4530-18-1

Basic information

• Product Name: BOC-DL-PHE-OH
• Synonyms: BOC-DL-PHENYLALANINE;BOC-DL-PHE-OH;N-ALPHA-T-BUTOXYCARBONYL-D-PHENYLALANINE;N-tert-Butoxycarbonyl-DL-phenylalanine;N-Methyl-Boc-D-phenylalanine;Boc-N-Me-Phe-OH;BOC-DL-Phenylalanine(Boc-DL-Phe-OH);2-(tert-butoxycarbonyl(Methyl)aMino)-3-phenylpropanoic acid
• CAS NO: 4530-18-1
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 279.33
• EINECS: 1533716-785-6
• Product Categories: Phenylalanine [Phe, F]
• Mol File: 4530-18-1.mol
• Article Data: 18

Chemical Properties

• Melting Point: 106-108 °C
• Boiling Point: 405oC at 760 mmHg
• Flash Point: 198.8oC
• Appearance: /Solid
• Density: 1.146g/cm3
• Vapor Pressure: 2.75E-07mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: Store at RT.
• PKA: 3.88±0.10(Predicted)
• CAS DataBase Reference: BOC-DL-PHE-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-DL-PHE-OH(4530-18-1)
• EPA Substance Registry System: BOC-DL-PHE-OH(4530-18-1)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 4530-18-1(Hazardous Substances Data)

Usage

General Description

BOC-DL-PHE-OH is a chemical compound with the molecular formula C15H21NO4. It is a derivative of phenylalanine, an essential amino acid that plays a key role in protein synthesis and is also a precursor for various neurotransmitters and hormones. BOC-DL-PHE-OH is often used as a protective group in peptide synthesis, where it serves to protect the amino group of phenylalanine from unwanted reactions and can be easily removed once the peptide chain is assembled. BOC-DL-PHE-OH is commonly employed in medicinal and pharmaceutical research, as well as in the production of biologically active peptides and proteins.

InChI:InChI=1/C15H21NO4/c1-15(2,3)20-14(19)16(4)12(13(17)18)10-11-8-6-5-7-9-11/h5-9,12H,10H2,1-4H3,(H,17,18)

Upstream product

• 4530-20-5 BOC-glycine 
• 100-39-0 benzyl bromide 
• 75-65-0 tert-butyl alcohol 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 74293-09-7 2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester 
• 35909-82-1 2,3,4,6-tetra-O-benzyl-1-O-(N-tert-butoxycarbonyl-L-phenylalanyl)-β-D-glucopyranose 
• 909114-65-4 tert-butyl 4,6-dimethoxy-1,3,5-triazinyl carbonate 
• 150-30-1 Phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4316-58-9 tris(p-bromophenyl)amine radical cation 
• 126686-59-7 (±)-(4-methoxyphenyl)methyl-2-[(tert-butoxycarbonyl)amino]phenylpropionate 
• 89037-64-9 1-tert-butoxycarbonyloxybenzotriazole 
• 13303-10-1 tert-Butyl 4-nitrophenyl carbonate 

Downstream Products

• 106572-02-5 N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester 
• 112700-37-5 5-[(2R)-2-(tert-Butoxycarbonylamino)-1-hydroxy-3-phenylpropylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 140647-62-7 N-t-butyloxycarbonyl-L-phenylalanyl-DL-3,3-difluoro-phenylalanine methyl ester 
• 125719-13-3 Boc-Phe-Gly-OEt 
• 53331-94-5 Boc-Phe-SePh 
• 58822-25-6 Leu-enkephalin 
• 150-30-1 Phenylalanine 
• 805230-93-7 methyl 11-({(2R,S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)undecanoate 
• 33365-35-4 H-Phe-OH p-toluenesulfonic acid salt 

Relevant articles and documents

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Synthesis and anti-tumor activity evaluation of novel 7-fluoro-4-(1-piperazinyl) quinolines

Background: Three series of new 7-fluoro-4-(1-piperazinyl) quinolines (I1~I6, II1~II2 and IV1~IV4) were synthesized. Their anti-tumor activity was evaluated in vitro against three human carcinoma cell lines, namely SGC-7901 cells, BEL-7402 cells and A549 cells expressing high levels of EGFR by Methyl Thiazolyl Terazolium (MTT) assay. Methods: Three series of quinoline derivatives were synthesized, characterized and evaluated for their in vitro anti-tumor activities. Results and Discussion: Structures of the newly synthesized compounds were confirmed by spectral analysis. The preliminary bioassay indicated that compounds I1, I10 and II1 exhibited better anti-tumor activity than the rest of the target compounds and gefitinib against A549 cell based assay, which demonstrated that compounds I1, I10 and II1 are potential agents for cancer therapy. Results suggested that the substitutes on piperazinyl influenced anti-tumor activities remarkably. Conclusion: These results are useful for discovering more potent novel anti-tumor compounds and further studies are ongoing.

Amino acid conjugated antimicrobial drugs: Synthesis, lipophilicity- activity relationship, antibacterial and urease inhibition activity

Present work describes the in vitro antibacterial evaluation of some new amino acid conjugated antimicrobial drugs. Structural modification was attempted on the three existing antimicrobial pharmaceuticals namely trimethoprim, metronidazole, isoniazid. Twenty one compounds from seven series of conjugates of these drugs were synthesized by coupling with some selected Boc-protected amino acids. The effect of structural features and lipophilicity on the antibacterial activity was investigated. The synthesized compounds were evaluated against five standard American type culture collection (ATCC) i.e. Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi strains of bacteria. Our results identified a close relationship between the lipophilicity and the activity. Triazine skeleton proved beneficial for the increase in hydrophobicity and potency. Compounds with greater hydrophobicity have shown excellent activities against Gram-negative strains of bacteria than Gram-positive. 4-amino unsubstituted trimethoprim-triazine derivative 7b have shown superior activity with MIC = 3.4 μM (2 μg/mL) for S. aureus and 1.1 μM (0.66 μg/mL) for E. coli. The synthesized compounds were also evaluated for their urease inhibition study. Microbial urease from Bacillus pasteurii was chosen for this study. Triazine derivative 7a showed excellent inhibition with IC50 = 6.23 ± 0.09 μM. Docking studies on the crystal structure of B. pasteurii urease (PDB ID 4UBP) were carried out.