Azalein - Misplaced Pages

Azalein
Names

IUPAC name 3′,4′,5-Trihydroxy-7-methoxy-3-(α-L-rhamnopyranosyloxy)flavone
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-3-{oxy}-4H-1-benzopyran-4-one
Other names Azaleatin 3-O-α-L-rhamnoside
Identifiers
CAS Number	29028-02-2
3D model (JSmol)	Interactive image
ChemSpider	26286942
PubChem CID	5321320
CompTox Dashboard (EPA)	DTXSID50487206
InChI InChI=1S/C22H22O11/c1-8-16(26)18(28)19(29)22(31-8)33-21-17(27)15-13(30-2)6-10(23)7-14(15)32-20(21)9-3-4-11(24)12(25)5-9/h3-8,16,18-19,22-26,28-29H,1-2H3/t8-,16-,18+,19+,22-/m0/s1Key: FYSMTINDJSASRR-UFGFRKJLSA-N InChI=1/C22H22O11/c1-8-16(26)18(28)19(29)22(31-8)33-21-17(27)15-13(30-2)6-10(23)7-14(15)32-20(21)9-3-4-11(24)12(25)5-9/h3-8,16,18-19,22-26,28-29H,1-2H3/t8-,16-,18+,19+,22-/m0/s1Key: FYSMTINDJSASRR-UFGFRKJLBS
SMILES CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)OC)O)C4=CC(=C(C=C4)O)O)O)O)O
Properties
Chemical formula	C₂₂H₂₂O₁₁
Molar mass	462.407 g·mol
Density	1.683 g/mL
Melting point	181 to 185 °C (358 to 365 °F; 454 to 458 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Azalein is a chemical compound. It is a flavonol, a type of flavonoid. It is the 3-O-α-L-rhamnoside of azaleatin. It can be found in the flowers of Plumbago and Rhododendron species.

References

Harborne, JB (January 1962). "Plant polyphenols. 5. Occurrence of azalein and related pigments in flowers of Plumbago and Rhododendron species". Arch. Biochem. Biophys. 96: 171–8. doi:10.1016/0003-9861(62)90467-8. PMID 13904580.

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

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

Conjugates of quercetin

Sulfates

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)

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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