4-Benzoyl-l-phenylalanine

Base Information

• Chemical Name: 4-Benzoyl-l-phenylalanine
• CAS No.: 104504-45-2
• Molecular Formula: C16H15NO3
• Molecular Weight: 269.3
• Hs Code.: 29225090
• UNII: 9RU6KQ9WYD
• DSSTox Substance ID: DTXSID20909021
• Nikkaji Number: J632.372C
• Wikidata: Q27097586
• Mol file: 104504-45-2.mol

Synonyms:4-benzoylphenylalanine;BzF amino acid;p-benzoyl-L-phenylalanine;p-benzoylphenylalanine;p-Bpa amino acid;pBpa amino acid

Chemical Property of 4-Benzoyl-l-phenylalanine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.616
• Boiling Point: 467.605 °C at 760 mmHg
• PKA: 2.16±0.10(Predicted)
• Flash Point: 236.599 °C
• PSA: 80.39000
• Density: 1.249 g/cm³
• LogP: 2.57230
• Storage Temp.: -15°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 269.10519334
• Heavy Atom Count: 20
• Complexity: 342

Purity/Quality:

98%,99%, ^*data from raw suppliers

H-p-Bz-Phe-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)CC(C(=O)O)N
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)C[C@@H](C(=O)O)N
• Recent ClinicalTrials: Study to Assess the Safety, Tolerability and Pharmacokinetic Profile of PBF-999 'After Multiple Oral Doses' in Healthy Volunteers
• Uses: 4-Benzoyl-L-phenylalanine is a photoreactive amino acid which can easily be incorporated into a peptide by solid-phase synthesis and finds application as phtolabel. It is an important raw material as well as an intermediate in organic synthesis.

Technology Process of 4-Benzoyl-l-phenylalanine

There total 4 articles about 4-Benzoyl-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: 28.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + benzoyl chloride (98-88-4) → p-Benzoyl-DL-Phenylalanine (104504-45-2)

Guidance literature:

With trifluorormethanesulfonic acid; at 0 - 20 ℃; for 12h;

DOI:10.3390/molecules18078393

Reference yield:

C19H16F3NO4 → p-Benzoyl-DL-Phenylalanine (104504-45-2)

Guidance literature:

With sodium hydroxide; In methanol; water; acetonitrile; at 20 ℃;

DOI:10.3987/COM-13-12815

Reference yield:

(S)-(-)-methyl N-(trifluoroacetyl)phenylalaninate (23635-30-5) + benzoyl chloride (98-88-4) → p-Benzoyl-DL-Phenylalanine (104504-45-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluorormethanesulfonic acid / 0 °C

1.2: 10 h / 20 °C

2.1: sodium hydroxide / methanol; water; acetonitrile / 20 °C

With trifluorormethanesulfonic acid; sodium hydroxide; In methanol; water; acetonitrile; 1.2: |Friedel-Crafts Acylation;

DOI:10.3987/COM-13-12815

upstream raw materials:

L-phenylalanine

benzoyl chloride

(S)-(-)-methyl N-(trifluoroacetyl)phenylalaninate

Downstream raw materials:

N-trifluoroacetyl 4-benzoylphenylalanine

Tyrocidine A

Refernces

• 1、 Wang, Lei,Hisano, Wataru,Murai, Yuta,Sakurai, Munenori,Muto, Yasuyuki,Ikemoto, Haruka,Okamoto, Masashi,Murotani, Takashi,Isoda, Reika,Kim, Dongyeop,Sakihama, Yasuko,Sitepu, Irnayuli R.,Hashidoko, Yasuyuki,Hatanaka, Yasumaru,Hashimoto, Makoto. "Distinct metabolites for photoreactive l-phenylalanine derivatives in Klebsiella sp. CK6 isolated from rhizosphere of a wild dipterocarp sapling". . p. 8393 - 8401. Retrieved 2013.