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Myricetin

Myricetin
Skeletal formula of myricetin
Ball-and-stick model of the myricetin molecule
Names
IUPAC name
3,3′,4′,5,5′,7-Hexahydroxyflavone
Systematic IUPAC name
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one
Other names
Cannabiscetin
Myricetol
Myricitin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.695 Edit this at Wikidata
EC Number
  • 208-463-2
KEGG
UNII
  • 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 checkY
    Key: IKMDFBPHZNJCSN-UHFFFAOYSA-N checkY
  • Oc1cc(O)c2c(=O)c(O)c(oc2c1)c3cc(O)c(O)c(O)c3
Properties
C15H10O8
Molar mass 318.237 g·mol−1
Density 1.912 g/mL
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Myricetin is a member of the flavonoid class of polyphenolic compounds, with antioxidant properties.[1] Common dietary sources[2] include vegetables (including tomatoes), fruits (including oranges), nuts, berries, tea,[3] and red wine.[4]

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.[3] Reported average intake of myricetin per day varies depending on diet, but has been shown in the Netherlands to average 23 mg/day.[5]

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.[6] Dihydromyricetin is frequently sold as a supplement and has controversial function as a partial GABAA receptor potentiator and treatment in Alcohol Use Disorder (AUD). Myricetin can alternatively be produced directly from kaempferol, which is another flavonol.[6]

  1. ^ Cite error: The named reference Ong was invoked but never defined (see the help page).
  2. ^ Holland, Thomas M.; Agarwal, Puja; Wang, Yamin; Leurgans, Sue E.; Bennett, David A.; Booth, Sarah L.; Morris, Martha Clare (2020-01-29). "Dietary flavonols and risk of Alzheimer dementia". Neurology. 94 (16): e1749–e1756. doi:10.1212/WNL.0000000000008981. ISSN 0028-3878. PMC 7282875. PMID 31996451.
  3. ^ a b Ross JA, Kasum CM (July 2002). "Dietary Flavonoids: Bioavailability, Metabolic Effects, and Safety". Annual Review of Nutrition. 22: 19–34. doi:10.1146/annurev.nutr.22.111401.144957. PMID 12055336.
  4. ^ Basli A, Soulet S, Chaher N, Merillon JM, Chibane M, Monti JP, Richard T (July 2012). "Wine polyphenols: potential agents in neuroprotection". Oxidative Medicine and Cellular Longevity. 2012: 805762. doi:10.1155/2012/805762. PMC 3399511. PMID 22829964.
  5. ^ Hollman PC, Katan MB (Dec 1999). "Health effects and bioavailability of dietary flavonols". Free Radical Research. 31 Suppl: Suppl S75–80. doi:10.1080/10715769900301351. PMID 10694044.
  6. ^ a b Flamini R, Mattivi F, De Rosso M, Arapitas P, Bavaresco L (Sep 2013). "Advanced knowledge of three important classes of grape phenolics: anthocyanins, stilbenes and flavonols". International Journal of Molecular Sciences. 14 (10): 19651–69. doi:10.3390/ijms141019651. PMC 3821578. PMID 24084717.

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