Combretol : Wikipedia, the free encyclopedia

Combretol

Combretol
Names

IUPAC name 5-Hydroxy-3,3′,4′,5′,7-pentamethoxyflavone
Preferred IUPAC name 5-Hydroxy-3,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one
Other names 3,7,3',4',5'-pentamethylmyricetin
Identifiers
CAS Number	5084-19-5^[1]
3D model (JSmol)	Interactive image
ChEBI	CHEBI:70005
ChEMBL	ChEMBL518300
ChemSpider	21131195^N
PubChem CID	12303802
UNII	2G3ZF4VTE5^Y
CompTox Dashboard (EPA)	DTXSID601029316
InChI 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^N Key: SUNUQCQIFHHEOW-UHFFFAOYSA-N^N InChI=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
SMILES COC1=CC(=C2C(=C1)OC(=C(C2=O)OC)C3=CC(=C(C(=C3)OC)OC)OC)O
Properties
Chemical formula	C₂₀H₂₀O₈
Molar mass	388.36 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

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

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

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)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates

Quercetin 3-O-sulfate
Quercetin 3,3'-bissulfate
Quercetin 3,4'-bissulfate

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
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)