26340-89-6

Basic information

• Product Name: Methyl L-argininate dihydrochloride
• Synonyms: ARGININE-OME 2 HCL;L-ARGININE METHYL ESTER DIHCL;L-ARGININE METHYL ESTER DIHYDROCHLORIDE;L-ARGININE METHYL ESTER DIHYDROCHLORIDE SALT;L-ARGININE METHYL ESTER HYDROCHLORIDE;H-ARG-OME 2HCL;methyl L-argininate dihydrochloride;L-Arginine Methyl Ester 2HCl
• CAS NO: 26340-89-6
• Molecular Formula: C₇H₁₆N₄O₂*ClH
• Molecular Weight: 261.15
• EINECS: 247-622-0
• Product Categories: Amino Acids;Arginine [Arg, R];Amino Acids and Derivatives;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry;Amino ester;Amino Acid Derivatives;Peptide Synthesis
• Mol File: 26340-89-6.mol

Chemical Properties

• Melting Point: ~190 °C (dec.)
• Boiling Point: 329.9 °C at 760 mmHg
• Flash Point: 153.3 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.31 g/cm³
• Vapor Pressure: 0.000172mmHg at 25°C
• Refractive Index: 21 ° (C=2.5, MeOH)
• Storage Temp.: Store at RT.
• Solubility: soluble in Methanol
• Sensitive: Hygroscopic
• BRN: 4159929
• CAS DataBase Reference: Methyl L-argininate dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl L-argininate dihydrochloride(26340-89-6)
• EPA Substance Registry System: Methyl L-argininate dihydrochloride(26340-89-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 26340-89-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl L-argininate dihydrochloride is used as a precursor for L-arginine in the pharmaceutical industry. L-arginine is an essential amino acid that plays a crucial role in various physiological processes, including the synthesis of proteins, hormones, and enzymes. It is also involved in the production of nitric oxide, a molecule that regulates blood flow and immune function.
Used in Nutritional Supplements:
Methyl L-argininate dihydrochloride is used as a nutritional supplement to provide L-arginine to the body. As a conditionally essential amino acid, L-arginine is necessary for maintaining optimal health, particularly during periods of increased demand, such as pregnancy or illness.
Used in Research Applications:
Methyl L-argininate dihydrochloride is used as a research tool in scientific studies. It can be used to investigate the role of L-arginine in various biological processes and to develop new therapeutic strategies for treating diseases and conditions related to L-arginine deficiency or dysfunction.
Used in Cosmetic Industry:
Methyl L-argininate dihydrochloride is used as an ingredient in cosmetic products for its potential skin benefits. L-arginine has been shown to improve skin elasticity, reduce the appearance of wrinkles, and promote wound healing, making it a valuable component in skincare formulations.
Used in Food Industry:
Methyl L-argininate dihydrochloride is used as a food additive to enhance the nutritional value of certain products. L-arginine is known to have various health benefits, including supporting immune function, promoting muscle growth, and improving cardiovascular health. By incorporating Methyl L-argininate dihydrochloride into food products, manufacturers can provide consumers with an additional source of this essential amino acid.

InChI:InChI=1/C7H16N4O2/c1-13-6(12)5(8)3-2-4-11-7(9)10/h5H,2-4,8H2,1H3,(H4,9,10,11)/p+2/t5-/m0/s1

Upstream product

• 22888-59-1 L-arginine methyl ester dihydrochloride 
• 67-56-1 methanol 
• 74-79-3 L-arginine 
• 627-75-8 arginine dihydrochloride 
• 157-06-2 D-arginine 

Downstream Products

• 63553-83-3 Boc-Phe-Arg-OMe 
• 102683-29-4 N-(benzyloxycarbonyl)-L-tyrosyl-L-arginine methyl ester 
• 85676-28-4 Boc-Tyr(Et)-Arg-OMe_.CH₃COOH 
• 85676-29-5 Boc-Tyr(3,5-diBr)-Arg-OMe_.0.5HCl 
• 85676-32-0 Boc-AlTyr-Arg-OMe_.HCl 
• 85717-89-1 C_.(-Phe-Arg-).HCl 
• 23815-23-8 H-Phe-Arg-OMe_.HCl 
• 85676-26-2 H-Tyr(Me)-Arg-OMe_.2HCl 
• 85676-21-7 H-Ser(Bzl)-Arg-OMe_.2HCl 
• 85675-72-5 C_.(-Cha-Arg-).1.5CH₃COOH 
• 85675-82-7 C.<-Tyr(Me)-Arg->.1.5CH3COOH 
• 85718-17-8 C_.(-MeTyr-Arg-).CH₃COOH 

