Quercitrin

Quercitrin is a glycoside formed from the flavonoid quercetin and the deoxy sugar rhamnose.

Not to be confused with quercetin or quercitron.
Quercitrin
Names
IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7- dihydroxy-3-[ [(2S,3R,4R,5R,6S)- 3,4,5-trihydroxy-6-methyl-2- tetrahydropyranyl]oxy]-4-chromenone
Other names
Quercetin 3-O-a-L-rhamnoside
Thujin
Quercetin 3-rhamnoside
Quercetin-3-rhamnoside
Quercetin-3-L-rhamnoside
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.567
UNII
Properties
C21H20O11
Molar mass 448.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Austrian chemist Heinrich Hlasiwetz (1825-1875) is remembered for his chemical analysis of quercitrin.

Occurrence

Quercitrin is a constituent of the dye quercitron. It can be found in Tartary buckwheat (Fagopyrum tataricum)[1] and in oaks species like the North American white oak (Quercus alba) and English oak (Quercus robur).[2] It is also found in Nymphaea odorata or Taxillus kaempferi.[3]

Metabolism

The enzyme quercitrinase catalyzes the chemical reaction between quercitrin and H2O to yield L-rhamnose and quercetin.

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References
  1. Tartary Buckwheat (Fagopyrum tataricum Gaertn.) as a Source of Dietary Rutin and Quercitrin. Nina Fabjan, Janko Rode, Iztok Jože Košir, Zhuanhua Wang, Zheng Zhang and Ivan Kreft, J. Agric. Food Chem., 2003, 51 (22), pp. 6452–6455, doi:10.1021/jf034543e
  2. Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry. Pirjo Mämmelä, Heikki Savolainen, Lasse Lindroos, Juhani Kangas and Terttu Vartiainen, Journal of Chromatography A, Volume 891, Issue 1, 1 September 2000, Pages 75-83, doi:10.1016/S0021-9673(00)00624-5
  3. The constituents of Taxillus kaempferi and the host, Pinus thunbergii. I. Catechins and flavones of Taxillus kaempferi. Konishi T, Nishio T, Kiyosawa S, Fujiwara Y and Konoshima T, Yakugaku Zasshi., February 1996, volume 116, issue 2, pages 148-157 (article in Japanese), doi:10.1248/yakushi1947.116.2_148
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