Calycosin

Calycosin
Names


IUPAC name 7-hydroxy-3-(3-hydroxy-4-methoxyphenyl)chromen-4-one
Other names 7,3'-dihydroxy-4'-methoxyisoflavone 3',7-dihydroxy-4'-methoxyisoflavone 3'-hydroxyformononetin
Identifiers
CAS Number	20575-57-9^N=
ChEBI	CHEBI:17793^Y
ChEMBL	ChEMBL241608^Y
ChemSpider	4444104^Y
Jmol interactive 3D	Image
PubChem	5280448
UNII	09N3E8P7TA^Y
InChI InChI=1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3^Y Key: ZZAJQOPSWWVMBI-UHFFFAOYSA-N^Y InChI=1/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3 Key: ZZAJQOPSWWVMBI-UHFFFAOYAR
SMILES O=C\1c3c(O/C=C/1c2ccc(OC)c(O)c2)cc(O)cc3
Properties
Chemical formula	C₁₆H₁₂O₅
Molar mass	284.26 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

Calycosin is an O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus^[1] and Trifolium pratense L. (red clover).^[2]

Biosynthesis

Isoflavone 3'-hydroxylase uses formononetin, NADPH, H⁺ and O₂ to produce calycosin, NADP⁺ and H₂O.

References

↑ Preparative isolation and purification of calycosin from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography. Xiaofeng Ma, Tianyou Zhang, Yun Wei, Pengfei Tu, Yingjie Chen and Yoichiro Ito, Journal of Chromatography A, Volume 962, Issues 1-2, 12 July 2002, Pages 243-247
↑ Identification of isoflavones calycosin and pseudobaptigenin in Trifolium pratense. David R. Biggs and Geoffrey A. Lane, Phytochemistry, Volume 17, Issue 9, 1978, Pages 1683-1684

Isoflavones and their glycosides

Isoflavones	Daidzein Genistein Irilone Orobol Pseudobaptigenin Anagyroidisoflavone A and B

O-methylated isoflavones	Biochanin A Calycosin Formononetin Glycitein Irigenin 5-O-methylgenistein Pratensein Prunetin Psi-tectorigenin Retusin Tectorigenin

Glycosides	Daidzin Genistin Iridin Ononin Puerarin Sophoricoside Tectoridin

Prenylated isoflavones	Bidwillol A Derrubone Luteone 7-O-Methylluteone Wighteone

Pyranoisoflavones	Alpinumisoflavone Barbigerone Di-O-methylalpinumisoflavone 4'-methyl-alpinumisoflavone

Misc	Rotenoids

Synthetic	Ipriflavone

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