Calycosin

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Calycosin
Chemical structure of calycosin
Calycosin molecule
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
20575-57-9 N=
ChEBI CHEBI:17793 YesY
ChEMBL ChEMBL241608 YesY
ChemSpider 4444104 YesY
Jmol 3D model Interactive image
PubChem 5280448
UNII 09N3E8P7TA YesY
  • 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 YesY
    Key: ZZAJQOPSWWVMBI-UHFFFAOYSA-N YesY
  • 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
  • O=C\1c3c(O/C=C/1c2ccc(OC)c(O)c2)cc(O)cc3
Properties
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 YesYN ?)
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

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  1. 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
  2. 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