13523-09-6

Basic information

• Product Name: 3,5-Cyclohexadiene-1,2-dione, 4-methoxy-5-methyl-
• CAS NO: 13523-09-6
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Mol File: 13523-09-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3,5-Cyclohexadiene-1,2-dione, 4-methoxy-5-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Cyclohexadiene-1,2-dione, 4-methoxy-5-methyl-(13523-09-6)
• EPA Substance Registry System: 3,5-Cyclohexadiene-1,2-dione, 4-methoxy-5-methyl-(13523-09-6)

Safety Data

• Hazardous Substances Data: 13523-09-6(Hazardous Substances Data)

Usage

General Description

3,5-Cyclohexadiene-1,2-dione, 4-methoxy-5-methyl, also known as scopoletin, is a natural chemical compound commonly found in a variety of plants such as Artemisia, Scopolia, and Angelica. It is known for its diverse biological activities including anti-inflammatory, anti-cancer, and anti-oxidative properties. Scopoletin has been used in traditional medicine for its anti-inflammatory and analgesic effects, and it also exhibits potential as a treatment for diabetes and cardiovascular diseases. Additionally, it has been studied for its antifungal and antimicrobial properties, making it a promising candidate for the development of new pharmaceutical products. Overall, 3,5-Cyclohexadiene-1,2-dione, 4-methoxy-5-methyl- has shown great potential for numerous health benefits and continues to be the subject of ongoing research.

Upstream product

• 124-41-4 sodium methylate 
• 452-86-8 4-methyl-1,2-dihydroxybenzene 
• 14786-82-4 4-hydroxy-2-methylanisole 
• 67-56-1 methanol 

Downstream Products

• 21086-80-6 4-methoxy-5-methylbenzene-1,2-diol 
• 614-13-1 2-methoxy-5-methyl-1,4-benzoquinone 

Relevant articles and documents

Oxidation of 4-Methylcatechol by Dioxygen Studied by ESR Spectroscopy. The Different Regioselectivity of OH(-) and MeO(-) Nucleophilic Attack and Kinetic Deuterium Isotope Effects

The oxidation of 4-methylcatechol by dioxygen and the subsequent reactions of the two nucleophiles OH(-) and MeO(-) with the oxidation products were studied by electron spin resonance (ESR) spectroscopy.These reactions are models for those of skin proteins with substituted 1,2-dihydroxybenzenes (catechols) which produce the serve allergic contact dermatitis associated with plants such as poison ivy, poison oak and the Japanese lac tree.The rates of formation of the primary and secondary semiquinone radical anions show a large kinetic deuterium isotope effect (ca 10) at 20 deg C, which is ascribed to a slow deprotonation of the hydrogen bridged 4-methylcatechol monoanion.There is a marked difference in regioselectivity for OH(-) and MeO(-) substitution of the 4-methylquinone; OH(-) reacts exclusively at the 3-position whereas MeO(-) attacks at the 5-position.This dissimilarity between two normally similar nucleophiles is also ascribed to the occurrence of hydrogen bridging between the substituting OH(-) at the 3-position and the adjacent quinone oxygen at the 2-position.The expected attack at the more electropositive 5-position occurs with MeO(-) because no such hydrogen bonding can occur.Disubstitution occurs for OH(-) but not for MeO(-), probably reflecting the greater nucleophilicity of the former. - Keywords: 4-Methylcatechol Autoxidation Electron spin resonance spectroscopy Nucleophiles Semiquinones Allergic contact dermatitis