5594-91-2

Basic information

• Product Name: 5-Acetoxyindole
• Synonyms: 5-Acetoxyindole
• CAS NO: 5594-91-2
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18396
• Mol File: 5594-91-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 113-114 °C
• Boiling Point: 339.08°C at 760 mmHg
• Flash Point: 158.87°C
• Appearance: /
• Density: 1.256g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.634
• PKA: 16.36±0.30(Predicted)
• CAS DataBase Reference: 5-Acetoxyindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Acetoxyindole(5594-91-2)
• EPA Substance Registry System: 5-Acetoxyindole(5594-91-2)

Safety Data

• Hazardous Substances Data: 5594-91-2(Hazardous Substances Data)

Usage

General Description

5-Acetoxyindole is a chemical compound with the molecular formula C10H9NO2. It is a derivative of indole, a heterocyclic aromatic organic compound. 5-Acetoxyindole is a white to off-white solid that is sparingly soluble in water. It is commonly used in organic synthesis, pharmaceuticals, and as a precursor in the synthesis of various natural and synthetic products. 5-Acetoxyindole has been studied for potential applications in the pharmaceutical industry due to its interesting biological activities, such as anti-inflammatory and anticancer properties. However, further research is needed to fully understand and exploit the potential uses of 5-Acetoxyindole.

InChI:InChI=1/C10H9NO2/c1-7(12)13-9-2-3-10-8(6-9)4-5-11-10/h2-6,11H,1H3

Upstream product

• 1953-54-4 indol-5-ol 
• 108-24-7 acetic anhydride 
• 26122-90-7 2-amino-3-(2,5-dihydroxyphenyl)propanoic acid 

Downstream Products

• 1953-54-4 indol-5-ol 
• 126963-80-2 1-(5-Hydroxy-1H-indol-4-yl)-ethanone 
• 126963-81-3 1-(5-Hydroxy-1H-indol-6-yl)-ethanone 
• 882803-11-4 5-hydroxy-1H-indazole-3-carbaldehyde 
• 487-93-4 bufotenin 

Relevant articles and documents

Ability of the Putative Decomposition Products of 2,3-dioxetanes of Indoles to Photosensitize Cyclobutane Pyrimidine Dimer (CPD) Formation and its Implications for the “Dark” (Chemisensitized) Pathway to CPDs in Melanocytes?

The formation of cyclobutane pyrimidine dimers (CPDs) by a “dark” pathway in melanocytes has been attributed to chemisensitization by dioxetanes produced from peroxynitrite oxidation of melanin or melanin precursors. These dioxetanes are proposed to decompose to triplet state compounds which sensitize CPD formation by triplet–triplet energy transfer. To determine whether such compounds are capable of sensitizing CPD formation, the putative decomposition products of 2,3-dioxetanes of variously substituted indoles were synthesized and their triplet state energies determined at 77?K. Their ability to photosensitize CPD formation was determined by an enzyme-coupled gel electrophoresis assay in comparison with norfloxacin (NFX) which has the lowest triplet energy known to sensitize CPD formation. The decomposition products of 2,3-dioxetanes of 5-hydroxy and 5,6-dimethoxy indoles used as models for melanin precursors had lower triplet energies and were incapable of photosensitizing CPD formation. Theoretical calculations suggest that the decomposition products of the 2,3-dioxetanes of melanin precursors DHI and DHICA will have similarly low triplet energies. Decomposition products of the 2,3-dioxetanes of indoles lacking oxygen substituents had higher triplet energies than NFX and were capable of photosensitizing CPD formation, suggesting that peroxynitrite oxidation of tryptophan could play a hitherto unrecognized role in the dark pathway to CPDs.

The first entry to 5,6-dihydroxy-3-mercaptoindole, 5-hydroxy-3-mercaptoindole and their 2-carbomethoxy derivatives by a mild thiocyanation/reduction methodology

The hitherto unknown 5,6-dihydroxy-3-mercaptoindole (4a) and its 2-carbomethoxy derivative (4b), as well as the analogous 5-hydroxy 3-mercaptoindoles, have been conveniently obtained as O,S-acetyl derivatives 3a-d by thiocyanation of the corresponding acetoxyindoles 1a-d with the NH4SCN/oxone system followed by SmI2 reduction and acetylation.