N-Acetyl-L-phenylalanine

Base Information

• Chemical Name: N-Acetyl-L-phenylalanine
• CAS No.: 2018-61-3
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• Hs Code.: 29242990
• European Community (EC) Number: 217-959-8
• NSC Number: 760131
• UNII: NP5BT39467
• DSSTox Substance ID: DTXSID20883539
• Nikkaji Number: J27.562J
• Wikidata: Q27101819
• Metabolomics Workbench ID: 37286
• ChEMBL ID: CHEMBL55743
• Mol file: 2018-61-3.mol

Synonyms:N-acetylphenylalanine;N-acetylphenylalanine, (D)-isomer;N-acetylphenylalanine, (D,L)-isomer, 3H-labeled;N-acetylphenylalanine, (L)-isomer;N-acetylphenylalanine, (L)-isomer, 3H-labeled

Chemical Property of N-Acetyl-L-phenylalanine

Chemical Property:

• Appearance/Colour: white to off-white fine cryst. powder or needles
• Vapor Pressure: 4.96E-09mmHg at 25°C
• Melting Point: 171-173 °C(lit.)
• Refractive Index: 40 ° (C=5, MeOH)
• Boiling Point: 453.9 °C at 760 mmHg
• PKA: 3.56±0.10(Predicted)
• Flash Point: 228.3 °C
• PSA: 66.40000
• Density: 1.199 g/cm³
• LogP: 1.20930
• Storage Temp.: -20°C
• Solubility.: Solubility in methanol (almost transparency). Soluble in acetone
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 207.08954328
• Heavy Atom Count: 15
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

N-Acetyl-L-Phenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O
• Uses: It is an essential amino acid produced for medical, feed, and nutritional applications such as in the preparation of aspartame. It is applied as an antidepressant. N-Acetyl-L-phenylalanine is an protected analogue of L-Phenylalanine (P319415), an essential amino acid produced for medical, feed, and nutritional applications such as in the preparation of Aspartame.

Technology Process of N-Acetyl-L-phenylalanine

There total 78 articles about N-Acetyl-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: 45.0%

ethyl N-acetyl-DL-phenylalaninate (4134-09-2) → (R)-N-acetylphenylalanin (10172-89-1) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) + (R)-ethyl N-acetylphenylalanine (2361-96-8,4134-09-2,57772-79-9,20918-84-7)

Guidance literature:

With water; In ethanol; at 25 ℃; for 2h; optical yield given as %ee; enantioselective reaction; Microbiological reaction;

DOI:10.1016/j.tetasy.2010.02.011

Reference yield:

N-acetyl-L-phenylalanine 4-nitrophenyl ester (14009-94-0) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Guidance literature:

PalHis; PalHis + 2C₁₄N₂C₁Br; In water; acetonitrile; at 25 ℃; Rate constant; furhter bilayer catalytic systems; k_cat;

DOI:10.1246/cl.1981.785

Reference yield:

1-tetradecyl-3-methylimidazolium L-2-aminohydrocinnamic acid salt + 4-nitrophenol acetate (830-03-5) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + (S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3)

Guidance literature:

In aq. buffer; at 25 ℃; pH=9; Kinetics;

DOI:10.1016/j.molliq.2020.113206

upstream raw materials:

(R,S)-N-acetyl phenylalanine

(1S)-endo-fenchylamine

(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol

L-phenylalanine

Downstream raw materials:

(S)-cyanomethyl 2-acetamido-3-phenylpropanoate

N-Acetyl-N'-methyl-L-phenylalaninamide

Ac-Phe-Lys-OH

2,3,4,6-tetra-O-acetyl-1-O-(N-acetyl-L-phenylalanyl)-β-D-glucopyranose

Refernces

• 1、 Tewari, Y. B.,Schantz, M. M.,Pandey, P. C.,Rekharsky, M. V.,Goldberg, R. N.. "Thermodynamics of the Hydrolysis of N-Acetyl-L-phenylalanine Ethyl Ester in Water and in Organic Solvents". . p. 1594 - 1601. Retrieved 1995.
• 2、 Cesarotti, E.,Chiesa, A.,D'Alfonso, G.. "ASYMMETRIC HYDROGENATION BY CHIRAL AMINOPHOSPHINE-PHOSPHINITE RHODIUM COMPLEXES". . p. 2995 - 2996. Retrieved 1982.
• 3、 Aso. "Enzymatic approach to the synthesis of a lysine-containing sweet peptide, N-acetyl-L-phenylalanyl-L-lysine". . p. 729 - 733. Retrieved 1989.
• 4、 Csuk, Rene,Glaenzer, Brigitte I.. "BIOCATALYTICAL TRANSFORMATIONS II. ENANTIOSELECTIVE HYDROLYSIS OF N-ACETYL-FLUORO-PHENYLALANINE-ETHYLESTERS BY LYOPHILISED YEAST". . p. 99 - 106. Retrieved 1988.
• 5、 Yan, Yongjun,Chi, Yongxiang,Zhang, Xumu. "Novel phosphine-phosphite and phosphine-phosphinite ligands for highly enantioselective asymmetric hydrogenation". . p. 2173 - 2175. Retrieved 2004.
• 6、 Dressen, Mark H. C. L.,Van De Kruijs, Bastiaan H. P.,Meuldijk, Jan,Vekemans, Jef A. J. M.,Hulshof, Lumbertus A.. "From batch to flow processing: Racemization of N-acetylamino acids under microwave heating". . p. 888 - 895. Retrieved 2009.
• 7、 Roper, Jerry M.,Bauer, Dennis P.. "Synthesis of Phenylalanines in High Enantiomeric Excess via Enzymatic Resolution". . p. 1041 - 1043. Retrieved 1983.
• 8、 Zanotti-Gerosa, Antonio,Malan, Christophe,Herzberg, Daniela. "Phosphonites based on the paracyclophane backbone: New ligands for highly selective rhodium-catalyzed asymmetric hydrogenation". . p. 3687 - 3690. Retrieved 2001.
• 9、 Figueroa, Roberto,Orth, Elisa,Pavez, Paulina,Rojas, Mabel,Santos, José G.. "The effect of imidazolium salts with amino acids as counterions on the reactivity of 4-nitrophenyl acetate: A kinetic study". . . Retrieved 2020/04/29.
• 10、 Moritz, Jan-Ole,Chakrabortty, Soumyadeep,Bernd H. Mu.ller,Spannenberg, Anke,Kamer, Paul C. J.. "P-chirogenic diphosphazanes with axially chiral substituents and their use in rh-catalyzed asymmetric hydrogenation". . p. 14537 - 14544. Retrieved 2020/12/29.