Azalein
Azalein
Azalein structure
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-{[(2S ,3R ,4R ,5R ,6S )-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H -1-benzopyran-4-one
Other names
Azaleatin 3-O -α-L -rhamnoside
Identifiers
ChemSpider
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/s1
Y Key: FYSMTINDJSASRR-UFGFRKJLSA-N
Y 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/s1
Key: FYSMTINDJSASRR-UFGFRKJLBS
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
C 22 H 22 O 11
Molar mass
462.407 g·mol−1
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 [77 °F], 100 kPa).
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.[ 1]
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
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
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
Pyranoflavonols
Furanoflavonols
Semisynthetic
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