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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:
529-44-2
Molecular Weight:
318.24
Beilstein:
332331
EC Number:
208-463-2
MDL number:
MFCD00006827
UNSPSC Code:
12352202
PubChem Substance ID:
57652239
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

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 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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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
R.B. Brandt et al.
International Journal of Quantum Chemistry, 11, 195-195 (1984)
Xiaominting Song et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 134, 111017-111017 (2020-12-19)
Myricetin(MYR) is a flavonoid compound widely found in many natural plants including bayberry. So far, MYR has been proven to have multiple biological functions and it is a natural compound with promising research and development prospects. This review comprehensively retrieved
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)
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Protocol for HPLC Analysis of Flavonoids on Ascentis® RP-Amide

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