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Myrislignan

Cat No.:V40805 Purity: ≥98%
Myrislignan is a lignan extracted from Myristica fragrans Houtt and has anti~inflammatory activity.
Myrislignan
Myrislignan Chemical Structure CAS No.: 171485-39-5
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
500mg
1g
Other Sizes

Other Forms of Myrislignan:

  • 1-(3,4-dimethoxyphenyl)-2-(4-allly-2,6-dimethoxyphenoxy)propan-1-ol
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Myrislignan is a lignan extracted from Myristica fragrans Houtt and has anti~inflammatory activity. Myrislignan reduces LPS-induced inflammatory response in mouse macrophages by inhibiting the activation of the NF-kB signaling pathway.
Myrislignan is a lignan isolated from Myristica fragrans Houtt (nutmeg). It has anti-inflammatory and anti-cancer activities. Myrislignan inhibits interleukin-6 (IL-6) and tumour necrosis factor-α (TNF-α). It significantly inhibits the expressions of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) in a dose-dependent manner in LPS-stimulated macrophage cells.
Biological Activity I Assay Protocols (From Reference)
Targets
Myrislignan targets the NF-κB signaling pathway. By inhibiting NF-κB signaling pathway activation, it reduces the expression of pro-inflammatory mediators such as IL-6, TNF-α, iNOS, and COX-2. Myrislignan also inhibits the proliferation of A549 cells in a dose- and time-dependent manner and significantly induces apoptosis and cell cycle arrest in A549 cells.
ln Vitro
In vitro, myrislignan inhibits IL-6 and TNF-α production. It significantly inhibits the expressions of iNOS and COX-2 in LPS-stimulated macrophage cells. It inhibits the proliferation of A549 cells in a dose- and time-dependent manner and significantly induces apoptosis and cell cycle arrest in A549 cells. Myrislignan attenuates LPS-induced inflammation in murine macrophage cells.
ln Vivo
In vivo, myrislignan has been reported to possess inhibition of neoplasm and vascular smooth muscle contraction, and cause a prolonging of hexobarbital-induced hypnosis in mice. Its anti-inflammatory and anti-cancer activities suggest potential therapeutic applications. Further in vivo studies are needed to evaluate its efficacy.
Enzyme Assay
The in vitro NF-κB inhibition assay for myrislignan measures its ability to inhibit NF-κB signaling pathway activation. Cells are treated with myrislignan and stimulated with LPS. NF-κB activation is assessed by measuring the phosphorylation and degradation of IκBα or by using NF-κB reporter gene assays. The expression of NF-κB target genes (IL-6, TNF-α, iNOS, COX-2) is measured by qRT-PCR or ELISA.
Cell Assay
In vitro cellular studies are conducted using macrophage cells (e.g., RAW 264.7) and cancer cell lines (e.g., A549 lung cancer cells). Cells are treated with myrislignan at various concentrations. Inflammatory cytokine production is measured by ELISA. iNOS and COX-2 expression is measured by Western blot or qRT-PCR. Cell proliferation is assessed using MTT or CellTiter-Glo assays. Apoptosis is measured by Annexin V/PI staining or caspase-3 activity assays.
Animal Protocol
In vivo animal experiments with myrislignan are limited. The compound is a natural product with potential anti-inflammatory and anti-cancer activities. Further in vivo studies are needed to evaluate its efficacy in models of inflammation and cancer. Animals would be administered myrislignan via injection or oral gavage, and endpoints would include tumor growth inhibition and inflammation reduction.
ADME/Pharmacokinetics
Myrislignan has a molecular formula of C21H26O6 and a molecular weight of 374.43 g/mol. It is an 8-O-4′ type neolignan isolated from Myristica fragrans Houtt (nutmeg). For storage, it should be kept at -20°C, protected from light and moisture. The compound is supplied with high purity for research purposes. It is a lignan with anti-inflammatory and anti-cancer activities.
Toxicity/Toxicokinetics
As a research chemical with potent biological activity, myrislignan is not intended for human use. Its toxicological profile is not fully characterized. Standard laboratory safety precautions should be followed when handling it. Its effects are related to its mechanism as an NF-κB inhibitor, which could have anti-inflammatory and anti-cancer effects.
References

[1]. 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.

Additional Infomation
Myrislignan is a phenylpropanoid compound. It has been reported that nutmeg (Myristica fragrans) contains Myrislignan, and relevant data are available for reference.
Myrislignan is a lignan isolated from Myristica fragrans Houtt (nutmeg). It has anti-inflammatory and anti-cancer activities. Myrislignan inhibits IL-6 and TNF-α and inhibits iNOS and COX-2 expression. It attenuates LPS-induced inflammation by inhibiting NF-κB signaling pathway activation. It inhibits the proliferation of A549 cells and induces apoptosis and cell cycle arrest.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H26O6
Molecular Weight
374.4275
Exact Mass
374.172
CAS #
171485-39-5
Related CAS #
(Rac)-Myrislignan; 41535-95-9; Myrislignan-13C,d2
PubChem CID
21636106
Appearance
White to off-white solid powder
Density
1.167
Boiling Point
537.6±50.0 °C at 760 mmHg
Flash Point
278.9±30.1 °C
Vapour Pressure
0.0±1.5 mmHg at 25°C
Index of Refraction
1.562
Source
Originated from plants: Myristicaceae Myristica fragrans Houtt.
LogP
2.54
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
9
Heavy Atom Count
27
Complexity
430
Defined Atom Stereocenter Count
2
SMILES
C[C@@H]([C@@H](C1=CC(=C(C=C1)O)OC)O)OC2=C(C=C(C=C2OC)CC=C)OC
InChi Key
ULZFTGWWPHYLGI-RBZFPXEDSA-N
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
Chemical Name
4-[(1R,2S)-2-(2,6-dimethoxy-4-prop-2-enylphenoxy)-1-hydroxypropyl]-2-methoxyphenol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~267.07 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.68 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (6.68 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (6.68 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.6707 mL 13.3536 mL 26.7073 mL
5 mM 0.5341 mL 2.6707 mL 5.3415 mL
10 mM 0.2671 mL 1.3354 mL 2.6707 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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