Azalein
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Names
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IUPAC name
3′,4′,5-Trihydroxy-7-methoxy-3-(α-L-rhamnopyranosyloxy)flavone
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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
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Other names
Azaleatin 3-O-α-L-rhamnoside
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Identifiers
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ChemSpider
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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
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CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)OC)O)C4=CC(=C(C=C4)O)O)O)O)O
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Properties
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C22H22O11
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Molar mass
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462.407 g·mol−1
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Density
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1.683 g/mL
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Melting point
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181 to 185 °C (358 to 365 °F; 454 to 458 K)
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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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 |
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Backbone | |
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Flavonols | Aglycones | |
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Conjugates | Glycosides of herbacetin | |
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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)
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Glycosides of myricetin | |
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Conjugates of quercetin | |
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O-Methylated flavonols | Aglycones | |
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Glycosides | of isorhamnetin |
- Narcissin (Isorhamnetin 3-O-rutinoside)
- Isorhamnetin 3-O-glucoside
- Tamarixetin 7-rutinoside
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other |
- (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)
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Derivative flavonols | Aglycones |
- Noricaritin
- Dihydronoricaritin
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Glycosides | |
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Pyranoflavonols | |
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Furanoflavonols | |
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Semisynthetic | |
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