23150-65-4

Basic information

• Product Name: L-Glutamic acid dimethyl ester hydrochloride
• Synonyms: H-GLU(OME)-OME HCL;GLUTAMIC ACID(OME)-OME HCL;Dimethyl L-glutamate hydrochloride~H-Glu(OMe)-OMe.HCl;dimethyl L-2-aminoglutarate hydrochloride;L-GUTAMINSAURE-DIMETHYLESTER HYDROCHLORIDE;L-Glutamic Acid Dimethyl Ester HCl;DimethylL-glutamateHCl~H-Glu(OMe)-OMe.HCl;H-Glu(OMe)-OMe•
• CAS NO: 23150-65-4
• Molecular Formula: C₇H₁₄NO₄*Cl
• Molecular Weight: 211.64
• EINECS: 245-461-0
• Product Categories: chiral;Amino Acids;Glutamic acid [Glu, E];Amino Acids and Derivatives;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Amino Acid Derivatives;Glutamic Acid;Peptide Synthesis
• Mol File: 23150-65-4.mol
• Article Data: 43

Chemical Properties

• Melting Point: 89-90°C
• Boiling Point: 224.3 °C at 760 mmHg
• Flash Point: 76.7 °C
• Appearance: White/Powder
• Density: 1.129 g/cm³
• Vapor Pressure: 0.0919mmHg at 25°C
• Refractive Index: 26 ° (C=5, H2O)
• Storage Temp.: 2-8°C
• Solubility: Methanol, Water
• Water Solubility: Soluble in water, methanol (50 mg/ml).
• Sensitive: Hygroscopic
• Stability: Hygroscopic
• BRN: 4238829
• CAS DataBase Reference: L-Glutamic acid dimethyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Glutamic acid dimethyl ester hydrochloride(23150-65-4)
• EPA Substance Registry System: L-Glutamic acid dimethyl ester hydrochloride(23150-65-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 23150-65-4(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline

Uses

Different sources of media describe the Uses of 23150-65-4 differently. You can refer to the following data:
1. L-Glutamic Acid Dimethyl Ester is a diester analogue of L-Glutamic Acid, a non-essential amino acid. L-Glutamic Acid Dimethyl Ester has been shown to antagonize the effects of morphine sulfate.
2. L-Glutamic acid dimethyl ester hydrochloride is used as a pharmaceutical intermediate.

InChI:InChI=1/C7H13NO4.ClH/c1-11-6(9)4-3-5(8)7(10)12-2;/h5H,3-4,8H2,1-2H3;1H/t5-;/m0./s1

Upstream product

• 67-56-1 methanol 
• 6893-26-1 D-Glutamic acid 
• 56-86-0 L-glutamic acid 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 617-65-2 Glutamic acid 
• 75-77-4 chloro-trimethyl-silane 
• 77-76-9 2,2-dimethoxy-propane 
• 138-15-8 l-glutamic acid hydrochloride 
• 129421-88-1 Lascivol 

Downstream Products

• 121187-76-6 (S)-2-{4-[2-(2,4-Diamino-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid dimethyl ester 
• 121187-70-0 (S)-2-{4-[2-(2-Amino-4-oxo-3,5,7,8-tetrahydro-4H-pyrido[4,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid dimethyl ester 
• 139455-91-7 3-[(S)-3-Acetyl-1-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-[1,2,4]triazin-5-yl]-propionic acid methyl ester 
• 136548-01-1 dimethyl N-<4-<5-(2,4-diamino-6(1H)-pyrimidinon-5-yl)-pent-1-en-2-yl>benzoyl>-L-glutamate 
• 139577-59-6 dimethyl N-<4-<5-(2,4-diamino-6(1H)-pyrimidinon-5-yl)-pent-2-en-2-yl>benzoyl>-L-glutamate 
• 101810-82-6 N-<4-<<(benzyloxy)carbonyl>methylamino>benzoyl>-L-glutamic acid dimethyl ester 
• 141019-17-2 dimethyl N-<4-<3-<(2-amino-6-methoxypyrimidin-4-yl)-amino>propyl>benzoyl>-L-glutamate 
• 141019-33-2 N-<4-<4-<(6-chloro-2-aminopyrimidin-4-yl)amino>butyl>benzoyl>-L-glutamic acid 
• 141019-08-1 dimethyl N-<4-<3-<(2-amino-1,6-dihydro-6-oxopyrimidin-4-yl)amino>propyl>benzoyl>-l-glutamate 
• 151937-11-0 dimethyl N-<4-<2-(2-amino-4(3H)-oxo-7H-pyrrolo<2,3-d>pyrimidin-6-yl)ethyl>benzoyl>-L-glutamate 
• 176208-39-2 dimethyl N-<4-<2-(2-amino-4(3H)-oxothieno<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate 
• 169134-88-7 Dimethyl N-<4-<2-<2-<<(N,N-dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidin-5-yl>ethyl>benzoyl>-L-glutamate 
• 169134-92-3 Dimethyl N-<4-<3-<2-<<(N,N-dimethylamino)methylene>amino>-4(3H)-oxo-3-<(pivaloyloxy)methyl>-5H-pyrrolo<3,2-d>pyrimidin-5-yl>propyl>benzoyl>-L-glutamate 
• 4931-66-2 methyl (S)-pyroglutamate 

