6519-67-1

Basic information

• Product Name: DL-TRYPTOPHAN ETHYL ESTER HCL
• Synonyms: DL-TRYPTOPHAN ETHYL ESTER HCL;DL -TRYPTOPHAN ETHYL ESTER HYDROCHLORIDE 99+%;Tryptophan, ethyl ester, monohydrochloride;H-DL-Trp-OEt;DL-Tryptophan Ethyl Ester Hydrochloride;DL-Trp-OEt·HCl
• CAS NO: 6519-67-1
• Molecular Formula: C₁₃H₁₆N₂O₂*ClH
• Molecular Weight: 268.73928
• Product Categories: Amino Acids;I - Z;Modified Amino Acids
• Mol File: 6519-67-1.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• Water Solubility: almost transparency in Water
• CAS DataBase Reference: DL-TRYPTOPHAN ETHYL ESTER HCL(CAS DataBase Reference)
• NIST Chemistry Reference: DL-TRYPTOPHAN ETHYL ESTER HCL(6519-67-1)
• EPA Substance Registry System: DL-TRYPTOPHAN ETHYL ESTER HCL(6519-67-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6519-67-1(Hazardous Substances Data)

Usage

General Description

DL-Tryptophan Ethyl Ester HCL is a chemical compound that is a derivative of the amino acid tryptophan. It is typically used in research and laboratory settings as a precursor to the neurotransmitter serotonin and the hormone melatonin. The ethyl ester form of tryptophan allows for better absorption and bioavailability in the body compared to the standard tryptophan compound. Additionally, the hydrochloride (HCL) salt of the compound enhances its stability and solubility, making it easier to work with in various applications. Overall, DL-Tryptophan Ethyl Ester HCL is important in the study of neurotransmitters and hormones and has potential therapeutic applications.

Upstream product

• 64-17-5 ethanol 
• 73-22-3 L-Tryptophan 

Downstream Products

• 130812-46-3 N^α-benzyloxycarbonyl-DL-tryptophan-methyl ester 
• 104951-44-2 ethyl benzyloxycarbonylthreonyltryptophanate 
• 87694-58-4 L-pyroglutamyl-L-tryptophan ethyl ester 
• 35937-24-7 L-pyroglutamyl-L-tryptophan 
• 7479-05-2 L-tryptophan ethyl ester 
• 1227610-57-2 trans-1-(4-tert-butyl-phenyl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acid ethyl ester 
• 1227610-56-1 cis-1-(4-tert-butyl-phenyl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acid ethyl ester 
• 1227610-61-8 trans-1-(4-fluoro-phenyl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acid ethyl ester 
• 1227610-60-7 cis-1-(4-fluoro-phenyl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acid ethyl ester 
• 1227610-59-4 trans-1-phenyl-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acid ethyl ester 
• 1227610-58-3 cis-1-phenyl-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acid ethyl ester 
• 1227610-63-0 trans-1-(4-bromo-phenyl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acid ethyl ester 
• 1227610-62-9 cis-1-(4-bromo-phenyl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acid ethyl ester 
• 1227610-53-8 trans-1-(4-ethyl-phenyl)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylic acid ethyl ester 

Relevant articles and documents

Solvent free three-component synthesis of 2,4,5-trisubstituted-1H-pyrrol-3-ol-type Compounds from L-tryptophan: DFT-B3LYP calculations for the reaction mechanism and 3H-pyrrol-3-one?1H-pyrrol-3-ol tautomeric equilibrium

In this paper, we describe the solvent-free three-component synthesis of 2,4,5-trisubstituted-1H-pyrrol-3-ol-type compounds from L-tryptophan. The first step of the synthetic methodology involved the esterification of L-tryptophan in excellent yields (93–98%). Equimolar mixtures of alkyl 2-aminoesters, 1,3-dicarbonyl compounds, and potassium hydroxide (0.1 eq.) were heated under solvent-free conditions. The title compounds were obtained in moderate to good yields (45%–81%). Density functional theory using “Becke, 3-parameter, Lee–Yang–Parr” correlational functional (DFT-B3LYP) calculations were performed to understand the molecular stability of the synthesized compounds and the tautomeric equilibrium from 3H-pyrrol-3-one type intermediates to 1H-pyrrol-3-ol type aromatized rings.

Tryptophan ester hydrochloride preparation method

The invention discloses a synthesizing method for tryptophan ester hydrochloride. The synthesizing method includes the steps that firstly, organic amine serves as catalysts, in proper solvents, tryptophan and hydrogen chloride generate tryptophan hydrochloride; secondly, the tryptophan hydrochloride and ester are esterified at the backflow temperature, generated water is taken away in an azeotropy mode, an esterification reaction is promoted, and after the reaction is completed, the tryptophan ester hydrochloride as the target product is obtained through postprocessing processes such as filtering, low-boiling-point substance low-pressure removing and recrystallization. Mother liquid obtained after recrystallization is repeatedly used indiscriminately, and the number of repeating times is larger than five. The synthesizing method has the advantages that the raw material cost is low, the conversion rate is high, postprocessing is simple, chlorinating agents such as thionyl chloride are not required, and three-waste discharging is less; the synthesizing method is suitable for industrial production.

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.