Laricitrin

Laricitrin
Names
	IUPAC name 3,3′,4′,5,7-Pentahydroxy-5′-methoxyflavone
	Systematic IUPAC name 2-(3,4-Dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
	Other names 3'-O-Methylmyricetin
Identifiers
CAS Number	53472-37-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:31763 ;
ChemSpider	4445351 ;
KEGG	C12633 ;
PubChem CID	5282154;
UNII	JQZ2DUC4C9 ;
CompTox Dashboard (EPA)	DTXSID40415210 ;
	InChI InChI=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 Key: CFYMYCCYMJIYAB-UHFFFAOYSA-N ; 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 Key: CFYMYCCYMJIYAB-UHFFFAOYAK;
	SMILES O=C1c3c(O/C(=C1/O)c2cc(O)c(O)c(OC)c2)cc(O)cc3O;
Properties
Chemical formula	C16H12O8
Molar mass	332.264 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Laricitrin is an O-methylated flavonol, a type of flavonoid. It is found in red grape (absent in white grape)^[1] and in Vaccinium uliginosum (bog bilberries).^[2] It is one of the phenolic compounds present in wine.^[3]

Metabolism

Laricitrin is formed from myricetin by the action of the enzyme myricetin O-methyltransferase.^[4] It is further methylated by laricitrin 5'-O-methyltransferase into syringetin.

Glycosides

Laricitrin 3-O-galactoside, found in grape^[1]
Laricitrin 3-glucoside found in Larix sibirica^[5]
Laricitrin 3,5’-di-O-β-glucopyranoside, found in Medicago littoralis^[6]

References

^ ^a ^b Mattivi, F; Guzzon, R; Vrhovsek, U; Stefanini, M; Velasco, R (October 2006). "Metabolite profiling of grape: Flavonols and anthocyanins". J. Agric. Food Chem. 54 (20): 7692–702. doi:10.1021/jf061538c. PMID 17002441.
^ Anja; Jaakola, Laura; Riihinen, Kaisu R.; Kainulainen, Pirjo S. (2010). "Anthocyanin and Flavonol Variation in Bog Bilberries (Vaccinium uliginosumL.) in Finland". Journal of Agricultural and Food Chemistry. 58 (1): 427–433. doi:10.1021/jf903033m. PMID 20000402.
^ Castillo-Munoz, Noelia; Gomez-Alonso, Sergio; Garcia-Romero, Esteban; Hermosin-Gutierrez, Isidro (2007). "Flavonol profiles of Vitis vinifera red grapes and their single-cultivar wines". Journal of Agricultural and Food Chemistry. 55 (3): 992–1002. doi:10.1021/jf062800k. PMID 17263504.
^ Syringetin biosynthesis pathway on metacyc.org
^ Tyukavkina, N. A.; Medvedeva, S. A.; Ivanova, S. Z. (1974). "New flavonol glycosides from the needles of Larix sibirica". Chemistry of Natural Compounds. 10 (2): 170–172. doi:10.1007/BF00563605.
^ Flavonoids isolated from Medicago littoralis Rhode (Fabaceae): their ecological and chemosystematic significance Archived 2011-07-22 at the Wayback Machine

[Mattivi-1] Mattivi, F; Guzzon, R; Vrhovsek, U; Stefanini, M; Velasco, R (October 2006). "Metabolite profiling of grape: Flavonols and anthocyanins". J. Agric. Food Chem. 54 (20): 7692–702. doi:10.1021/jf061538c. PMID 17002441.

[2] Anja; Jaakola, Laura; Riihinen, Kaisu R.; Kainulainen, Pirjo S. (2010). "Anthocyanin and Flavonol Variation in Bog Bilberries (Vaccinium uliginosumL.) in Finland". Journal of Agricultural and Food Chemistry. 58 (1): 427–433. doi:10.1021/jf903033m. PMID 20000402.

[3] Castillo-Munoz, Noelia; Gomez-Alonso, Sergio; Garcia-Romero, Esteban; Hermosin-Gutierrez, Isidro (2007). "Flavonol profiles of Vitis vinifera red grapes and their single-cultivar wines". Journal of Agricultural and Food Chemistry. 55 (3): 992–1002. doi:10.1021/jf062800k. PMID 17263504.

[4] Syringetin biosynthesis pathway on metacyc.org

[5] Tyukavkina, N. A.; Medvedeva, S. A.; Ivanova, S. Z. (1974). "New flavonol glycosides from the needles of Larix sibirica". Chemistry of Natural Compounds. 10 (2): 170–172. doi:10.1007/BF00563605.

[6] Flavonoids isolated from Medicago littoralis Rhode (Fabaceae): their ecological and chemosystematic significance Archived 2011-07-22 at the Wayback Machine

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