Article · Wikipedia archive · Last revised Jun 5, 2026

Isoquercetin

Isoquercetin 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. It is also present in the leaves of Annona squamosa, Camellia sinensis (tea), and Vestia foetida.

Last revised
Jun 5, 2026
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≈ 2 min
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Citations
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Source
Wikipedia ↗
Isoquercetin
Isoquercitrin structure
Isoquercitrin structure source ↗
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
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
  • 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).

Isoquercetin (also known as isoquercitrin or isotrifoliin1) 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),34 and Vestia foetida.5

Spectral data

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

Biosynthesis and metabolism

Isoquercetin if formed from quercetin by action of the enzyme flavonol 3-O-glucosyltransferase in plants such as the tulip.6

2D representation of the chemical structure of quercetin .
quercetin
+ UDP-glucose
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of isoquercetin .
isoquercetin


The enzyme flavonol-3-O-glucoside L-rhamnosyltransferase in tulips converts isoquercetin to rutin by adding an L-rhamnose sugar unit from UDP-L-rhamnose, with uridine diphosphate (UDP) as byproduct.7

isoquercetin + UDP-L-rhamnose
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of rutin .
rutin


Potential clinical uses

Isoquercetin is presently being investigated for prevention of thromboembolism in selected cancer patients8 and as an anti-fatigue agent in kidney cancer patients treated with sunitinib.9

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.10

Isoquercetin belongs to the class of chemical compounds known as pan-assay interference compounds (PAINS), which frequently give false positive results in assays for pharmacological activities.11

See also

See also

References

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. Bibcode:2003JAFC...51..571S. doi:10.1021/jf020926l. PMID 12537425.
  5. Brevis, C.; Quezada, M.; Bustamante, P.; Carrasco, L.; Ruiz, A.; Donoso, S. (2005). "Huevil ( Vestia foetida ) poisoning of cattle in Chile". Veterinary Record. 156 (14): 452–453. doi:10.1136/vr.156.14.452. PMID 15828729.
  6. Kleinehollenhorst, G.; Behrens, H.; Pegels, G.; Srunk, N.; Wiermann, R. (1982). "Formation of Flavonol 3-O-Diglycosides and Flavonol 3-O-Triglycosides by Enzyme Extracts from Anthers of Tulipa cv. Apeldoorn / Characterization and Activity of Three Different O -Glycosyltransferases during Anther Development". Zeitschrift für Naturforschung C. 37 (7–8): 587–599. doi:10.1515/znc-1982-7-808.
  7. Wiermann R (1982). "Formation of flavonol 3-O-diglycosides and flavonol 3-O-triglycosides by enzyme extracts from anthers of Tulipa cv apeldoorn - characterization and activity of 3 different O-glycosyltransferases during anther development". Z. Naturforsch. C. 37: 587–599. doi:10.1515/znc-1982-7-808.
  8. NCT02195232
  9. NCT02446795
  10. 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. PMID 29141065.
  11. J Baell & M A Walters (2014). "Chemistry: Chemical con artists foil drug discovery". Nature. 513 (7519): 481–483. Bibcode:2014Natur.513..481B. doi:10.1038/513481a. PMID 25254460.