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L-Glutamic acid dimethyl ester hydrochloride is a diester analogue of L-Glutamic Acid, a non-essential amino acid. It is a crystalline compound known for its ability to antagonize the effects of morphine sulfate.

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  • 23150-65-4 Structure
  • Basic information

    1. Product Name: L-Glutamic acid dimethyl ester hydrochloride
    2. 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•
    3. CAS NO:23150-65-4
    4. Molecular Formula: C7H14NO4*Cl
    5. Molecular Weight: 211.64
    6. EINECS: 245-461-0
    7. 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
    8. Mol File: 23150-65-4.mol
  • Chemical Properties

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

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 23150-65-4(Hazardous Substances Data)

23150-65-4 Usage

Uses

Used in Pharmaceutical Industry:
L-Glutamic acid dimethyl ester hydrochloride is used as a pharmaceutical intermediate for the development of medications targeting various medical conditions. Its antagonistic properties against morphine sulfate make it a valuable compound in the research and production of drugs aimed at treating opioid addiction or dependence.
Used in Research and Development:
In the field of scientific research, L-Glutamic acid dimethyl ester hydrochloride serves as an essential compound for studying the effects of morphine and other opioids on the nervous system. This helps researchers better understand the mechanisms of action and develop new therapeutic strategies to combat opioid-related issues.
Used in Drug Delivery Systems:
Similar to gallotannin, L-Glutamic acid dimethyl ester hydrochloride can be incorporated into drug delivery systems to enhance its bioavailability and therapeutic outcomes. By utilizing various organic and metallic nanoparticles as carriers, the compound can be more effectively delivered to target cells, improving its overall efficacy in treating specific medical conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 23150-65-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,1,5 and 0 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 23150-65:
(7*2)+(6*3)+(5*1)+(4*5)+(3*0)+(2*6)+(1*5)=74
74 % 10 = 4
So 23150-65-4 is a valid CAS Registry Number.
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

23150-65-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • TCI America

  • (D3353)  Dimethyl L-Glutamate Hydrochloride  >98.0%(N)(T)

  • 23150-65-4

  • 5g

  • 250.00CNY

  • Detail
  • TCI America

  • (D3353)  Dimethyl L-Glutamate Hydrochloride  >98.0%(N)(T)

  • 23150-65-4

  • 25g

  • 750.00CNY

  • Detail
  • Alfa Aesar

  • (L03764)  L-Glutamic acid dimethyl ester hydrochloride, 98+%   

  • 23150-65-4

  • 5g

  • 347.0CNY

  • Detail
  • Alfa Aesar

  • (L03764)  L-Glutamic acid dimethyl ester hydrochloride, 98+%   

  • 23150-65-4

  • 25g

  • 1420.0CNY

  • Detail
  • Aldrich

  • (49560)  L-Glutamicaciddimethylesterhydrochloride  ≥99.0% (dried material, AT)

  • 23150-65-4

  • 49560-10G

  • 934.83CNY

  • Detail
  • Aldrich

  • (49560)  L-Glutamicaciddimethylesterhydrochloride  ≥99.0% (dried material, AT)

  • 23150-65-4

  • 49560-50G

  • 3,446.82CNY

  • Detail

23150-65-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name dimethyl (2S)-2-aminopentanedioate,hydrochloride

1.2 Other means of identification

Product number -
Other names L-Glutamic acid dimethyl ester hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:23150-65-4 SDS

23150-65-4Downstream Products

23150-65-4Relevant articles and documents

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

Liakopoulou-Kyriakides,Lagopodi,Thanassoulopoulos,Stavropoulos,Magafa

, p. 37 - 40 (1997)

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.

Synthesis of 4-N-α-coumaryl amino acids and investigation of their antioxidant, antimicrobial activities and fluorescence spectra

Ghalehshahi, Hajar Golshadi,Balalaie, Saeed,Aliahmadi, Atousa,Moghimi, Roya

, p. 1461 - 1470 (2018)

An efficient metal-free approach for the synthesis of N-coumaryl amino acids and the first one-step synthesis of 4-hydrazinocoumarin from 4-hydroxycoumarin was developed. The nucleophilic addition of amino acid methyl esters to 4-tosylcoumarins produced a series of 4-N-α-coumaryl amino acids in good to excellent yields without racemization. The antioxidant activities of the synthesized compounds were investigated using DPPH and FRAP methods. 4-Hydrazinocoumarin and N-coumaryl tyrosine had the best antioxidant activity. The antimicrobial activities of the compounds against Gram-positive was stronger than Gram-negative. 4-Hydrazinocoumarin showed the best antibacterial effect.

