110139-35-0

Basic information

• Product Name: 1-Methoxy-1H-Indole-3-Methanol
• Synonyms: 1-Methoxy-1H-Indole-3-Methanol
• CAS NO: 110139-35-0
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.19984
• Mol File: 110139-35-0.mol

Chemical Properties

• Boiling Point: 92-94 °C(Press: 0.1 Torr)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• PKA: 14.38±0.10(Predicted)
• CAS DataBase Reference: 1-Methoxy-1H-Indole-3-Methanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methoxy-1H-Indole-3-Methanol(110139-35-0)
• EPA Substance Registry System: 1-Methoxy-1H-Indole-3-Methanol(110139-35-0)

Safety Data

• Hazardous Substances Data: 110139-35-0(Hazardous Substances Data)

Usage

Methoxylated derivative

1H-indole-3-methanol
1-Methoxy-1H-Indole-3-Methanol is modified from 1H-indole-3-methanol by the addition of a methoxy group.

Synthesis method

Methylation
The compound can be synthesized through a series of chemical reactions involving the methylation of 1H-indole-3-methanol.

Usage

Synthesis of pharmaceutical compounds and organic molecules
1-Methoxy-1H-Indole-3-Methanol is used as a building block in the production of various pharmaceutical compounds and organic molecules.

Chemical structure

Indole ring with methoxy and hydroxyl groups
The compound's structure contains an indole ring system with a methoxy group and a hydroxyl group attached to it.

Versatility

Complex organic compound production
The presence of the methoxy and hydroxyl groups makes the compound a versatile building block for creating complex organic compounds.

Importance in medicinal chemistry and drug design

Potential biological activities
The compound and its derivatives may exhibit potential biological activities, making it significant in the fields of medicinal chemistry and drug design.

Upstream product

• 32991-03-0 trans-β-dimethylamino-2-nitrostyrene 
• 126769-93-5 1-methoxyindolyl-3-methyl isothiocyanate 
• 67282-55-7 1-methoxy-1H-indole-3-carbaldehyde 
• 67-56-1 methanol 
• 88-72-2 1-methyl-2-nitrobenzene 
• 54698-11-2 1-methoxyindole 
• 3289-82-5 1-hydroxyindole 
• 5187-84-8 1-methoxy-3-indolylmethyl glucosinolate 

Relevant articles and documents

Investigation of neoascorbigen

The synthesis of N-methoxyascorbigen (neoascorbigen) - a natural substance from plants of the Cruciferae family - and also N-ethoxyascorbigen is described. In an acidic media under drastic conditions N-alkoxyascorbigens undergo transformations with the release of ascorbic acid and the formation of oligomers of 1-alkoxy-3-methyleneindolenine or with opening of the lactone ring, decarboxylation, and dehydration and the formation of 2-hydroxy-3-(1-alkoxy,-3-indolyl)-4-hydroxymethylcyclopent-2-enone. Amides of neoascorbigen, 3-O-methylglycoside of N-ethoxyascorbigen, and the product of the reduction of N-ethoxyascorbigen by sodium borohydride were obtained for the first time.

Application of indole-3-carbinol and diindolylmethane and derivatives thereof in preparation of medicines for treating lupus erythematosus

The invention provides an application of indole-3-carbinol and diindolylmethane and derivatives thereof in preparation of medicines for treating lupus erythematosus. The medicines of the type can enhance ability of initiatively scavenging free radicals for cells by improving expression of specific genes in the cells, which resist the free radicals, and then reduce injury of the free radicals to the cells and tissue. Simultaneously, the used small molecule medicines are easy to obtain, low in cost, stable in quality, and convenient to save and transport, and have a wide application prospect.

Application of indol-3-methyl alcohol and diindolylmethane and derivatives thereof to preparation of medicines for treating organ transplant rejection

The invention provides application of indol-3-methyl alcohol and diindolylmethane and derivatives thereof to preparation of medicines for treating organ transplant rejection. The medicines are capable of enhancing the capability of cells of actively removing free radicals by improving expression of specific genes with resistance to the free radicals in the cells, so as to relieve damage of the free radicals to the cells and tissues. Meanwhile, the used micro-molecule medicines are easy to get, low in costs, stable in properties and convenient to preserve and transport, and have broad application prospects.

Initial and Final Products, Nitriles, and Ascorbigens Produced in Myrosinase-Catalyzed Hydrolysis of Indole Glucosinolates

Micellar electrokinetic capillary chromatography (MECC) was used to follow the myrosinase (β-thioglucoside glucohydrolase EC 3.2.3.1)-catalyzed transformation of glucobrassicin (indol-3-ylmethylglucosinolate, 1a) and neoglucobrassicin (N-methoxyglucobrassicin, 1b) into nitriles, ascorbigens, and other products. The influence of pH, ascorbic acid, and Fe(II) ions was investigated. In the presence of ascorbic acid, (5 mM), thiocyanate ion and ascorbigens were the dominating products from 1a and 1b. In the presence of Fe(II) ions (2.5 mM), nitriles were the dominating products between pH 4 and 6-7. During hydrolysis of 1b in neutral or weakly basic solution, an unstable intermediate was detected by MECC. Comparisons of the rate of ascorbigen formation from 1a, 1b, and indol-3-ylcarbinol showed that ascorbigens were formed directly from ascorbate and unstable products of the hydrolysis of indole glucosinolates and that indol-3-ylcarbinols were not important intermediates. Structures of 1a, 1b, and products of 1b were confirmed by 1H NMR, MS, and UV spectroscopy.

Chemistry of Indole Glucosinolates: Intermediacy of Indol-3-ylmethyl Isothiocyanates in the Enzymic Hydrolysis of Indole Glucosinolates

The enzymic hydrolysis of 1-methoxyindol-3-ylmethyl glucosinolate (1b) proceeds via the corresponding isothiocyanate (2b), thus providing evidence for a previously unsubstantiated breakdown pathway and establishing a link with 1-methoxycyclobrassinin (4b) and related indole phytoalexins.

IDENTIFICATION OF 1-METHOXYINDOLYL-3-METHYL ISOTHIOCYANATE AS AN INDOLE GLUCOSINOLATE BREAKDOWN PRODUCT

The putative indole glucosinolate enzymic hydrolysis product, 1-methoxyindolyl-3-methyl isothiocyanate has been detected for the first time using low and high resolution mass spectrometry.