Syringetin

Syringetin

Chemical structure of 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 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18215 ☒N
ChEMBL	ChEMBL489142 ☒N
ChemSpider	4445230 ☒N
ECHA InfoCard
E number
PubChem CID	5281953
UNII	J68JG79B9W checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
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 checkY☒N ?) Infobox references

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

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

Metabolism

Syringetin is formed from laricitrin by the action of the enzyme laricitrin 5′-O-methyltransferase (myricetin O-methyltransferase).

Glycosides

• Syringetin-3-O-galactoside
• Syringetin-3-O-glucoside
• Syringetin 3-rhamnoside (CAS number 93126-00-2)
• Syringetin-3-O-rutinoside found in Larix sibirica
• Syringetin 3-O-(6′′-acetyl)-β-glucopyranoside found in Picea abies (Norway spruce)