Myristicin | CAS#607-91-0 | apoptosis inducer | decreases pro-inflammatory cytokine expression

MedKoo Cat#: 540306 | Name: Myristicin

Featured

Description:

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

Myristicin is a natural product found in spices and umbelliferous plants. It induces apoptosis in leukemia cells, decreases pro-inflammatory cytokine expression in alveolar epithelial cells, and suppresses growth of Clostridium, Enterococcus, Candida.

Chemical Structure

Myristicin

CAS#607-91-0

Theoretical Analysis

MedKoo Cat#: 540306

Name: Myristicin

CAS#: 607-91-0

Chemical Formula: C11H12O3

Exact Mass: 192.0786

Molecular Weight: 192.21

Elemental Analysis: C, 68.74; H, 6.29; O, 24.97

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 180.00
50mg	USD 200.00
100mg	USD 545.00

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Myristicin; HSDB 3516; HSDB3516; HSDB-3516

IUPAC/Chemical Name

6-allyl-4-methoxybenzo[d][1,3]dioxole

InChi Key

BNWJOHGLIBDBOB-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H12O3/c1-3-4-8-5-9(12-2)11-10(6-8)13-7-14-11/h3,5-6H,1,4,7H2,2H3

SMILES Code

COC1=C2OCOC2=CC(CC=C)=C1

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:

Myristicine acts as a serotonin receptor antagonist, a weak monamine oxidase (MAO) inhibitor.

In vitro activity:

The aim of this work was to identify whether the role of myristicin in CYP enzyme inhibition is mechanism-based inhibition and to gain further information regarding the structure of the resulting reactive metabolites. CYP cocktail assays showed that myristicin most significantly inhibits CYP1A2 among five CYP enzymes (CYP1A2, CYP2D6, CYP2E1, CYP3A4 and CYP2C19) from human liver microsomes. Reference: Chem Biol Interact. 2015 Jul 25;237:133-40. https://pubmed.ncbi.nlm.nih.gov/26091900/

In vivo activity:

The results indicated the potential upregulation of ERS, pro-apoptotic, lipid peroxidation, and pro-inflammatory cascades by induction of UC in rats. However, myristicin could effectively reverse the deteriorated effects of ulceration in colonic mucosa. It was mediated through downregulation of the ERS markers GRP78 and CHOP genes expression, reduction of NF-κB mRNA expression, DNA fragmentation, reduced lipid peroxidation, myeloperoxidase (MPO) activity and pro-inflammatory markers (Tumor necrosis factor-α (TNF-α), Interleukin-1β (IL-1β) and cyclo‑oxygenase (COX-2) activity). Reference: Life Sci. 2022 Dec 15;311(Pt B):121187. https://pubmed.ncbi.nlm.nih.gov/36403646/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	130.06
	DMSO	62.5	325.16
	Ethanol	30.0	156.08
	Ethanol:PBS (pH 7.2) (1:1)	0.5	2.60

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 192.21 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. Luo L, Liang H, Liu L. Myristicin regulates proliferation and apoptosis in oxidized low-density lipoprotein-stimulated human vascular smooth muscle cells and human umbilical vein endothelial cells by regulating the PI3K/Akt/NF-κB signalling pathway. Pharm Biol. 2022 Dec;60(1):56-64. doi: 10.1080/13880209.2021.2010775. PMID: 34905418; PMCID: PMC8676624. 2. Yang AH, He X, Chen JX, He LN, Jin CH, Wang LL, Zhang FL, An LJ. Identification and characterization of reactive metabolites in myristicin-mediated mechanism-based inhibition of CYP1A2. Chem Biol Interact. 2015 Jul 25;237:133-40. doi: 10.1016/j.cbi.2015.06.018. Epub 2015 Jun 16. PMID: 26091900. 3. Song J, Xu X, He S, Wang N, Bai Y, Chen Z, Li B, Zhang S. Myristicin Suppresses Gastric Cancer Growth via Targeting the EGFR/ERK Signaling Pathway. Curr Mol Pharmacol. 2023 Jan 3. doi: 10.2174/1874467216666230103104600. Epub ahead of print. PMID: 36597605. 4. Ismail Abo El-Fadl HM, Mohamed MFA. Targeting endoplasmic reticulum stress, Nrf-2/HO-1, and NF-κB by myristicin and its role in attenuation of ulcerative colitis in rats. Life Sci. 2022 Dec 15;311(Pt B):121187. doi: 10.1016/j.lfs.2022.121187. Epub 2022 Nov 17. PMID: 36403646.

