Quercitrin: Difference between revisions

{{Refimprove|date=December 2009}}

{{distinguish|quercetin|quercitron}}

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| verifiedrevid = 412196077

| ImageFile=Quercitrin.png

| ImageSize=250px

| ImageFile2=Quercitrin 3D BS.png

| ImageSize2=250px

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

| SystematicName=2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2''S'',3''R'',4''R'',5''R'',6''S'')-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4''H''-1-benzopyran-4-one

| OtherNames=Quercetin 3-''O''-a-L-rhamnoside<br>Thujin<br>Quercetin 3-rhamnoside<br>Quercetin-3-rhamnoside<br>Quercetin-3-L-rhamnoside

|Section1={{Chembox Identifiers

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

| 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.<ref name="pmid36500458">{{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 }} </ref>

== Occurrence ==

Quercitrin is a constituent of the dye [[quercitron]]. It can be found in Tartary buckwheat (''[[Fagopyrum tataricum]]'')<ref>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}}</ref> and in oaks species like the North American white oak (''[[Quercus alba]]'') and English oak (''[[Quercus robur]]'').<ref>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}}</ref> It is also found in ''[[Nymphaea odorata]]'' or ''[[Taxillus kaempferi]]''.<ref name=Konishi>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}}</ref>

== 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}}