N-Methyl-L-phenylalanine CAS#: 2566-30-5; ChemWhat Code: 92482
Identification
| Product Name | N-Methyl-L-phenylalanine |
| IUPAC Name | (2S)-2-(methylamino)-3-phenylpropanoic acid |
| Molecular Structure |  |
| CAS Registry Number | 2566-30-5 |
| EINECS Number | No data available |
| MDL Number | MFCD00037757 |
| Beilstein Registry Number | No data available |
| Synonyms | N-Methyl-L-phenylalanine;L-phenylalanine, N-methyl-;N-Me-Phe-OH;N-Methyl-L-phenylalanin;N-Méthyl-L-phénylalanine;N-methyl-L-phenylalanine zwitterion;CAS Number: 2566-30-5 |
| Molecular Formula | C10H13NO2 |
| Molecular Weight | 179.22 |
| InChI | InChI=1S/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 |
| InChI Key | SCIFESDRCALIIM-VIFPVBQESA-N |
| Canonical SMILES | CN[C@@H](CC1=CC=CC=C1)C(=O)O |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| US2015/152139 | Peptide Tyrosinase Activators | 2015 |
| US4178371 | Tetrapeptide derivatives | 1979 |
| US4199568 | Tetrapeptide amides | 1980 |
Physical Data
| Appearance | White or off-white crystalline powder |
| Melting Point, °C | Solvent (Melting Point) |
| 243 – 246 | |
| 253 – 254 | |
| 255 – 260 | H2O |
| 233 – 237 | |
| 260 | H2O |
| 258 – 260 | aq. ethanol |
| 278 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | water-d2, deuteriated sodium hydroxide | 400 |
| Chemical shifts, Spectrum | 13C | water-d2, deuteriated sodium hydroxide | 101 |
| Chemical shifts | 1H | D2O, O-deuterio-2,2,2-trifluoro-acetic acid | 300 |
| 1H | D2O, O-deuterio-2,2,2-trifluoro-acetic acid | 300 | |
| Chemical shifts | 13C | ||
| Chemical shifts | 1H | D2O, various solvent(s) | |
| Chemical shifts | 1H | D2O | |
| Spin-spin coupling constants | D2O |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Comment (IR Spectroscopy) |
| Bands | KBr | |
| Bands | KBr | 3200 – 700 cm**(-1) |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) | Comment (UV/VIS Spectroscopy) | Absorption Maxima (UV/VIS), nm | Ext./Abs. Coefficient, l·mol-1cm-1 |
| Absorption maxima | methanol | 264, 258, 252 | 250, 310, 240 | |
| Absorption maxima | HCl, methanol | Ratio of solvents: 0.1 M | 263, 257, 252 | 130, 170, 140 |
| Spectrum |
Route of Synthesis (ROS)
| Conditions | Yield |
| With sodium hydrogencarbonate In water; acetone at 40℃; for 1h; Experimental Procedure General procedure: Samples of each 0.4 mg of 1 and 2 were hydrolyzed by heating in 1 ml 6 N HCl for 24 h at 110 °C. After cooling, the solution was evaporated to dryness and the residue redissolved in H2O (50 μL). To each of these hydrolyzate solutions, or to a solution of the reference amino acid (50 μL; 50 mM), a solution of FDAA (Marfey’s reagent, N-(2,4-dinitro-5-fluorophenyl)-l-alaninamide) in acetone (100 μL of 1% (w/v) solution) was added. After addition of NaHCO3 solution (20 μL; 1 M), the mixture was incubated for 1 h at 40 °C. The reaction was stopped by addition of HCl (10 μL; 2 M), the solvents were evaporated, and the residue was redissolved in acetonitrile (1 ml). An aliquot of this solution (20 μL) was analyzed by HPLC (Phenomenex Luna C18, 250 4.6 mm, 5 μm; solvents: A is H2O + 0.05% HCOOH, B is MeOH + 0.05% HCOOH; linear gradient from 10% B in A at t = 0 min to 90% B in A within 20 min; 25 °C; 300 μL min-1). Configuration of the amino acid units were determined by comparing the chromatograms with those of derivatives of commercially available amino acids. The retention times (min) were as follows: l-Val (15.1), d-Val (16.9), N-Me-l-Val (16.0), N-Me-d-Val (17.0), l-Phe (16.4), d-Phe (18.1), N-Me-l-Phe (15.9), and N-Me-d-Phe (11.6). 26 In independent experiments, all 1/2-derived amino acids were shown to have the l-configuration. | |
| Stage #1: N-Methyl-L-phenylalanine; N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide With sodium hydrogencarbonate In water; acetone at 40℃; for 1h; Stage #2: With hydrogenchloride In water; acetone | |
| With sodium hydrogencarbonate In water; acetone at 70℃; for 2h; |
Safety and Hazards
| GHS Hazard Statements | Not Classified |
| For more detailed information, please visit ECHA C&L website |
| Source: European Chemicals Agency (ECHA) License Note: Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: “Source: European Chemicals Agency, http://echa.europa.eu/”. Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. License URL: https://echa.europa.eu/web/guest/legal-notice Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446 Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database |
Other Data
| Transportation | Under the room temperature and away from light |
| HS Code | No data available |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price | USD |
| Use Pattern |
| N-Methyl-L-phenylalanine CAS#: 2566-30-5 Often used as an amino acid. |
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