Relevant articles and documents

Isolation and synthesis of a host-selective toxin produced by Alternaria alternata

Two phytotoxins are isolated from culture filtrates of an Alternaria alternata pathogenic to sunflower. One was identified by chemical and physicochemical techniques as the tetrapeptide Ser-Val-Gly-Glu. This peptide, for which we suggested the name AS-I toxin, was further characterised by synthesis and by its phytotoxic effect on sunflower and other plants.

Ribose conversion with amino acids into pyrraline platform chemicals-expeditious synthesis of diverse pyrrole-fused alkaloid compounds

One-pot conversion of sustainable d-ribose with l-amino acid, methyl esters produced pyrrole-2-carbaldehydes 5 in reasonable yields (32-63%) under pressurized conditions of 2.5 atm at 80 °C. The value-added pyrraline compounds 5 as platform chemicals were utilized for quick installation of poly-heterocyclic cores for the development of pyrrole-motif natural and artificial therapeutic agents. A pyrrole-fused piperazin-2-one scaffold 6 was prepared by reductive amination of pyrralines 5 with benzylamine. While further cyclization of pyrralines 5 with ethane-1,2-diamine produced pyrrolo-piperazin-2-ones 7 with an extra imidazolidine ring, the reaction with 2-amino alcohols derived from natural l-amino acids, alanine, valine, and phenylalanine, respectively provided pyrrolo-piperazin-2-ones 8, 9, and 10 with oxazolidine as the third structural core. Cell viability and an anti-inflammatory effect of the synthesized compounds were briefly tested by the MTT method and the Griess assay, among which 8h and 10g exhibited significant anti-inflammatory effects with negligible cell toxicity.

Post-synthetic functionalization of tryptophan protected peptide sequences through indole (C-2) photocatalytic alkylation

We report a selective, mild, and efficient C-H functionalization of tryptophan and tryptophan-containing peptides with activated α-bromo-carbonyl compounds under visible-light irradiation. The protocol efficiency is outlined by the wide substrate scope and excellent tolerance of sensitive functional groups present in the amino acid side chains. The method can be successfully extended to access pharmaco-peptide conjugate scaffolds.

Amino acid conjugates of 2-mercaptobenzimidazole provide better anti-inflammatory pharmacology and improved toxicity profile

Benzimidazole is an important pharmacophore for clinically active drugs against inflammation and treatment of pain, however, it is associated with gastrointestinal side effects. Here we synthesized benzimidazole based agents with significant analgesic/anti-inflammatory potential but with less gastrointestinal adverse effects. In this study, we synthesized novel, orally bioavailable 2-mercaptobenzimidazole amino acid conjugates (4a–4o) and screened them for analgesic, anti-inflammatory and gastro-protective effects. The synthesized 2-mercaptbenzimidazole derivatives were characterized for their structure using FTIR, 1H NMR and 13C NMR spectroscopic techniques. The 2-mercaptobenzimidazole amino acid conjugates have found to possess potent analgesic, anti-inflammatory and gastroprotective activities, particularly with compound 4j and 4k. Most of the compounds exhibited remarkable anti-ulcer and antisecretory effects. Molecular docking studies were carried out to study the binding affinities and interactions of the synthesized compounds with target proteins COX-2 (PDB ID: 3LN1) and H+/K+-ATPase (PDB ID: 5Y0B). Our results support the clinical promise of these newly synthesized 2-mercaptobezimidazol conjugates as a component of therapeutic strategies for inflammation and analgesia, for which the gastric side effects are always a major limitation.