DL-Phenylalanine

Base Information

• Chemical Name: DL-Phenylalanine
• CAS No.: 150-30-1
• Molecular Formula: C9H11NO2
• Molecular Weight: 165.192
• Hs Code.: 29224995
• European Community (EC) Number: 205-756-7
• NSC Number: 620354,79477,25005,9959
• UNII: 8P946UF12S
• DSSTox Substance ID: DTXSID9023463
• Nikkaji Number: J1.258K
• Wikidata: Q27103475
• NCI Thesaurus Code: C61713
• ChEMBL ID: CHEMBL25080
• Mol file: 150-30-1.mol

Synonyms:1,2-dilauroylphosphatidic acid;1,2-dilauroylphosphatidic acid, sodium salt;DLPA

Chemical Property of DL-Phenylalanine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.000313mmHg at 25°C
• Melting Point: 266-267 °C
• Refractive Index: 1.576
• Boiling Point: 307.5 °C at 760 mmHg
• Flash Point: 139.771 °C
• PSA: 63.32000
• Density: 1.202 g/cm³
• LogP: 1.34130
• Water Solubility.: 14.11 g/L (25℃)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: Xi,C
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)N

Technology Process of DL-Phenylalanine

There total 165 articles about DL-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: 81.8%

threo-O-Acetyl-β-phenyl-L-serine hydrochloride (88854-16-4,88854-17-5) → Phenylalanine (150-30-1,25191-15-5,658-69-5,67675-33-6) + (R,S)-N-acetyl phenylalanine (2901-75-9) + threo-2-amino-3-hydroxy-3-phenylpropanoic acid (69-96-5,1078-17-7,2584-74-9,2584-75-0,6254-48-4,7352-06-9,7687-36-7,7695-56-9,32946-42-2,50897-27-3,68296-26-4,109120-55-0)

Guidance literature:

With hydrogen; Pd-BaSO₄; In water; acetic acid; at 60 ℃; for 8h; under 2585.7 Torr; Yields of byproduct given;

DOI:10.1021/jo00180a038

Reference yield: 33.0%

4-benzyl-2-phenyl-2-oxazolin-5-one (5874-61-3,21453-79-2,51127-19-6,75658-67-2) → Phenylalanine (150-30-1,25191-15-5,658-69-5,67675-33-6) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With potassium; In tetrahydrofuran; for 4h;

Reference yield: 30.0%

phenyllactic acid (828-01-3) → Phenylalanine (150-30-1,25191-15-5,658-69-5,67675-33-6)

Guidance literature:

With ammonium hydroxide; hydrogen; at 219.84 ℃; for 2h; under 7500.75 Torr; Autoclave;

DOI:10.1073/pnas.1800272115

upstream raw materials:

5-benzylidene-2-thiohydantoin

4-benzyl-oxazolidine-2,5-dione

5-phenylimidazolidine-2,4-dione

diethyl ether

Downstream raw materials:

3-acetylamino-4-phenyl-2-butanone

N-hexahydroazepin-2-ylidene-DL-phenylalanine

(+/-)-phenylalanine propyl ester

4-benzyl-oxazolidine-2,5-dione

Refernces

• 1、 Micskei, Károly,Holczknecht, Orsolya,Hajdu, Csongor,Patonay, Tamás,Marchis, Valér,Meo, Milena,Zucchi, Claudia,Pályi, Gyula. "Asymmetric synthesis of amino acids by Cr(II) complexes of natural amino acids". . p. 143 - 148. Retrieved 2003.
• 2、 Xie, Zhenbing,Chen, Bingfeng,Peng, Fangfang,Liu, Mingyang,Liu, Huizhen,Yang, Guanying,Han, Buxing. "Highly Efficient Synthesis of Amino Acids by Amination of Bio-Derived Hydroxy Acids with Ammonia over Ru Supported on N-Doped Carbon Nanotubes". . p. 5683 - 5689. Retrieved 2020.
• 3、 Tripathi, Y. C.,Maurya, S. K.,Spingh, V. P.,Pandey, V. B.. "CYCLOPEPTIDE ALKALOIDS FROM ZIZYPHUS RUGOSA BARK". . p. 1563 - 1565. Retrieved 1989.
• 4、 Bernauer, Klaus,Deschenaux, Robert,Taura, Toshiaki. "Stereoselectivity in Reactions of Metal Complexes VII. Asymmetric Synthesis of Amino Acids by Metal Ion-Promoted Transamination". . p. 2049 - 2058. Retrieved 1983.
• 5、 Gouverneur,Ghosez. "Electrophilic amination of 2-azadienes". . p. 7585 - 7598. Retrieved 1996.
• 6、 Tabushi et al.. "-". . p. 4343. Retrieved 1976.
• 7、 Baryshnikov, A. T.,Belikov, V. M.,Latov, V. K.,Saporovskaya, M. B.. "CATALYSTS FOR THE HYDROGENATION OF DEHYDRO(ACETYLAMINO ACIDS) BASED ON PALLADIUM AND RHODIUM COMPLEXES OF BISSALICYLIDENE DERIVATIVES". . p. 1206 - 1209. Retrieved 1981.
• 8、 Nakahara,Nishikawa,Mitani. "The direct derivations of some amino acids from glycine.". . p. 2212 - 2212. Retrieved 1967.
• 9、 Galat. "-". . p. 965. Retrieved 1947.
• 10、 Homer,R.B. et al.. "-". . p. 4403 - 4409. Retrieved 1965.