2445-80-9

Basic information

• Product Name: 7,8-dimethoxycoumarin
• Synonyms: Daphnetin dimethyl ether;Daphnetin dimetyl ether;etin dimetyl ether
• CAS NO: 2445-80-9
• Molecular Formula: C₁₁H₁₀O₄
• Molecular Weight: 206.19
• Mol File: 2445-80-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 118-119 °C
• Boiling Point: 370.9°Cat760mmHg
• Flash Point: 167.6°C
• Appearance: /
• Density: 1.248
• Vapor Pressure: 1.07E-05mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 7,8-dimethoxycoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 7,8-dimethoxycoumarin(2445-80-9)
• EPA Substance Registry System: 7,8-dimethoxycoumarin(2445-80-9)

Safety Data

• Hazardous Substances Data: 2445-80-9(Hazardous Substances Data)

Usage

General Description

7,8-dimethoxycoumarin, also known as umbelliferone, is a chemical compound that belongs to the coumarin family. It is a naturally occurring organic compound found in plants such as citrus fruits, carrots, and parsley. 7,8-dimethoxycoumarin has been shown to possess anti-inflammatory, antioxidant, and anti-cancer properties. It has also been used in traditional medicine for its potential medicinal benefits. Additionally, 7,8-dimethoxycoumarin is known for its fluorescent properties, making it useful in various applications such as in the field of fluorescence bioimaging and as a fluorescent probe for the detection of metal ions. Overall, 7,8-dimethoxycoumarin is a versatile chemical compound with potential therapeutic and analytical applications.

InChI:InChI=1/C11H10O4/c1-13-8-5-3-7-4-6-9(12)15-10(7)11(8)14-2/h3-6H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 19492-03-6 8-hydroxy-7-methoxy-2H-chromen-2-one 
• 486-35-1 daphnetin 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 152821-16-4 2,2-dimethyl-5-<(2,3,4-trimethoxyphenyl)-methylene>-1,3-dioxane-4,6-dione 
• 76474-93-6 7-methoxy-8-[(3-methyl-2-butenyl)oxy]-2H-1-benzopyran-2-one 
• 67-56-1 methanol 
• 106-28-5 Farnesol 
• 77-78-1 dimethyl sulfate 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 19283-70-6 3,4-dimethoxysalicylaldehyde 
• 152821-20-0 7,8-dimethoxy-2-oxo-2H-1-benzopyran-3-carboxylic acid 
• 74-88-4 methyl iodide 
• 485-90-5 hydrangetin 

Downstream Products

• 19492-03-6 8-hydroxy-7-methoxy-2H-chromen-2-one 
• 486-35-1 daphnetin 
• 855410-03-6 2-Hydroxy-3.4-dimethoxy-styrol 
• 76474-94-7 dihydrocinnamic acid 

Relevant articles and documents

SINGLE ELECTRON TRANSFER INITIATED PHOTOCYCLIZATION OF SUBSTITUTED CINNAMIC ACIDS TO CORRESPONDING COUMARINS

Efficient photocyclization of substituted cinnamic acids to corresponding coumarins, initiated by single electron transfer processes, have been reported.A probabale mechanism has been discussed.

Study of the Oxidative Cleavage Proposed in the Biogenesis of Transtaganolides/Basiliolides: Pyran-2-one Aromaticity-Mediated Regioselective Control and Biogenetic Implications

The synthetic feasibility of the oxidative cleavage: epoxidation of 7-O-geranylscopoletin followed by electrocyclic ring-opening, proposed in the biogenesis of transtaganolides/basiliolides is studied. Unlike the proposed pericyclic reactions, this pathway has not yet been addressed. Three synthetic strategies have been tested consisting of: i) Baeyer–Villiger oxidation of p-quinoids, ii) hydrolysis of quinone monoketals, or iii) direct fragmentation by using oxygen donors. Oxidation of the benzene ring of hydroxylated coumarins has been achieved using peroxyacids, but cleavage took place between undesired positions. The aromaticity conservation of the pyran-2-one cycle during oxidation is the controlling factor of these observed regioselectivities. The use of a 4,5-dihydroxy-2-methoxycinnamate model, in which the pyran-2-one ring does not exert influence on oxidation, has allowed the design of a synthetic sequence toward an analogue of the natural pyran-2-one isolated from Thapsia transtagana, key in the biogenesis. Mechanistic proposals for the obtained results as well as their biogenetic implications are raised.

Monoalkylation of dihydroxycoumarins via Mitsunobu dehydroalkylation under high intensity ultrasound. The synthesis of ferujol

Monoalkylation of natural dihydroxycoumarins was carried out by Mitsunobu dehydroalkylation under sonochemical conditions. Aesculetin (6,7-dihydroxycoumarin) was selectively alkylated in good yield with prenyl alcohols at position 7, as clearly shown by N