In vitro protocol:

In vivo protocol:

1. Song J, Xu X, He S, Wang N, Bai Y, Chen Z, Li B, Zhang S. Myristicin Suppresses Gastric Cancer Growth via Targeting the EGFR/ERK Signaling Pathway. Curr Mol Pharmacol. 2023 Jan 3. doi: 10.2174/1874467216666230103104600. Epub ahead of print. PMID: 36597605. 2. Ismail Abo El-Fadl HM, Mohamed MFA. Targeting endoplasmic reticulum stress, Nrf-2/HO-1, and NF-κB by myristicin and its role in attenuation of ulcerative colitis in rats. Life Sci. 2022 Dec 15;311(Pt B):121187. doi: 10.1016/j.lfs.2022.121187. Epub 2022 Nov 17. PMID: 36403646.

1: Yang AH, He X, Chen JX, He LN, Jin CH, Wang LL, Zhang FL, An LJ. Identification and characterization of reactive metabolites in myristicin-mediated mechanism-based inhibition of CYP1A2. Chem Biol Interact. 2015 Jul 25;237:133-40. doi: 10.1016/j.cbi.2015.06.018. Epub 2015 Jun 16. PubMed PMID: 26091900. 2: Martins C, Doran C, Silva IC, Miranda C, Rueff J, Rodrigues AS. Myristicin from nutmeg induces apoptosis via the mitochondrial pathway and down regulates genes of the DNA damage response pathways in human leukaemia K562 cells. Chem Biol Interact. 2014 Jul 25;218:1-9. doi: 10.1016/j.cbi.2014.04.014. Epub 2014 Apr 29. PubMed PMID: 24792648. 3: Dawidowicz AL, Dybowski MP. Simple and rapid determination of myristicin in human serum. Forensic Toxicol. 2013 Jan;31(1):119-123. Epub 2012 Aug 15. PubMed PMID: 23440626; PubMed Central PMCID: PMC3573713. 4: Lee JY, Park W. Anti-inflammatory effect of myristicin on RAW 264.7 macrophages stimulated with polyinosinic-polycytidylic acid. Molecules. 2011;16(8):7132-42. PubMed PMID: 21991618. 5: Sivathanu S, Sampath S, David HS, Rajavelu KK. Myristicin and phenytoin toxicity in an infant. BMJ Case Rep. 2014 Jun 5;2014. pii: bcr2013203000. doi: 10.1136/bcr-2013-203000. PubMed PMID: 24903724; PubMed Central PMCID: PMC4054332. 6: Leiter E, Hitchcock G, Godwin S, Johnson M, Sedgwick W, Jones W, McCall S, Ceremuga TE. Evaluation of the anxiolytic properties of myristicin, a component of nutmeg, in the male Sprague-Dawley rat. AANA J. 2011 Apr;79(2):109-14. PubMed PMID: 21560973. 7: Dawidowicz AL, Dybowski MP. Determination of myristicin in commonly spices applying SPE/GC. Food Chem Toxicol. 2012 Jul;50(7):2362-7. doi: 10.1016/j.fct.2012.04.013. Epub 2012 Apr 16. PubMed PMID: 22525861. 8: Raffo A, D'Aloise A, Magrì AL, Leclercq C. Quantitation of tr-cinnamaldehyde, safrole and myristicin in cola-flavoured soft drinks to improve the assessment of their dietary exposure. Food Chem Toxicol. 2013 Sep;59:626-35. doi: 10.1016/j.fct.2013.06.058. Epub 2013 Jul 8. PubMed PMID: 23845511. 