7524-52-9

Basic information

• Product Name: Methyl L-tryptophanate hydrochloride
• Synonyms: L-A-AMINO-3-INDOLEPROPIONIC ACID METHYL ESTER HYDROCHLORIDE;L-2-AMINO-3-INDOLYLPROPANOIC ACID METHYL ESTER HYDROCHLORIDE;L-B-3-INDOLYLALANINE METHYL ESTER HYDROCHLORIDE;H-TRP-OME HCL;L-TRYPTOPHAN METHYL ESTER HCL;L-TRYPTOPHAN METHYL ESTER HYDROCHLORIDE;L-TRYPTOPHAN METHYL ESTER HYDROCHLORIDE SALT;METHYL L-TRYPTOPHANATE HYDROCHLORIDE
• CAS NO: 7524-52-9
• Molecular Formula: C₁₂H₁₄N₂O₂*ClH
• Molecular Weight: 254.71
• EINECS: 231-385-5
• Product Categories: Amino Acids;Tryptophan [Trp, W];Amino Acids and Derivatives;Amino Acids 13C, 2H, 15N;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry;Indoles;Tryptophans;Amino hydrochloride;Amino Acids & Derivatives;Amino Acid Derivatives;Peptide Synthesis;Tryptophan;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 7524-52-9.mol
• Article Data: 106

Chemical Properties

• Melting Point: 218-220 °C(lit.)
• Boiling Point: 390.6oC at 760 mmHg
• Flash Point: 190oC
• Appearance: White to off-white/Powder
• Vapor Pressure: 2.62E-06mmHg at 25°C
• Refractive Index: 19.5 ° (C=5, MeOH)
• Storage Temp.: -15°C
• Solubility: DMSO (Slightly), Methanol (Sparingly)
• BRN: 4240280
• CAS DataBase Reference: Methyl L-tryptophanate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl L-tryptophanate hydrochloride(7524-52-9)
• EPA Substance Registry System: Methyl L-tryptophanate hydrochloride(7524-52-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 7524-52-9(Hazardous Substances Data)

Usage

Chemical Properties

Methyl L-tryptophanate hydrochloride is White to off-white powder

Uses

Different sources of media describe the Uses of 7524-52-9 differently. You can refer to the following data:
1. L-Tryptophan methyl ester hydrochloride can be used as a reactant to prepare: Oxamoyl derivatives of N-(2-aminobenzoyl)-L-tryptophan (dipeptides) by acylation reaction with 3,1-benzoxazinones.Tadalafil (Cialis), a type-V phosphodiesterase (PDE5) inhibitor. Isoroquefortine C.
2. Methyl L-tryptophanate hydrochloride may be used to prepare the corresponding amino acid amide L-Tryptophanamide Hydrochloride (Cat. #T89550)

InChI:InChI=1/C12H14N2O2/c1-16-12(15)10(13)6-8-7-14-11-5-3-2-4-9(8)11/h2-5,7,10,14H,6,13H2,1H3/p+1/t10-/m0/s1

Upstream product

• 67-56-1 methanol 
• 73-22-3 L-Tryptophan 
• 6159-33-7 L-tryptophan hydrochloride 
• 153-94-6 D-tryptophan 
• 141595-98-4 D-tryptophan benzyl ester 
• 5619-09-0 methyl tryptophanate hydrochloride 
• 153-94-6 D-tryptophan 
• 54-12-6 Trp 
• 120-72-9 indole 
• 118553-32-5 Methyl N-(diphenylmethylene)-D,L-tryptophanates 
• 141215-69-2 methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate 
• 1198605-52-5 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate 

Downstream Products

• 139456-02-3 (S)-3-Acetyl-1-(4-chloro-phenyl)-5-(1H-indol-3-ylmethyl)-4,5-dihydro-1H-[1,2,4]triazin-6-one 
• 72254-56-9 (S,S)-methyl 2-[2-tert-butoxycarbonylamino-3-(indol-3-yl)-propionylamino]-3-(indol-3-yl)propanoate 
• 73054-11-2 methyl N-(4-methoxybenzoyl)-L-tryptophanate 
• 65474-80-8 methyl N-(phenylacetyl)-l-tryptophanate 
• 62056-80-8 Nα-diphenylphosphinyltryptophan methyl ester 
• 139258-97-2 (S)-2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 238428-14-3 (1S,3S)-1-(3-Bromo-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 238428-12-1 (1S,3S)-methyl 1-(4-methylphenyl)-2,3,4,9-tetrahydo-1H-pyrido[3,4-b]indole-3-carboxylate 
• 238428-10-9 (1S,3S)-methyl 1-(4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 238428-08-5 (1S,3S)-methyl 1-(4-chlorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 238428-19-8 methyl 1-(2-chlorophenyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate 
• 238428-17-6 (1S,3S)-1-(3-Chloro-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 238428-21-2 cis-1-(2-fluorophenyl)-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline 
• 82789-39-7 1-(4-Fluorophenyl)-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-β-carboline 

