Methyl p-coumarate
(Synonyms: 4-羟基肉桂酸甲酯; Methyl 4-hydroxycinnamate) 目录号 : GC61670
Methylp-coumarate(Methyl4-hydroxycinnamate)，一种从Trixismichuacanavarlongifolia的花中分离出来的对香豆酸(pCA)的酯化衍生物。Methylp-coumarate可抑制B16小鼠黑素瘤细胞中黑色素的形成。Methylp-coumarate对链格孢菌和其他病原体也具有很强的体外抑制作用。
Cas No.:3943-97-3
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
Methyl p-coumarate (Methyl 4-hydroxycinnamate), an esterified derivative of p-Coumaric acid (pCA), is isolated from the flower of Trixis michuacana var longifolia. Methyl p-coumarate could inhibit the melanin formation in B16 mouse melanoma cells. Methyl p-coumarate also has strong in vitro inhibitory effect on A. alternata and other pathogens[1][2].
[1]. Kubo I, et, al. Methyl p-coumarate, a melanin formation inhibitor in B16 mouse melanoma cells. Bioorg Med Chem. 2004 Oct 15;12(20):5349-54. [2]. Yuan S, et, al. Defense Responses, Induced by p-Coumaric Acid and Methyl p-Coumarate, of Jujube ( Ziziphus jujuba Mill.) Fruit against Black Spot Rot Caused by Alternaria alternate. J Agric Food Chem. 2019 Mar 13;67(10):2801-2810.
| Cas No. | 3943-97-3 | SDF | |
| 别名 | 4-羟基肉桂酸甲酯; Methyl 4-hydroxycinnamate | ||
| Canonical SMILES | O=C(OC)/C=C/C1=CC=C(O)C=C1 | ||
| 分子式 | C10H10O3 | 分子量 | 178.18 |
| 溶解度 | 储存条件 | Store at -20°C | |
| 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 | 5.6123 mL | 28.0615 mL | 56.123 mL |
| 5 mM | 1.1225 mL | 5.6123 mL | 11.2246 mL |
| 10 mM | 0.5612 mL | 2.8062 mL | 5.6123 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。
Producing Methyl p-coumarate from Herbaceous Lignin via a "Clip-Off" Strategy
J Agric Food Chem 2022 May 11;70(18):5624-5633.PMID:35473308DOI:10.1021/acs.jafc.1c08353.
As the most abundant renewable aromatic resource on Earth, lignin is a preferred starting material for producing bulk chemicals via a sustainable route. In this study, we provide a novel and efficient "clip-off" approach for producing Methyl p-coumarate, an important and versatile fine chemical by selective cleavage of the ester linkage in herbaceous lignin in the presence of commercial metal chlorides. When bagasse lignin was depolymerized at 155 °C for 4 h, a 12.7% yield of aromatic chemicals was obtained in the presence of CuCl2, 71.7% of which was identified as Methyl p-coumarate (the yield was 9.1%). Further investigation of the structural evolution of lignin revealed that the ester linkages in lignin were efficiently broken via intensive transesterification with methanol accompanied by the simultaneous weakening of the inter-/intramolecular hydrogen bonds. Moreover, this observation of selective cleavage of ester linkages could be further confirmed by the conversion of model compounds with characteristic bonds under identical reaction conditions. Therefore, this work provides a new insight into the production of value-added chemicals from renewable resources.
Methyl p-coumarate Ameliorates the Inflammatory Response in Activated-Airway Epithelial Cells and Mice with Allergic Asthma
Int J Mol Sci 2022 Nov 28;23(23):14909.PMID:36499236DOI:10.3390/ijms232314909.
Methyl p-coumarate (methyl p-hydroxycinnamate) (MH) is a natural compound found in a variety of plants. In the present study, we evaluated the ameliorative effects of MH on airway inflammation in an experimental model of allergic asthma (AA). In this in vitro study, MH was found to exert anti-inflammatory activity on PMA-stimulated A549 airway epithelial cells by suppressing the secretion of IL-6, IL-8, MCP-1, and ICAM-1. In addition, MH exerted an inhibitory effect not only on NF-κB (p-NF-κB and p-IκB) and AP-1 (p-c-Fos and p-c-Jun) activation but also on A549 cell and EOL-1 cell (eosinophil cell lines) adhesion. In LPS-stimulated RAW264.7 macrophages, MH had an inhibitory effect on TNF-α, IL-1β, IL-6, and MCP-1. The results from in vivo study revealed that the increases in eosinophils/Th2 cytokines/MCP-1 in the bronchoalveolar lavage fluid (BALF) and IgE in the serum of OVA-induced mice with AA were effectively inhibited by MH administration. MH also exerted a reductive effect on the immune cell influx, mucus secretion, and iNOS/COX-2 expression in the lungs of mice with AA. The effects of MH were accompanied by the inactivation of NF-κB. Collectively, the findings of the present study indicated that MH attenuates airway inflammation in mice with AA, suggesting its potential as an adjuvant in asthma therapy.