9: Martins C, Doran C, Laires A, Rueff J, Rodrigues AS. Genotoxic and apoptotic activities of the food flavourings myristicin and eugenol in AA8 and XRCC1 deficient EM9 cells. Food Chem Toxicol. 2011 Feb;49(2):385-92. doi: 10.1016/j.fct.2010.11.013. Epub 2010 Nov 16. PubMed PMID: 21087650. 10: Smaili T, Zellagui A, Cioni PL, Flamini G. A myristicin-rich essential oil from Daucus sahariensis growing in Algeria. Nat Prod Commun. 2011 Jun;6(6):883-6. PubMed PMID: 21815432. 11: Lee BK, Kim JH, Jung JW, Choi JW, Han ES, Lee SH, Ko KH, Ryu JH. Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells. Toxicol Lett. 2005 May 16;157(1):49-56. PubMed PMID: 15795093. 12: Hallström H, Thuvander A. Toxicological evaluation of myristicin. Nat Toxins. 1997;5(5):186-92. Review. PubMed PMID: 9496377. 13: Jeong HG, Yun CH. Induction of rat hepatic cytochrome P450 enzymes by myristicin. Biochem Biophys Res Commun. 1995 Dec 26;217(3):966-71. PubMed PMID: 8554622. 14: Mao W, Zangerl AR, Berenbaum MR, Schuler MA. Metabolism of myristicin by Depressaria pastinacella CYP6AB3v2 and inhibition by its metabolite. Insect Biochem Mol Biol. 2008 Jun;38(6):645-51. doi: 10.1016/j.ibmb.2008.03.013. Epub 2008 Apr 9. PubMed PMID: 18510976. 15: Jeong HG, Lee SS, Kim HK, Yang KH. Murine Cyp1a-1 induction in mouse hepatoma Hepa-1C1C7 cells by myristicin. Biochem Biophys Res Commun. 1997 Apr 28;233(3):619-22. PubMed PMID: 9168900. 16: Zheng GQ, Kenney PM, Zhang J, Lam LK. Inhibition of benzo[a]pyrene-induced tumorigenesis by myristicin, a volatile aroma constituent of parsley leaf oil. Carcinogenesis. 1992 Oct;13(10):1921-3. PubMed PMID: 1423855. 17: Ahmad H, Tijerina MT, Tobola AS. Preferential overexpression of a class MU glutathione S-transferase subunit in mouse liver by myristicin. Biochem Biophys Res Commun. 1997 Jul 30;236(3):825-8. PubMed PMID: 9245741. 18: Lee HS, Jeong TC, Kim JH. In vitro and in vivo metabolism of myristicin in the rat. J Chromatogr B Biomed Sci Appl. 1998 Feb 13;705(2):367-72. PubMed PMID: 9521577. 19: Al-Malahmeh AJ, Al-Ajlouni A, Wesseling S, Soffers AE, Al-Subeihi A, Kiwamoto R, Vervoort J, Rietjens IM. Physiologically based kinetic modeling of the bioactivation of myristicin. Arch Toxicol. 2017 Feb;91(2):713-734. doi: 10.1007/s00204-016-1752-5. Epub 2016 Jun 22. PubMed PMID: 27334372; PubMed Central PMCID: PMC5306082. 20: Morita T, Jinno K, Kawagishi H, Arimoto Y, Suganuma H, Inakuma T, Sugiyama K. Hepatoprotective effect of myristicin from nutmeg (Myristica fragrans) on lipopolysaccharide/d-galactosamine-induced liver injury. J Agric Food Chem. 2003 Mar 12;51(6):1560-5. PubMed PMID: 12617584.