{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 449562314 | Name = Laricitrin | ImageFile = Laricitrin.svg | ImageName = Chemical structure of laricitrin | IUPACName = 3,3′,4′,5,7-Pentahydroxy-5′-methoxyflavone | SystematicName = 2-(3,4-Dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-4''H''-1-benzopyran-4-one | OtherNames = 3'-''O''-Methylmyricetin |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 53472-37-0 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = JQZ2DUC4C9 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 31763 | CASNoOther = | PubChem = 5282154 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4445351 | SMILES = O=C1c3c(O/C(=C1/O)c2cc(O)c(O)c(OC)c2)cc(O)cc3O | InChI = 1/C16H12O8/c1-23-11-3-6(2-9(19)13(11)20)16-15(22)14(21)12-8(18)4-7(17)5-10(12)24-16/h2-5,17-20,22H,1H3 | InChIKey = CFYMYCCYMJIYAB-UHFFFAOYAK | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C16H12O8/c1-23-11-3-6(2-9(19)13(11)20)16-15(22)14(21)12-8(18)4-7(17)5-10(12)24-16/h2-5,17-20,22H,1H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = CFYMYCCYMJIYAB-UHFFFAOYSA-N | RTECS = | MeSHName = | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C12633 }} |Section2={{Chembox Properties | C=16 | H=12 | O=8 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} }}
'''Laricitrin''' is an ''O''-methylated flavonol, a type of flavonoid. It is found in red grape (absent in white grape)<ref name=Mattivi>{{cite journal|doi=10.1021/jf061538c | pmid=17002441 | volume=54 | title=Metabolite profiling of grape: Flavonols and anthocyanins | date=October 2006 | journal=J. Agric. Food Chem. | pages=7692–702 | last1 = Mattivi | first1 = F | last2 = Guzzon | first2 = R | last3 = Vrhovsek | first3 = U | last4 = Stefanini | first4 = M | last5 = Velasco | first5 = R| issue=20 | bibcode=2006JAFC...54.7692M }}</ref> and in ''Vaccinium uliginosum'' (bog bilberries).<ref>{{cite journal|doi=10.1021/jf903033m | volume=58 | title=Anthocyanin and Flavonol Variation in Bog Bilberries (Vaccinium uliginosumL.) in Finland | year=2010 | journal=Journal of Agricultural and Food Chemistry | pages=427–433 | last1 = Anja | last2 = Jaakola | first2 = Laura | last3 = Riihinen | first3 = Kaisu R. | last4 = Kainulainen | first4 = Pirjo S. | issue=1 | pmid = 20000402| bibcode=2010JAFC...58..427L }}</ref> It is one of the phenolic compounds present in wine.<ref>{{cite journal | first1 = Noelia | last1 = Castillo-Munoz | first2 = Sergio | last2 = Gomez-Alonso | first3 = Esteban | last3 = Garcia-Romero | first4 = Isidro | last4 = Hermosin-Gutierrez | year = 2007 | title = Flavonol profiles of Vitis vinifera red grapes and their single-cultivar wines | url = http://cat.inist.fr/?aModele=afficheN&cpsidt=18502213 | journal = Journal of Agricultural and Food Chemistry | volume = 55 | issue = 3| pages = 992–1002 | doi=10.1021/jf062800k| pmid = 17263504 | bibcode = 2007JAFC...55..992C | url-access = subscription }}</ref>
==Metabolism== Laricitrin is formed from myricetin by the action of the enzyme myricetin O-methyltransferase.<ref>[http://metacyc.org/META/new-image?type=PATHWAY&object=PWY-5391 Syringetin biosynthesis pathway on metacyc.org]</ref> It is further methylated by <!-- the same enzyme -->laricitrin 5'-O-methyltransferase into syringetin.
=== Glycosides === * Laricitrin 3-O-galactoside, found in grape<ref name=Mattivi/> * Laricitrin 3-glucoside found in ''Larix sibirica''<ref>{{cite journal | doi=10.1007/BF00563605 | volume=10 | title=New flavonol glycosides from the needles of Larix sibirica | year=1974 | journal=Chemistry of Natural Compounds | pages=170–172 | last1 = Tyukavkina | first1 = N. A. | last2 = Medvedeva | first2 = S. A. | last3 = Ivanova | first3 = S. Z.| issue=2 | bibcode=1974CNatC..10..170T }}</ref> * Laricitrin 3,5’-di-O-β-glucopyranoside, found in ''Medicago littoralis''<ref>[http://www1.unifi.it/caryologia/past_volumes/63_1/63_1_12.pdf Flavonoids isolated from ''Medicago littoralis'' Rhode (Fabaceae): their ecological and chemosystematic significance] {{webarchive|url=https://web.archive.org/web/20110722063750/http://www1.unifi.it/caryologia/past_volumes/63_1/63_1_12.pdf |date=2011-07-22 }}</ref>
== References == {{reflist}}
{{flavonol}}
Category:O-methylated flavonols Category:Resorcinols Category:Catechols