Calycosin

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

Calycosin
Chemical structure of calycosin
Calycosin molecule
Names
IUPAC name
3′,7-Dihydroxy-4′-methoxyisoflavone
Systematic IUPAC name
7-Hydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Other names
7,3′-Dihydroxy-4′-methoxyisoflavone
3′-Hydroxyformononetin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.222.904
UNII
  • 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 checkY
    Key: ZZAJQOPSWWVMBI-UHFFFAOYSA-N checkY
  • O=C\1c3c(O/C=C/1c2ccc(OC)c(O)c2)cc(O)cc3
Properties
C16H12O5
Molar mass 284.267 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Biosynthesis

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

References
  1. Ma, Xiaofeng; Zhang, Tianyou; Wei, Yun; Tu, Pengfei; Chen, Yingjie; Ito, Yoichiro (2002). "Preparative isolation and purification of calycosin from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography". Journal of Chromatography A. 962 (1–2): 243–7. doi:10.1016/S0021-9673(02)00535-6. PMID 12198969.
  2. Biggs, David R; Lane, Geoffrey A (1978). "Identification of isoflavones calycosin and pseudobaptigenin in Trifolium pratense". Phytochemistry. 17 (9): 1683. doi:10.1016/S0031-9422(00)94679-X.
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