Relevant articles and documents

Convenient method for the synthesis of some novel chiral methyl 2-(2-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)propanoate derivatives and biological evaluation of their antioxidant, cytotoxic, and molecular docking properties

Ten chiral methyl 2-(2-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)propanoate derivatives 6a-6j have been synthesized from optically pure amino methyl phenol 5 and 4-nitrophenyl chloroformate. These derivatives 6a-6j are characterized by 1H NMR, 13C NMR, FT-IR, and HRMS spectral techniques. Optical purity of these derivatives was confirmed by chiral HPLC method. Ten synthesized ester derivatives 6a-6j were screened for their in vitro antioxidant activity. Among the compounds 6b-d and 6h-j have exhibited comparable antioxidant activity with ascorbic acid as a standard. Compounds 6a and 6e-g have shown moderate antioxidant activity. Further, the in vitro cytotoxicity of these compounds were studied through MTT cell proliferation assay in addition the effect on LDH leakage and NO release. Among the derivatives, 6j showed extremely best activity and the IC50 value (12.54 ± 0.71 μM) is very close to doxorubicin (7.2 ± 0.58 μM) as a standard. Compounds 6b, 6h, and 6i showed better inhibition next to compound 6j on the viability of HepG2 cells with an IC50 value (μM) of 56.02 ± 1.4, 41.76 ± 0.58, and 38.17 ± 0.34, respectively. Also, molecular docking studies have been carried out with STAT-3 (PDB ID: 1BG1) and BCL-2 (PDB ID: 4AQ3) proteins against the four active compounds 6b, 6h, 6i, and 6j. The binding energies of the tested compounds were in the range of ?7.76 to ?8.41 kcal/mol, which is very close to doxorubicin (?8.53 kcal/mol) as a standard. These molecular docking results are in good agreement with the in vitro studies.

Lithocholic acid-tryptophan conjugate (UniPR126) based mixed micelle as a nano carrier for specific delivery of niclosamide to prostate cancer via EphA2 receptor

Targeted delivery of chemotherapeutic agents is considered a prominent strategy for the treatment of cancer due to its site-specific delivery, augmented penetration, bioavailability, and improved therapeutic efficiency. In the present study, we employed UniPR126 as a carrier in a mixed nanomicellar delivery system to target and deliver anticancer drug NIC specifically to cancer cells via EphA2 receptors as these receptors are overexpressed in cancer cells but not in normal cells. The specificity of the carrier was confirmed from the significant enhancement in the uptake of coumarin-6 loaded mixed nanomicelle by EphA2 highly expressed PC-3 cells compared to EphA2 low expressed H4 cells. Further, niclosamide-loaded lithocholic acid tryptophan conjugate-based mixed nanomicelle has shown significant synergistic cytotoxicity in PC-3 but not in H4 cells. In vivo anticancer efficacy data in PC-3 xenograft revealed a significant reduction in the tumor volume (66.87%) with niclosamide-loaded lithocholic acid tryptophan conjugate nanomicelle, where pure niclosamide showed just half of the activity. Molecular signaling data by western blotting also indicated that niclosamide-loaded lithocholic acid tryptophan conjugate nanomicelle interfered with the EphA2 receptor signaling and inhibition of the Wnt/beta-catenin pathway and resulted in the synergistic anticancer activity compared to niclosamide pure drug.

A fast and direct iodide-catalyzed oxidative 2-selenylation of tryptophan

A metal-free 2-selenylation of tryptophan derivatives is reported, where the use of iodide as the catalyst and oxone as the oxidant is key to obtain high yields. Various functional groups within the di-seleny and the indole ring are tolerated, and no racemization is generally observed.