25197-96-0

Basic information

• Product Name: 5-METHOXY-L-TRYPTOPHAN
• Synonyms: 5-METHOXY-L-TRYPTOPHAN;L-2-AMINO-3-(5-METHOXYINDOLYL)PROPIONIC ACID;L-5-METHOXYTRYPTOPHAN;H-5-MEO-TRP-OH;5-Methoxy-L-tryptophan, (S)-2-Amino-3-(5-methoxyindolyl)propionic acid, 98%;H-L-Trp(5-OMe)-OH;(S)-2-AMino-3-(5-Methoxy-1H-indol-3-yl)propanoic acid;L-Tryptophan, 5-methoxy-
• CAS NO: 25197-96-0
• Molecular Formula: C₁₂H₁₄N₂O₃
• Molecular Weight: 234.25
• EINECS: 248-800-0
• Product Categories: Indoles and derivatives
• Mol File: 25197-96-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 253-256 °C
• Boiling Point: 478.3°C at 760 mmHg
• Flash Point: 243.1°C
• Appearance: /
• Density: 1.347g/cm³
• Vapor Pressure: 5.87E-10mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 2.22±0.10(Predicted)
• CAS DataBase Reference: 5-METHOXY-L-TRYPTOPHAN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-L-TRYPTOPHAN(25197-96-0)
• EPA Substance Registry System: 5-METHOXY-L-TRYPTOPHAN(25197-96-0)

Safety Data

• Hazardous Substances Data: 25197-96-0(Hazardous Substances Data)

Usage

Uses

(S)?-?2-?Amino-?3-?(5-?methoxy-?1H-?indol-?3-?yl)?propanoic Acid is a reagent used in the preparation of anti-HIV agent flazine analogues.

InChI:InChI=1/C12H14N2O3/c1-17-8-2-3-11-9(5-8)7(6-14-11)4-10(13)12(15)16/h2-3,5-6,10,14H,4,13H2,1H3,(H,15,16)/t10-/m0/s1

Upstream product

• 43167-40-4 N^α-acetyl-5-methoxy-D,L-tryptophan 
• 74761-41-4 (S)-1-(methoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 68-95-1 (S)-acetylproline 
• 147-85-3 L-proline 
• 72458-83-4 5-methoxy-N_b-methoxycarbonyl-L-tryptophan methyl ester 
• 93299-30-0 N-methoxycarbonyl-L-glutamine methyl ester 
• 93271-96-6 (2S,5RS)-1,2-dimethyl-5-hydroxypyrrolidine-1,2-dicarboxylate 
• 154005-67-1 (S)-1-Acetyl-5-hydroxy-pyrrolidine-2-carboxylic acid methyl ester 
• 93271-98-8 N-methoxycarbonyl-4-cyano-L-2-aminobutyric acid methyl ester 
• 93272-00-5 5-methoxy-N_b-acetyl-L-tryptophan methyl ester 
• 2311-25-3 N-acetyl-L-proline methyl ester 
• 83541-81-5 (S)-dimethyl pyrrolidine-1,2-dicarboxylate 
• 89434-07-1 5-methoxy-L-tryptophan methyl ester 
• 93299-32-2 5-methoxy-N_b-methoxycarbonyl-L-tryptophan 

Downstream Products

• 460751-69-3 (S)-N-(fluoren-9-ylmethoxycarbonyl)-5-methoxy-tryptophan 
• 67010-09-7 N^α-acetyl-5-methoxy-L-tryptophan 
• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 

Relevant articles and documents

The facile synthesis of a series of tryptophan derivatives

This study reports a facile method for the synthesis of a variety of 5- and 6-substituted tryptophan derivatives that are difficult to prepare using alternative enzymatic approaches. Acylation of an activated amino acid, derived from serine in situ, is coupled with an enzymatic resolution step to furnish enantiopure analogues bearing a range of electron withdrawing and releasing substituents. Isolation of a dehydroalanine derivative as a by-product from some reactions provides some insights into the likely mechanism of the reaction.

Syntheses of Substituted L- and D-Tryptophans

Several 5-substituted nb-methoxycarbonyl-L- and -D-tryptophan derivatives were synthesized from proline by a new route involving electrochemical oxidation, as well as by the known procedures.Removal of the Nb-methoxycarbonyl group was accomplished by treatment with Me3SiI in refluxing chloroform, then alkaline hydrolysis of the methyl esters afforded 5-substituted L- and D-tryptophans with high optical purities.Keywords - L-tryptophan 5-substituted; D-tryptophan 5-substituted; anodic oxidation; N-methoxycarbonyl group deprotection; Fischer indole synthesis; iodotrimethylsilane