Ayanin Chemical structure of ayanin |
| Names |
| IUPAC name 3′,5-Dihydroxy-3,4′,7-trimethoxyflavone |
Systematic IUPAC name 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxy-4H-1-benzopyran-4-one |
Other names - 3,7,4'-Tri-O-methylquercetin
- 3,7,4'-Trimethylquercetin
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| Identifiers |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
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| UNII | |
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InChI=1S/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-13(23-2)11(19)6-9/h4-8,19-20H,1-3H3 YKey: KPCRYSMUMBNTCK-UHFFFAOYSA-N YInChI=1/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-13(23-2)11(19)6-9/h4-8,19-20H,1-3H3 Key: KPCRYSMUMBNTCK-UHFFFAOYAE |
COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)O O=C1c3c(O/C(=C1/OC)c2ccc(OC)c(O)c2)cc(OC)cc3O |
| Properties |
| | C18H16O7 |
| Molar mass | 344.319 g·mol−1 |
| Density | 1.454 g/mL |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Ayanin is an O-methylated flavonol, a type of flavonoid. It is the 3,7,4'-tri-O-methylated derivative of quercetin.
It can be found in Croton schiedeanus. It can also be synthesized.[1]
Biosynthesis
The enzyme 3,7-dimethylquercetin 4'-O-methyltransferase uses S-adenosyl methionine and rhamnazin to produce S-adenosylhomocysteine and ayanin.
References
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 | - 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)
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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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