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Pinosylvin monomethyl ether

Cat No.:V53114 Purity: ≥98%
Pinosylvin monomethyl ether has antibacterial and antifungal activity.
Pinosylvin monomethyl ether
Pinosylvin monomethyl ether Chemical Structure CAS No.: 35302-70-6
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
10mg
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Product Description
Pinosylvin monomethyl ether has antibacterial and antifungal activity.
Pinosylvin monomethyl ether (PME) is a naturally occurring methylated stilbenoid phytoalexin predominantly found in the heartwood and induced defense tissues of Pinus species and Cajanus cajan. It possesses inhibitory activity against several Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), Mycobacterium bovis BCG, and Bacillus anthracis. The compound also exhibits antibacterial and antifungal activity. Structurally related to resveratrol, it exhibits antimicrobial, anticancer, and neuroprotective effects.
Biological Activity I Assay Protocols (From Reference)
Targets
Pinosylvin monomethyl ether targets bacterial pathogens, particularly Gram-positive bacteria including MRSA. The compound's mechanism involves antibacterial and fungicidal activity. It also demonstrates inhibitory activity against A2780, J774, and HEK293 cells. Its antioxidant and anti-inflammatory properties suggest additional targets in oxidative stress and inflammatory pathways.
ln Vitro
Pinosylvin monomethyl ether demonstrates potent in vitro antibacterial activity against several Gram-positive bacteria, including isolates of methicillin-resistant Staphylococcus aureus (MRSA), Mycobacterium bovis BCG, and avirulent Bacillus anthracis. It exhibits fungicidal activity. The compound also demonstrates inhibitory activity against A2780, J774, and HEK293 cells, suggesting potential anticancer activity.
ln Vivo
In vivo activity of pinosylvin monomethyl ether has been suggested by its antibacterial, antifungal, antioxidant, anti-inflammatory, and anticancer properties. As a natural stilbenoid phytoalexin, it plays a role in plant defense mechanisms. Further in vivo studies are needed to evaluate its therapeutic potential in animal models of infection, inflammation, and cancer.
Enzyme Assay
In vitro antimicrobial assays for pinosylvin monomethyl ether involve testing its effectiveness against various bacterial and fungal strains using standard susceptibility testing methods. Minimum inhibitory concentration (MIC) values are determined against Gram-positive bacteria including MRSA, M. bovis BCG, and B. anthracis. Antifungal activity is assessed using standard fungal growth inhibition assays.
Cell Assay
In vitro cellular assays for pinosylvin monomethyl ether involve treating cancer cell lines such as A2780, J774, and HEK293 cells with varying concentrations of the compound and measuring cell viability using MTT or other assays. Antibacterial activity is assessed by culturing bacterial cells in the presence of the compound and measuring inhibition of growth.
Animal Protocol
In vivo animal experiments for pinosylvin monomethyl ether are not extensively documented. If used in animal models of bacterial infection, inflammation, or cancer, typical protocols would involve administering the compound to infected or tumor-bearing animals and evaluating efficacy by measuring bacterial load, inflammatory markers, or tumor growth.
ADME/Pharmacokinetics
Pharmacokinetic data for pinosylvin monomethyl ether are limited. The compound has a molecular formula of C15H14O2. It is a natural stilbenoid found in pine species and pigeon pea. Its absorption, distribution, metabolism, and excretion properties have not been fully characterized. Further pharmacokinetic studies are needed to determine its bioavailability.
Toxicity/Toxicokinetics
Toxicological data for pinosylvin monomethyl ether are limited. As a natural product-derived compound, it is generally considered to have low toxicity, but comprehensive toxicological studies have not been reported. The compound is intended for research use only. Standard laboratory safety precautions should be followed when handling this compound.
References

[1]. Lindberg LE, Willför SM, Holmbom BR. Antibacterial effects of knotwood extractives on paper mill bacteria. J Ind Microbiol Biotechnol. 2004;31(3):137-147.

[2]. Structure-fungicidal properties of some 3- and 4-hydroxylated stilbenes and bibenzyl analogues. Phytochemistry, 1992, 31(11):3801–3806.

Additional Infomation
Pinosylvin methyl ether is a stilbene compound. It has been reported to exist in pine trees, Scots pine, and other organisms with relevant data.
Pinosylvin monomethyl ether (PME; (E)-3-hydroxy-5-methoxystilbene) (CAS#: 35302-70-6) has the molecular formula C15H14O2. It is a naturally occurring methylated stilbenoid phytoalexin found in Pinus species and Cajanus cajan. The compound has antibacterial activity against MRSA, M. bovis BCG, and B. anthracis, as well as antifungal, antioxidant, anti-inflammatory, and anticancer properties. It is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H14O2
Molecular Weight
226.27
Exact Mass
226.099
CAS #
35302-70-6
PubChem CID
5281719
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
405.8±24.0 °C at 760 mmHg
Flash Point
245.6±7.8 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.662
LogP
4.34
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
3
Heavy Atom Count
17
Complexity
243
Defined Atom Stereocenter Count
0
SMILES
COC1=CC(=CC(=C1)O)/C=C/C2=CC=CC=C2
InChi Key
JVIXPWIEOVZVJC-BQYQJAHWSA-N
InChi Code
InChI=1S/C15H14O2/c1-17-15-10-13(9-14(16)11-15)8-7-12-5-3-2-4-6-12/h2-11,16H,1H3/b8-7+
Chemical Name
3-methoxy-5-[(E)-2-phenylethenyl]phenol
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 (441.95 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.05 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.

Solubility in Formulation 2: ≥ 2.5 mg/mL (11.05 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 4.4195 mL 22.0975 mL 44.1950 mL
5 mM 0.8839 mL 4.4195 mL 8.8390 mL
10 mM 0.4419 mL 2.2097 mL 4.4195 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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  • 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
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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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