Quercitrin

Quercitrin
Names


IUPAC name 3′,4′,5,7-Tetrahydroxy-3-(α-L-rhamnopyranosyloxy)flavone
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names Quercetin 3-O-a-L-rhamnoside Thujin Quercetin 3-rhamnoside Quercetin-3-rhamnoside Quercetin-3-L-rhamnoside
Identifiers
CAS Number	522-12-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17558^N
ChEMBL	ChEMBL82242^N
ChemSpider	4444112^N
ECHA InfoCard	100.007.567
KEGG	C01750^Y
PubChem CID	5280459
UNII	2Y8906LC5P^N
CompTox Dashboard (EPA)	DTXSID50200230
InChI InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m0/s1^N Key: OXGUCUVFOIWWQJ-HQBVPOQASA-N^N InChI=1/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m0/s1 Key: OXGUCUVFOIWWQJ-HQBVPOQABA
SMILES C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
Properties
Chemical formula	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). N verify (what is ^YN ?) Infobox references

Chemical compound

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

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

It has also been investigated as a potential dietary supplement.^[1]

Occurrence

Quercitrin is a constituent of the dye quercitron. It can be found in Tartary buckwheat (Fagopyrum tataricum)^[2] and in oaks species like the North American white oak (Quercus alba) and English oak (Quercus robur).^[3] It is also found in Nymphaea odorata or Taxillus kaempferi.^[4]

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

^ Audah KA, Ettin J, Darmadi J, Azizah NN, Anisa AS, Hermawan TDF; et al. (2022). "Indonesian Mangrove Sonneratia caseolaris Leaves Ethanol Extract Is a Potential Super Antioxidant and Anti Methicillin-Resistant Staphylococcus aureus Drug". Molecules. 27 (23): 8369. doi:10.3390/molecules27238369. PMC 9735687. PMID 36500458.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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
^ 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
^ 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

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Aglycones

Conjugates

Glycosides of herbacetin

Glycosides of kaempferol

Glycosides of myricetin

Conjugates of quercetin

Sulfates

Glycosides

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)