3182-93-2

Basic information

• Product Name: Ethyl L-phenylalaninate hydrochloride
• Synonyms: PHENYLALANINE-OET HCL;L-phenylalanine ethylester;ethyl L-phenylalaninate hydrochloride;Phe-OEt HCl;L-PhenylalanineEthylEster>99%;L-PHANYLALANINEETHYLESTERHCL;H-L-Phe-OEt*HCl;L-Phenylalanine ethyl ester hydrochlorid
• CAS NO: 3182-93-2
• Molecular Formula: C₁₁H₁₅NO₂*ClH
• Molecular Weight: 229.7
• EINECS: 221-673-9
• Product Categories: Amino Acids;Phenylalanine [Phe, F];Amino hydrochloride;Amino Acid Derivatives;Peptide Synthesis;Phenylalanine;Other enzyme inhibitors and activators;Other Enzyme Inhibitors and Activators.
• Mol File: 3182-93-2.mol
• Article Data: 42

Chemical Properties

• Melting Point: 155-156 °C(lit.)
• Boiling Point: 281.3 °C at 760 mmHg
• Flash Point: 140.3 °C
• Appearance: White/Fine Needle-Like Crystalline Solid
• Vapor Pressure: 0.00359mmHg at 25°C
• Storage Temp.: Store at RT.
• Solubility: Methanol, Water
• Water Solubility: Soluble in methanol and water.
• Sensitive: Hygroscopic
• BRN: 3657823
• CAS DataBase Reference: Ethyl L-phenylalaninate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl L-phenylalaninate hydrochloride(3182-93-2)
• EPA Substance Registry System: Ethyl L-phenylalaninate hydrochloride(3182-93-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26
• WGK Germany: 3
• Hazardous Substances Data: 3182-93-2(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline

Uses

L-Phenylalanine Ethyl Ester Hydrochloride is an derivative of L-Phenylalanine (P319415), an essential amino acid.

InChI:InChI=1/C11H15NO2/c1-2-14-11(13)10(12)8-9-6-4-3-5-7-9/h3-7,10H,2,8,12H2,1H3/p+1/t10-/m0/s1

Upstream product

• 100-39-0 benzyl bromide 
• 64-17-5 ethanol 
• 150-30-1 Phenylalanine 
• 63-91-2 L-phenylalanine 
• 1416989-77-9 ethyl ((S)-tert-butylsulfinyl)phenylalaninate 
• 6378-11-6 ethyl chlorosulfite 
• 3081-24-1 H-Phe-OEt 
• 121269-47-4 (3R,5R)-3-benzyl-4-tert-butyloxycarbonyl-5-phenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 121269-56-5 (3S,5R)-2,3,5,6-tetrahydro-5-phenyl-3,4-bis(phenylmethyl)-4H-1,4-oxazin-2-one 
• 100-44-7 benzyl chloride 

Downstream Products

• 97437-59-7 N-(3-Carboxy-propionyl)-D,L-phenylalanin-ethylester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 106302-39-0 Bernsteinsaeure-glycin-ethylester-DL-phenylalanin-ethylester 
• 1170-76-9 Z-Gly-(L)-Phe 
• 3182-95-4 L-Phenylalaninol 
• 52558-43-7 N-acetyl-phenylalanine hexadecyl ester 
• 37682-80-7 2-isocyanato-3-phenyl-propionic acid ethyl ester 
• 83597-39-1 (S)-2-{2-[((S)-1-Ethoxycarbonyl-2-phenyl-ethylcarbamoyl)-methoxy]-acetylamino}-3-phenyl-propionic acid ethyl ester 
• 82827-51-8 (S)-3-Phenyl-2-[(piperidine-4-carbonyl)-amino]-propionic acid ethyl ester 
• 79868-78-3 (S)-(-)-2-amino-1,1,3-triphenyl-1-propanol 
• 82827-41-6 (S)-3-Phenyl-2-[(quinoline-2-carbonyl)-amino]-propionic acid ethyl ester 
• 122334-63-8 (S)-2-[2-(1H-Indol-3-yl)-2-oxo-acetylamino]-3-phenyl-propionic acid ethyl ester 
• 3956-78-3 CbzGly-L-PheOEt 
• 52961-44-1 rac-2-amino-3-phenylpropanal diethyl acetal 

Relevant articles and documents

Juvenile hormone mimics with phenyl ether and amide functionality to be insect growth regulators (IGRs): synthesis, characterization, computational and biological study

