N-Methyl-L-phenylalanine

Base Information

• Chemical Name: N-Methyl-L-phenylalanine
• CAS No.: 2566-30-5
• Molecular Formula: C10H13 N O2
• Molecular Weight: 179.219
• UNII: X4UR82KST1
• DSSTox Substance ID: DTXSID80426229
• Nikkaji Number: J594.824J
• Wikidata: Q27104520
• Metabolomics Workbench ID: 52354
• ChEMBL ID: CHEMBL1234265
• Mol file: 2566-30-5.mol

Synonyms:N-Methyl-L-phenylalanine;2566-30-5;N-Methylphenylalanine;(S)-2-(Methylamino)-3-phenylpropanoic acid;(2S)-2-(methylamino)-3-phenylpropanoic acid;N-Me-Phe-OH;N-Me-Phe;L-Phenylalanine, N-methyl-;N-Me-L-Phe;X4UR82KST1;H-MePhe-OH;methyl-l-phenylalanine;H-Me-L-Phe-OH;N-Me-L-Phe-OH;UNII-X4UR82KST1;(S)-2-Methylamino-3-phenylpropionic acid;CHEBI:43980;MFCD00037757;(S)-2-(N-methylamino)-3-phenylpropionic acid;MePhe;N-Methyl phenylalanine;N-Methyl-L-phenylalamne;(S)-N-Methylphenylalanine;(2S)-2-(methylamino)-3-phenyl-propanoic acid;SCHEMBL38480;CHEMBL1234265;DTXSID80426229;SCIFESDRCALIIM-VIFPVBQESA-N;AKOS015850642;CS-W005388;GS-4210;HY-W005388;AC-24114;PD196440;(2S)-2-(Methylamino)-3-phenylpropanoate;(S)-2-methylamino-3-phenyl-propionic acid;AM20060576;N12075;EN300-1132087;A877514;Q27104520

Chemical Property of N-Methyl-L-phenylalanine

Chemical Property:

• Vapor Pressure: 0.000297mmHg at 25°C
• Melting Point: 254-256 °C
• Boiling Point: 308.3oC at 760 mmHg
• PKA: 2.22±0.10(Predicted)
• Flash Point: 140.3oC
• Density: 1.126g/cm3
• Storage Temp.: −20°C
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

97%, ^*data from raw suppliers

N-Methyl-1-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(CC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CN[C@@H](CC1=CC=CC=C1)C(=O)O
• Uses: N-Methyl-1-L-phenylalanine can be used as anti-insect agents.

Technology Process of N-Methyl-L-phenylalanine

There total 73 articles about N-Methyl-L-phenylalanine 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:

Neopeptin A (83855-20-3) → 2,3-diaminopropanoic acid (515-94-6) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + threo-β-hydroxy-L-glutamic acid (threo-L-BHGA) (6208-98-6) + N-Methyl-L-phenylalanine (2566-30-5) + N-methyl-L-aspartic acid (4226-18-0) + (2S,3R)-2-amino-3-methylpentanedioic acid (33511-69-2,274255-87-7)

Guidance literature:

With hydrogenchloride; hydrogen; platinum(IV) oxide; Product distribution; 1.) 4 atm; 2.) 110 deg C;

DOI:10.1080/00021369.1986.10867376

Reference yield:

N-methylphenylalanine (2566-35-0) → N-Methyl-L-phenylalanine (2566-30-5) + N-methyl-D-phenylalanine (56564-52-4)

Guidance literature:

With C₂₄H₂₉CoN₂O₄; In dichloromethane; water; at 10 ℃; for 24h; optical yield given as %ee; Resolution of racemate;

DOI:10.1002/ejoc.200701101

Reference yield:

grassypeptolide A (1010433-25-6) → N-Methyl-L-phenylalanine (2566-30-5) + N-methyl-D-phenylalanine (56564-52-4)

Guidance literature:

grassypeptolide A; With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 1h;

With hydrogenchloride; In water; at 110 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jo1013564

upstream raw materials:

formaldehyd

L-phenylalanine

(+)-2-bromo-3-phenyl-propionic acid

methylamine

Downstream raw materials:

N-Nitroso-N-methyl-L-phenylalanin

L-N^α-methyl-4-nitrophenylalanine

N-methyl-L-tyrosine

tert-butyl (2S)-2-(methylamino)-3-phenylpropanoate

Refernces

• 1、 Chen, Yanchun,Cui, Xuexian,Cui, Yinglu,Li, Chuijian,Li, Ruifeng,Li, Tao,Sun, Jinyuan,Wu, Bian,Zhu, Tong. "Exploration of Transaminase Diversity for the Oxidative Conversion of Natural Amino Acids into 2-Ketoacids and High-Value Chemicals". . p. 7950 - 7957. Retrieved 2020/08/21.
• 2、 Surup, Frank,Chauhan, Dhruv,Niggemann, Jutta,Bartok, Eva,Herrmann, Jennifer,Keck, Matthias,Zander, Wiebke,Stadler, Marc,Hornung, Veit,Müller, Rolf. "Activation of the NLRP3 Inflammasome by Hyaboron, a New Asymmetric Boron-Containing Macrodiolide from the Myxobacterium Hyalangium minutum". . p. 2981 - 2988. Retrieved 2018/09/27.