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M6760

Sigma-Aldrich

Myricetin

≥96.0%, crystalline

Synonym(s):
3,3′,4′,5,5′,7-Hexahydroxyflavone, Cannabiscetin, Myricetol
Empirical Formula (Hill Notation):
C15H10O8
CAS Number:
Molecular Weight:
318.24
Beilstein:
332331
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥96.0%

form

crystalline

mp

>300 °C (lit.)

solubility

absolute ethanol: 10 mg/mL, clear to slightly hazy, yellow to very deep greenish-yellow

SMILES string

Oc1cc(O)c2C(=O)C(O)=C(Oc2c1)c3cc(O)c(O)c(O)c3

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

InChI key

IKMDFBPHZNJCSN-UHFFFAOYSA-N

Gene Information

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Application

Myricetin has been used:
  • to investigate its effect on end product (AGE)- bovine serum albumin mediated phosphorylation of mitogen-activated protein kinase(ERK1)
  • as a standard for the quantification of phenolics from noni plant extracts using high performance liquid chromatography(HPLC)
  • as a standard for characterization of phenolic compounds from Hibiscus sabdariffa using ultra-high performance liquid chromatography(UHPLC)

Biochem/physiol Actions

Myricetin is a naturally occurring flavonol with antioxidant property. It displays moderate membrane permeability and it degrades rapidly at elevated pH. Myricetin is one of the major flavonoid present in edible plants and has anticarcinogenic and antimutagenic functionality. It comprises of two benzene rings A and B. Ring B intercalates with nucleotide staking and inhibits bacterial DNA synthesis. Myricetin elicits protective function against oxidative stress generated by tert-butylhydroperoxide (t-BHP) in diabetic rat and improves glutathione peroxidase (GPx) and xanthine oxidase (XO) enzyme activity. It also lowers the glycation of low-density lipoprotein.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M6760.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Chemistry and biological activities of flavonoids: an overview
Kumar S and Pandey AK
TheScientificWorldJournal, 2013, 119-138 (2013)
Medicinal uses and chemistry of flavonoid contents of some common edible tropical plants
Asif M and Khodadadi E
Journal of Paramedical Sciences, 4(3), 119-138 (2013)
Preformulation studies of myricetin: a natural antioxidant flavonoid
Yao Y, et al.
Pharmazie, 69(1), 19-26 (2014)
Noni (Morinda citrifolia L.) fruit extracts improve colon microflora and exert anti-inflammatory activities in Caco-2 cells
Huang HL, et al.
Journal of Medicinal Food, 18(6), 663-676 (2015)
Antioxidant and anti-aging assays of Hibiscus sabdariffa extract and its compounds
Widowati W, et al.
Natural Product Sciences, 23(3), 192-200 (2017)

Articles

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

Protocols

HPLC Analysis of Flavonoids on Ascentis® RP-Amide

Protocol for HPLC Analysis of Flavonoids on Ascentis® RP-Amide

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