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

MedKoo CAT#: 464672

CAS#: 171485-39-5

Description: Myrislignan is a lignan that has been found in M. fragrans and has diverse biological activities. It inhibits hypocotyl or root growth of cress (IC50s = 429 and 517 µM, respectively). Myrislignan (50 µg/ml) inhibits production of nitric oxide (NO), increases in inducible nitric oxide synthase (iNOS) and COX-2 levels, and release of TNF-α and IL-6 in LPS-stimulated RAW 264.7 cells. It inhibits the proliferation of, and induces apoptosis in, A549 lung cancer cells. Myrislignan (3, 5, and 8 mg/kg) reduces tumor growth in an A549 lung cancer mouse xenograft model. It decreases parasite burden in the liver, brain, and spleen in a mouse model of T. gondii infection when administered at a dose of 100 mg/kg.

Chemical Structure

CAS# 171485-39-5

Theoretical Analysis

MedKoo Cat#: 464672
Name: Myrislignan
CAS#: 171485-39-5
Chemical Formula: C21H26O6
Exact Mass: 374.1729
Molecular Weight: 374.433
Elemental Analysis: C, 67.36; H, 7.00; O, 25.64

Price and Availability

Size Price Availability Quantity
1.0mg USD 260.0 2 Weeks
5.0mg USD 650.0 2 Weeks
10.0mg USD 1040.0 2 Weeks
25.0mg USD 1640.0 2 Weeks
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Synonym: Myrislignan;

IUPAC/Chemical Name: 4-((1R,2S)-2-(4-allyl-2,6-dimethoxyphenoxy)-1-hydroxypropyl)-2-methoxyphenol


InChi Code: InChI=1S/C21H26O6/c1-6-7-14-10-18(25-4)21(19(11-14)26-5)27-13(2)20(23)15-8-9-16(22)17(12-15)24-3/h6,8-13,20,22-23H,1,7H2,2-5H3/t13-,20-/m0/s1

SMILES Code: COC1=C(O[C@H]([C@H](O)C(C=C2)=CC(OC)=C2O)C)C(OC)=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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
DMF 15.0 40.06
DMF:PBS (pH 7.2) (1:2) 0.33 0.88
DMSO 5.0 13.35
Ethanol 1.0 2.67

Preparing Stock Solutions

The following data is based on the product molecular weight 374.433 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: Zhang J, Si H, Li B, Zhou X, Zhang J. Myrislignan Exhibits Activities Against Toxoplasma gondii RH Strain by Triggering Mitochondrial Dysfunction. Front Microbiol. 2019 Sep 18;10:2152. doi: 10.3389/fmicb.2019.02152. PMID: 31620108; PMCID: PMC6759950.

2: Yang X, Zan T, Yan H, Liu B. UPLC-MS/MS determination of flavokawain B, a novel anti-tumor chemotherapeutic agent in rat plasma and its application to a pharmacokinetic study in rats. Biomed Chromatogr. 2019 Feb;33(2):e4391. doi: 10.1002/bmc.4391. Epub 2018 Oct 15. PMID: 30238480.

3: Zhao Q, Zhang JL, Li F. Application of Metabolomics in the Study of Natural Products. Nat Prod Bioprospect. 2018 Aug;8(4):321-334. doi: 10.1007/s13659-018-0175-9. Epub 2018 Jun 29. PMID: 29959744; PMCID: PMC6102178.

4: Yang XN, Liu XM, Fang JH, Zhu X, Yang XW, Xiao XR, Huang JF, Gonzalez FJ, Li F. PPARα Mediates the Hepatoprotective Effects of Nutmeg. J Proteome Res. 2018 May 4;17(5):1887-1897. doi: 10.1021/acs.jproteome.7b00901. Epub 2018 Apr 25. PMID: 29664296; PMCID: PMC6628927.

5: Lu X, Yang L, Chen J, Zhou J, Tang X, Zhu Y, Qiu H, Shen J. The action and mechanism of myrislignan on A549 cells in vitro and in vivo. J Nat Med. 2017 Jan;71(1):76-85. doi: 10.1007/s11418-016-1029-6. Epub 2016 Aug 4. PMID: 27491743.

6: Wu N, Xu W, Cao GY, Yang YF, Yang XB, Yang XW. The Blood-Brain Barrier Permeability of Lignans and Malabaricones from the Seeds of Myristica fragrans in the MDCK-pHaMDR Cell Monolayer Model. Molecules. 2016 Jan 22;21(2):134. doi: 10.3390/molecules21020134. PMID: 26805808; PMCID: PMC6274353.

7: Zhu Z, Yang S, Zhao W, Li R, Zhao C. A Comparative Pharmacokinetic Study of Myrislignan by UHPLC-MS After Oral Administration of a Monomer and Myristica fragrans Extract to Rats. J Chromatogr Sci. 2016 May-Jun;54(5):689-96. doi: 10.1093/chromsci/bmv227. Epub 2016 Jan 15. PMID: 26774114; PMCID: PMC4890437.

8: Cao GY, Xu W, Yang XW, Gonzalez FJ, Li F. New neolignans from the seeds of Myristica fragrans that inhibit nitric oxide production. Food Chem. 2015 Apr 15;173:231-7. doi: 10.1016/j.foodchem.2014.09.170. Epub 2014 Oct 13. PMID: 25466017; PMCID: PMC6338084.

9: Jin H, Zhu ZG, Yu PJ, Wang GF, Zhang JY, Li JR, Ai RT, Li ZH, Tian YX, Zhang WX, Wu SG. Myrislignan attenuates lipopolysaccharide-induced inflammation reaction in murine macrophage cells through inhibition of NF-κB signalling pathway activation. Phytother Res. 2012 Sep;26(9):1320-6. doi: 10.1002/ptr.3707. Epub 2012 Feb 1. PMID: 22294521.

10: Li F, Yang X. Quantification of myrislignan in rat plasma by solid-phase extraction and reversed-phase high-performance liquid chromatography. Biomed Chromatogr. 2008 Jun;22(6):601-5. doi: 10.1002/bmc.975. PMID: 18254153.

11: Li F, Yang XW. Biotransformation of myrislignan by rat liver microsomes in vitro. Phytochemistry. 2008 Feb;69(3):765-71. doi: 10.1016/j.phytochem.2007.09.008. Epub 2007 Oct 26. PMID: 17964618.