Relevant articles and documents

Synthesis, molecular docking, and antiepileptic activity of new N-phthaloylglycine derivatives

Thalidomide (α-N-phthalimido-glutarimide), the withdrawn sedative compound, has recently been reemerged as a potent agent against epilepsy. In this study, five l-amino acid derivatives of N-phthaloylglycine were synthesized and were tested on pentylenetetrazole (PTZ) induced seizure mice model. N-phthaloylglycine was prepared by reaction of phthalic anhydride and glycine in the presence of triethylamine in toluene under reflux. Arginine, glutamine, leucine, phenylalanine, and tryptophan methyl ester were prepared and coupled with N-phthaloylglycine using coupling agents (EDC and HOBt). The final compounds were characterized by spectroscopic methods (1H NMR, 13 CNMR, IR, and MS). A docking study using AutoDock 4.2 was performed to predict the possible interactions of synthesized compounds on the GABAA receptor. All compounds were characterized, docked into the binding pocket of the GABAA receptor, and tested on pentylenetetrazole-induced seizures in mice. As expected, in silico studies demonstrated that all compounds interact efficiently with the GABAA receptor. All synthesized compounds showed satisfactory results leading to increased latency time to the first symptom of a seizure. The phenylalanine methyl ester derivative of N-phthaloylglycine (6d) had antiepileptic effects even more potent than thalidomide. Increasing lipophilicity and facilitating compounds delivery through l-amino acid carriers to the brain appear to be responsible for the remarkable activity of these compounds. Both in silico and in vivo results suggest that the l-amino acid derivatives of N-phthaloylglycine act as a novel compound against chemically induced seizures through interaction with the binding pocket of the GABAA receptor.

New cationic vesicles prepared with double chain surfactants from arginine: Role of the hydrophobic group on the antimicrobial activity and cytotoxicity

Cationic double chain surfactants have attracted much interest because they can give rise to cationic vesicles that can be used in biomedical applications. Using a simple and economical synthetic approach, we have synthesized four double-chain surfactants with different alkyl chain lengths (LANHC. x). The critical aggregation concentration of the double chain surfactants is at least one order of magnitude lower than the CMC of their corresponding single-chain LAM and the solutions prepared with the LANHC. x contain stable cationic vesicles. Encouragingly, these new arginine derivatives show very low haemolytic activity and weaker cytotoxic effects than conventional dialkyl dimethyl ammonium surfactants. In addition, the surfactant with the shortest alkyl chain exhibits good antimicrobial activity against Gram-positive bacteria. The results show that a rational design applied to cationic double chain surfactants might serve as a promising strategy for the development of safe cationic vesicular systems.

Synthesis and antimicrobial activities of His(2-aryl)-Arg and Trp-His(2-aryl) classes of dipeptidomimetics

In this communication, we report the design, synthesis and in vitro antimicrobial activity of ultra short peptidomimetics. Besides producing promising antibacterial activities against Staphylococcus aureus and methicillin-resistant S. aureus (MRSA), the dipeptidomimetics exhibited high antifungal activity against C. neoformans with IC50 values in the range of 0.16-19 μg mL-1. The most potent analogs exhibited 4-fold higher activity than the currently used drug amphotericin B, with no apparent cytotoxicity in a panel of mammalian cell lines. This journal is the Partner Organisations 2014.

Synthesis, characterization and pharmacological evaluation of amino acid conjugates of ketoprofen

Ketoprofen is used for its antipyretic, analgesic and antiinflammatory properties by inhibiting cyclooxygenase-1 and cyclooxygenase-2 enzymes reversibly, which decreases production of proinflammatory prostaglandin precursors. Ketoprofen suffers from the general side effects of nonsteroidal antiinflammatory drugs, owing to presence of free carboxylic acid group. The study aimed to retard the adverse effects of gastrointestinal origin. Different conjugates of ketoprofen have been synthesized by amidation with methyl esters of amino acids namely, phenylalanine, lysine, arginine, glycine, cysteine, valine, glutamine, serine, proline and alanine. Synthesized conjugates were characterized and evaluated for analgesic and antiinflammatory activities.