Methyl p-coumarate, a melanin formation inhibitor in B16 mouse melanoma cells
Bioorg Med Chem 2004 Oct 15;12(20):5349-54.PMID:15388162DOI:10.1016/j.bmc.2004.07.052.
p-Coumaric acid (4-hydroxycinnamic acid) and Methyl p-coumarate (methyl 4-hydroxycinnamate) inhibit the oxidation of L-tyrosine catalyzed by mushroom tyrosinase. However, both were oxidized as monophenol substrate analogues at an extremely slow rate. This oxidation was significantly accelerated as soon as catalytic amounts (0.01 mM) of L-3,4-dihydroxyphenylalanine (L-DOPA) became available as a co-factor. Methyl p-coumarate significantly suppressed the melanin formation in B16 mouse melanoma cells, whereas p-coumaric acid did not show this activity.
Defense Responses, Induced by p-Coumaric Acid and Methyl p-coumarate, of Jujube ( Ziziphus jujuba Mill.) Fruit against Black Spot Rot Caused by Alternaria alternata
J Agric Food Chem 2019 Mar 13;67(10):2801-2810.PMID:30794401DOI:10.1021/acs.jafc.9b00087.
The esterified fraction of jujube ( Ziziphus jujuba Mill.) peel extract showed strong antifungal activity on Alternaria alternata. p-Coumaric acid (pCA) was found to be the most predominant individual phenolic acid that was correlated highly with the antifungal activity of the esterified fraction. Thus, effects of postharvest treatments with pCA and its simplest esterified derivative Methyl p-coumarate (MeCA) against black spot rot on jujube fruit caused by A. alternata were investigated. pCA and MeCA strongly suppressed in vitro growth of the fungus and significantly reduced postharvest Alternaria rot on fresh jujubes. Biochemical and transcriptional analysis revealed that pCA and MeCA regulated the expression of some genes encoding antioxidant enzymes and their enzymatic activities, enhanced the phenylpropanoid pathway metabolism, and activated the expression of genes encoding pathogenesis-related proteins. These results suggested that, apart from its direct antifungal activity, pCA and MeCA induced defense responses in jujube fruit against postharvest Alternaria rot.
In vitro and in vivo toxicological evaluations of methyl ferulate, Methyl p-coumarate, and pulegone 1,2-epoxide
Pharm Biol 2016;54(3):523-9.PMID:26067677DOI:10.3109/13880209.2015.1052148.
Context: Toxicological screening of natural compounds for medicinal purposes. Objectives: The objective of this study is to evaluate the toxicity of methyl ferulate (MF), Methyl p-coumarate (MpC), and pulegone 1,2-epoxide (PE) with in vitro and in vivo assays. Materials and methods: The in vitro toxicity of MF, MpC, and PE was assessed at a concentration of 10 mg/ml with the Ames assay using two strains of Salmonella typhimurium TA98 and TA100. Human red blood cells (RBC) were used to determine the hemolytic activity of these compounds. The cytotoxicity of above compounds was determined with brine shrimp lethality bioassay (BSLB) at the concentrations of 0.1-20 mg/ml. While dermal and ocular irritation studies were conducted on healthy rabbits (n = 8) for 96 and 12 h post-topical application of test compounds, respectively. Results: PE produced 6-8% hemolysis of RBCs at all the tested concentrations while MF and MpC produced 10-5% hemolysis up to 20 mg/ml, and 50-85% hemolysis at concentrations of 40 and 80 mg/ml, respectively. The Ames assay indicated that MF, MpC, and PE were non-mutagenic as the test values were not significantly higher as compared with background values of the assay. BSLB suggested the lethal concentration (LC50) values of MF, MpC, and PE as 4.38, 6.74, and 25.91 mg/ml, respectively. In vivo ocular and dermal irritation scores of MF, MpC, and PE were comparable with ethanol (control) in rabbits indicating the non-irritant nature of these natural compounds. Conclusion: The present studies suggest that these compounds are non-toxic/non-irritant and might be used for medicinal purposes.