2-Methoxy-4-vinylphenol
(Synonyms: 4-乙烯基-2-甲氧基苯酚) 目录号 : GC62777
2-Methoxy-4-vinylphenol (2M4VP) 是天然的发芽抑制剂，具有抗炎活性。
Cas No.:7786-61-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-Methoxy-4-vinylphenol (2M4VP), a naturally Germination inhibitor, exerts potent anti-inflammatory effects[1][2].
2-Methoxy-4-vinylphenol (2M4VP) potently inhibits the translocation of NF-κB p65 into the nucleus by IκB degradation following IκB-α phosphorylation and the phosphorylation of MAPKs such as p38, ERK1/2, and JNK[1]. 2-Methoxy-4-vinylphenol (2M4VP) inhibits hyper-acetylation of histone H3 (Lys9/Lys14) induced by LPS[1].
[1]. Jin Boo Jeong, et al. 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]. Hossein Reza Darabi, et al. 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.
| Cas No. | 7786-61-0 | SDF | |
| 别名 | 4-乙烯基-2-甲氧基苯酚 | ||
| 分子式 | C9H10O2 | 分子量 | 150.17 |
| 溶解度 | 储存条件 | Store at -20°C, stored under nitrogen | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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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 |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
2-Methoxy-4-vinylphenol Attenuates Migration of Human Pancreatic Cancer Cells via Blockade of FAK and AKT Signaling
Anticancer Res 2019 Dec;39(12):6685-6691.PMID:31810933DOI:10.21873/anticanres.13883.
Background/aim: No effective therapeutics have yet been developed for pancreatic cancer. 2-Methoxy-4-vinyl phenol (2M4VP), a member of the class of phenols, has been demonstrated to have anti-inflammatory properties and cause cell cycle arrest making it an attractive candidate drug for the treatment of pancreatic cancer. Materials and methods: The effects of 2M4VP were examined in Panc-1 and SNU-213 human pancreatic cancer cells. Results: 2M4VP had anticancer effects on pancreatic cancer cell lines, Panc-1 and SNU-213. 2M4VP reduced the viability of Panc-1 cells by inhibiting the expression of the cell nuclear antigen (PCNA) protein. 2M4VP also suppressed the migratory activity of both cell lines. In addition, treatment with 2M4VP effectively decreased the phosphorylation of Focal Adhesion Kinase (FAK) and AKT. Conclusion: 2M4VP might be used as a pancreatic cancer treatment supplement.
Bioactive Potential of 2-Methoxy-4-vinylphenol and Benzofuran from Brassica oleracea L. var. capitate f, rubra (Red Cabbage) on Oxidative and Microbiological Stability of Beef Meat
Foods 2020 May 4;9(5):568.PMID:32375308DOI:10.3390/foods9050568.
In the future, plant based phytochemicals will be considered as efficient replacement sources of chemical preservatives, to act as potential bio-preservatives. We investigated the antibacterial and antioxidant activity of red cabbage (RC) extracts using different solvents. Among all extracts, chloroform extract exhibited strong antimicrobial and antioxidant activities. Hence, the phytochemical constitutions of the RC chloroform extract was examined by GC-MS analysis, and further, based on molecular docking analysis, revealed 2-Methoxy-4-vinylphenol and benzofuran as two major compounds found to be possessing higher degrees of interaction with DNA gyrase (4PLB; -8.63 Kcal.mol-1) and lipoprotein (LpxC-8.229 Kcal.mol-1), respectively, of the bacterial cell wall, which leads to higher antimicrobial efficacy. Further, it was confirmed with that the in vivo Caenorhabditis elegans model (but no cytotoxic effect) was exhibited in the MCF-7 cell line. Thus, we investigated the influence of this extract on the shelf life of meat under refrigeration storage. The physicochemical properties were observed periodically, and microbial analysis was conducted. The shelf life of the beef was enhanced (up to eight days) in terms of microbial and physiochemical properties, at 4 ± 2 °C when compared to control. We concluded that chloroform extract of RC has potential as a natural preservative in the meat processing industry.
Anti-inflammatory activity of 2-Methoxy-4-vinylphenol involves inhibition of lipopolysaccharide-induced inducible nitric oxidase synthase by heme oxygenase-1
Immunopharmacol Immunotoxicol 2023 Apr 5;1-8.PMID:36995736DOI:10.1080/08923973.2023.2197141.
