Axillarin

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Axillarin
Chemical structure of axillarin
Names
Preferred IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4H-1-benzopyran-4-one
Other names
  • 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4H-chromen-4-one
  • DMQT
  • 3,6-Dimethoxyquercetagetin
  • Quercetagetin 3,6-dimethyl ether
  • 3',4',5,7-Tetrahydroxy-3,6-dimethoxyflavone
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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 checkY
    Key: KIGVXRGRNLQNNI-UHFFFAOYSA-N checkY
  • 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 346.291 g·mol−1
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 checkY☒N ?)

Axillarin is an

Wyethia bolanderi in Balsamorhiza macrophylla[2] and in Tanacetum vulgare.[3] It can also be synthesized.[4]

Glycosides

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

References

  1. PMID 10650074
    .
  2. doi:10.1016/S0031-9422(00)83143-X
    .
  3. S2CID 9011931
    .
  4. S2CID 33789154
    .
  5. ^ Guillermo Schmeda-Hirschmann, Alejandro Tapia, Cristina Theoduloz, Jaime Rodrıguez, Susana Lopez and Gabriela Egly Feresin (2004). "Free Radical Scavengers and Antioxidants from Tagetes mendocina" (PDF). Verlag der Zeitschrift für Naturforschung. 59c: 345–353.{{cite journal}}: CS1 maint: multiple names: authors list (link)


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