Synthesis, characterization and biological evaluation of amino acid conjugates of mefenamic acid

Mefenamic acid is used for its antipyretic, analgesic, antiinflammatory properties and also inhibits cyclooxygenase-1 and cyclooxygenase- 2 (COX-1 and COX-2) enzymes reversibly, which decreases production of pro-inflammatory prostaglandin precursors. Mefenamic acid suffers from the general side effects of non-steroidal antiinflammatory drugs, owing to presence of free carboxylic acid group. The study aimed to retard the adverse effects of gastrointestinal origin. Amino acid conjugates of mefenamic acid were synthesized by amidation with methyl esters of amino acids namely, phenylalanine, cysteine, glycine, lysine, arginine, valine, proline, serine, alanine and methionine. Synthesized conjugates were characterized by melting point, TLC, 1H NMR and mass spectroscopy. Synthesized conjugates were also evaluated for their analgesic and antiinflammatory activities. Comparable analgesic and anti-inflammatory activities were obtained as compared to mefenamic acid.

Ultrasound accelerated synthesis of proteinogenic and α,α- dialkylamino acid ester salts

A simple and efficient sonochemical esterification of proteinogenic as well as cyclic α,α-dialkyl amino acid methyl and ethyl ester hydrochloride salts employing thionyl chloride and alcohol has been reported. All the amino acid esters made have been obtained in good yield (94-98%) as pure compounds.

Inhibitory effects of L-arginine derivatives on endothelium-dependent vasorelaxing response to acetylcholine of the rat aorta

Nω-nitro-L-arginine alkyl esters (A-1-A-B) and L-arginine alkyl esters (E-1-E-B) were synthesized, and the vasorelaxing effects of acetylcholine were studied in the absence or presence of these compounds in rat aortic rings with intact endothelium that was precontracted with phenylephrine. These compounds revealed that the nitro group is an essential inhibiting group of these inhibitors, and that hydrophobic functional groups can fine-tune the binding effects. Among them, A-3 is the most potent inhibitor.

A chiral sensor for arginine and lysine

(Graph presented) We provide access to a new class of C1-or C2-symmetrical host molecules 1 and 2 based on a spirobisindane skeleton. Whereas 1 is selective for short, rigid diamines, 2 prefers longer α,ω-dications. Of all the amino acid methyl esters, only those of lysine and arginine with the correct distance between their cationic groups form strong 1:1 complexes in DMSO with 2. NMR titrations reveal high association constants as well as discrimination between the enantiomers of lysine and arginine.

New alquil amide type cationic surfactants from arginine

The synthesis, stability, surface activity and antimicrobial properties of a new family of cationic surfactants (the long chain arginylalkylamide dihydrochloride salts) derived from the condensation of the amino acid arginine and a long chain alkylamine are described. The surface active parameters reported are c.m.c. (critical micellar concentration), pC20 (negative log of the surfactant molar concentration required to reduce the surface tension of the solvent by 20 mN m-1), γc.m.c (the surface tension at the c.m.c.), Γmax (the maximum surface excess concentration) and Amin (the minimum area per surfactant molecule at the interface). These data and those obtained from the evaluation of the antimicrobial properties are compared with the data corresponding to another family of cationic surfactants reported earlier by our group: the long chain Nα-acylarginine methyl ester salts. Moreover, the synthesis of analogues possessing a reactive group capable of bonding to wool or cotton fibres is described: the long chain Nα-dichlorotriazinylarginylalkylamide monohydrochloride salts. We expect these compounds to bond to the textile substrate by the formation of a covalent bond. Confirmation of this is, however, necessary.

Enzyme-Catalyzed Irreversible Formation of Peptides Containing D-Amino Acids

Procedures have been developed for the preparation of dipeptides Z-L-Tyr-D-X and Z-L-Phe-D-X using Z-L-Tyr-OMe (or Z-L-Phe-OMe) and D-amino acid esters or amides (D-X) as substrates and soluble or immobilized α-chymotrypsin as a catalyst.The formation of each of these peptides in miscible or immiscible organic solvent-water systems in a kinetically controlled approach is virtually irreversible with no side reactions or racemization.Kinetic studies indicate that D-amino acid esters are about 100 times that of water and 10percent that of L-amino acid esters as a nucleophile in deacylation reactions.The effects of pH, organic solvents, temperature, and substrate and enzyme concentrations on the yield and the stability of the enzyme in syntheses have been studied and the results compared with those in the enzyme-catalyzed formation of L-L-dipeptides.