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trans-3,5-Dimethoxystilbene

Cat No.:V45891 Purity: ≥98%
trans-3,5-Dimethoxystilbene (cis-Pinosylvin dimethyl ether) is a naturally occurring compound extracted from the benzene extract of jack pine (Pinus bunksiuna) bark.
trans-3,5-Dimethoxystilbene
trans-3,5-Dimethoxystilbene Chemical Structure CAS No.: 21956-56-9
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
trans-3,5-Dimethoxystilbene (cis-Pinosylvin dimethyl ether) is a naturally occurring compound extracted from the benzene extract of jack pine (Pinus bunksiuna) bark.
trans-3,5-Dimethoxystilbene (cis-Pinosylvin dimethyl ether) is a naturally occurring stilbene compound isolated from the bark of jack pine (Pinus banksiana). It has the molecular formula C₁₆H₁₆O₂ and molecular weight 240.30. The compound exhibits activity against Leishmania braziliensis amastigotes with an LC₅₀ of 4.18 µg/mL (17.40 µM), but shows only moderate activity against Trypanosoma cruzi. trans-3,5-Dimethoxystilbene is used in research on antiparasitic agents, natural product chemistry, and inflammation/immunology.
Biological Activity I Assay Protocols (From Reference)
Targets
trans-3,5-Dimethoxystilbene targets Leishmania parasites, exhibiting activity against Leishmania braziliensis amastigotes with an LC₅₀ of 4.18 µg/mL (17.40 µM). It shows only moderate activity against Trypanosoma cruzi. As a stilbene compound, it may also interact with various cellular targets involved in oxidative stress and inflammation. The compound's mechanism of action against Leishmania may involve disruption of parasite metabolism or membrane integrity. Specific molecular targets in parasites are not extensively characterized.
ln Vitro
trans-3,5-Dimethoxystilbene exhibits activity against Leishmania braziliensis amastigotes with an LC₅₀ of 4.18 µg/mL (17.40 µM). It shows moderate activity against Trypanosoma cruzi. The compound is also used in research on inflammation and immunology. Specific IC₅₀ values for other activities are not extensively documented. The compound's antiparasitic activity makes it a potential lead for drug discovery against leishmaniasis.
ln Vivo
In vivo activity data for trans-3,5-Dimethoxystilbene are limited in the literature. Based on its in vitro activity against Leishmania parasites, it is anticipated to have potential in vivo efficacy in animal models of leishmaniasis. However, specific animal studies detailing its therapeutic effects, dosing, and pharmacokinetics are not extensively documented.
Enzyme Assay
The non-cellular enzyme/receptor binding assays for trans-3,5-Dimethoxystilbene would typically involve antiparasitic activity evaluation using cell-free systems. For Leishmania, assays could involve measuring the compound's effect on parasite enzyme activity or metabolic processes. However, antiparasitic activity is typically assessed in cell-based assays using infected macrophages. The compound's antioxidant activity could be evaluated using DPPH, ABTS, or FRAP assays.
Cell Assay
In vitro cellular assays for trans-3,5-Dimethoxystilbene typically use Leishmania-infected macrophage cultures to evaluate antiparasitic activity. Macrophages are infected with Leishmania braziliensis amastigotes and treated with various concentrations of the compound. Parasite load is determined by counting intracellular parasites or by measuring parasite-specific markers. The LC₅₀ is calculated from dose-response curves. Cell viability of host macrophages is assessed to ensure selectivity. Activity against Trypanosoma cruzi is evaluated similarly.
Animal Protocol
In vivo animal studies for trans-3,5-Dimethoxystilbene are not extensively documented. Based on its anti-Leishmanial activity, typical study designs would involve mouse models of cutaneous or visceral leishmaniasis. The compound would be administered orally or intraperitoneally. Parasite burden in target organs, lesion size (for cutaneous), and immune responses would be evaluated. Efficacy would be compared to standard anti-Leishmanial drugs.
ADME/Pharmacokinetics
Pharmacokinetic properties of trans-3,5-Dimethoxystilbene are not extensively characterized. As a stilbene with molecular weight 240.30, it is expected to have moderate lipophilicity and reasonable oral absorption. The compound is soluble in DMSO (100 mg/mL). Metabolic pathways likely involve phase I oxidation of the methoxy groups and phase II conjugation. Specific PK parameters such as half-life, Cmax, and bioavailability are not well documented.
Toxicity/Toxicokinetics
Toxicological data for trans-3,5-Dimethoxystilbene are limited. As a naturally occurring stilbene, it is generally considered to have low toxicity. However, comprehensive toxicology studies are not available. The compound may cause skin and eye irritation upon contact. Standard laboratory safety precautions should be observed when handling this compound.
Additional Infomation
(E)-3,5-Dimethoxystilbene is a stilbene compound. It has been reported to exist in holly-leaved hibiscus, ginger, and other organisms with relevant data.
trans-3,5-Dimethoxystilbene 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 antiparasitic agents against Leishmania, investigating the bioactivity of stilbene compounds, and serving as a reference standard in natural product chemistry and inflammation/immunology research. The compound is also known as cis-Pinosylvin dimethyl ether.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H16O2
Molecular Weight
240.2970
Exact Mass
240.115
CAS #
21956-56-9
PubChem CID
5316874
Appearance
Off-white to light yellow solid powder
Density
1.089g/cm3
Boiling Point
376.5ºC at 760mmHg
Flash Point
150.7ºC
Vapour Pressure
1.56E-05mmHg at 25°C
Index of Refraction
1.615
LogP
3.874
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
4
Heavy Atom Count
18
Complexity
244
Defined Atom Stereocenter Count
0
SMILES
O(C([H])([H])[H])C1C([H])=C(C([H])=C(/C(/[H])=C(\[H])/C2C([H])=C([H])C([H])=C([H])C=2[H])C=1[H])OC([H])([H])[H]
InChi Key
BIYGTLDPTJMNET-CMDGGOBGSA-N
InChi Code
InChI=1S/C16H16O2/c1-17-15-10-14(11-16(12-15)18-2)9-8-13-6-4-3-5-7-13/h3-12H,1-2H3/b9-8+
Chemical Name
1,3-dimethoxy-5-[(E)-2-phenylethenyl]benzene
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 (~416.15 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.40 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 4.1615 mL 20.8073 mL 41.6146 mL
5 mM 0.8323 mL 4.1615 mL 8.3229 mL
10 mM 0.4161 mL 2.0807 mL 4.1615 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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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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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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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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