A series of substituted phenyl ethers derivatives as juvenile hormone (JH) mimics (V1-V8) have been synthesized. Substituted phenoxyacetic acid and amino acid ethyl ester hydrochloride were prepared using NaOH, SOCl2. DCC method has been used for amide linkage. The structure of prepared compounds has been confirmed by Fourier Transform Infra-Red (FT-IR), Electrospray ionization-Mass spectrometry (ESI-MS), Proton and Carbon-13 nuclear magnetic resonance (1H-NMR, 13C-NMR) spectroscopic techniques. Biological efficacy of synthesized analogs has been carried out under laboratory conditions. Galleria mellonella (honey bee pest) has been chosen as testing insect. Juvenile hormone (JH) activity of synthesized compounds has been tested at different concentrations and compared with the standard juvenile hormone analogs (JHAs) pyriproxyfen (M1) and fenoxycarb (M2) against the fifth larval instar of G. mellonella. Compound ethyl 2-[2-(4-methylphenoxy)aminoacetyl]-3-phenyl-propanoate (V6) exhibited better activity among all the synthesized compounds (V1-V8) with LC50 and LC90 values of 0.11 mg/mL and 0.56 mg/mL respectively. Compounds showed insect growth regulating (IGR) activity at lower concentrations. In silico screening of all synthesized compounds with the W-cavity of juvenile hormone-binding protein (JHBP) of insect G. mellonella has been carried out. Chemical reactivity of synthesized series has been studied using DFT/B3LYP/6-311 + G(d,2p) method. Non-toxic behavior of molecules has also been observed from ADMET (Absorption, Distribution, Metabolism, Excretion, and Toxicity) study using discovery studio client 3.0. Communicated by Ramaswamy H. Sarma.

Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids

The technological utility of active pharmaceutical ingredients (APIs) is greatly enhanced when they are transformed into ionic liquids (ILs). API-ILs have better solubility, thermal stability, and the efficacy in topical delivery than solid or crystalline drugs. However, toxicological issue of API-ILs is the main challenge for their application in drug delivery. To address this issue, 11 amino acid esters (AAEs) were synthesized and investigated as biocompatible counter cations for the poorly water-soluble drug salicylic acid (Sal) to form Sal-ILs. The AAEs were characterized using 1H and 13C NMR, FTIR, elemental, and thermogravimetric analyses. The cytotoxicities of the AAE cations, Sal-ILs, and free Sal were investigated using mammalian cell lines (L929 and HeLa). The toxicities of the AAE cations greatly increased with inclusion of long alkyl chains, sulfur, and aromatic rings in the side groups of the cations. Ethyl esters of alanine, aspartic acid, and proline were selected as a low cytotoxic AAE. The cytotoxicities of the Sal-ILs drastically increased compared with the AAEs on incorporation of Sal into the cations, and were comparable to that of free Sal. Interestingly, the water miscibilities of the Sal-ILs were higher than that of free Sal, and the Sal-ILs were miscible with water at any ratio. A skin permeation study showed that the Sal-ILs penetrated through skin faster than the Sal sodium salt. These results suggest that AAEs could be used in biomedical applications to eliminate the use of traditional toxic solvents for transdermal delivery of poorly water-soluble drugs.

Synthesis, spectroscopic characterization, and in vitro antibacterial evaluation of novel functionalized sulfamidocarbonyloxyphosphonates

Several new sulfamidocarbonyloxyphosphonates were prepared in two steps, namely carbamoylation and sulfamoylation, by using chlorosulfonyl isocyanate (CSI), α-hydroxyphosphonates, and various amino derivatives and related (primary or secondary amines, β-amino esters, and oxazolidin-2-ones). All structures were confirmed by 1H, 13C, and 31P NMR spectroscopy, IR spectroscopy, and mass spectroscopy, as well as elemental analysis. Eight compounds were evaluated for their in vitro antibacterial activity against four reference bacteria including Gram-positive Staphylococcus aureus (ATCC 25923), and Gram-negative Escherichia coli (ATCC 25922), Klebsiella pneumonia (ATCC 700603), Pseudomonas aeruginosa (ATCC 27853), in addition to three clinical strains of each studied bacterial species. Compounds 1a–7a and 1b showed significant antibacterial activity compared to sulfamethoxazole/trimethoprim, the reference drug used in this study.