CAS 2566-22-5 Benzoyl-L-phenylalanine (HCID 97370)

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Basic information

CAS: 2566-22-5
Standard SMILES: O=C(N[C@@H](Cc1ccccc1)C(=O)O)c1ccccc1
InChIKey: NPKISZUVEBESJI-AWEZNQCLSA-N
Molecular formula: C16H15NO3
Average molar mass: 269.29 g/mol
Monoisotopic mass: 269.10519334

Names & identifiers

Preferred name: Benzoyl-L-phenylalanine
IUPAC: (2S)-2-benzamido-3-phenylpropanoic acid
English name: Bz-Phe-OH
Molecular formula: C16H15NO3
Molecular weight: 269.3

Names & synonyms

2566-22-5Benzoyl-l-phenylalanineBenzoylphenylalanine9S304JL9M7DTXSID701313598NSC-118532RefChem:916971DTXCID601743413N-Benzoyl-l-phenylalanineBz-Phe-OHBz-L-Phe-OHMFCD00063153

Show more names

NSC 167264BENZOYL-PHE-OHBZ-PHENYLALANINEBZ-PHE-OH USP/EP/BPN-Benzoylphenylalanine

Bzo-Phe-OH(2S)-3-phenyl-2-(phenylformamido)propanoic acidL-Phenylalanine, N-benzoyl-(2S)-2-benzamido-3-phenylpropanoic acidPhenylalanine, N-benzoyl-(2S)-2-(Benzoylamino)-3-phenylpropanoic acid(s)-2-benzamido-3-phenylpropanoic acidUNII-9S304JL9M7

Database identifiers

CAS: 2566-22-5
PubChem CID: 97370
DTXSID: DTXSID701313598
ChEMBL: CHEMBL22685
ChEBI: CHEBI:90412
UNII: 9S304JL9M7
Nikkaji: J231.705B

Properties

Computed structural properties

XLogP: 2.8
Topological polar surface area: 66.4 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 5
Heavy atoms: 20
Formal charge: 0
Complexity: 331

Physicochemical properties

Melting point: 184 °C · 184 °C (decomp)
Boiling point: 532 · 532.0±43.0 °C(Predicted)
Density: 1.232 · 1.232±0.06 g/cm3(Predicted)
RTECS: 7326700 · SQ7326700
storage temp.: -20 °C · Sealed in dry,Store in freezer, under -20°C
pka: 3.8 · 3.80±0.10(Predicted)
form: Powder
color: Off-white to white
optical activity: Consistent with structure
CAS DataBase Reference: 2566 · 2566-22-5(CAS DataBase Reference)
FDA UNII: 9 S304JL9M7 · 9S304JL9M7
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338

Safety & regulation

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

Biologically active molecules which are covalently bound to the enzymes or binding proteins normally acting on them. Binding occurs due to activation of the label by ultraviolet light. These labels are used primarily to identify binding sites on proteins.

Applications

UsesN-Benzoyl-L-phenylalanine is used in the preparation of α-di/monoketo ester derivatives of n-protected amino acids as inhibitors of cysteine of serine proteinases, as well as calpain inhibitors.