isorhamnetin

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 400271366

| Name = Isorhamnetin

| ImageFile = 3-methylquercetin.svg

| ImageSize = 250px

| ImageName = Isorhamnetin structure

| ImageFile2 = Isorhamnetin.png

| ImageSize2 = 250px

| ImageName2 = Isorhamnetin 3D structure

| IUPACName = 3,4′,5,7-Tetrahydroxy-3′-methoxyflavone

| SystematicName = 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one

| OtherNames = 3-methylquercetin
3-Methylquercetin
Isorhamnetol
isorhamentin
isorhamnetine
iso-rhamnetin
3'-Methoxyquercetin

|Section1={{Chembox Identifiers

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

| CASNo = 480-19-3

| PubChem = 5281654

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

| ChEBI = 6052

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

| ChEMBL = 379064

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

| UNII = 07X3IB4R4Z

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C10084

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

| ChemSpiderID = 4444973

| SMILES = COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O

| InChI = 1/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3

| InChIKey = IZQSVPBOUDKVDZ-UHFFFAOYAD

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

| StdInChI = 1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3

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

| StdInChIKey = IZQSVPBOUDKVDZ-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula = C₁₆H₁₂O₇

| MolarMass = 316.26 g/mol

| Density =

| MeltingPtC = 307

| BoilingPt =

}}

}}

Isorhamnetin is an O-methylated flavon-ol from the class of flavonoids. A common food source of this 3'-methoxylated derivative of quercetin and its glucoside conjugates are pungent yellow or red onions, in which it is a minor pigment, quercetin-3,4'-diglucoside and quercetin-4'-glucoside and the aglycone quercetin being the major pigments.{{cite journal | pmid = 17997520 | doi=10.1021/jf0712503 | volume=55 | title=Onions: a source of unique dietary flavonoids | date=December 2007 | journal=J. Agric. Food Chem. | pages=10067–80 | last1 = Slimestad | first1 = R | last2 = Fossen | first2 = T | last3 = Vågen | first3 = IM| issue=25 | bibcode=2007JAFC...5510067S }} Pears, olive oil, wine and tomato sauce are rich in isorhamnetin.{{Cite journal|last1=Holland|first1=Thomas M.|last2=Agarwal|first2=Puja|last3=Wang|first3=Yamin|last4=Leurgans|first4=Sue E.|last5=Bennett|first5=David A.|last6=Booth|first6=Sarah L.|last7=Morris|first7=Martha Clare|author-link7=Martha Clare Morris|date=2020-01-29|title=Dietary flavonols and risk of Alzheimer dementia|journal=Neurology|language=en|volume=94|issue=16|pages=e1749–e1756|doi=10.1212/WNL.0000000000008981|issn=0028-3878|pmc=7282875|pmid=31996451}} Almond skin is a rich source of isorhamnetin-3-O-rutinoside and

isorhamnetin-3-O-glucoside, in some cultivars they comprise 75% of the polyphenol content, the total of which can exceed 10 mg/100 gram almond.PMID 25544797 PMC4276397 Others sources include the spice, herbal medicinal{{cite journal|doi=10.1021/jf053071w | volume=54 | title=Antifungal and Antibacterial Activities of Mexican Tarragon (Tagetes lucida) | journal=Journal of Agricultural and Food Chemistry | pages=3521–3527 | last1 = Céspedes | first1 = Carlos L.| year=2006 | issue=10 | pmid=19127719 | bibcode=2006JAFC...54.3521C }} and psychoactive Mexican tarragon (Tagetes lucida), which is described as accumulating isorhamnetin and its 7-O-glucoside derivate.Abdala, 1999 Nopal (Opuntia ficus-indica (L.)) is also a good source of isorhamnetin, which can be extracted by supercritical fluid extraction assisted by enzymes.{{cite journal|doi=10.1016/j.supflu.2017.11.030 | volume=141 | title=Supercritical CO2 enzyme hydrolysis as a pretreatment for the release of isorhamnetin conjugates from Opuntia ficus-indica (L.) Mill | date=November 2018 | journal=The Journal of Supercritical Fluids | pages=21–28 |vauthors=Antunes-Ricardo M, Garcia-Cayuela T, Mendiola JA, Ibañez E, Gutierrez-Uribe JA, Cano MP, Guajardo-Flores D| s2cid=103893093 }}