Okanin

Okanin
Names

IUPAC name (E)-3-(3,4-dihydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)prop-2-en-1-one
Other names 3-(3,4-dihydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)prop-2-en-1-one
Identifiers
CAS Number	484-76-4^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:7734^N
ChemSpider	4444680^N
PubChem	5281294
InChI InChI=1S/C15H12O6/c16-10(9-3-6-12(18)15(21)14(9)20)4-1-8-2-5-11(17)13(19)7-8/h1-7,17-21H/b4-1+^N Key: GSBNFGRTUCCBTK-DAFODLJHSA-N^N InChI=1/C15H12O6/c16-10(9-3-6-12(18)15(21)14(9)20)4-1-8-2-5-11(17)13(19)7-8/h1-7,17-21H/b4-1+ Key: GSBNFGRTUCCBTK-DAFODLJHBD
SMILES C1=CC(=C(C=C1C=CC(=O)C2=C(C(=C(C=C2)O)O)O)O)O
Properties
Chemical formula	C₁₅H₁₂O₆
Molar mass	288.25 g/mol
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

Okanin is a chalconoid. It can be found in the plant Bidens pilosa (Picao preto).^[1]

Glycosides / Acetylations

Marein is the 4'-O-glucoside of okanin.

Methylated okanin derivatives can be isolated from Bidens torta. Those include okanin 3,4,3′,4′-tetramethyl ether, okanin 3,4,3′-trimethyl ether 4′-glucoside, okanin 4-methyl ether 4′-glucoside and okanin 4-methyl ether 4′-glucoside monoacetate. Okanin 3,4-dimethyl ether 4′-glucoside can also be isolated.^[2]

References

↑ Presence of Compounds in Picao preto (Bidens pilosa)
↑ Methylated Chalcones from Bidens torta. Susan P. McCormick, Bruce A. Bohm and Fred R. Ganders, Phytochemistry, Volume 23, Issue 10, 1984, Pages 2400-2401, doi:10.1016/S0031-9422(00)80570-1

Chalconoids and their glycosides

Chalconoids	Butein Isoliquiritigenin Methyl hydroxychalcone Okanin

Chalconoid glycosides	Carthamin Marein okanin 3,4,3′-trimethyl ether 4′-glucoside okanin 4-methyl ether 4′-glucoside okanin 4-methyl ether 4′-glucoside monoacetate Okanin 3,4-dimethyl ether 4′-glucoside

Acylated chalconoids	Licochalcone A Sophoradin (prenylated) Tephrospinosin (3′,5′-diisopentenyl-2′,4′-dihydroxychalcone) (prenylated) Xanthohumol (prenylated)

O-methylated chalconoids	Cardamomin Flavokawin B Okanin 3,4,3′,4′-tetramethyl ether Pashanone (2',6'-Dihydroxy-3',4'-dimethoxychalcone)

Flavokavains	Flavokavain A Flavokavain B Flavokavain C

Synthetic	Sofalcone

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