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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:31763^N
ChemSpider	4445351^N
KEGG	C12633^N
PubChem CID	5282154
UNII	JQZ2DUC4C9^Y
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^N Key: CFYMYCCYMJIYAB-UHFFFAOYSA-N^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). N verify (what is ^YN ?) Infobox references

Chemical compound

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 billberries).^[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

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates

Quercetin 3-O-sulfate
Quercetin 3,3'-bissulfate
Quercetin 3,4'-bissulfate

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)