Physicochemical Properties
| Molecular Formula | C9H10O2 |
| Molecular Weight | 150.17 |
| Exact Mass | 150.068 |
| CAS # | 7786-61-0 |
| Related CAS # | 31853-85-7 |
| PubChem CID | 332 |
| Appearance | Colorless to light yellow liquid |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 245.0±20.0 °C at 760 mmHg |
| Melting Point | 25-29°C |
| Flash Point | 111.3±6.7 °C |
| Vapour Pressure | 0.0±0.5 mmHg at 25°C |
| Index of Refraction | 1.578 |
| LogP | 1.93 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 11 |
| Complexity | 134 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O(C([H])([H])[H])C1=C(C([H])=C([H])C(C([H])=C([H])[H])=C1[H])O[H] |
| InChi Key | YOMSJEATGXXYPX-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 |
| Chemical Name | 4-ethenyl-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: 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) |
Biological Activity
| Targets | Human Endogenous Metabolite |
| ln Vitro | 2-Methoxy-4-vinylphenol (2M4VP) phosphorylates MAPKs such p38, ERK1/2, and JNK and potently inhibits IκB degradation that leads to NF-κB p65 translocation into the nucleus[1]. LPS-induced hyper-acetylation of histone H3 (Lys9/Lys14) is inhibited by 2-methyl-4-vinylphenol (2M4VP)[1]. |
| Cell Assay |
Western Blot Analysis[1] Cell Types: RAW264.7 cells. Tested Concentrations: 0-40 μM. Incubation Duration: 24 h. Experimental Results: Inhibited the over-expression of iNOS and COX-2 protein in LPS-stimulated RAW264.7 cells. |
| References |
[1]. Anti-inflammatory Effect of 2-methoxy-4-vinylphenol via the Suppression of NF-κB and MAPK Activation, and Acetylation of Histone H3. Arch Pharm Res. 2011 Dec;34(12):2109-16. [2]. A Structure-Activity Relationship Study on a Natural Germination Inhibitor, 2-methoxy-4-vinylphenol (MVP), in Wheat Seeds to Evaluate Its Mode of Action. Z Naturforsch C J Biosci. Sep-Oct 2007;62(9-10):694-700. |
| Additional Infomation |
2-methoxy-4-vinylphenol is a member of the class of phenols that is guaiacol in which the hydrogen para- to the hydroxy group is replaced by a vinyl group. It has a role as a pheromone, a flavouring agent and a plant metabolite. 2-Methoxy-4-vinylphenol has been reported in Angelica gigas, Humulus lupulus, and other organisms with data available. 4-Vinylguaiacol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Moringa oleifera leaf oil (part of). |
Solubility Data
| Solubility (In Vitro) | DMSO: 100 mg/mL (665.91 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.65 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 (16.65 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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 3: ≥ 2.5 mg/mL (16.65 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 | 6.6591 mL | 33.2956 mL | 66.5912 mL | |
| 5 mM | 1.3318 mL | 6.6591 mL | 13.3182 mL | |
| 10 mM | 0.6659 mL | 3.3296 mL | 6.6591 mL |