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| Targets |
Methyl syringate targets the transient receptor potential ankyrin 1 (TRPA1) channel, of which it is an agonist. TRPA1 is a non-selective cation channel expressed in sensory neurons and various other cell types, involved in the detection of noxious stimuli, pain, and inflammation. By activating TRPA1, methyl syringate suppresses hypoxia-induced inflammation and inhibits the hypoxic induction of COX-2 expression and cell invasion. The compound also has unique inhibitory activity toward aflatoxin production and serves as a bacterial and fungal laccase mediator. Its multiple biological activities make it a compound of interest in both microbiology and inflammation research.
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| ln Vitro |
In vitro, Methyl syringate demonstrates unique inhibitory activity toward aflatoxin production. It is effective in suppressing hypoxia-induced inflammation and inhibits the hypoxic induction of COX-2 expression and cell invasion through TRPA1 activation. The compound acts as a TRPA1 agonist and serves as a bacterial and fungal laccase mediator. As a chemical marker of narcissus nectar, it is used in analytical chemistry for the identification and characterization of nectar sources. Its in vitro activities are concentration-dependent, with efficacy observed at various concentrations depending on the assay and target. Methyl syringate is a versatile compound with applications in microbiology, inflammation research, and analytical chemistry.
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| ln Vivo |
In vivo data for Methyl syringate are limited as the compound is primarily used as a research tool and analytical standard. As a TRPA1 agonist with anti-inflammatory activity, the compound would be expected to modulate pain and inflammatory responses in animal models. TRPA1 activation can produce both pro- and anti-inflammatory effects depending on the context and duration of activation. The compound's ability to suppress hypoxia-induced inflammation suggests potential applications in conditions involving tissue hypoxia. However, detailed in vivo efficacy, pharmacokinetic, and toxicological data for Methyl syringate require further investigation from primary research publications.
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| Enzyme Assay |
In vitro enzyme/receptor binding (non-cellular) assays for Methyl syringate involve measuring its interaction with the TRPA1 channel. Radioligand binding assays using membrane preparations from cells expressing TRPA1 can measure displacement of labeled ligands by Methyl syringate. Alternatively, calcium flux assays using isolated membrane preparations or purified TRPA1 protein can assess channel activation. The compound's laccase mediator activity can be assessed using purified laccase enzymes with appropriate substrates, measuring the compound's ability to facilitate electron transfer and substrate oxidation. Aflatoxin production inhibition assays may use cell-free systems or purified enzymes involved in aflatoxin biosynthesis.
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| Cell Assay |
In vitro cellular experiments with Methyl syringate are performed using various cell lines to assess its anti-inflammatory and TRPA1-mediated activities. Cells expressing TRPA1 are cultured in appropriate media and treated with varying concentrations of Methyl syringate (typically 1-100 μM) for varying durations. TRPA1 activation is assessed by measuring intracellular calcium levels using fluorescent calcium indicators. For inflammation studies, cells are exposed to hypoxic conditions and treated with Methyl syringate. COX-2 expression is measured by RT-qPCR or Western blot. Cell invasion is assessed using transwell invasion assays. Cell viability is evaluated using MTT or CellTiter-Glo assays. Cells are maintained at 37°C in 5% CO₂ with appropriate media supplements.
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| Animal Protocol |
In vivo animal studies with Methyl syringate have not been extensively reported. As a TRPA1 agonist with anti-inflammatory activity, the compound would be expected to demonstrate efficacy in animal models of inflammation or pain. Standard studies could include rodent models of hypoxia-induced inflammation, where Methyl syringate is administered via oral or intraperitoneal routes. Efficacy is assessed by measuring inflammatory markers, COX-2 expression, and tissue histopathology. TRPA1 activation can be confirmed by measuring calcium flux or behavioral responses. However, detailed in vivo studies are needed to establish its therapeutic potential. The compound is intended for research use only.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Methyl syringate are not extensively characterized. The compound has molecular formula C₁₀H₁₂O₅ and molecular weight 212.2 g/mol. It has a melting point of 103-107°C and is soluble in alcohol and ether, slightly soluble in water. Topological polar surface area and monoisotopic mass data are available from PubChem. Storage: follow manufacturer's guidelines. As a small molecule (molecular weight 212.2) with moderate polarity, it is expected to have reasonable oral bioavailability. Detailed pharmacokinetic parameters including half-life, clearance, and bioavailability require further investigation.
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| Toxicity/Toxicokinetics |
Toxicological information for Methyl syringate is not extensively detailed in the available literature. As a naturally occurring compound found in narcissus nectar and used as an analytical standard, it is generally considered to have a favorable safety profile at research-use concentrations. Standard safety precautions for handling research chemicals apply, including use of personal protective equipment (gloves, safety goggles, lab coat) and working in a well-ventilated area. The compound is for research use only and is not approved for human therapeutic use. Purity: >98.0%.
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| References |
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| Additional Infomation |
Methyl eugenol is a benzoic acid ester formed by the condensation of the carboxyl group of eugenol with methanol. It is a plant metabolite. It is a benzoic acid ester, dimethoxybenzene, belonging to the phenolic class of compounds. Its function is related to eugenol. Methyl 4-hydroxy-3,5-dimethoxybenzoate has been reported to exist in Taraxacum formosanum, Litsea hypophaea, and other organisms with relevant data.
Methyl syringate (CAS 884-35-5) is a chemical marker of narcissus nectar and a potent bacterial and fungal laccase mediator. The compound has molecular formula C₁₀H₁₂O₅ and molecular weight 212.2 g/mol. Methyl syringate is an agonist of TRPA1. It has unique inhibitory activity toward aflatoxin production and is effective in suppressing hypoxia-induced inflammation, inhibiting the hypoxic induction of COX-2 expression and cell invasion through TRPA1 activation. Also known as methyl 4-hydroxy-3,5-dimethoxybenzoate, syringic acid methyl ester, and 4-Hydroxy-3,5-dimethoxy-benzoic Acid Methyl Ester. Purity: >98.0%. |
| Molecular Formula |
C10H12O5
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| Molecular Weight |
212.1993
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| Exact Mass |
212.068
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| CAS # |
884-35-5
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| Related CAS # |
Methyl syringate-d6;1182838-09-0
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| PubChem CID |
70164
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
339.9±37.0 °C at 760 mmHg
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| Melting Point |
103-107 °C
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| Flash Point |
132.4±20.0 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.525
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| LogP |
1.1
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
15
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| Complexity |
204
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
ZMXJAEGJWHJMGX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H12O5/c1-13-7-4-6(10(12)15-3)5-8(14-2)9(7)11/h4-5,11H,1-3H3
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| Chemical Name |
methyl 4-hydroxy-3,5-dimethoxybenzoate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~471.25 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.78 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 (11.78 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (11.78 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 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 |
*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.
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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