Axillarin

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Axillarin
Chemical structure of axillarin
Names
IUPAC name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxychromen-4-one
Other names
DMQT
3,6-Dimethoxyquercetagetin
Quercetagetin 3,6-dimethyl ether
3',4',5,7-Tetrahydroxy-3,6-dimethoxyflavone
Identifiers
5188-73-8 N=
ChEBI CHEBI:2941 N
ChEMBL ChEMBL487810 YesY
ChemSpider 4444922 YesY
Jmol 3D model Interactive image
PubChem 5281603
  • InChI=1S/C17H14O8/c1-23-16-10(20)6-11-12(13(16)21)14(22)17(24-2)15(25-11)7-3-4-8(18)9(19)5-7/h3-6,18-21H,1-2H3 YesY
    Key: KIGVXRGRNLQNNI-UHFFFAOYSA-N YesY
  • InChI=1/C17H14O8/c1-23-16-10(20)6-11-12(13(16)21)14(22)17(24-2)15(25-11)7-3-4-8(18)9(19)5-7/h3-6,18-21H,1-2H3
    Key: KIGVXRGRNLQNNI-UHFFFAOYAX
  • COC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)OC)O
Properties
C17H14O8
Molar mass 346.28 g/mol
Density 1.659 g/mL
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

Axillarin is an O-methylated flavonol. It can be found in Pulicaria crispa, Filifolium sibiricum, Inula britannica,[1] Wyethia bolanderi in Balsamorhiza macrophylla[2] and in Tanacetum vulgare.[3] It can also be synthetized.[4]

Glycosides

Axillarin 7-O-β-D-glucoside can be found in Tagetes mendocina, a medicinal plant widely used in the Andean provinces of Argentina.[5]

References

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  1. Acylated Flavonol Glycosides from the Flower of Inula britannica. Eun Jung Park, Youngleem Kim, and Jinwoong Kim, J. Nat. Prod., 2000, 63 (1), pp 34–36
  2. Methylated flavonols from Wyethia bolanderi and Balsamorhiza macrophylla. Susan McCormick, Kathleen Robson and Bruce Bohm, Phytochemistry, Volume 24, Issue 9, 1985, Page 2133
  3. Lua error in package.lua at line 80: module 'strict' not found.
  4. The syntheses of axillarin and its related compounds. K. Fukui, M. Nakayama and T. Horie, Cellular and Molecular Life Sciences, Volume 24, Number 8 / August 1968, Pages 769-770
  5. Free Radical Scavengers and Antioxidants from Tagetes mendocina. Guillermo Schmeda-Hirschmann, Alejandro Tapia, Cristina Theoduloz, Jaime Rodrıguez, Susana Lopez and Gabriela Egly Feresin.