Methyl syringate
(Synonyms: 丁香酸甲酯) 目录号 : GC39117
Methyl syringate (Syringic Acid Methyl Ester), a plant phenolic compound, is a specific and selective TRPA1 agonist.
Cas No.:884-35-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Methyl syringate (Syringic Acid Methyl Ester), a plant phenolic compound, is a specific and selective TRPA1 agonist.
Methyl syringate increases cytosolic Ca2+ in human TRPA1 (hTRPA1)-transfected cells[1]. Methyl syringate selectively activated hTRPA1 (EC(50) = 507.4 μM), but not hTRPV1[2].
Methyl syringate regulates food intake and gastric emptying through a TRPA1-mediated pathway and, by extension, can contribute to weight suppression in ICR mice[1].
[1] Kim MJ, et al. PLoS One. 2013, 8(8):e71603. [2] Son HJ, et al. Arch Pharm Res. 2012, 35(12):2211-8. [3] Park J, et al. Phytomedicine. 2016, 23(3):324-9.
| Cas No. | 884-35-5 | SDF | |
| 别名 | 丁香酸甲酯 | ||
| Canonical SMILES | O=C(OC)C1=CC(OC)=C(O)C(OC)=C1 | ||
| 分子式 | C10H12O5 | 分子量 | 212.2 |
| 溶解度 | DMSO : 100 mg/mL (471.25 mM; ultrasonic and warming and heat to 60°C) | 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 | 4.7125 mL | 23.5627 mL | 47.1254 mL |
| 5 mM | 0.9425 mL | 4.7125 mL | 9.4251 mL |
| 10 mM | 0.4713 mL | 2.3563 mL | 4.7125 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。
Methyl syringate, a TRPA1 agonist represses hypoxia-induced cyclooxygenase-2 in lung cancer cells
Phytomedicine 2016 Mar 15;23(3):324-9.PMID:26969386DOI:10.1016/j.phymed.2016.01.009.
Background: We have previously found that Methyl syringate is a specific and selective agonist of the human transient receptor potential channel ankyrin 1 (TRPA1) and suppresses food intake and gastric emptying in imprinting control region mice. Because TRPA1 has been implicated in inflammatory responses, and inflammation and tumorigenesis are stimulated by the cyclooxygenase-2 (COX-2)/prostaglandin E2 pathway in hypoxic cancer cells. Purpose: This study examined the effects of Methyl syringate on hypoxia-induced COX-2 in human distal lung epithelial A549 cells. Study design: The effect of the Methyl syringate on suppression of hypoxia-induced COX-2 in A549 cells were determined by Western blot and/or quantitative real-time polymerase chain reaction. The anti-invasive effect of Methyl syringate was evaluated on A549 cells using matrigel invasion assay. Results: Methyl syringate suppressed hypoxia-induced COX-2 protein and mRNA expression and promoter activity and reduced hypoxia-induced cell migration and invasion and secretion of vascular endothelial growth factor. These effects were antagonized by a TRPA1 antagonist, implying their mediation by the TRPA1 pathway. Conclusion: Together, these results indicate that Methyl syringate inhibits the hypoxic induction of COX-2 expression and cell invasion through TRPA1 activation. These findings suggest that Methyl syringate could be effective to suppress hypoxia-induced inflammation and indicate an additional functional effect of Methyl syringate.
Methyl syringate, a low-molecular-weight phenolic ester, as an activator of the chemosensory ion channel TRPA1
Arch Pharm Res 2012 Dec;35(12):2211-8.PMID:23263817DOI:10.1007/s12272-012-1220-6.
