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Isoquercetin

Names
IUPAC name 3-(β-D-Glucopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{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
CAS Number	482-35-9
3D model (JSmol)	Interactive image
ChemSpider	4444361
ECHA InfoCard	100.123.856
KEGG	C05623
PubChem CID	5280804
UNII	6HN2PC637T
CompTox Dashboard (EPA)	DTXSID3041110
InChI 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/s1Key: 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/s1Key: OVSQVDMCBVZWGM-QSOFNFLRBX
SMILES C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O4((((O4)CO)O)O)O)O)O
Properties
Chemical formula	C21H20O12
Molar mass	464.379 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Isoquercetin, isoquercitrin or isotrifoliin 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) and Rheum nobile (the Noble rhubarb). It is also present in the leaves of Annona squamosa, Camellia sinensis (tea). and Vestia foetida

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 and as an anti-fatigue agent in kidney cancer patients treated with sunitinib.

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.

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

References

1. "Isoquercetin". PubChem. Retrieved 2018-09-11.
2. Singh UP, Singh DP, Singh M, et al. (2004). "Characterization of phenolic compounds in some Indian mango cultivars". International Journal of Food Sciences and Nutrition. 55 (2): 163–9. doi:10.1080/09637480410001666441. PMID 14985189.
3. Panda S, Kar A (2007). "Antidiabetic and antioxidative effects of Annona squamosa leaves are possibly mediated through quercetin-3-O-glucoside". BioFactors. 31 (3–4): 201–210. doi:10.1002/biof.5520310307. PMID 18997283.
4. Sakakibara, H; Honda, Y; Nakagawa, S; Ashida, H; Kanazawa, K (2003). "Simultaneous determination of all polyphenols in vegetables, fruits, and teas". Journal of Agricultural and Food Chemistry. 51 (3): 571–81. doi:10.1021/jf020926l. PMID 12537425.
5. C. Brevis, M. Quezada, P. Bustamante, L. Carrasco, A. Ruiz, S. Donoso, Huevil (Vestia foetida) poisoning of cattle in Chile The Veterinary record 156(14):452-3 May 2005
6. NCT02195232
7. NCT02446795
8. Pennesi, Christine M.; Neely, John; Marks Jr., Ames G.; Alison Basak, S. (November 2017). "Use of Isoquercetin in the Treatment of Prurigo Nodularis". Journal of Drugs in Dermatology. 16 (11): 1156–1158.
9. J Baell & M A Walters (2014). "Chemistry: Chemical con artists foil drug discovery". Nature. 513 (7519): 481–483. doi:10.1038/513481a. PMID 25254460.

See also

• Quercitrin

• Quercetin glycosides
• Flavonoid glucosides