Myricetin

Myricetin

Names
IUPAC name 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4-chromenone
Other names Cannabiscetin Myricetol Myricitin
Identifiers
CAS Number	529-44-2 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:18152 N
ChEMBL	ChEMBL164 Y
ChemSpider	4444991 Y
DrugBank	DB02375 N
ECHA InfoCard	100.007.695
PubChem	5281672
InChI InChI=1S/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H Y Key: IKMDFBPHZNJCSN-UHFFFAOYSA-N Y
SMILES Oc1cc(O)c2c(=O)c(O)c(oc2c1)c3cc(O)c(O)c(O)c3
Properties
Chemical formula	C15H10O8
Molar mass	318.24 g·mol−1
Density	1.912 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Myricetin is a member of the flavonoid class of polyphenolic compounds, with antioxidant properties. It is commonly derived from vegetables, fruits, nuts, berries, tea, and is also found in red wine. Myricetin is structurally similar to fisetin, luteolin, and quercetin and is reported to have many of the same functions as these other members of the flavonol class of flavonoids. Reported average intake of myricetin per day varies depending on diet, but has been shown in the Netherlands to average 23 mg/day.

Myricetin is produced from the parent compound taxifolin through the (+)-dihydromyricetin intermediate and can be further processed to form laricitrin and then syringetin, both members of the flavonol class of flavonoids. Dihydromyricetin is frequently sold as a supplement and has controversial function as a partial GABA_A receptor potentiator and treatment in Alcohol Use Disorder (AUD). Myricetin can alternatively be produced directly from kaempferol, which is another flavonol.

Antioxidants are molecules present in fruits and vegetables that have been demonstrated to protect against some forms of cancer and cardiovascular disease. Biomolecules and cell structures can experience oxidative stress due to the presence and activity of reactive oxygen species (ROS). ROS like •OH, •O₂⁻, and H₂O₂ are produced during cellular metabolism processes (aerobic respiration). ROS can cause damage to lipids, DNA, and proteins. Gradual but steady accretion of ROS and the biomolecules they damage can lead to the development of many diseases and conditions including thrombosis, diabetes, persistent inflammation, cancer, and atherosclerosis. Flavonoids including myricetin are able to scavenge for ROS and can chelate intracellular transition metal ions that ultimately produce ROS. Myricetin also enhances the effects of other antioxidants. Myricetin can induce the enzyme glutathione S-transferase (GST). GST has been suggested to protect cells against oxidative stress by protecting cells against free-radicals. In vitro studies have shown that myricetin significantly increased GST activity.