324028-06-0

Basic information

• Product Name: N-ACETYL-3-(3,4,5-TRIFLUORO-PHENYL)-DL-ALANINE
• Synonyms: N-ACETYL-3-(3,4,5-TRIFLUORO-PHENYL)-DL-ALANINE ;2-Acetylamino-3-(3,4,5-trifluoro-phenyl)-propionic acid;5-trifluoro-phenyl)-DL-alanine;N-Acetyl-3-(3;2-Acetamido-3-(3,4,5-trifluorophenyl)propanoic acid
• CAS NO: 324028-06-0
• Molecular Formula: C₁₁H₁₀F₃NO₃
• Molecular Weight: 261.1972096
• Mol File: 324028-06-0.mol

Chemical Properties

• Boiling Point: 446.7 °C at 760 mmHg
• Flash Point: 223.9 °C
• Appearance: /
• Density: 1.409 g/cm³
• Vapor Pressure: 9.23E-09mmHg at 25°C
• Refractive Index: 1.503
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-ACETYL-3-(3,4,5-TRIFLUORO-PHENYL)-DL-ALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYL-3-(3,4,5-TRIFLUORO-PHENYL)-DL-ALANINE(324028-06-0)
• EPA Substance Registry System: N-ACETYL-3-(3,4,5-TRIFLUORO-PHENYL)-DL-ALANINE(324028-06-0)

Safety Data

• Hazardous Substances Data: 324028-06-0(Hazardous Substances Data)

Usage

Uses

Used in Ophthalmic Applications:
N-Acetyl-3-(3,4,5-trifluoro-phenyl)-DL-alanine is used as an ophthalmic solution for the treatment of ocular cancers, such as intraocular melanoma and retinoblastoma. Its application in this field is due to its ability to penetrate the blood-retina barrier and exert a localized effect on cancer cells in the eye, minimizing systemic side effects.
Used in Combination Therapy:
In the field of oncology, N-Acetyl-3-(3,4,5-trifluoro-phenyl)-DL-alanine is used as a component of combination therapy for the treatment of various types of cancer. Its synergistic effect with other medications or treatments enhances the overall therapeutic outcome, providing a more comprehensive approach to cancer management.
Used in Pharmaceutical Research and Development:
N-Acetyl-3-(3,4,5-trifluoro-phenyl)-DL-alanine serves as a valuable compound in pharmaceutical research and development. Its unique mechanism of action and potential applications in cancer treatment make it an attractive candidate for further investigation and development of new drugs and therapies.

InChI:InChI=1/C11H10F3NO3/c1-5(16)15-9(11(17)18)4-6-2-7(12)10(14)8(13)3-6/h2-3,9H,4H2,1H3,(H,15,16)(H,17,18)

Upstream product

• 324027-94-3 diethyl 2-acetamido-2-(3,4,5-trifluorobenzyl)malonate 
• 220141-72-0 3,4,5-trifluorobenzyl bromide 
• 324028-00-4 2-acetylamino-2-(3,4,5-trifluoro-benzyl)-malonic acid 

Downstream Products

• 646066-73-1 3,4,5-trifluoro-L-phenylalanine 
• 324028-12-8 acetyl-D-3,4,5-trifluorophenylalanine 
• 1217684-62-2 3,4,5-trifluoro-D-phenylalanine 

Relevant articles and documents

Exploration of the role of phenylalanine in the thrombin receptor tethered-ligand peptide by substitution with a series of trifluorophenylalanines

The thrombin receptor-tethered ligand SFLLRNP (abbreviation formed by one letter amino acid codes expressing Ser-Phe-Leu-Leu-Arg-Asn-Pro) consists of the Phe-2 residue essential for the receptor activation. In order to explore the molecular characteristics of this Phe-2-phenyl, a series of trifluorophenylalanines [(F3)Phe] was incorporated into this S/Phe/LLRNP for evaluation of their ability to induce the human platelet aggregation. A complete set of (F3)Phe in the L-configuration, namely, (2,3,4-F3)Phe, (2,3,5-F3)Phe, (2,3,6-F3)Phe, (2,4,5-F3)Phe, (2,4,6-F3)Phe, and (3,4,5-F3)Phe, was prepared from trifluorobenzyl bromides and diethyl acetamidomalonate. S/(2,3,4-F3)Phe/LLRNP was equipotent to S/Phe/LLRNP, while (2,4,5-F3)Phe-containing analog was almost twice as potent as those. (2,4,6-F3)Phe-analog exhibited about a half of the activity of S/Phe/LLRNP. (3,4,5-F3)Phe-, (2,3,5-F3)Phe-, and (2,3,6-F3)Phe-analogs were very weak. The analysis of these assay results suggested that Phe-2-phenyl of SFLLRNP is in the edge-to-face CH/π interaction with the receptor aromatic group, utilizing the Phe-2-phenyl edge along with benzene hydrogens at position 2-3 or 5-6. The computer-assisted semi-empirical molecular orbital calculations by MOPAC showed that the fluorine atom decreases the electron density of its ortho, meta, and para hydrogens, and thus increases their acidity more strongly in that order. All these suggested that H → F replacements reinforce the edge-to-face CH/π interaction to enhance biological activity. The H → F replacement on the Phe-phenyl group was found to render an effective structural examination; i.e., to identify the hydrogens in the CH/π interaction, and to intensify the CH/π interaction.