Myricetin
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MedKoo CAT#: 540305

CAS#: 529-44-2

Description: Myricetin is a COMT inhibitor found in fruits and vegetables. It exhibits a wide variety of biological activities, including decreasing cholesterol, triglyceride, and lipid levels, inhibiting amyloid-B-induced neurodegeneration, activating Wnt/B-catenin signaling to increase osteoclast differentiation, and inducing cell cycle arrest in oral squamous cell carcinoma cells.


Chemical Structure

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Myricetin
CAS# 529-44-2

Theoretical Analysis

MedKoo Cat#: 540305
Name: Myricetin
CAS#: 529-44-2
Chemical Formula: C15H10O8
Exact Mass: 318.0376
Molecular Weight: 318.23
Elemental Analysis: C, 56.61; H, 3.17; O, 40.22

Price and Availability

Size Price Availability Quantity
25.0mg USD 225.0 2 Weeks
50.0mg USD 365.0 2 Weeks
100.0mg USD 650.0 2 Weeks
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Synonym: Cannabiscetin; HSDB 7682; HSDB7682; HSDB-7682; Myricetin

IUPAC/Chemical Name: 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

InChi Key: IKMDFBPHZNJCSN-UHFFFAOYSA-N

InChi Code: 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 Code: O=C1C(O)=C(C2=CC(O)=C(O)C(O)=C2)OC3=C1C(O)=CC(O)=C3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 318.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Ma Z, Wang G, Cui L, Wang Q. Myricetin Attenuates Depressant-Like Behavior in Mice Subjected to Repeated Restraint Stress. Int J Mol Sci. 2015 Nov 30;16(12):28377-85. doi: 10.3390/ijms161226102. PubMed PMID: 26633366; PubMed Central PMCID: PMC4691049.

2: Feng J, Chen X, Wang Y, Du Y, Sun Q, Zang W, Zhao G. Myricetin inhibits proliferation and induces apoptosis and cell cycle arrest in gastric cancer cells. Mol Cell Biochem. 2015 Oct;408(1-2):163-70. doi: 10.1007/s11010-015-2492-1. Epub 2015 Jun 27. PubMed PMID: 26112905.

3: Yao Y, Lin G, Xie Y, Ma P, Li G, Meng Q, Wu T. Preformulation studies of myricetin: a natural antioxidant flavonoid. Pharmazie. 2014 Jan;69(1):19-26. PubMed PMID: 24601218.

4: Yuan X, Liu Y, Hua X, Deng X, Sun P, Yu C, Chen L, Yu S, Liu S, Pang H. Myricetin ameliorates the symptoms of collagen-induced arthritis in mice by inhibiting cathepsin K activity. Immunopharmacol Immunotoxicol. 2015;37(6):513-9. doi: 10.3109/08923973.2015.1096942. Epub 2015 Nov 2. PubMed PMID: 26525510.

5: Wu C, Wang W, Tian B, Liu X, Qu X, Zhai Z, Li H, Liu F, Fan Q, Tang T, Qin A, Zhu Z. Myricetin prevents titanium particle-induced osteolysis in vivo and inhibits RANKL-induced osteoclastogenesis in vitro. Biochem Pharmacol. 2015 Jan 1;93(1):59-71. doi: 10.1016/j.bcp.2014.10.019. Epub 2014 Nov 7. PubMed PMID: 25449599.

6: Chang Y, Chang CY, Wang SJ, Huang SK. Myricetin inhibits the release of glutamate in rat cerebrocortical nerve terminals. J Med Food. 2015 May;18(5):516-23. doi: 10.1089/jmf.2014.3219. Epub 2014 Oct 23. PubMed PMID: 25340625; PubMed Central PMCID: PMC4410760.

7: Mendes V, Vilaça R, de Freitas V, Ferreira PM, Mateus N, Costa V. Effect of myricetin, pyrogallol, and phloroglucinol on yeast resistance to oxidative stress. Oxid Med Cell Longev. 2015;2015:782504. doi: 10.1155/2015/782504. Epub 2015 Apr 27. PubMed PMID: 26000072; PubMed Central PMCID: PMC4427115.

8: Okan A, Barlas N, Karabulut G. Investigation of effects of myricetin on thyroid-gonadal axis of male rats at prepubertal period. Environ Toxicol Pharmacol. 2015 Jul;40(1):268-79. doi: 10.1016/j.etap.2015.04.015. Epub 2015 Apr 27. PubMed PMID: 26164744.