Photochemical Deracemization at sp3-Hybridized Carbon Centers via a Reversible Hydrogen Atom Transfer

Bach, Thorsten,Breitenlechner, Stefan,Gro?kopf, Johannes,Plaza, Manuel,Seitz, Antonia,Storch, Golo

supporting information, p. 21241 - 21245 (2021/12/27)

A photochemical deracemization of 5-substituted 3-phenylimidazolidine-2,4-diones (hydantoins) is reported (27 examples, 69%-quant., 80–99% ee). The reaction is catalyzed by a chiral diarylketone which displays a two-point hydrogen bonding site. Mechanistic evidence (DFT calculations, radical clock experiments, H/D labeling) suggests the reaction to occur by selective hydrogen atom transfer (HAT). Upon hydrogen binding, one substrate enantiomer displays the hydrogen atom at the stereogenic center to the photoexcited catalyst allowing for a HAT from the substrate and eventually for its conversion into the product enantiomer. The product enantiomer is not processed by the catalyst and is thus enriched in the photostationary state.

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

Ackermann, Lutz,Berlinck, Roberto G. S.,Bernardi, Darlon I.,Delgado, José A. C.,Kaplaneris, Nikolaos,Lima, Rafaely N.,Paix?o, Márcio W.

supporting information, p. 5758 - 5761 (2021/06/16)

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.

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

Cho, Soohyeon,Gu, Lina,In, Ik Joon,Kim, Hakwon,Koo, Sangho,Lee, Taehoon,Wu, Bo

, p. 31511 - 31525 (2021/11/30)

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.

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

Khan, Muhammad T.,Nadeem, Humaira,Khan, Arif-ullah,Abbas, Muzaffar,Arif, Muazzam,Malik, Nadia Shamshad,Malik, Zulkifal,Javed, Ibrahim

, p. 1057 - 1072 (2020/08/13)

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.

Synthesis and Penicillin-binding Protein Inhibitory Assessment of Dipeptidic 4-Phenyl-β-lactams from α-Amino Acid-derived Imines

Decuyper, Lena,Juki?, Marko,Sosi?, Izidor,Amoroso, Ana Maria,Verlaine, Olivier,Joris, Bernard,Gobec, Stanislav,D'hooghe, Matthias

supporting information, p. 51 - 55 (2019/11/28)

Monocyclic β-lactams revive the research field on antibiotics, which are threatened by the emergence of resistant bacteria. A six-step synthetic route was developed, providing easy access to new 3-amino-1-carboxymethyl-4-phenyl-β-lactams, of which the penicillin-binding protein (PBP) inhibitory potency was demonstrated biochemically.

L-glutamic acid derivative and synthesis method and application thereof

-

Paragraph 0044-0047; 0056-0059; 0066-0069; 0076-0079; 0086, (2020/11/01)

The invention belongs to the technical field of synthesis of medical and traditional Chinese medicine intermediates, and discloses an L-glutamic acid derivative and a synthesis method and applicationthereof. All the steps in the synthesis method are simple and in order , the obtained L-dimethyl glutamate hydrochloride oily matter is directly put into the next step of reaction through a one-pot method, L-dimethyl glutamate hydrochloride solids do not need to be obtained, the use of all the raw materials can be effectively reduced, and the cost is reduced; ethyl acetate is selected as a reaction solvent and can be effectively recycled, the utilization rate of the ethyl acetate is remarkably increased, and pollution to the environment is reduced; a final product is obtained in a crystallization manner so that the convenience and the storage convenience during transportation are improved, and the quality and the yield of the product can be further improved. The technical scheme of the synthesis method is complete and simple, the produced product is high in crystallization yield and better in quality, the overall yield of the product is conveniently, rapidly, scientifically and effectively increased to 85% or above, and raw materials are provided for research and development of new drugs.

Synthesis, CYP 450 evaluation, and docking simulation of novel 4-aminopyridine and coumarin derivatives

Ghalehshahi, Hajar G.,Balalaie, Saeed,Sohbati, Hamid R.,Azizian, Homa,Alavijeh, Mohammad S.

, (2019/01/21)

Four series of novel compounds based on 4-aminopyridine, glatiramer acetate, pyrone, and coumarin backbones were sufficiently synthesized and identified by spectroscopic methods. CYP enzyme inhibition assays of five predominate human P450 isozymes indicate that all compounds, except for 4-hydrazide pyridine 1c, seem to be less toxic than 4-aminopyridine. Further investigation of the compounds using molecular docking experiments revealed different, the same, or stronger binding modes for most of the synthesized compounds, with both polar and hydrophobic interactions with the 1WDA and 1J95 receptors compared to benzoyl l-arginine amide and 4-aminopyridine, respectively. These results introduce the synthesized compounds as K+ channel blockers that could be considered for in vivo CNS disease studies.

PRODRUGS ACTIVATED BY REACTIVE OXYGEN SPECIES FOR USE IN THE TREATMENT OF INFLAMMATORY DISEASES AND CANCER

-

Page/Page column 27; 32, (2018/09/25)

Prodrugs activated predominantly or exclusively in inflammatory tissue, more particularly prodrugs of methotrexate and derivatives thereof, which are selectively activated by Reactive Oxygen Species (ROS) in inflammatory tissues associated with cancer and inflammatory diseases, as well as method for preparing said prodrugs.

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