Azaleatin - Misplaced Pages

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Azaleatin
Names
Azaleatin structure
IUPAC name 3,3′,4′,7-Tetrahydroxy-5-methoxyflavone
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-4H-1-benzopyran-4-one
Other names 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-4H-chromen-4-one 5-O-Methylquercetin Quercetin 5-methyl ether
Identifiers
CAS Number	529-51-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:2945
ChEMBL	ChEMBL470848
ChemSpider	4444923
PubChem CID	5281604
UNII	SO52512D8G
CompTox Dashboard (EPA)	DTXSID80200945
InChI InChI=1S/C16H12O7/c1-22-11-5-8(17)6-12-13(11)14(20)15(21)16(23-12)7-2-3-9(18)10(19)4-7/h2-6,17-19,21H,1H3Key: RJBAXROZAXAEEM-UHFFFAOYSA-N InChI=1/C16H12O7/c1-22-11-5-8(17)6-12-13(11)14(20)15(21)16(23-12)7-2-3-9(18)10(19)4-7/h2-6,17-19,21H,1H3Key: RJBAXROZAXAEEM-UHFFFAOYAA
SMILES O=C1c3c(O/C(=C1/O)c2ccc(O)c(O)c2)cc(O)cc3OC
Properties
Chemical formula	C₁₆H₁₂O₇
Molar mass	316.26 g/mol
Density	1.634 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Azaleatin is a chemical compound. It is an O-methylated flavonol, a type of flavonoid. It was first isolated from the flowers of Rhododendron mucronatum in 1956 and has since been recorded in 44 other Rhododendron species, in Plumbago capensis, in Ceratostigma willmottiana and in Carya pecan. It has also been found in the leaves of Eucryphia.

Glycosides

Azalein is the 3-O-α-L-rhamnoside of azaleatin.

Wada, Einosuke (1956). "On a Flavonol Glycoside Isolated from Flowers of a White Azalea (Rhododendron mucronatum G. Don)". Journal of the American Chemical Society. 78 (18): 4725–6. Bibcode:1956JAChS..78.4725W. doi:10.1021/ja01599a052.
Harborne, J.B. (1962). "Plant polyphenols: 5. Occurrence of azalein and related pigments in flowers of Plumbago and Rhododendro species". Archives of Biochemistry and Biophysics. 96: 171–8. doi:10.1016/0003-9861(62)90467-8. PMID 13904580.
Sasaki, T; Mikami, M (1963). "Studies on the Components of Pecan (Carya Pecan Engl. & Graebn). I. On the Flavon Isolated from the Bark of Pecan". Yakugaku Zasshi. 83: 897–900. doi:10.1248/yakushi1947.83.9_897. PMID 14085492.
Bate-Smith, E. C.; Harborne, J. B.; Davenport, S. M. (1966). "Occurrence of Azaleatin and Caryatin in Eucryphia". Nature. 212 (5066): 1065–6. Bibcode:1966Natur.212.1065B. doi:10.1038/2121065a0. S2CID 4258930.

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Aglycones

Conjugates

Glycosides of herbacetin

Glycosides of kaempferol

Glycosides of myricetin

Conjugates of quercetin

Sulfates

Glycosides

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)

Derivative flavonols

Aglycones	Noricaritin Dihydronoricaritin
Glycosides	Amurensin Icariin Phelloside Dihydrophelloside Rutin S

Pyranoflavonols

Aglycones	Karanjachromene

Furanoflavonols

Aglycones	Karanjin
Glycosides	Pongamoside A, B and C

Semisynthetic

Glycosides	Hydroxyethylrutosides Monoxerutin Troxerutin

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