L-Glutamic acid 1-methyl ester
[CAS# 6384-08-3]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Glutamic acid derivative
• Name: L-Glutamic acid 1-methyl ester
• Synonyms: H-Glu-OMe
• Protein Sequence: E
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.16
• CAS Registry Number: 6384-08-3
• EC Number: 873-237-8
• SMILES: COC(=O)[C@H](CCC(=O)O)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 145 ºC (decomp.)
• Index of Refraction: 1.477, Calc.^*
• Boiling Point: 303.3±32.0 ºC (760 mmHg), Calc.^*
• alpha: 35
• Flash Point: 137.2±25.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

L-Glutamic acid 1-methyl ester, also known as methyl L-glutamate, is an organic compound with the molecular formula C6H11NO4. It is an ester derivative of L-glutamic acid, an important amino acid that plays a crucial role in various biological processes. L-Glutamic acid 1-methyl ester is typically a white crystalline powder and is soluble in water and alcohol.

The discovery of L-glutamic acid 1-methyl ester can be traced back to the early 20th century, shortly after the identification of glutamic acid itself, which was first isolated in 1866 by the German chemist Karl Heinrich Ritthausen from wheat gluten. The methyl ester form was subsequently synthesized to study the compound's properties and biological activities. The esterification of glutamic acid with methanol, typically in the presence of an acid catalyst, yields L-glutamic acid 1-methyl ester. This transformation highlights the significance of ester derivatives in expanding the chemical properties and functionalities of amino acids.

L-Glutamic acid 1-methyl ester has various applications, particularly in the fields of biochemistry, pharmaceuticals, and food science. One of its primary uses is as a building block in the synthesis of peptides and proteins. The methyl ester form of glutamic acid can be incorporated into peptide sequences, facilitating the study of protein structure and function. Researchers often utilize L-glutamic acid 1-methyl ester as a protected form of glutamic acid in peptide synthesis, allowing for selective reactions while preserving the integrity of the amino acid.

In pharmaceuticals, L-glutamic acid 1-methyl ester has been investigated for its potential neuroprotective properties. Glutamic acid is a key neurotransmitter in the central nervous system, and its esters have been studied for their ability to modulate glutamatergic signaling. Some research suggests that L-glutamic acid 1-methyl ester may have therapeutic applications in treating neurodegenerative diseases, such as Alzheimer's disease, where glutamate signaling is disrupted. However, further studies are necessary to establish its efficacy and safety in clinical settings.

L-Glutamic acid 1-methyl ester is also used in food science as a flavor enhancer. It is a component of monosodium glutamate (MSG), which is widely used to enhance the umami taste in various food products. The ester form contributes to the flavor profile and overall sensory experience of food, making it a valuable additive in the food industry.

Additionally, L-glutamic acid 1-methyl ester has applications in biochemical research, where it serves as a substrate in enzymatic assays. It can be used to study enzymes involved in amino acid metabolism and related pathways, providing insights into various physiological processes.

Despite its numerous applications, safety considerations are essential when handling L-glutamic acid 1-methyl ester. While it is generally recognized as safe in food applications, some individuals may have sensitivities to glutamate-containing compounds. Therefore, it is important to monitor consumption and adhere to recommended guidelines.

In summary, L-glutamic acid 1-methyl ester is a significant chemical compound with a notable history of discovery and diverse applications in biochemistry, pharmaceuticals, and food science. Its unique properties and versatility continue to make it a subject of interest in contemporary research, highlighting its relevance across multiple fields.

References

1976. Labile protein-methyl ester: Comparison between chemically and enzymatically synthesized. Cellular and Molecular Life Sciences, 32(8).
DOI: 10.1007/bf01933924

2008. Semisynthesis of H-Ras with a glutamic acid methylester at position 61. Peptide Science, 88(1).
DOI: 10.1002/bip.20797

2024. Synthesis, characterization and pharmacological screening of etodolac amino acid's mutual prodrugs. Chemical Papers, 78(8).
DOI: 10.1007/s11696-024-03322-8