Quercitrin

{{Refimprove|date=December 2009}}

{{distinguish|quercetin|quercitron}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 412196077

| ImageFile=Quercitrin.png

| ImageSize=250px

| ImageFile2=Quercitrin 3D BS.png

| ImageSize2=250px

| IUPACName=3′,4′,5,7-Tetrahydroxy-3-(α-L-rhamnopyranosyloxy)flavone

| SystematicName=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

| OtherNames=Quercetin 3-O-a-L-rhamnoside
Thujin
Quercetin 3-rhamnoside
Quercetin-3-rhamnoside
Quercetin-3-L-rhamnoside

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=522-12-3

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 17558

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 82242

| PubChem=5280459

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 2Y8906LC5P

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C01750

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4444112

| 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

| 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

| InChIKey = OXGUCUVFOIWWQJ-HQBVPOQABA

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = OXGUCUVFOIWWQJ-HQBVPOQASA-N

}}

|Section2={{Chembox Properties

| Formula=C21H20O11

| MolarMass= 448.38 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt=

}}

}}

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.{{cite journal| author=Audah KA, Ettin J, Darmadi J, Azizah NN, Anisa AS, Hermawan TDF | display-authors=etal| title=Indonesian Mangrove Sonneratia caseolaris Leaves Ethanol Extract Is a Potential Super Antioxidant and Anti Methicillin-Resistant Staphylococcus aureus Drug. | journal=Molecules | year= 2022 | volume= 27 | issue= 23 | page=8369| pmid=36500458 | doi=10.3390/molecules27238369 | doi-access=free| pmc=9735687 }}

Occurrence

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

Metabolism

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

References

{{reflist}}

{{Flavonol}}

Category:Quercetin glycosides

Category:Flavonol rhamnosides

{{aromatic-stub}}