Axillarin

Axillarin
Chemical structure of 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).
X markN verify (what is checkYX markN ?)

Axillarin is an O-methylated flavonol. It can be found in Pulicaria crispa, Filifolium sibiricum, Inula britannica, Wyethia bolanderi in Balsamorhiza macrophylla and in Tanacetum vulgare. It can also be synthesized.

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.

References

  1. ↑ Jung Park, Eun; Kim, Youngleem; Kim, Jinwoong (2000). "Acylated Flavonol Glycosides from the Flower ofInula britannica". Journal of Natural Products. 63 (1): 34–36. doi:10.1021/np990271r. PMID 10650074.
  2. ↑ McCormick, Susan; Robson, Kathleen; Bohm, Bruce (1985). "Methylated flavonols from Wyethia bolanderi and Balsamorhiza macrophylla". Phytochemistry. 24 (9): 2133. Bibcode:1985PChem..24.2133M. doi:10.1016/S0031-9422(00)83143-X.
  3. ↑ Álvarez, Ángel L.; Habtemariam Solomon; Juan-Badaturuge Malindra; Jackson Caroline; Parra Francisco (2011). "In vitro anti HSV-1 and HSV-2 activity of Tanacetum vulgare extracts and isolated compounds: An approach to their mechanisms of action". Phytotherapy Research (Submitted manuscript). 25 (2): 296–301. doi:10.1002/ptr.3382. hdl:10651/8271. PMID 21171142. S2CID 9011931.
  4. ↑ Fukui, K.; Nakayama, M.; Horie, T. (1968). "The syntheses of axillarin and its related compounds". Experientia. 24 (8): 769–770. doi:10.1007/BF02144856. 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)