2566-30-5

Basic information

• Product Name: N-Methyl-L-phenylalanine
• Synonyms: (2S)-2-Amino-3-methyl-3-phenylpropanoic acid;N-Methyl phenylalanine;(2S)-2-(MethylaMino)-3-phenylpropanoic acid;Arg(pbf)oMe.HCl;(S)-2-(MethylaMino)-3-phenylpropanoic acid;H-L-MePhe-OH hydrochloride;L-Arg(Pbf)-OMeHCl;N-Me-L-Phe-OH·HCl
• CAS NO: 2566-30-5
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• Product Categories: Amino Acid Derivatives;Amino Acids;I - Z;Modified Amino Acids;amino acid
• Mol File: 2566-30-5.mol
• Article Data: 41

Chemical Properties

• Melting Point: 254-256 °C
• Boiling Point: 308.3oC at 760 mmHg
• Flash Point: 140.3oC
• Appearance: /
• Density: 1.126g/cm3
• Vapor Pressure: 0.000297mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: −20°C
• PKA: 2.22±0.10(Predicted)
• CAS DataBase Reference: N-Methyl-L-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-L-phenylalanine(2566-30-5)
• EPA Substance Registry System: N-Methyl-L-phenylalanine(2566-30-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2566-30-5(Hazardous Substances Data)

Usage

Description

N-Methyl-L-phenylalanine, also known as N-Methyl-1-L-phenylalanine, is an amino acid derivative with the chemical formula C10H13NO2. It is a white to off-white powder and is characterized by its unique chemical properties that make it suitable for various applications.

Uses

Used in Pest Control Industry:
N-Methyl-L-phenylalanine is used as an anti-insect agent for controlling and managing insect populations. Its application in this industry is due to its ability to disrupt the normal growth and development of insects, making it an effective tool in integrated pest management strategies.
Used in Pharmaceutical Industry:
N-Methyl-L-phenylalanine is also used in the pharmaceutical industry as a building block for the synthesis of various drugs and pharmaceutical compounds. Its unique chemical structure allows for the development of new medications with potential therapeutic applications.
Used in Research and Development:
In addition to its practical applications, N-Methyl-L-phenylalanine is utilized in research and development for studying the properties and functions of amino acids and their derivatives. This helps scientists gain a better understanding of their role in biological systems and can lead to the discovery of new applications and uses for this compound.

InChI:InChI=1/C10H13NO2/c1-11-9(10(12)13)7-8-5-3-2-4-6-8/h2-6,9,11H,7H2,1H3,(H,12,13)/t9-/m0/s1

Upstream product

• 14464-19-8 (+)-N-methyl-N-benzyl-(S)-β-Phe 
• 37553-65-4 Boc-N-Me-Phe-OH 
• 109171-13-3 cycloaspeptide A 
• 55740-07-3 (4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 83855-20-3 Neopeptin A 
• 83855-21-4 Neopeptin B 
• 89838-29-9 Neopeptin C 
• 2899-07-2 (S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine 
• 63-91-2 L-phenylalanine 
• 1276072-29-7 cocosamide A 
• 1276072-31-1 cocosamide B 
• 50-00-0 formaldehyd 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 74-89-5 methylamine 

Downstream Products

• 55260-07-6 N-methyl-N-acetyl-L-phenylalanine 
• 1655-54-5 N(2,4-dinitrophenyl)-(S)-phenylalanine 
• 50886-63-0 (3S)-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione 
• 74530-80-6 4-Benzyliden-3-methyl-2-trifluormethyl-1,3-oxazolidin-5-on 
• 162258-11-9 Boc-Tyr(Bzl)-D-Ala-Gly-(Me)Phe-OH 
• 37553-65-4 Boc-N-Me-Phe-OH 
• 37553-65-4 N-tert-butoxycarbonyl-N-methyl-D-phenylalanine 
• 537-49-5 N-methyl-L-tyrosine 
• 1563182-63-7 (S)-tert-butyl (1-((2-(((benzyloxy)carbonyl)amino)ethyl)amino)-1-oxo-3-phenylpropan-2-yl)(methyl)carbamate 
• 1563182-64-8 (S)-benzyl 2-(2-(methylamino)-3-phenylpropanamido)ethylcarbamate 
• 1563182-77-3 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylbutanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester 
• 1563182-78-4 2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylbutanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester 
• 1563182-79-5 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-hydroxy-N-methylpentanamido)-3-phenylpropanamido)-ethyl carbamic acid benzylester 
• 1563182-81-9 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-5-oxopentanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester 

Relevant articles and documents

Komesuamide and odopenicillatamide, two linear lipopeptides from the marine cyanobacterium Caldora penicillata

The linear lipopeptides komesuamide (1) and odopenicillatamide (2) were isolated from Caldora penicillata a marine cyanobacterium collected in Okinawa. The structures of these compounds were established by spectroscopic analyses, and the absolute configurations were determined by HPLC analyses of the acid hydrolysates. Both compounds showed glucose uptake activity at 40 μM in cultured L6 myotubes.

Isolation and Total Synthesis of Mabuniamide, a Lipopeptide from an Okeania sp. Marine Cyanobacterium

The bioassay-guided fractionation of an Okeania sp. marine cyanobacterium collected in Okinawa led to the isolation of the lipopeptide mabuniamide (1). The gross structure of 1 was determined by spectroscopic analyses, and its absolute configuration was determined using Marfey's analysis of the acid hydrolysate of 1. The absolute configuration of 1 was confirmed by total synthesis. Mabuniamide (1) stimulated glucose uptake in cultured rat L6 myotubes. In addition, mabuniamide (1) and its stereoisomer (2) exhibited moderate antimalarial activity.

Biocatalytic Synthesis of Chiral N-Functionalized Amino Acids

N-Functionalized amino acids are important building blocks for the preparation of diverse bioactive molecules, including peptides. The development of sustainable manufacturing routes to chiral N-alkylated amino acids remains a significant challenge in the pharmaceutical and fine-chemical industries. Herein we report the discovery of a structurally diverse panel of biocatalysts which catalyze the asymmetric synthesis of N-alkyl amino acids through the reductive coupling of ketones and amines. Reactions have been performed on a gram scale to yield optically pure N-alkyl-functionalized products in high yields.