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Merck

70050

Myricetin

≥96.0% (HPLC)

Synonym(s):

3,3′,4′,5,5′,7-Hexahydroxyflavone, Cannabiscetin, Myricetol

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About This Item

Empirical Formula (Hill Notation):
C15H10O8
CAS Number:
529-44-2
Molecular Weight:
318.24
UNSPSC Code:
12352202
NACRES:
NA.77
PubChem Substance ID:
57652239
EC Number:
208-463-2
Beilstein/REAXYS Number:
332331
MDL number:
MFCD00006827

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InChI key

IKMDFBPHZNJCSN-UHFFFAOYSA-N

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

SMILES string

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

assay

≥96.0% (HPLC)

form

powder

mp

≥300 °C, >300 °C (lit.)

solubility

ethanol: 10 mg/mL, clear to very faintly turbid, yellow to very deep greenish-yellow

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

200

Gene Information

human ... CYP1A2(1544)
mouse ... Hexa(15211)
rat ... Il4(287287), Tnf(24835)

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General description

Myricetin (MYR) is a natural polyhydroxyflavonol compound, first isolated from the bark of Morella rubra (Myrica rubra) tree.

Application

Myricetin has been used:
  • to study its preventive effect as an antioxidant on noise-induced hearing loss (NIHL) in rats
  • as a flavonoid compound to test antiviral activity of Bourbon virus (BRBV) and in inhibition of RNA-dependent RNA polymerase (RdRP)
  • to study its effect as a treatment on biofilms of Streptococcus mutans and Candida albicans
  • as a reference standard for the quantification of phenolic compounds from Juniperus species

Biochem/physiol Actions

Myricetin exerts anti-oxidant effects, and anti-inflammatory effects by regulating multiple signal pathways. It also displays anti-diabetic and hepatoprotective effects. Myricetin strongly inhibits yeast α-glucosidase, glyoxalase I in vitro, and bovine milk xanthine oxidase. It also promotes complex formation between DNA and both topoisomerase I and II, an effect that may have implications in cancer chemotherapy. Myricetin also has various nutraceuticals values and therapeutic effects.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

70050-BULK: + 70050-100MG: + 70050-25MG: + 70050-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG0319
BCCD4602
BCCC1735
BCBW0114
BCCB0851

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R.B. Brandt et al.
International Journal of Quantum Chemistry, 11, 195-195 (1984)
Guilherme Roncari Rocha et al.
BMC complementary and alternative medicine, 18(1), 61-61 (2018-02-16)
Dental caries is considered a multifactorial disease, in which microorganisms play an important role. The diet is decisive in the biofilm formation because it provides the necessary resources for cellular growth and exopolysaccharides synthesis. Exopolysaccharides are the main components of
M. Iio et al.
Agricultural and Biological Chemistry, 49, 2173-2173 (1985)
M. Iio, et al.
Agricultural and Biological Chemistry, 48, 1559-1559 (1984)
Miguel López-Lázaro et al.
Mutation research, 696(1), 41-47 (2009-12-23)
DNA topoisomerases (topos) are the target of several drugs commonly used in cancer chemotherapy; these drugs induce topo-DNA complexes with either topo I or topo II that eventually trigger cell death. The inhibition of these enzymes induces DNA alterations that
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Protocols

HPLC Analysis of Flavonoids on Ascentis® RP-Amide

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

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