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4-Methoxycinnamaldehyde

Cat No.:V45788 Purity: ≥98%
4-Methoxycinnamaldehyde (p-Methoxycinnamaldehyde), an active component of Agastache rugosa, has cytoprotective activity against respiratory syncytial virus (RSV) in human laryngeal carcinoma cell lines.
4-Methoxycinnamaldehyde
4-Methoxycinnamaldehyde Chemical Structure CAS No.: 1963-36-6
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
4-Methoxycinnamaldehyde (p-Methoxycinnamaldehyde), an active component of Agastache rugosa, has cytoprotective activity against respiratory syncytial virus (RSV) in human laryngeal carcinoma cell lines. 4-Methoxycinnamaldehyde effectively inhibits the cytopathic effects of RSV with IC50 of about 0.055 μg/mL.
4-Methoxycinnamaldehyde (p-Methoxycinnamaldehyde) is an active constituent of Agastache rugosa. It exhibits potent cytoprotective activity against respiratory syncytial virus (RSV) in human larynx carcinoma cell lines, effectively inhibiting the cytopathic effect of RSV with an IC₅₀ of approximately 0.055 µg/mL and a selectivity index of 898.2. The compound also exhibits antioxidant, anti-inflammatory, and antimicrobial properties. It shows potential in modulating cellular signaling pathways involved in oxidative stress and inflammation.
Biological Activity I Assay Protocols (From Reference)
Targets
4-Methoxycinnamaldehyde targets the respiratory syncytial virus (RSV) by inhibiting its cytopathic effect in infected cells. The compound may interfere with viral entry, replication, or assembly. It also modulates cellular signaling pathways involved in oxidative stress and inflammation, suggesting interactions with NF-κB, MAPK, or other stress-responsive pathways. The compound's antioxidant and anti-inflammatory activities are mediated through radical scavenging and modulation of inflammatory mediators.
ln Vitro
4-Methoxycinnamaldehyde effectively inhibits the cytopathic effect of RSV with an IC₅₀ of approximately 0.055 µg/mL and a selectivity index of 898.2. It exhibits antioxidant activity through radical scavenging mechanisms. The compound also shows anti-inflammatory activity by reducing the production of pro-inflammatory mediators. Antimicrobial properties have also been reported. These activities make it valuable for studying viral infections and inflammatory conditions.
ln Vivo
In vivo activity data for 4-Methoxycinnamaldehyde are limited in the literature. Based on its potent in vitro anti-RSV activity, it is anticipated to have potential in vivo efficacy in animal models of RSV infection. The compound's antioxidant and anti-inflammatory properties also suggest potential in vivo effects in models of oxidative stress and inflammation. However, specific animal studies are not extensively documented.
Enzyme Assay
The non-cellular enzyme/receptor binding assays for 4-Methoxycinnamaldehyde would typically involve antiviral activity evaluation using cell-free systems. For antioxidant activity, DPPH, ABTS, and FRAP assays can be employed to measure radical scavenging capacity. The compound's ability to inhibit viral enzymes such as viral polymerases or proteases could be assessed using enzyme inhibition assays. However, specific assays for RSV inhibition are typically cell-based.
Cell Assay
In vitro cellular assays for 4-Methoxycinnamaldehyde typically use human larynx carcinoma cell lines infected with RSV. Cells are treated with various concentrations of the compound, and the cytopathic effect is assessed microscopically or using colorimetric methods such as XTT or MTT assays. The IC₅₀ and selectivity index are calculated. Anti-inflammatory activity can be evaluated using LPS-stimulated macrophages, measuring nitric oxide and cytokine production. Antioxidant activity is assessed using cell-based ROS measurement.
Animal Protocol
In vivo animal studies for 4-Methoxycinnamaldehyde are not extensively documented. Based on its anti-RSV activity, typical study designs would involve mouse models of RSV infection. The compound would be administered orally or intranasally. Viral load in lungs, inflammatory markers, and histopathological changes would be evaluated. Efficacy would be compared to standard antiviral treatments.
ADME/Pharmacokinetics
Pharmacokinetic properties of 4-Methoxycinnamaldehyde are not extensively characterized. As a small lipophilic aldehyde (molecular weight 162.19), it is expected to have good oral absorption and membrane permeability. Metabolic pathways likely involve oxidation of the aldehyde group to the corresponding carboxylic acid, as well as phase II conjugation. The compound may undergo extensive first-pass metabolism. Specific PK parameters such as half-life, Cmax, and bioavailability are not well documented.
Toxicity/Toxicokinetics
Toxicological data for 4-Methoxycinnamaldehyde are limited. As a naturally occurring cinnamaldehyde derivative, it is generally considered to have moderate toxicity at high concentrations. Skin and eye irritation may occur upon contact. The compound may cause allergic reactions in sensitive individuals. Comprehensive toxicology studies are not available. Standard laboratory safety precautions should be observed.
References

[1]. 4-Methoxycinnamaldehyde inhibited human respiratory syncytial virus in a human larynx carcinoma cell line. Phytomedicine. 2009 Sep;16(9):882-6.

Additional Infomation
3-(4-Methoxyphenyl)-2-propenal is one of the cinnamaldehyde compounds. It has been reported that 4-methoxycinnamal exists in Pogostemon cablin and Artemisia annua, and relevant data are available for reference.
4-Methoxycinnamaldehyde is a research-grade natural product intended for laboratory use only. It is not approved for clinical use as a therapeutic agent. Its primary applications include studying antiviral mechanisms against RSV, investigating antioxidant and anti-inflammatory activities, and serving as a reference standard for the analysis of cinnamaldehyde derivatives. It is also used in structure-activity relationship studies of para-substituted cinnamaldehyde analogs.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H10O2
Molecular Weight
162.1852
Exact Mass
162.068
CAS #
1963-36-6
PubChem CID
641294
Appearance
Light yellow to yellow solid powder
Density
1.1±0.1 g/cm3
Boiling Point
308.7±17.0 °C at 760 mmHg
Melting Point
55-60ºC(lit.)
Flash Point
146.5±14.5 °C
Vapour Pressure
0.0±0.7 mmHg at 25°C
Index of Refraction
1.559
LogP
2.07
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
3
Heavy Atom Count
12
Complexity
155
Defined Atom Stereocenter Count
0
SMILES
COC1=CC=C(C=C1)/C=C/C=O
InChi Key
AXCXHFKZHDEKTP-NSCUHMNNSA-N
InChi Code
InChI=1S/C10H10O2/c1-12-10-6-4-9(5-7-10)3-2-8-11/h2-8H,1H3/b3-2+
Chemical Name
(E)-3-(4-methoxyphenyl)prop-2-enal
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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.1656 mL 30.8280 mL 61.6561 mL
5 mM 1.2331 mL 6.1656 mL 12.3312 mL
10 mM 0.6166 mL 3.0828 mL 6.1656 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.

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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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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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
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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  • The answer appears in the Volume (to add to vial) box
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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