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

Description

7,8-Dimethoxycoumarin, also known as umbelliferone, is a naturally occurring organic compound belonging to the coumarin family. It is found in various plants such as citrus fruits, carrots, and parsley. This versatile chemical compound exhibits anti-inflammatory, antioxidant, and anti-cancer properties, and has been utilized in traditional medicine for its potential medicinal benefits. Furthermore, its fluorescent properties make it valuable in applications like fluorescence bioimaging and as a fluorescent probe for detecting metal ions.

Uses

Used in Pharmaceutical Industry:
7,8-Dimethoxycoumarin is used as a therapeutic agent for its anti-inflammatory, antioxidant, and anti-cancer properties, offering potential benefits in the treatment of various diseases and conditions.
Used in Traditional Medicine:
7,8-Dimethoxycoumarin is used as a medicinal component in traditional medicine, leveraging its natural healing properties for various health applications.
Used in Analytical Chemistry:
7,8-Dimethoxycoumarin is used as a fluorescent probe for the detection of metal ions, thanks to its fluorescent properties, which aid in sensitive and selective analysis in various chemical and environmental samples.
Used in Fluorescence Bioimaging:
7,8-Dimethoxycoumarin is used as a fluorescent marker in fluorescence bioimaging, allowing for the visualization and tracking of biological processes and molecules within living organisms or cells.

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

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

Downstream Products

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

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