Axillarin

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
CAS Number	5188-73-8^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:2941^N
ChEMBL	ChEMBL487810^Y
ChemSpider	4444922^Y
PubChem CID	5281603
UNII	CF7D7U7ZK2^Y
CompTox Dashboard (EPA)	DTXSID80199840
InChI 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^Y Key: KIGVXRGRNLQNNI-UHFFFAOYSA-N^Y 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
SMILES COC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)OC)O
Properties
Chemical formula	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 ^YN ?) Infobox references

Chemical compound

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 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

^ 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.
^ McCormick, Susan; Robson, Kathleen; Bohm, Bruce (1985). "Methylated flavonols from Wyethia bolanderi and Balsamorhiza macrophylla". Phytochemistry. 24 (9): 2133. doi:10.1016/S0031-9422(00)83143-X.
^ 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. PMID 21171142. S2CID 9011931.
^ 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.
^ 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)

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates

Quercetin 3-O-sulfate
Quercetin 3,3'-bissulfate
Quercetin 3,4'-bissulfate

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)