Transient receptor potential channel ankryn 1 (TRPA1) and transient receptor potential channel vanilloid 1 (TRPV1) are members of the TRP superfamily of structurally related, nonselective cation channels and are often coexpressed in sensory neurons. Extracts of the first leaves of Kalopanax pictus Nakai (Araliaceae) have been shown to activate hTRPA1 and hTRPV1. Therefore, the effects of six commercially available chemicals (Methyl syringate, coniferyl alcohol, protocatechuic acid, hederacoside C, α-hederin, and eleutheroside B) found in K. pictus were investigated on cultured cells expressing hTRPA1 and hTRPV1. Of the six compounds, Methyl syringate selectively activated hTRPA1 (EC(50) = 507.4 μM), but not hTRPV1. Although Methyl syringate had a higher EC(50) compared with allyl isothiocyanate (EC(50) = 7.4 μM) and cinnamaldehyde (EC(50) = 22.2 μM), the present study provides evidence that Methyl syringate from K. pictus is a specific and selective activator of hTRPA1.
The TRPA1 agonist, Methyl syringate suppresses food intake and gastric emptying
PLoS One 2013 Aug 21;8(8):e71603.PMID:23990963DOI:10.1371/journal.pone.0071603.
Transient receptor potential channel ankryn 1 (TRPA1) expressed in the gastrointestinal tract is associated with gastric motility, gastric emptying, and food intake. In this study, we investigated the effects of Methyl syringate, a specific and selective TRPA1 agonist, on food intake, gastric emptying, and gut hormone levels in imprinting control region (ICR) mice. The administration of Methyl syringate suppressed cumulative food intake and gastric emptying. In addition, treatment with ruthenium red (RR), a general cation channel blocker, and HC-030031, a selective TRPA1 antagonist, inhibited methyl syringate-induced reduction of food intake and delayed gastric emptying in ICR mice. Methyl syringate also increased plasma peptide YY (PYY) levels, but not glucagon-like peptide-1 (GLP-1) levels. The elevation in PYY was blocked by treatment with RR and HC-030031. The present findings indicate that Methyl syringate regulates food intake and gastric emptying through a TRPA1-mediated pathway and, by extension, can contribute to weight suppression.
Characterization of a Monoclonal Antibody against Syringate Derivatives: Application of Immunochemical Detection of Methyl syringate in Honey
J Agric Food Chem 2016 Aug 24;64(33):6495-501.PMID:27477590DOI:10.1021/acs.jafc.6b01328.
Syringic acid is one of the key skeletal structures of plant-derived chemicals. The derivatives of syringic acid have certain biological functions. In this study, a monoclonal antibody to syringic acid-based phytochemicals was prepared and characterized. The obtained antibody reacted with Methyl syringate, syringic acid, and leonurine. Methyl syringate is a characteristic compound found in manuka honey, other honey varieties, and plants. Manuka honey was fractionated using HPLC, and the reactivity of the fractions with the antibody was examined. The antibody reacted with the fraction in which Methyl syringate was eluted. The amount of Methyl syringate in honeys as estimated by ELISA using the antibody had a good linearity compared with that estimated by HPLC. These results suggest that the antibody is applicable for the immunochemical detection of syringic acid derivatives in plants and foods.
Methyl syringate: an efficient phenolic mediator for bacterial and fungal laccases
Bioresour Technol 2012 Nov;124:371-8.PMID:22995168DOI:10.1016/j.biortech.2012.08.023.
The aim of the present work is to provide insight into the mechanism of laccase reactions using syringyl-type mediators. We studied the pH dependence and the kinetics of oxidation of syringyl-type phenolics using the low CotA and the high redox potential TvL laccases. Additionally, the efficiency of these compounds as redox mediators for the oxidation of non-phenolic lignin units was tested at different pH values and increasing mediator/non-phenolic ratios. Finally, the intermediates and products of reactions were identified by LC-MS and (1)H NMR. These approaches allow concluding on the (1) mechanism involved in the oxidation of phenolics by bacterial laccases, (2) importance of the chemical nature and properties of phenolic mediators, (3) apparent independence of the enzyme's properties on the yields of non-phenolics conversion, (4) competitive routes involved in the catalytic cycle of the laccase-mediator system with several new C-O coupling type structures being proposed.