Rhamnazin

Rhamnazin
Rhamnazin structure
Rhamnazin structure
Rhamnazin structure
Rhamnazin structure
Names
IUPAC name
3,4′,5-Trihydroxy-3′,7-dimethoxyflavone
Systematic IUPAC name
3,5-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
Other names
3′,7-Dimethylquercetin
3,5,4′-Trihydroxy-7,3′-dimethoxyflavone
5,3′,4′-Trihydroxy-3,7-dimethoxyflavone
Flavone, 3,4′,5-trihydroxy-3′,7-dimethoxy-
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C17H14O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-10(18)12(5-8)23-2/h3-7,18-19,21H,1-2H3 ☒N
    Key: MYMGKIQXYXSRIJ-UHFFFAOYSA-N ☒N
  • InChI=1/C17H14O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-10(18)12(5-8)23-2/h3-7,18-19,21H,1-2H3
    Key: MYMGKIQXYXSRIJ-UHFFFAOYAP
  • COC1=CC(=C2C(=C1)OC(=C(C2=O)O)C3=CC(=C(C=C3)O)OC)O
Properties
C17H14O7
Molar mass 330.292 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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Rhamnazin is an O-methylated flavonol, a type of chemical compound. It can be found in Rhamnus petiolaris,[1] a buckthorn plant native to Iraq, Lebanon, Syria, and Turkey.[2]

Metabolism

The enzyme 3-methylquercetin 7-O-methyltransferase uses S-adenosyl methionine and isorhamnetin to produce S-adenosyl homocysteine and rhamnazin.

The enzyme 3,7-dimethylquercetin 4'-O-methyltransferase uses S-adenosyl methionine and rhamnazin to produce S-adenosyl homocysteine and ayanin.

References

  1. ^ Wagner, H.; Ertan, M.; Seligmann, O. (1974). "Rhamnazin- und rhamnetin-3-O-trioside aus Rhamnus petiolaris". Phytochemistry (in German). 13 (5): 857–860. Bibcode:1974PChem..13..857W. doi:10.1016/S0031-9422(00)91151-8.
  2. ^ "Rhamnus petiolaris Boiss. & Balansa". Plants of the World Online. The Trustees of the Royal Botanic Gardens, Kew. n.d. Retrieved January 9, 2025.