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M6760

Sigma-Aldrich

Myricetin

≥96.0%, crystalline

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%

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.

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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Chemistry and biological activities of flavonoids: an overview
Kumar S and Pandey AK
TheScientificWorldJournal, 2013, 119-138 (2013)
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)
Preformulation studies of myricetin: a natural antioxidant flavonoid
Yao Y, et al.
Pharmazie, 69(1), 19-26 (2014)
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)
Antioxidant and anti-aging assays of Hibiscus sabdariffa extract and its compounds
Widowati W, et al.
Natural Product Sciences, 23(3), 192-200 (2017)

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