Myricetin | CAS#529-44-2 | COMT inhibitor

MedKoo Cat#: 540305 | Name: Myricetin

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

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: 318.24

Elemental Analysis: C, 56.61; H, 3.17; O, 40.22

Price and Availability

Size	Price	Availability
1g	USD 205.00	2 Weeks
2g	USD 365.00	2 Weeks
5g	USD 650.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities.

In vitro activity:

The aim of the present study was to assess whether these two apoptotic pathways are involved in myricetin‑induced cell death in SKOV3 ovarian cancer cells. The results revealed that treatment with myricetin inhibited viability of SKOV3 cells in a dose‑dependent manner. Myricetin induced nuclear chromatin condensation and fragmentation, and also upregulated the protein levels of active caspase 3 in a time‑dependent manner. In addition, myricetin upregulated ER stress‑associated proteins, glucose‑regulated protein‑78 and C/EBP homologous protein in SKOV3 cells. Reference: Mol Med Rep. 2016 Mar;13(3):2094-100. https://pubmed.ncbi.nlm.nih.gov/26782830/

In vivo activity:

After 21 days of treatment, it was found that myricetin significantly alleviated myocardial injury in EAM (autoimmune myocarditis) mice. The serum anti-cardiac myosin antibody, immunoglobulin (Ig) G, IgM levels and the proportion of T helper 17 (Th17) cells were decreased and the proportion of regulatory T (Treg) cells was increased with the treatment of myricetin in EAM mice. The myosin-specific T cell proliferation was inhibited by myricetin. Meanwhile, myricetin suppressed the expressions of monocyte chemoattractant protein-1 (MCP-1), phospho (p)-p65, p-c-Jun and Act1/TRAF6/TAK1 in H9C2 cells and myocardial tissues of EAM mice. Reference: Eur J Pharmacol. 2023 Mar 5;942:175549. https://pubmed.ncbi.nlm.nih.gov/36708976/

	Solvent	mg/mL	mM
Solubility
	Ethanol	14.8	46.46

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 318.24 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.

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

Formulation protocol:

1. Xu Y, Xie Q, Wu S, Yi D, Yu Y, Liu S, Li S, Li Z. Myricetin induces apoptosis via endoplasmic reticulum stress and DNA double-strand breaks in human ovarian cancer cells. Mol Med Rep. 2016 Mar;13(3):2094-100. doi: 10.3892/mmr.2016.4763. Epub 2016 Jan 12. PMID: 26782830; PMCID: PMC4768956. 2. Lee KW, Kang NJ, Rogozin EA, Kim HG, Cho YY, Bode AM, Lee HJ, Surh YJ, Bowden GT, Dong Z. Myricetin is a novel natural inhibitor of neoplastic cell transformation and MEK1. Carcinogenesis. 2007 Sep;28(9):1918-27. doi: 10.1093/carcin/bgm110. Epub 2007 Aug 11. PMID: 17693661. 3. Nie N, Li Z, Li W, Huang X, Jiang Z, Shen Y. Myricetin ameliorates experimental autoimmune myocarditis in mice by modulating immune response and inhibiting MCP-1 expression. Eur J Pharmacol. 2023 Mar 5;942:175549. doi: 10.1016/j.ejphar.2023.175549. Epub 2023 Jan 25. PMID: 36708976. 4. Phillips PA, Sangwan V, Borja-Cacho D, Dudeja V, Vickers SM, Saluja AK. Myricetin induces pancreatic cancer cell death via the induction of apoptosis and inhibition of the phosphatidylinositol 3-kinase (PI3K) signaling pathway. Cancer Lett. 2011 Sep 28;308(2):181-8. doi: 10.1016/j.canlet.2011.05.002. Epub 2011 Jun 14. PMID: 21676539; PMCID: PMC3126884.

In vitro protocol:

In vivo protocol:

1. Nie N, Li Z, Li W, Huang X, Jiang Z, Shen Y. Myricetin ameliorates experimental autoimmune myocarditis in mice by modulating immune response and inhibiting MCP-1 expression. Eur J Pharmacol. 2023 Mar 5;942:175549. doi: 10.1016/j.ejphar.2023.175549. Epub 2023 Jan 25. PMID: 36708976. 2. Phillips PA, Sangwan V, Borja-Cacho D, Dudeja V, Vickers SM, Saluja AK. Myricetin induces pancreatic cancer cell death via the induction of apoptosis and inhibition of the phosphatidylinositol 3-kinase (PI3K) signaling pathway. Cancer Lett. 2011 Sep 28;308(2):181-8. doi: 10.1016/j.canlet.2011.05.002. Epub 2011 Jun 14. PMID: 21676539; PMCID: PMC3126884.

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.

View History

C.I. 37585

MedKoo CAT#: 462633

CAS#: 1830-77-9