Combretol
Combretol
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Names
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IUPAC name
5-Hydroxy-3,3′,4′,5′,7-pentamethoxyflavone
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Preferred IUPAC name
5-Hydroxy-3,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one
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Other names
3,7,3',4',5'-pentamethylmyricetin
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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/C20H20O8/c1-23-11-8-12(21)16-13(9-11)28-18(20(27-5)17(16)22)10-6-14(24-2)19(26-4)15(7-10)25-3/h6-9,21H,1-5H3 NKey: SUNUQCQIFHHEOW-UHFFFAOYSA-N NInChI=1/C20H20O8/c1-23-11-8-12(21)16-13(9-11)28-18(20(27-5)17(16)22)10-6-14(24-2)19(26-4)15(7-10)25-3/h6-9,21H,1-5H3 Key: SUNUQCQIFHHEOW-UHFFFAOYAT
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COC1=CC(=C2C(=C1)OC(=C(C2=O)OC)C3=CC(=C(C(=C3)OC)OC)OC)O
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Properties
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C20H20O8
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Molar mass
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388.36 g/mol
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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
Combretol is an O-methylated flavonol, a type of flavonoid. It is the 3,7,3',4',5'-O-methylation of myricetin and can be extracted from Combretum quadrangulare[2] and from Rhodomyrtus tomentosa.[3]
References
- ^ "KNApSAcK Metabolite Information - C00004777". www.knapsackfamily.com.
- ^ Combretol from Combretum quadrangulare. Stang Mongkolsuk, F. M. Dean and L. E. Houghton, J. Chem. Soc. C, 1966, page 125, doi:10.1039/J39660000125
- ^ 5-Hydroxy-3,3',4',5',7-pentamethoxyflavone (combretol). Dachriyanus, R. Fahmi, M. V. Sargent, B. W. Skelton and A. H. White, Acta Crystallogr. (2004). E60, o86-o88
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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