2491-20-5

Basic information

• Product Name: L-Alanine methyl ester hydrochloride
• Synonyms: L-ALANINE METHYL ESTER HYDROCHLORIDE;METHYL L-ALANINATE HYDROCHLORIDE;H-L-ALA-OME HCL;H-ALA-OME HCL;H-ALA-OME HYDROCHLORIDE;(S)-2-AMINOPROPIONIC ACID METHYL ESTER HYDROCHLORIDE;A-Ala-OMe·HCl ;L-ALANINE METHYL ESTER HYDROCHLORIDE, 99 %
• CAS NO: 2491-20-5
• Molecular Formula: C₄H₁₀NO₂*Cl
• Molecular Weight: 139.58
• EINECS: 219-652-4
• Product Categories: Amino Acids Derivatives;AMINOACIDS DERIVATIVES;Amino Acids;Alanine [Ala, A];Amino Acids and Derivatives;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Alanine;Amino Acid Derivatives;Peptide Synthesis;amino acid;amino;Piperazines ,Oxazolines/Oxazolidines
• Mol File: 2491-20-5.mol

Chemical Properties

• Melting Point: 109-111 °C(lit.)
• Boiling Point: 101.5 °C at 760 mmHg
• Appearance: White to off-white/Powder
• Vapor Pressure: 35mmHg at 25°C
• Refractive Index: 6.5 ° (C=2, MeOH)
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• Water Solubility: Soluble in Water (100 mg/ml).
• Sensitive: Hygroscopic
• BRN: 3594033
• CAS DataBase Reference: L-Alanine methyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine methyl ester hydrochloride(2491-20-5)
• EPA Substance Registry System: L-Alanine methyl ester hydrochloride(2491-20-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 2491-20-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-Alanine methyl ester hydrochloride is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows for the development of new drugs with potential applications in treating a range of medical conditions.
Used in Diagnostic Applications:
L-Alanine methyl ester hydrochloride is used as a diagnostic aid for in-vivo measurement of glucose and alanine metabolism in studies of patients with diabetes. Its ability to be easily detected and monitored in the body makes it a valuable tool for understanding the metabolic processes in diabetic patients and for the development of new treatments for diabetes.
Used in Research and Development:
Due to its unique chemical properties, L-Alanine methyl ester hydrochloride is used in research and development for the study of amino acid metabolism, protein synthesis, and other biological processes. It can also be used as a building block for the synthesis of novel peptides and other bioactive molecules with potential applications in medicine and biotechnology.
Used in Chemical Synthesis:
L-Alanine methyl ester hydrochloride is used as a reagent in various chemical synthesis processes, particularly in the production of chiral compounds. Its optical activity and stability make it a valuable starting material for the synthesis of enantiomerically pure compounds, which are important in the pharmaceutical and agrochemical industries.

InChI:InChI=1/C4H9NO2/c1-3(5)4(6)7-2/h3H,5H2,1-2H3/p+1/t3-/m0/s1

Upstream product

• 67-56-1 methanol 
• 56-41-7 L-alanin 
• 77-76-9 2,2-dimethoxy-propane 
• 13515-97-4 methyl 2-aminopropanoate monohydrochloride 
• 640-68-6 D-Val-OH 
• 16948-16-6 N-(tert-butoxycarbonyl)-N-methyl-L-alanine 
• 28819-05-8 (S)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 10065-72-2 L-Alanine methyl ester 
• 28875-17-4 (S)-N-(tert-butoxycarbonyl)alanine methyl ester 
• 75-36-5 acetyl chloride 
• 74-88-4 methyl iodide 
• 129178-93-4 L-alanine acid chloride 
• 15761-38-3 L-N-Boc-Ala 
• 6003-05-0 L-alanine hydrochloride 

Downstream Products

• 21679-94-7 N-(S-benzyl-N-benzyloxycarbonyl-L-cysteinyl)-L-alanine methyl ester 
• 80514-64-3 2-(tritylamino)propanoic acid 
• 56120-14-0 methyl N-(3-(((benzyloxy)carbonyl)amino)propanoyl)-L-alaninate 
• 16816-28-7 methyl 2-[({[(benzyloxy)carbonyl]amino}acetyl)amino]propanoate 
• 24955-56-4 Z-Gly-D-Ala-OMe 
• 5249-68-3 N-benzyloxycarbonyl-γ-tert-butyl-L-glutamyl-L-alanine methyl ester 
• 3057-69-0 N-[(benzyloxy)carbonyl]-L-alanyl-L-alanyl-L-alanine methyl ester 
• 111609-44-0 (S)-2-[(R)-3-Phenyl-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-propionic acid methyl ester 
• 854-34-2 (S)-2-[(S)-3-Phenyl-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-propionic acid methyl ester 
• 63236-33-9 Z-DL-(Me)Leu-Ala-OMe 
• 117290-42-3 Z-(Me)Leu-Ala-OMe 
• 96393-24-7 (S)-N-(1-Methoxycarbonylethyl)-4-phenyl-5-methyl-Δ⁴-thiazoline-2-thione 
• 138995-97-8 (S)-2-(2-Methyl-4-nitro-imidazol-1-yl)-propionic acid methyl ester 
• 62056-76-2 (S)-N-diphenylphosphinoylalanine methyl ester 

Relevant articles and documents

Development of a prodrug of salicylic acid, salicylic Acid-L-alanine conjugate, utilizing hydrolysis by rabbit intestinal microorganisms

