4-Acetyl-L-phenylalanine

Base Information

• Chemical Name: 4-Acetyl-L-phenylalanine
• CAS No.: 122555-04-8
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• Hs Code.: 2922500090
• UNII: Y61IJN1HNY
• DSSTox Substance ID: DTXSID401346627
• Nikkaji Number: J1.854.447D
• Wikidata: Q27454549
• Mol file: 122555-04-8.mol

Synonyms:3-(4-acetylphenyl)-2-aminopropanoic acid;p-acetyl-L-phenylalanine;p-acetylphenylalanine

Chemical Property of 4-Acetyl-L-phenylalanine

Chemical Property:

• Melting Point: >300°C (dec.)
• Boiling Point: 396.7±37.0 °C(Predicted)
• PKA: 2.15±0.10(Predicted)
• PSA: 80.39000
• Density: 1.226±0.06 g/cm3(Predicted)
• LogP: 1.54390
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 207.08954328
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

≥99.0% ^*data from raw suppliers

L-4-Acetylphenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC=C(C=C1)CC(C(=O)O)N
• Isomeric SMILES: CC(=O)C1=CC=C(C=C1)C[C@@H](C(=O)O)N
• Uses: 4-Acetyl-L-phenylalanine is the 4-acetyl analogue of the essential amino acid L-phenylaniline. 4-Acetyl-L-phenylalanine as well as other unnatural amino acids can be genetically incorporated successfully into proteins in Escherichia coli as well as mammalian cells.

Technology Process of 4-Acetyl-L-phenylalanine

There total 15 articles about 4-Acetyl-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: 100.0%

diethyl 2-acetamido-2-(4-acetylbenzyl)malonate (522601-20-3) → para-acetylphenylalanine (18910-27-5,22888-49-9,122555-04-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 8h; Reflux;

DOI:10.1039/c1cc13533c

Reference yield: 98.0%

C15H19NO4 → p-acetyl-L-phenylalanine (122555-04-8)

Guidance literature:

With hydrogenchloride; In water; at 90 ℃; for 6h;

Reference yield: 88.0%

→ p-acetyl-L-phenylalanine (122555-04-8)

Guidance literature:

upstream raw materials:

(4-Acetyl-benzyl)-formamido-malonsaeurediethylester

4-chloromethylacetophenone

diethyl 2-acetamido-2-(4-acetylbenzyl)malonate

4-acetylbenzyl bromide

Downstream raw materials:

C₁₉H₂₆BNO₃

para-acetyl-phenylalanine

C₁₃H₁₅NO₄

(S)-3-(4-Acetyl-phenyl)-2-amino-propionic acid methyl ester

Refernces

Click strategies for single-molecule protein fluorescence

10.1021/ja210587q

The study systematically investigates various clickable UAAs for their potential in high-resolution smFRET, focusing on parameters such as probe accessibility, protein expression yield, and quantitative labeling. The researchers found that genetically encoding propargyllysine (UAA 5) offers significant advantages for state-of-the-art measurements compared to other UAAs. Using this optimized system, they presented a biocompatible one-step dual-labeling strategy for the regulatory protein RanBP3, demonstrating that a region with two FxFG repeat sequences adopts a disordered but collapsed state. Key chemicals used in the process include UAAs such as p-acetylphenylalanine (1), p-azidophenylalanine (2), p-(propargyloxy)-phenylalanine (3), and aliphatic alkyne UAAs (4 and 5), as well as fluorescent dyes like Alexa 488 and Alexa 594 for labeling and smFRET measurements.

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