Isoquercetin

Chemical compound From Wikipedia, the free encyclopedia

Isoquercetin, isoquercitrin or isotrifoliin[1] is a flavonoid, a type of chemical compound. It is the 3-O-glucoside of quercetin. Isoquercitrin can be isolated from various plant species including Mangifera indica (mango)[2] and Rheum nobile (the Noble rhubarb). It is also present in the leaves of Annona squamosa, Camellia sinensis (tea).[3][4] and Vestia foetida[5]

Quick facts Names, Identifiers ...
Isoquercetin
Isoquercitrin structure
Isoquercitrin structure
Names
IUPAC name
3-(β-D-Glucopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names
Isoquercitroside
Isoquercitrin
Isoquercetin
Trifoliin
Isotrifolin
Trifoliin A
Isohyperoside
Isotrifoliin
Quercetin-3-glucoside
Quercetin-3-O-glucoside
Quercetin 3-O-β-D-glucopyranoside
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.123.856 Edit this at Wikidata
EC Number
  • 640-533-1
KEGG
UNII
  • InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1
    Key: OVSQVDMCBVZWGM-QSOFNFLRSA-N
  • InChI=1/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1
    Key: OVSQVDMCBVZWGM-QSOFNFLRBX
  • C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
Properties
C21H20O12
Molar mass 464.379 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Spectral data

The lambda-max for isoquercetin is 254.8 and 352.6 nm.

Potential clinical uses

Isoquercetin is presently being investigated for prevention of thromboembolism in selected cancer patients[6] and as an anti-fatigue agent in kidney cancer patients treated with sunitinib.[7]

There is a single case report of its use in the successful treatment of prurigo nodularis, a difficult to treat pruritic eruption of the skin.[8]

However it belongs to the PAINS (Pan-assay interference compounds) categories of chemicals.[9]

References

See also

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