57105-53-0

Basic information

• Product Name: Tryptophan, N-indol-3-ylacetyl- (6CI)
• Synonyms: Tryptophan, N-indol-3-ylacetyl- (6CI);INDOLE-3-ACETYL-L-TRYPTOPHAN (IATrp);(S)-2-(2-(1H-indol-3-yl)acetamido)-3-(1H-indol-3-yl)propanoic acid
• CAS NO: 57105-53-0
• Molecular Formula: C₂₁H₁₉N₃O₃
• Molecular Weight: 361.39386
• Mol File: 57105-53-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 181-183 °C
• Boiling Point: 767.2°Cat760mmHg
• Flash Point: 417.8°C
• Appearance: /
• Density: 1.399g/cm³
• Vapor Pressure: 9.31E-25mmHg at 25°C
• Refractive Index: 1.737
• PKA: 3?+-.0.10(Predicted)
• CAS DataBase Reference: Tryptophan, N-indol-3-ylacetyl- (6CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Tryptophan, N-indol-3-ylacetyl- (6CI)(57105-53-0)
• EPA Substance Registry System: Tryptophan, N-indol-3-ylacetyl- (6CI)(57105-53-0)

Safety Data

• Hazardous Substances Data: 57105-53-0(Hazardous Substances Data)

Usage

Uses

Indole-3-acetyl-L-tryptophan is an indole-3-acetyl-amino acid conjugate involved in regulatory mechanisms for the control of auxin activity during physiological and pathophysiological responses. It may also be used in the synthesis of β-D-galactosidase and β-D-glucosidase inhibitors.

InChI:InChI=1/C21H19N3O3/c25-20(10-14-12-23-18-8-4-2-6-16(14)18)24-19(21(26)27)9-13-11-22-17-7-3-1-5-15(13)17/h1-8,11-12,19,22-23H,9-10H2,(H,24,25)(H,26,27)/t19-/m0/s1

Upstream product

• 87-51-4 indole-3-acetic acid 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 1080025-88-2 1-(1H-benzotriazol-1-yl)-2-(1H-indol-3-yl)ethanone 
• 73-22-3 L-Tryptophan 
• 50720-05-3 indolyl acetyl chloride 

Relevant articles and documents

Preparation of synthetic auxin-amino acid conjugates

Auxin amide conjugates are regulators of the most important auxin, indole-3-acetic acid (IAA), which is considered responsible for many important processes within the plants. Herein, amide conjugates of IAA were synthesized employing a simple and efficient coupling method with WSCI·HCl, a water-soluble condensing reagent, in the presence of 1-hydroxybenzotriazole. IAA conjugates with 10 amino acids along with their corresponding methyl esters were prepared in excellent yields, up to 95%, aiming to facilitate their identification in plant species. Eight IAA-amino acid methyl ester conjugates are characterized here for the first time.

Syntheses of IAA- and IPA-amino acid conjugates

(Chemical Equation Presented) Amino acid derivatives of IAA and IPA are prepared conveniently and efficiently by coupling of readily available 2a-b with diverse free amino acids 3a-g and (3c+3c′) to give compounds 4a-j, (4c+4c′) and (4h+4h′) in 38-70% yie