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Sigma-Aldrich

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:
Molecular Weight:
318.24
Beilstein:
332331
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

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

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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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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R.B. Brandt et al.
International Journal of Quantum Chemistry, 11, 195-195 (1984)
Maryam Bahaloo et al.
Iranian journal of otorhinolaryngology, 31(106), 273-279 (2019-10-11)
Exposure to hazardous noise induces one of the forms of acquired and preventable hearing loss that is noise-induced hearing loss (NIHL). Considering oxidative stress as the main mechanism of NIHL, it is possible that myricetin can protect NIHL by its
M. Iio et al.
Agricultural and Biological Chemistry, 49, 2173-2173 (1985)
M. Iio, et al.
Agricultural and Biological Chemistry, 48, 1559-1559 (1984)
Deepak Kumar Semwal et al.
Nutrients, 8(2), 90-90 (2016-02-20)
Myricetin is a common plant-derived flavonoid and is well recognised for its nutraceuticals value. It is one of the key ingredients of various foods and beverages. The compound exhibits a wide range of activities that include strong anti-oxidant, anticancer, antidiabetic

Articles

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

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

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