Azalein : Wikipedia, the free encyclopedia

Azalein

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-{[(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
CAS Number	29028-02-2^Y
3D model (JSmol)	Interactive image
ChemSpider	26286942^Y
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/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
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⁻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). Y verify (what is ^YN ?) 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.^[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

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

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

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates

Quercetin 3-O-sulfate
Quercetin 3,3'-bissulfate
Quercetin 3,4'-bissulfate

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)