Ayanin
Ayanin
Chemical structure of ayanin
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Names
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IUPAC name
3′,5-Dihydroxy-3,4′,7-trimethoxyflavone
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Systematic IUPAC name
5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxy-4H-1-benzopyran-4-one
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Other names
- 3,7,4'-Tri-O-methylquercetin
- 3,7,4'-Trimethylquercetin
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Identifiers
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ChEBI
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ChEMBL
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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
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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
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Molar mass
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344.319 g·mol−1
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Density
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1.454 g/mL
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
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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