33140-80-6

Basic information

• Product Name: Methyl indole-1-acetate
• Synonyms: Methyl indole-1-acetate;Indol-1-yl-acetic acid methyl ester
• CAS NO: 33140-80-6
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21054
• EINECS: -0
• Mol File: 33140-80-6.mol

Chemical Properties

• Boiling Point: 318.6 °C at 760 mmHg
• Flash Point: 146.5 °C
• Appearance: /
• Density: 1.13 g/cm³
• CAS DataBase Reference: Methyl indole-1-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl indole-1-acetate(33140-80-6)
• EPA Substance Registry System: Methyl indole-1-acetate(33140-80-6)

Safety Data

• Hazardous Substances Data: 33140-80-6(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
Methyl indole-1-acetate is used as a fixative and modifier for [imparting a deep, woody aroma to perfumes and colognes]. Its ability to add depth and complexity to fragrances makes it a valuable component in the creation of various scented products.
Used in Flavorings Production:
Although known for its strong odor, Methyl indole-1-acetate is used in small amounts as a flavoring agent for [enhancing the taste profiles of certain food products]. Its controlled use allows for the subtle enhancement of flavors without overpowering the overall taste experience.
Used in Medical Research:
Methyl indole-1-acetate is studied for its potential applications as a [treatment for gastrointestinal conditions]. The exploration of its medicinal properties aims to leverage its characteristics for therapeutic benefits in the management of specific health conditions.
Safety and Handling:
Methyl indole-1-acetate is considered safe for use in fragrances and flavorings when used appropriately. However, it is important to handle this chemical with caution, as it can cause [irritation to the skin and eyes if not properly handled]. Proper safety measures should be taken to minimize risks during its use in various applications.

Upstream product

• 186581-53-3 diazomethane 
• 24297-59-4 1-indolylacetic acid 
• 271-63-6 7-Azaindole 
• 96-32-2 bromoacetic acid methyl ester 
• 40899-71-6 1-benzenesulfonylindole 
• 120-72-9 indole 
• 102235-21-2 methyl α-(3-ethyl-4-pyridyl)-1-indoleacetate 
• 102235-20-1 1-(3-ethyl-4-pyridylmethyl)indole 
• 102260-95-7 methyl (Z)-α-<1-(2-acetoxy-ethyl)-3-ethyl-1,4-dihydro-4-pyridylidene>-1-indoleacetate 
• 10468-64-1 o-tolyl isocyanide 
• 16982-67-5 sodium salt of indole 
• 96-34-4 methyl chloroacetate 
• 67-56-1 methanol 

Downstream Products

• 24297-59-4 1-indolylacetic acid 
• 27640-31-9 2,3-Dihydro-1H-indol-2-ylmethanol 
• 121459-15-2 2-(1H-indol-1-yl)ethanol 

Relevant articles and documents

Br?nsted Acid-Promoted Cyclodimerization of Indolyl Ketones: Construction of Indole Fused-Oxabicyclo[3.3.1]nonane and -Cyclooctatetraene Ring Systems

A Br?nsted acid-promoted cyclodimerization of C(3)-, C(2)-, or N(1)-substituted indole ketone derivatives is described. A wide range of structurally diverse bisindole fused-9-oxabicyclo[3.3.1]nonane and bisindole fused-cyclooctatetraene (COT) derivatives can be prepared in good to high yields with high efficiency.

Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls

The functionalization of aryl and heteroaryls using α-carbonyl sulfoxonium ylides without the help of a directing group has remained so far a neglected area, despite the advantageous safety profile of sulfoxonium ylides. Described herein are the cyclizations of α-carbonyl sulfoxonium ylides onto benzenes, benzofurans and N-p-toluenesulfonyl indoles in the presence of a base in HFIP, whereas pyrroles and N-methyl indoles undergo cyclization in the presence of an iridium catalyst. Significantly, these two sets of conditions are chemospecific for each groups of substrates.

Catalytic Tandem Friedel-Crafts Alkylation/C4-C3 Ring-Contraction Reaction: An Efficient Route for the Synthesis of Indolyl Cyclopropanecarbaldehydes and Ketones

A general strategy for the synthesis of indolyl cyclopropanecarbaldehydes and ketones via a Br?nsted acid-catalyzed indole nucleophilic addition/ring-contraction reaction sequence has been exploited. The procedure leads to a wide panel of cyclopropyl carbonyl compounds in generally high yields with a broad substrate scope.

Novel hits for acetylcholinesterase inhibition derived by docking-based screening on ZINC database

The inhibition of the enzyme acetylcholinesterase (AChE) increases the levels of the neurotransmitter acetylcholine and symptomatically improves the affected cognitive function. In the present study, we searched for novel AChE inhibitors by docking-based virtual screening of the standard lead-like set of ZINC database containing more than 6 million small molecules using GOLD software. The top 10 best-scored hits were tested in vitro for AChE affinity, neurotoxicity, GIT and BBB permeability. The main pharmacokinetic parameters like volume of distribution, free fraction in plasma, total clearance, and half-life were predicted by previously derived models. Nine of the compounds bind to the enzyme with affinities from 0.517 to 0.735 μM, eight of them are non-toxic. All hits permeate GIT and BBB and bind extensively to plasma proteins. Most of them are low-clearance compounds. In total, seven of the 10 hits are promising for further lead optimisation. These are structures with ZINC IDs: 00220177, 44455618, 66142300, 71804814, 72065926, 96007907, and 97159977.

HETEROCYCLIC COMPOUNDS AS INHIBITORS OF LEUKOTRIENE PRODUCTION

The present invention relates to compound of formula (I): or pharmaceutically acceptable salts thereof, wherein R1-R7, A and HET are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes

Indolyl and dihydroindolyl N-glycinamides as potent and in vivo active NPY5 antagonists

A novel series of indolyl and dihydroindolyl glycinamides were identified as potent NPY5 antagonists with in vivo activity from screen hit 1. The dihydroindolyl glycinamide 10a significantly inhibits NPY5 agonist induced feeding at a dose of 0.1 mg/kg. The indolyl glycinamide 12c also inhibits NPY5 agonist induced feeding at a dose of 1 mg/kg. Both compounds 10a and 12c represent potential tools for further investigation into the biology of the NPY5 receptor.

INDOLE-DERIVATIVE MODULATORS OF STEROID HORMONE NUCLEAR RECEPTORS

The present invention provides a compound of formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising an effective amount of a compound of Formula I in combination with a suitable carrier, diluent, or excipient, and methods for treating physiological disorders, particularly congestive heart disease, comprising administering to a patient in thereof an effective amount of a compound of Formula I.

4-AMINOMETHYL-1-ARYL-CYCLOHEXYLAMINE DERIVATIVES

The invention concerns 4-aminomethyl-1-aryl-cyclohexylamine derivatives, methods for producing same, medicines containing said compounds and the use of 4-aminomethyl-1-aryl-cyclohexylamine derivatives for producing medicines.

Heterocyclic compounds having anti-diabetic activity and their use

Compounds of formula (I): STR1 [wherein: X represents an unsubstituted or substituted indolyl, indolinyl, azaindolyl, azaindolinyl, imidazopyridyl or imidazopyrimidinyl group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethyl group; R represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a nitro group, an aralkyl group or a unsubstituted or substituted amino group; and m is an integer of from 1 to 5] have hypoglycemic and anti-diabetic activities.

Pharmaceutical compounds

A compound having pharmaceutical activity, of the formula STR1 in which A is hydrogen or --(CR1 R2)x R3 where x is 0 or 1 to 4, R1 and R2 are each hydrogen or C1-4 alkyl and Rsu