N-Acetyl-D-phenylalanine

Base Information

• Chemical Name: N-Acetyl-D-phenylalanine
• CAS No.: 10172-89-1
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• Hs Code.: 2924299090
• European Community (EC) Number: 233-447-7
• UNII: 606E063065
• DSSTox Substance ID: DTXSID90144144
• Nikkaji Number: J207.899F
• Wikidata: Q27103564
• Metabolomics Workbench ID: 51620
• ChEMBL ID: CHEMBL174089
• Mol file: 10172-89-1.mol

Synonyms:N-Acetyl-D-phenylalanine;10172-89-1;Acetyl-D-phenylalanine;Ac-D-Phe-OH;D-Phenylalanine, N-acetyl-;N-Acetylphenylalanine, D-;N-Acetyl-3-phenyl-D-alanine;(R)-2-acetamido-3-phenylpropanoic acid;(2R)-2-acetamido-3-phenylpropanoic acid;(2R)-2-acetamido-3-phenyl-propanoic acid;CHEBI:28203;EINECS 233-447-7;UNII-606E063065;606E063065;N-Acetylphenylalanine #;MFCD00002664;NSC-523830;D-N-acetylphenylalanine;N-Ac-D-Phe-OH;(R)-N-acetylphenylalanine;AFALANINE, (R)-;bmse000479;SCHEMBL331330;CHEMBL174089;DTXSID90144144;N-ACETYL-(R)-PHENYLALANINE;D-(-)-N-ACETYLPHENYLALANINE;(-)-N-ACETYL-D-PHENYLALANINE;AKOS015841021;AM82154;CCG-233383;CS-W015269;HY-W014553;NSC 523830;(R)-(-)-N-ACETYLPHENYLALANINE;AC-24139;AS-12783;ALANINE, N-ACETYL-3-PHENYL-, D-;A0105;C05620;EN300-962030;A800443;J-300204;W-108904;Q27103564;Z1455311715;(2R)-2-(1-hydroxyvinylamino)-3-phenyl-propanoic acid

Chemical Property of N-Acetyl-D-phenylalanine

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 4.96E-09mmHg at 25°C
• Melting Point: 167 °C
• Refractive Index: -41 ° (C=5, MeOH)
• Boiling Point: 453.944 °C at 760 mmHg
• PKA: 3.56±0.10(Predicted)
• Flash Point: 228.338 °C
• PSA: 66.40000
• Density: 1.2 g/cm³
• LogP: 1.20930
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Sparingly)
• 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-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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: Protected amino acid.

Technology Process of N-Acetyl-D-phenylalanine

There total 44 articles about N-Acetyl-D-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: 96.2%

(Z)-2-acetamidocinnamic acid → (R)-N-acetylphenylalanin (10172-89-1)

Guidance literature:

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: 41.0%

D-phenylalanine hydrochloride (28069-46-7) + acetyl chloride (75-36-5) → (R)-N-acetylphenylalanin (10172-89-1)

Guidance literature:

With sodium hydroxide; water; at 0 ℃; for 1h;

DOI:10.1039/b802311e

upstream raw materials:

(R,S)-N-acetyl phenylalanine

(1S)-endo-fenchylamine

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

D-(R)-phenylalanine

Downstream raw materials:

D-(R)-phenylalanine

(2R,3R)-2-((R)-2-Acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid benzyl ester

4-(BOC-tyrosylamino)-1-(N-acetyl-D-phenylalanyl)piperidine

(R,S)-N-acetyl phenylalanine

Refernces

• 1、 Zhu,Cao,Jiang,Zhang. "Highly enantioselective Rh-catalyzed hydrogenations with a new chiral 1,4-bisphosphine containing a cyclic backbone". . p. 1799 - 1800. Retrieved 1997.
• 2、 Fadnavis,Jadhav, Vasudev. "Enantioselective hydrolytic reactions of rice bran lipase (RBL): A first report". . p. 2361 - 2366. Retrieved 1997.
• 3、 Miyano, Sotaro,Nawa, Masayoshi,Hashimoto, Harukichi. "ASYMMETRIC HYDROGENATION OF α-ACYLAMINOACRYLIC ACIDS AND ESTERS WITH AXIALLY DISSYMMETRIC BISAMINOPHOSPHINE-RHODIUM COMPLEXES". . p. 729 - 730. Retrieved 1980.
• 4、 Jamis, Jim,Anderson, John R.,Dickson, Ron S.,Campi, Eva M.,Jackson, W. Roy. "Modified silica-heterogenised catalysts for use in aqueous enantioselective hydrogenations". . p. 37 - 43. Retrieved 2001.
• 5、 Sakurai, Takayasu,Margolin, Alexey L.,Russell, Alan J.,Klibanov, Alexander M.. "Control of Enzyme Enantioselectivity by the Reaction Medium". . p. 7236 - 7237. Retrieved 1988.
• 6、 Dahlenburg, Lutz,Eckert, Christine. "Chirale Bisphosphane VIII. Die enantioselektive Hydrierung von α-Acetamidozimtsaeure durch kationische Rhodium(I)-Komplexe mit optisch reinen (1S,2S)-Cyclopentan-1,2-diyl-bis(phosphonigsaeurediester)- und (1S,2S)-Cyclopentan-1,2-diyl-bis(phosphonigsaeurediamid)-Liganden1". . p. 227 - 232. Retrieved 1998.
• 7、 Honda, Takeshi,Miyazaki, Masaya,Nakamura, Hiroyuki,Maeda, Hideaki. "Facile preparation of an enzyme-immobilized microreactor using a cross-linking enzyme membrane on a microchannel surface". . p. 2163 - 2171. Retrieved 2006.
• 8、 Nagel, Ulrich,Leipold, Joachim. "Synthesis of bis(phosphane) palladium and rhodium complexes on a polyethylene oxide grafted polystyrene matrix (tentagel) and the catalytic behavior of the rhodium". . p. 815 - 821. Retrieved 1996.
• 9、 Almena Perea, Juan J.,Boerner, Armin,Knochel, Paul. "A versatile modular approach to new chiral C2-symmetrical ferrocenyl ligands: Highly enantioselective Rh-catalyzed hydrogenation of α- acetamidoacrylic acid derivatives". . p. 8073 - 8076. Retrieved 1998.
• 10、 Rocha Gonsalves,Bayon,Pereira,Serra,Pereira. "Asymmetric transfer hydrogenation of acrylic acids catalyzed by rhodium(I) complexes of diphosphine ligands". . p. 199 - 204. Retrieved 1998.