Background: 2-Methoxy-4-vinylphenol (2M4VP) is a natural anti-inflammatory compound derived from red wine, but its underlying mechanism remains unclear. Heme oxygenase-1 (HO-1), an anti-inflammatory enzyme, inhibits NO gene expression, while nuclear factor erythroid 2-related factor 2 (Nrf2), a transcription factor involved in HO-1 production, binds to the antioxidant response element (ARE) in the nucleus and promotes HO-1 transcription. Based on the hypothesis that the inhibitory effect of 2M4VP on NO production is mediated by HO-1, we examined the possible mechanism of the anti-inflammatory activity of 2M4VP in this study. Materials and methods: The anti-inflammatory activity of 2M4VP was analyzed by Griess method, ELISA, qPCR, and Western blotting using LPS-treated macrophage lineage RAW264.7 cells. The impact of 2M4VP on the Nrf2/ARE pathway was also analyzed using immunocytochemistry and an ARE luciferase reporter using HEK293 cells. Results: The results showed that 2M4VP reduced the production of LPS-induced NO and inducible nitric oxidase synthase (iNOS). In addition, 2M4VP increased the expression of HO-1, while pretreatment with the Nrf2 inhibitor ML385 downregulated HO-1 expression. 2M4VP induced Kelch-like ECH-associated protein 1 (Keap1) degradation. Furthermore, it promoted Nrf2 nuclear translocation and increased luciferase activity by binding to the ARE. Conclusions: 2M4VP induces Keap1 degradation and promotes Nrf2 nuclear translocation. Activation of Nrf2/ARE pathway enhances HO-1 expression and leads to iNOS inhibition for anti-inflammatory function.
2-Methoxy-4-vinylphenol can induce cell cycle arrest by blocking the hyper-phosphorylation of retinoblastoma protein in benzo[a]pyrene-treated NIH3T3 cells
Biochem Biophys Res Commun 2010 Oct 1;400(4):752-7.PMID:20816752DOI:10.1016/j.bbrc.2010.08.142.
Benzo[a]pyrene (BaP) is an environment carcinogen that can enhance cell proliferation by disturbing the signal transduction pathways in cell cycle regulation. In this study, the effects of 2M4VP on cell proliferation, cell cycle and cell cycle regulatory proteins were studied in BaP-treated NIH 3T3 cells to establish the molecular mechanisms of 2M4VP as anti-proliferative agents. 2M4VP exerted a dose-dependent inhibitory effect on cell growth correlated with a G1 arrest. Analysis of G1 cell cycle regulators expression revealed 2M4VP increased expression of CDK inhibitor, p21Waf1/Cip1 and p15 INK4b, decreased expression of cyclin D1 and cyclin E, and inhibited kinase activities of CDK4 and CDK2. However, 2M4VP did not affect the expression of CDK4 and CDK2. Also, 2M4VP inhibited the hyper-phosphorylation of Rb induced by BaP. Our results suggest that 2M4VP induce growth arrest of BaP-treated NIH 3T3 cells by blocking the hyper-phosphorylation of Rb via regulating the expression of cell cycle-related proteins.
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.PMID:22210037DOI:10.1007/s12272-011-1214-9.
Although inflammation acts as host defense mechanism against infection or injury and is primarily a self limiting process, inadequate resolution of inflammatory responses leads to various chronic disorders. This work aimed to elucidate the anti-inflammatory effects of 2-Methoxy-4-vinylphenol (2M4VP) isolated from pine needles in LPS-stimulated RAW264.7 cells. Some key pro-inflammatory mediators including nitric oxide (NO), prostaglandins (PGE(2)), inducible NO synthase (iNOS), and cyclooxygenase-2 (COX-2) were studied by sandwich ELISA and western blot. In addition, suppression of NF-κB and MAPK activation, and histone acetylation was studied by western blot analysis and immunostaining. 2M4VP dosedependently inhibited NO and PGE(2) production and also blocked LPS-induced iNOS and COX-2 expression. In addition, 2M4VP potently inhibited the translocation of NF-κB p65 into the nucleus by IκB degradation following IκB-α phosphorylation and the phosphorylation of MAPKs such as p38, ERK1/2, and JNK. Also, 2M4VP inhibited hyper-acetylation of histone H3 (Lys9/Lys14) induced by LPS. Taken together, our results suggest that 2M4VP, a naturally occurring phenolic compound, exert potent anti-inflammatory effects by inhibiting LPS-induced NO, PGE(2), iNOS, and COX-2 in RAW264.7 cells. These effects are mediated by suppression of NF-κB and MAPK activation and histone acetylation.