Azaleatin

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[1] and has since been recorded in 44 other Rhododendron species, in Plumbago capensis, in Ceratostigma willmottiana[2] and in Carya pecan.[3] It has also been found in the leaves of Eucryphia.[4]

Azaleatin
Azaleatin structure
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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,1H3 checkY
    Key: RJBAXROZAXAEEM-UHFFFAOYSA-N checkY
  • 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,1H3
    Key: RJBAXROZAXAEEM-UHFFFAOYAA
  • O=C1c3c(O/C(=C1/O)c2ccc(O)c(O)c2)cc(O)cc3OC
Properties
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 [77 °F], 100 kPa).
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Infobox references

Glycosides

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

References
  1. 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. doi:10.1021/ja01599a052.
  2. 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.
  3. 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.
  4. Bate-Smith, E. C.; Harborne, J. B.; Davenport, S. M. (1966). "Occurrence of Azaleatin and Caryatin in Eucryphia". Nature. 212 (5066): 1065–6. doi:10.1038/2121065a0. S2CID 4258930.
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