Dimethyl DL-Glutamate Hydrochloride

Base Information

• Chemical Name: Dimethyl DL-Glutamate Hydrochloride
• CAS No.: 13515-99-6
• Molecular Formula: C₇H₁₄NO₄*Cl
• Molecular Weight: 211.645
• Hs Code.: 2922499990
• NSC Number: 83254
• UNII: 16247QSY33
• DSSTox Substance ID: DTXSID40388975
• Wikidata: Q27251762
• Mol file: 13515-99-6.mol

Synonyms:13515-99-6;Dimethyl DL-Glutamate Hydrochloride;dimethyl 2-aminopentanedioate hydrochloride;H-DL-Glu(OMe)-OMe.HCl;H-DL-Glu(Ome)-OMe;dimethyl 2-aminopentanedioate;hydrochloride;Glutamic acid, dimethyl ester, hydrochloride;UNII-16247QSY33;DL-Glutamic acid, dimethyl ester, hydrochloride;Glutamic acid, dimethyl ester, hydrochloride, DL-;16247QSY33;Glutamic acid, 1,5-dimethyl ester, hydrochloride (1:1);DIMETHYL 2-AMINOPENTANEDIOATE HCL;H-Glu(OMe)-OMe HCl;MFCD00235872;NSC-83254;1,5-dimethyl 2-aminopentanedioate hydrochloride;H-Glu-(Ome)-Omehydrochloride;SCHEMBL1238805;DTXSID40388975;NSC83254;AR2240;dimethyl (rs)-glutamate hydrochloride;MFCD00266895;AKOS015847816;AKOS015892894;HY-W098059;DS-16144;SY036573;4-DIAZO-4-METHOXYDIPHENYLAMINESULFATE;CS-0150701;D3305;FT-0627830;FT-0654147;FT-0686507;FT-0705575;DL-Glutamic Acid Dimethyl Ester Hydrochloride;EN300-296312;A849968;J-006655;Q27251762;2-AMINO-PENTANEDIOIC ACID DIMETHYL ESTER, HYDROCHLORIDE

Chemical Property of Dimethyl DL-Glutamate Hydrochloride

Chemical Property:

• Vapor Pressure: 0.0919mmHg at 25°C
• Melting Point: 154 °C
• Boiling Point: 224.3oC at 760 mmHg
• Flash Point: 76.7oC
• PSA: 78.62000
• LogP: 0.94220
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 211.0611356
• Heavy Atom Count: 13
• Complexity: 169

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dimethyl DL-Glutamate Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC(C(=O)OC)N.Cl
• Description: While extracellular glutamic acid is an excitatory neurotransmitter, intracellular glutamic acid is an amino acid that serves numerous metabolic roles. Dimethyl DL-glutamate is a cell-permeant glutamic acid derivative that enhances insulin release in response to glucose in isolated islets and in animal models of diabetes. It also potentiates the insulinotropic potential of glyburide and glucagon-like peptide 1. Dimethyl DL-glutamate is used as a cell-permeable form of glutamate in studies of glutamate action in β-cells. However, it can be cytotoxic to myeloid cells and act as an antagonist of glutamate-mediated neurosignaling.
• Uses: While extracellular glutamic acid is an excitatory neurotransmitter, intracellular glutamic acid is an amino acid that serves numerous metabolic roles. Dimethyl DL-glutamate Hydrochloride is a cell-permeant glutamic acid derivative that enhances insulin release in response to glucose in isolated islets and in animal models of diabetes. It also potentiates the insulinotropic potential of glyburide and glucagon-like peptide 1. Dimethyl DL-glutamate Hydrochloride is used as a cell-permeable form of glutamate in studies of glutamate action in β-cells. However, it can be cytotoxic to myeloid cells and act as an antagonist of glutamate-mediated neurosignaling.

Technology Process of Dimethyl DL-Glutamate Hydrochloride

There total 3 articles about Dimethyl DL-Glutamate Hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methanol (67-56-1) + D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → D-glutamic acid dimethyl ester hydrochloride (13515-99-6,23150-65-4,27025-25-8)

Guidance literature:

With chloro-trimethyl-silane; at 20 ℃; for 16h;

DOI:10.1016/j.bmc.2008.01.004

Reference yield: 100.0%

methanol (67-56-1) + Glutamic acid (617-65-2,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → dimethyl glutamate hydrochloride (23150-65-4,27025-25-8,13515-99-6)

Guidance literature:

With thionyl chloride; at 0 - 70 ℃; for 16h;

DOI:10.1021/jacs.1c11266

Reference yield:

→ dimethyl glutamate hydrochloride (23150-65-4,27025-25-8,13515-99-6)

Guidance literature:

upstream raw materials:

methanol

Glutamic acid

D-Glutamic acid

Downstream raw materials:

N-(N-benzoyl-glycyl)-glutamic acid dimethyl ester

N-{4-[(2-oxo-benzooxazol-3-ylmethyl)-amino]-benzoyl}-glutamic acid dimethyl ester

N-{4-[(2-thioxo-benzothiazol-3-ylmethyl)-amino]-benzoyl}-glutamic acid dimethyl ester

C₁₆H₂₀N₂O₇S

Refernces

• 1、 Khan, Muhammad T.,Nadeem, Humaira,Khan, Arif-ullah,Abbas, Muzaffar,Arif, Muazzam,Malik, Nadia Shamshad,Malik, Zulkifal,Javed, Ibrahim. "Amino acid conjugates of 2-mercaptobenzimidazole provide better anti-inflammatory pharmacology and improved toxicity profile". . p. 1057 - 1072. Retrieved 2020/08/13.
• 2、 Dumbre, Shrinivas,Derouaux, Adeline,Lescrinier, Eveline,Piette, Andre,Joris, Bernard,Terrak, Mohammed,Herdewijn, Piet. "Synthesis of modified peptidoglycan precursor analogues for the inhibition of glycosyltransferase". supporting information; experimental part. p. 9343 - 9351. Retrieved 2012/07/14.