organic compound with the formula C6H4OC3H(Ph)O. A white solid, flavone is a derivative of chromone with a phenyl (Ph) substituent adjacent to the ether group. The compound is of little direct practical importance, but substituted derivatives, the flavones and flavonoids are a large class of nutritionally important natural products.[2] Flavone can be prepared in the laboratory by cyclization of 2-hydroxacetophenone.[3] Isomeric with flavone is isoflavone, where the phenyl group is adjacent to the ketone.

## References

[edit]

1. ^ https://iupac.qmul.ac.uk/flavonoid/index.html#Flv321
2. ^ Gaspar, Alexandra; Matos, Maria João; Garrido, Jorge; Uriarte, Eugenio; Borges, Fernanda (2014). "Chromone: A Valid Scaffold in Medicinal Chemistry". Chemical Reviews. 114 (9): 4960–4992\. doi:10.1021/cr400265z.
3. ^ T. S. Wheeler (1952). "Flavone". Organic Syntheses. 32: 72. doi:10.15227/orgsyn.032.0072.

* v
* t
* e

Flavones and their conjugates

Aglycones|

| Monohydroxyflavone|

* 3-Hydroxyflavone
* 6-Hydroxyflavone

|

Dihydroxyflavones|

* Chrysin
* 4',7-Dihydroxyflavone
* 7,8-Dihydroxyflavone

Trihydroxyflavones|

* Apigenin
* Baicalein
* Galangin
* Norwogonin
* 7,8,3'-Trihydroxyflavone
* 6,7,4'-Trihydroxyflavone

Tetrahydroxyflavones|

* Fisetin
* Kaempferol
* Isoscutellarein
* Luteolin
* Norartocarpetin
* Scutellarein

Pentahydroxyflavones|

* Herbacetin
* Morin
* Quercetin
* Nortangeretin
* 6-Hydroxyluteolin
* Norwightin
* Hypolaetin
* Tricetin

O-methylated flavones|

* 4',7-Dihydroxy-6-methoxyflavone
* Acacetin
* Alnetin
* Artocarpetin
* Chrysoeriol
* Cirsilineol
* Cirsiliol
* Cirsimaritin
* Diosmetin
* Eupatilin
* Genkwanin
* Hispidulin
* Nepetin
* Nobiletin
* Oroxylin A
* Pratol
* Salvigenin
* Sinensetin
* Tangeretin
* Techtochrysin
* Tricin
* Wogonin
* Zapotin

Glycosides|

| of apigenin|

* Apiin
* Apigetrin
* Isovitexin
* Rhoifolin
* Saponarin
* Schaftoside
* Vicenin-2
* Vitexin

|

of baicalein|

* Baicalin
* Tetuin

of hypolaetin|

* Hypolaetin 8-glucoside
* Hypolaetin 8-glucuronide

of luteolin|

* Cynaroside
* Isoorientin
* Orientin
* Veronicastroside
* Luteolin-7-O-glucuronide

* Giraldiin A and B
* Nepitrin
* Oroxindin
* Scutellarin

Acetylated|

* Artocarpetin A
* Artoindonesianin P

Sulfated glycosides|

Theograndin I and II

Polymers|

* Amentoflavone
* Ochnaflavone

Drugs|

* Diosmin
* Hidrosmin

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template