Ayanin
Ayanin
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Names |
IUPAC name
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxychromen-4-one |
Other names
3,7,4'-Tri-O-methylquercetin 3,7,4'-trimethylquercetin 5,3'-dihydroxy-3,7,4'-trimethoxyflavone |
Identifiers |
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572-32-7 Y= |
3D model (Jmol) |
Interactive image Interactive image |
ChEBI |
CHEBI:27825 Y |
ChEMBL |
ChEMBL74898 Y |
ChemSpider |
4444274 Y |
PubChem |
5280682 |
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
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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
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Properties |
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C18H16O7 |
Molar mass |
344.31 g/mol |
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). |
Y verify (what is YN ?) |
Infobox references |
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Ayanin is an O-methylated flavonol, a type of flavonoid. It is the 3,7,4'-tri-O-methylation of quercetin.
It can be found in Croton schiedeanus. It can also be synthetized.[1]
Biosynthesis
The enzyme 3,7-dimethylquercetin 4'-O-methyltransferase uses S-adenosyl methionine and 5,3',4'-trihydroxy-3,7-dimethoxyflavone (rhamnazin) to produce S-adenosylhomocysteine and 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (ayanin).
References
Flavonols and their conjugates |
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Backbone | |
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Flavonols | Aglycones | |
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| Conjugates | | |
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- 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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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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