The hydrolysis of salicylic acid-L-alanine conjugate (salicyl-L-alanine) following oral, intravenous, intracaecal and rectal administration (60, 10, 5 and 5 mg kg-1 respectively: salicylic acid equivalent) was examined in rabbits. Salicylic acid was detected in the blood 2 h after oral administration of salicyl-L-alanine and reached a maximum concentration at 10 h, whereas salicyl-L-alanine was rapidly eliminated. In contrast, unchanged salicyl-L-alanine only was found following intravenous administration of salicyl-L-alanine, suggesting that presystemic de-conjugation of salicyl-L-alanine was involved. The intestinal mucosal de-conjugation of salicyl-L-alanine was not recognized in the in-situ intestinal sac preparation with complete mesenteric venous blood collection. Immediate and very extensive salicylic acid formation in the caecum was found following intracaecal administration of salicyl-L-alanine. After oral pretreatment of rabbits with kanamycin sulphate, a significant inhibition of salicylic acid formation following intracaecal administration of salicyl-L-alanine was observed, indicating that the intestinal microorganisms were responsible for the biotransformation of salicyl-L-alanine. In-vitro incubation of salicyl-L-alanine with gut contents showed that the major source of its hydrolysis was the hind gut. Consequently, the blood concentration of salicylic acid was prolonged extensively following rectal administration of salicyl-L-alanine, suggesting the usefulness of salicyl-L-alanine as a prodrug of salicylic acid.

Synthesis and structure of α/δ-hybrid peptides - Access to novel helix patterns in foldamers

Stimulated by an overview on all periodic folding patterns of α/δhybrid peptides with 1:1 alternating backbone provided by ab initio molecular orbital theory, the first representatives of this foldamer class were synthesized connecting novel C-linked carb

Three new metabolites from the endophytic fungus Climacocystis montana isolated from the root bark of Paeonia ostia

Two new pyridine derivatives climacomontaninates A–B (1–2), and a new sesquiterpenoid derivative climacomontanetate (3), together with twelve known compounds (4–15) were isolated from the culture extract of the fungal strain Climacocystis montana from the root bark of Paeonia ostii. The structures of these compounds were determined through spectroscopic methods such as NMR and HRMS. Moreover, we expound the absolute configuration of 1 using the organic synthesis method. The cytotoxicity against five human cancer cell lines of new compounds were evaluated by SRB assay.

ENANTIOSELECTIVE ALKYLATION OF ENOLATE DERIVED FROM GLYCINE INFLUENCE OF THE IMINE MOIETY

Optically active alanine was obtained by asymmetric one carbon transfer reaction.Variation of the nature of the imine moiety in the enantioselective alkylation of Schiff bases derived from glycine caused the enantiomeric excess to shift from 0 to 70 percent.

Triazolyl-donor-acceptor chromophore-decorated unnatural amino acids and peptides: FRET events in a β-turn conformation

The β-turn conformation and FRET process were established in the designed tripeptide containing fluorescent triazolyl donor and acceptor-decorated unnatural amino acids separated by a natural alanine.

2-Methyltetrahydro-3-benzazepin-1-ols – The missing link in SAR of GluN2B selective NMDA receptor antagonists

The NMDA receptor containing GluN2B subunits represents a promising target for the development of drugs for the treatment of various neurological disorders including neurodegenerative diseases. In order to study the role of CH3 and OH moieties trisubstituted tetrahydro-3-benzazepines 4 were designed as missing link between tetra- and disubstituted 3-benzazepines 2 and 5. The synthesis of 4 comprises eight reaction steps starting from alanine. The intramolecular Friedel-Crafts acylation to obtain the ketone 12 and the base-catalyzed elimination of trifluoromethanesulfinate (CF3SO2?) followed by NaBH4 reduction represent the key steps. The GluN2B affinity of the cis-configured 3-benzazepin-1-ol cis-4a with a 4-phenylbutyl side chain (Ki = 252 nM) is considerably lower than the GluN2B affinity of (R,R)-2 (Ki = 17 nM) indicating the importance of the phenolic OH moiety for the interaction with the receptor protein. Introduction of an additional CH3 moiety in 2-position led to a slight decrease of GluN2B affinity as can be seen by comparing the affinity data of cis-4a and 5. The homologous phenylpentyl derivative cis-4b shows the highest GluN2B affinity (Ki = 56 nM) of this series of compounds. According to docking studies cis-4a adopts the same binding mode as the cocrystallized ligand ifenprodil-keto 1A and 5 at the interface of the GluN2B and GluN1a subunits. The same crucial H-bonds are formed between the C([dbnd]O)NH2 moiety of Gln110 within the GluN2B subunit and the protonated amino moiety and the OH moiety of (R,R)-cis-4a.

Novel emissive bio-inspired non-proteinogenic coumarin-Alanine amino acid: Fluorescent probe for polyfunctional systems

Two new bio-inspired non-proteinogenic compounds L1 and L2, containing coumarin and/or acridine chromophores and bearing as spacer an alanine amino acid were successfully synthesized and fully characterized by elemental analysis, 1H and 13

Synthesis of β 3-amino acid and peptides from D-ribose

Synthesis of new β 3-amino acid, peptides and conformational analysis are reported from d-ribose, using Wittig olefination and Aza-Michael addition.

Design and synthesis of hydrophobic and chiral anions from amino acids as precursor for functional ionic liquids

Hydrophobic ionic liquids composed of tetrabutylphosphonium cation and chiral anions derived from amino acids modified with trifluoromethane sulfonyl groups have been synthesized using a simple method. The Royal Society of Chemistry 2006.

New generation ionic liquids: Cations derived from amino acids

Two families of a new generation of ionic liquids, in which the chiral cations are directly derived from naturally occurring α-amino acids and α-amino acid ester salts, have been obtained via very simple preparations. The Royal Society of Chemistry 2005.