Azaleatin

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477369517

| Name = Azaleatin

| ImageFile = Azaleatin.svg

| ImageSize = 200px

| ImageName = Azaleatin structure

| IUPACName = 3,3′,4′,7-Tetrahydroxy-5-methoxyflavone

| SystematicName = 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-4H-1-benzopyran-4-one

| OtherNames = 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-4H-chromen-4-one
5-O-Methylquercetin
Quercetin 5-methyl ether

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 529-51-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = SO52512D8G

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 2945

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 470848

| PubChem = 5281604

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4444923

| SMILES = O=C1c3c(O/C(=C1/O)c2ccc(O)c(O)c2)cc(O)cc3OC

| 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

| InChIKey = RJBAXROZAXAEEM-UHFFFAOYAA

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = RJBAXROZAXAEEM-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula = C16H12O7

| MolarMass = 316.26 g/mol

| Density = 1.634 g/mL

| MeltingPt =

| BoilingPt =

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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{{cite journal |doi=10.1021/ja01599a052 |year=1956 |last1=Wada |first1=Einosuke |journal=Journal of the American Chemical Society |volume=78 |issue=18 |pages=4725–6 |title=On a Flavonol Glycoside Isolated from Flowers of a White Azalea (Rhododendron mucronatum G. Don)|bibcode=1956JAChS..78.4725W }} and has since been recorded in 44 other Rhododendron species, in Plumbago capensis, in Ceratostigma willmottiana{{cite journal |doi=10.1016/0003-9861(62)90467-8 |title=Plant polyphenols: 5. Occurrence of azalein and related pigments in flowers of Plumbago and Rhododendro species |year=1962 |last1=Harborne |first1=J.B. |authorlink1=Jeffrey Harborne |journal=Archives of Biochemistry and Biophysics |volume=96 |pages=171–8 |pmid=13904580}} and in Carya pecan.{{cite journal |pmid=14085492 |year=1963 |last1=Sasaki |first1=T |last2=Mikami |first2=M |title=Studies on the Components of Pecan (Carya Pecan Engl. & Graebn). I. On the Flavon Isolated from the Bark of Pecan |volume=83 |pages=897–900 |journal=Yakugaku Zasshi|doi=10.1248/yakushi1947.83.9_897 |doi-access=free }} It has also been found in the leaves of Eucryphia.{{cite journal |doi=10.1038/2121065a0 |title=Occurrence of Azaleatin and Caryatin in Eucryphia |year=1966 |last1=Bate-Smith |first1=E. C. |authorlink1=Edgar Charles Bate-Smith |last2=Harborne |first2=J. B. |authorlink2=Jeffrey Harborne |last3=Davenport |first3=S. M. |journal=Nature |volume=212 |issue=5066 |pages=1065–6|bibcode=1966Natur.212.1065B |s2cid=4258930 }}

Glycosides

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

References

{{Reflist}}

{{Flavonol}}

Category:O-methylated flavonols

Category:Catechols

Category:Tetrols

{{Aromatic-stub}}