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| Other Sizes |
| Targets |
Methyl L-pyroglutamate has been reported to exhibit anti-inflammatory activity. The compound’s mechanism of action is not fully elucidated but may involve modulation of inflammatory signaling pathways. As a derivative of pyroglutamic acid, it may interact with enzymes or receptors involved in glutamate metabolism or neurotransmission. Pyroglutamate derivatives are known to affect neurotransmitter systems, and methyl L-pyroglutamate is used in neurochemical studies to investigate these effects. Its chiral nature makes it a valuable tool for studying stereospecific interactions in biological systems.
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| ln Vitro |
Methyl L-pyroglutamate exhibits in vitro anti-inflammatory activity. In cell-based assays, it has been shown to reduce the production of pro-inflammatory cytokines such as TNF-α and IL-6. It may also modulate the activity of enzymes involved in inflammation, such as cyclooxygenase (COX) or lipoxygenase (LOX). The compound is used in neurochemical studies to investigate neurotransmitter synthesis and release. Its effects on neurotransmitter systems have been studied in neuronal cell cultures. These in vitro activities confirm its potential as a research tool for inflammation and neuroscience.
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| ln Vivo |
In vivo studies with methyl L-pyroglutamate have been conducted in animal models of inflammation and neurological disorders. Its anti-inflammatory activity has been evaluated in models such as carrageenan-induced paw edema or acetic acid-induced vascular permeability. In these models, the compound has shown efficacy in reducing inflammation. It has also been studied in models of cognitive function and neurodegenerative diseases due to its effects on neurotransmitter systems. Further in vivo studies are needed to fully characterize its pharmacokinetic and pharmacodynamic properties.
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| Enzyme Assay |
In vitro enzyme assays for methyl L-pyroglutamate are not commonly performed for a specific enzyme target. However, its activity as a pyroglutamate derivative may be studied in assays measuring pyroglutamate aminopeptidase or other enzymes involved in glutamate metabolism. The compound’s anti-inflammatory activity can be assessed in enzyme assays for COX-1, COX-2, or LOX. These assays involve incubating the enzyme with substrate and measuring the production of inflammatory mediators in the presence and absence of the compound. Such assays help elucidate its mechanism of action.
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| Cell Assay |
In vitro cellular assays for methyl L-pyroglutamate are conducted in various cell types, including immune cells (e.g., macrophages) and neuronal cells. In immune cells, the compound’s anti-inflammatory activity is assessed by measuring cytokine production (e.g., TNF-α, IL-6, IL-1β) using ELISA or qPCR after stimulation with LPS or other inflammatory stimuli. In neuronal cells, its effects on neurotransmitter synthesis and release are studied by measuring neurotransmitter levels (e.g., glutamate, GABA) using HPLC or LC-MS. Cytotoxicity is assessed using standard cell viability assays. These experiments characterize the compound’s biological activity.
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| Animal Protocol |
In vivo animal experiments with methyl L-pyroglutamate are conducted in rodent models of inflammation and neurological disorders. In inflammation models, the compound is administered orally or intraperitoneally, and inflammation is induced by carrageenan or other irritants. Paw edema or other inflammatory markers are measured. In neurological models, the compound is administered and its effects on behavior, cognition, and neurotransmitter levels are assessed. These studies help define the compound’s in vivo efficacy and potential therapeutic applications. Further studies are needed to fully characterize its effects.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for methyl L-pyroglutamate are limited. The compound has a molecular weight of 143.14 and is a small, polar molecule. It is soluble in organic solvents such as chloroform, dichloromethane, ethyl acetate, DMSO, and acetone. Its bioavailability and half-life have not been extensively characterized. The compound is typically stored at -20°C and is air-sensitive. Further PK studies would be needed if the compound were to be developed as a therapeutic agent.
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| Toxicity/Toxicokinetics |
Methyl L-pyroglutamate is considered to have low toxicity based on its use as a research compound. It has been used in various in vitro and in vivo studies without significant adverse effects reported at relevant concentrations. However, comprehensive toxicological evaluations have not been extensively published. As with any chemical, standard laboratory safety precautions should be followed when handling this compound. Further toxicity studies would be required to support any potential clinical development.
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| References | |
| Additional Infomation |
Reports indicate that 5-oxo-L-proline methyl esters have been found in Taraxacum officinale and Pseudochloa heterophylla, and relevant data are available for reference.
Methyl L-pyroglutamate is a chiral alpha amino acid ester used in neurochemical studies and as a building block in organic synthesis. It has anti-inflammatory activity and is extracted from cabbage. The compound is also known as L-pyroglutamic acid methyl ester. It is used to investigate neurotransmitter synthesis and release. The compound is available in high purity (>98%) for research applications. Its chiral nature makes it valuable for studying stereospecific interactions. It should be stored desiccated at -20°C and handled under inert atmosphere due to air sensitivity. |
| Molecular Formula |
C₆H₉NO₃
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|---|---|
| Molecular Weight |
143.14
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| Exact Mass |
143.058
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| CAS # |
4931-66-2
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| PubChem CID |
78646
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| Appearance |
Colorless to light yellow liquid（Density：1.226 g/cm3）
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
304.7±35.0 °C at 760 mmHg
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| Flash Point |
138.1±25.9 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.465
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| LogP |
-1.92
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
10
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| Complexity |
166
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O(C([H])([H])[H])C([C@]1([H])C([H])([H])C([H])([H])C(N1[H])=O)=O
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| InChi Key |
HQGPKMSGXAUKHT-BYPYZUCNSA-N
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| InChi Code |
InChI=1S/C6H9NO3/c1-10-6(9)4-2-3-5(8)7-4/h4H,2-3H2,1H3,(H,7,8)/t4-/m0/s1
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| Chemical Name |
methyl (2S)-5-oxopyrrolidine-2-carboxylate
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| Synonyms |
Methyl Lpyroglutamate; Methyl L pyroglutamate
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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 (~698.62 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (17.47 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 (17.47 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 (17.47 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 | 6.9862 mL | 34.9308 mL | 69.8617 mL | |
| 5 mM | 1.3972 mL | 6.9862 mL | 13.9723 mL | |
| 10 mM | 0.6986 mL | 3.4931 mL | 6.9862 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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