9: Zang W, Wang T, Wang Y, Li M, Xuan X, Ma Y, Du Y, Liu K, Dong Z, Zhao G. Myricetin exerts anti-proliferative, anti-invasive, and pro-apoptotic effects on esophageal carcinoma EC9706 and KYSE30 cells via RSK2. Tumour Biol. 2014 Dec;35(12):12583-92. doi: 10.1007/s13277-014-2579-4. Epub 2014 Sep 6. PubMed PMID: 25192723.

10: Zhang S, Wang L, Liu H, Zhao G, Ming L. Enhancement of recombinant myricetin on the radiosensitivity of lung cancer A549 and H1299 cells. Diagn Pathol. 2014 Mar 20;9:68. doi: 10.1186/1746-1596-9-68. PubMed PMID: 24650056; PubMed Central PMCID: PMC3994494.

11: Huang H, Chen AY, Rojanasakul Y, Ye X, Rankin GO, Chen YC. Dietary compounds galangin and myricetin suppress ovarian cancer cell angiogenesis. J Funct Foods. 2015 May 1;15:464-475. PubMed PMID: 26113875; PubMed Central PMCID: PMC4476554.

12: Grenier D, Chen H, Ben Lagha A, Fournier-Larente J, Morin MP. Dual Action of Myricetin on Porphyromonas gingivalis and the Inflammatory Response of Host Cells: A Promising Therapeutic Molecule for Periodontal Diseases. PLoS One. 2015 Jun 29;10(6):e0131758. doi: 10.1371/journal.pone.0131758. eCollection 2015. PubMed PMID: 26121135; PubMed Central PMCID: PMC4487256.

13: Kim ME, Ha TK, Yoon JH, Lee JS. Myricetin induces cell death of human colon cancer cells via BAX/BCL2-dependent pathway. Anticancer Res. 2014 Feb;34(2):701-6. PubMed PMID: 24511002.

14: Devi KP, Rajavel T, Habtemariam S, Nabavi SF, Nabavi SM. Molecular mechanisms underlying anticancer effects of myricetin. Life Sci. 2015 Dec 1;142:19-25. doi: 10.1016/j.lfs.2015.10.004. Epub 2015 Oct 8. Review. PubMed PMID: 26455550.

15: Büchter C, Ackermann D, Honnen S, Arnold N, Havermann S, Koch K, Wätjen W. Methylated derivatives of myricetin enhance life span in Caenorhabditis elegans dependent on the transcription factor DAF-16. Food Funct. 2015 Oct;6(10):3383-92. doi: 10.1039/c5fo00463b. PubMed PMID: 26281763.

16: Huang J, Wu C, Tian B, Zhou X, Ma N, Qian Y. Myricetin Prevents Alveolar Bone Loss in an Experimental Ovariectomized Mouse Model of Periodontitis. Int J Mol Sci. 2016 Mar 22;17(3):422. doi: 10.3390/ijms17030422. PubMed PMID: 27011174; PubMed Central PMCID: PMC4813273.

17: Hobbs CA, Swartz C, Maronpot R, Davis J, Recio L, Koyanagi M, Hayashi SM. Genotoxicity evaluation of the flavonoid, myricitrin, and its aglycone, myricetin. Food Chem Toxicol. 2015 Sep;83:283-92. doi: 10.1016/j.fct.2015.06.016. Epub 2015 Jul 2. PubMed PMID: 26142838.

18: Hong C, Dang Y, Lin G, Yao Y, Li G, Ji G, Shen H, Xie Y. Effects of stabilizing agents on the development of myricetin nanosuspension and its characterization: an in vitro and in vivo evaluation. Int J Pharm. 2014 Dec 30;477(1-2):251-60. doi: 10.1016/j.ijpharm.2014.10.044. Epub 2014 Oct 18. PubMed PMID: 25445518.

19: Ying X, Chen X, Feng Y, Xu HZ, Chen H, Yu K, Cheng S, Peng L. Myricetin enhances osteogenic differentiation through the activation of canonical Wnt/β-catenin signaling in human bone marrow stromal cells. Eur J Pharmacol. 2014 Sep 5;738:22-30. doi: 10.1016/j.ejphar.2014.04.049. Epub 2014 May 27. PubMed PMID: 24876056.

20: Yao Y, Xie Y, Hong C, Li G, Shen H, Ji G. Development of a myricetin/hydroxypropyl-β-cyclodextrin inclusion complex: preparation, characterization, and evaluation. Carbohydr Polym. 2014 Sep 22;110:329-37. doi: 10.1016/j.carbpol.2014.04.006. Epub 2014 Apr 18. PubMed PMID: 24906763.