Syringetin

Syringetin is an O-methylated flavonol, a type of flavonoid. It is found in red grape (absent in white grape),^[1] in Lysimachia congestiflora^[2] and in Vaccinium uliginosum (bog bilberries).^[3] It is one of the phenolic compounds present in wine.^[4]

Syringetin

Chemical structure of syringetin
Names
IUPAC name 3,4′,5,7-Tetrahydroxy-3′,5′-dimethoxyflavone
Systematic IUPAC name 3,5,7-Trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-one
Other names 3′,5′-O-Dimethylmyricetin 3′,5′-Dimethoxy-3,5,7,4′-tetrahydroxyflavone 3,5,7,4′-Tetrahydroxy-3′,5′-dimethoxyflavone
Identifiers
CAS Number	4423-37-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18215 N
ChEMBL	ChEMBL489142 N
ChemSpider	4445230 N
PubChem CID	5281953
UNII	J68JG79B9W Y
CompTox Dashboard (EPA)	DTXSID60196074
InChI InChI=1S/C17H14O8/c1-23-11-3-7(4-12(24-2)14(11)20)17-16(22)15(21)13-9(19)5-8(18)6-10(13)25-17/h3-6,18-20,22H,1-2H3 N Key: UZMAPBJVXOGOFT-UHFFFAOYSA-N N InChI=1/C17H14O8/c1-23-11-3-7(4-12(24-2)14(11)20)17-16(22)15(21)13-9(19)5-8(18)6-10(13)25-17/h3-6,18-20,22H,1-2H3 Key: UZMAPBJVXOGOFT-UHFFFAOYAJ
SMILES COc1cc(cc(OC)c1O)C=3Oc2cc(O)cc(O)c2C(=O)C=3O
Properties
Chemical formula	C17H14O8
Molar mass	346.291 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

It induces human osteoblast differentiation through bone morphogenetic protein-2/extracellular signal-regulated kinase 1/2 pathway.^[4]

Metabolism

Syringetin is formed from laricitrin by the action of the enzyme laricitrin 5′-O-methyltransferase^[1][5] (myricetin O-methyltransferase).^[6]

Glycosides

• Syringetin-3-O-galactoside^[1][7]
• Syringetin-3-O-glucoside^[8][9]
• Syringetin 3-rhamnoside (CAS number 93126-00-2)
• Syringetin-3-O-rutinoside^[9] found in Larix sibirica^[10]
• Syringetin 3-O-(6′′-acetyl)-β-glucopyranoside found in Picea abies (Norway spruce)^[11]