31338-08-6

Basic information

• Product Name: tryptophan butyl ester
• Synonyms: tryptophan butyl ester;(S)-2-Amino-3-(1H-indol-3-yl)propionic acid butyl ester;L-Tryptophan butyl ester
• CAS NO: 31338-08-6
• Molecular Formula: C₁₅H₂₀N₂O₂
• Molecular Weight: 260.33
• Mol File: 31338-08-6.mol

Chemical Properties

• Boiling Point: 423.714°C at 760 mmHg
• Flash Point: 210.055°C
• Appearance: /
• Density: 1.158g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.596
• CAS DataBase Reference: tryptophan butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: tryptophan butyl ester(31338-08-6)
• EPA Substance Registry System: tryptophan butyl ester(31338-08-6)

Safety Data

• Hazardous Substances Data: 31338-08-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H20N2O2/c1-2-3-8-19-15(18)13(16)9-11-10-17-14-7-5-4-6-12(11)14/h4-7,10,13,17H,2-3,8-9,16H2,1H3/t13-/m0/s1

Upstream product

• 6330-20-7 L-tryptophan n-butyl ester hydrochloride 
• 73-22-3 L-Tryptophan 
• 71-36-3 butan-1-ol 

Downstream Products

• 71-36-3 butan-1-ol 

Relevant articles and documents

Synthesis and antifungal activity against fusarium oxysporum of some brassinin analogs derived from L-Tryptophan: A DFT/B3LYP study on the reaction mechanism

An efficient methodology to obtain novel antifungal analogs of brassinin 1 is described. Starting from L-Tryptophan 2, N,N0-dialkylthiourea 4, 4-[(1H-indol-3-yl)methylene]-2-sulfanylidene- 1,3-Thiazolidin-5-one 5 and alkyl (2S)-3-(1H-indol-3-yl)-2-{[(alkylsulfanyl)carbonothioyl]amino} propanoate 6 type compounds were obtained as main products in different ratios depending on the reaction conditions via a tandem dithiocarbamate formation and Michael addition reaction. In order to understand the dependence of the reaction conditions on the mechanism pathway, a DFT/B3LYP study was performed. The results suggested the existence of competitive mechanistic routes which involve the presence of an ionic dithiocarbamate intermediate 9. Antifungal activities of all products were then evaluated against Fusarium oxysporum through mycelial growth inhibition using a microscale amended-medium assay. IC50 values were thus determined for each compound. These results showed that 6-related compounds can be considered as promissory antifungal agents.

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.

COMPOUND SUITABLE FOR THE TREATMENT OF SYNUCLEOPATHIES

The present invention relates to a compound of formula (I): Wherein R1 is a substituted or unsubstituted aromatic hetero- or homocyclic or a substituted or unsubstituted alicyclic hetero- or homocyclic group; R2 is an alkyl group with 1 to 18 carbon atoms or a substituted or unsubstituted cycloalkyl or aryl group; R3 is a substituted or unsubstituted aromatic hetero- or homocyclic or a substituted or unsubstituted alicyclic hetero- or homocyclic group; L is a single bond, an alkyl group having 1 to 6 carbon atoms, NHCO, O, S, NHCONH or NHCOO; X, Y and Z are independently 0, N, NH, S or CH; W is a single bond or an alkyl group having from 1 to 6 carbon atoms; or a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable solvate of said compound or salt. I

Determination of the rates of formation and hydrolysis of the schiff bases formed by pyridoxal 5′-phosphate with L-tryptophan and its methyl and n-butyl esters

The apparent rate constants of the formation (k1) and hydrolysis (k2) of the Schiff bases formed by pyridoxal 5′-phosphate with L-tryptophan and their methyl and n-butyl esters at a variable pH, 25 °C, and an ionic strength of 0.1 M were determined, along with the equilibrium constant (KpH). The individual rate constants of formation and hydrolysis of the Schiff bases of systems corresponding to different chemical species present in the medium as a function of its acidity were also determined, as were the pK values for the Schiff bases. The influence of the α-carboxyl group on the formation and hydrolysis constants of the Schiff bases, and also on their pK values, is demonstrated.