19492-03-6

Usage

Uses

Used in Pharmaceutical Industry:
8-HYDROXY-7-METHOXYCOUMARIN is used as a potential therapeutic agent for its antioxidant, anti-inflammatory, and antimicrobial properties. Its diverse pharmacological activities make it a promising candidate for the development of new drugs to treat various health conditions.
Used in Cancer Research:
8-HYDROXY-7-METHOXYCOUMARIN is used as a subject of interest in cancer research due to its anti-cancer properties. It is being investigated for its potential to inhibit tumor growth and progression, as well as its ability to enhance the efficacy of conventional chemotherapeutic drugs in resistant cases.
Used in Antioxidant Applications:
8-HYDROXY-7-METHOXYCOUMARIN is used as an antioxidant agent to protect cells from oxidative stress and damage, which can contribute to various health conditions and diseases.
Used in Anti-inflammatory Applications:
8-HYDROXY-7-METHOXYCOUMARIN is used as an anti-inflammatory agent to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Antimicrobial Applications:
8-HYDROXY-7-METHOXYCOUMARIN is used as an antimicrobial agent to combat bacterial, fungal, and other microbial infections, potentially leading to the development of new antimicrobial drugs.

InChI:InChI=1/C10H8O4/c1-13-7-4-2-6-3-5-8(11)14-10(6)9(7)12/h2-5,12H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 477770-79-9 8-acetoxy-7-hydroxycoumarin 
• 4055-69-0 2,3-dihydroxy-4-methoxybenzaldehyde 
• 108-24-7 acetic anhydride 
• 2445-80-9 7,8-dimethoxy-chromen-2-one 
• 77369-03-0 Villosin 
• 76474-93-6 7-methoxy-8-[(3-methyl-2-butenyl)oxy]-2H-1-benzopyran-2-one 
• 934-00-9 3-methocycatechol 
• 110-16-7 maleic acid 
• 160820-51-9 7-methoxy-8-methoxymethoxy-2H-1-benzopyran-2-one 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 160820-50-8 2-hydroxy-4-methoxy-3-methoxymethoxybenzaldehyde 
• 486-35-1 daphnetin 
• 471-25-0 Propiolic acid 

Downstream Products

• 2445-80-9 7,8-dimethoxy-chromen-2-one 
• 76474-93-6 7-methoxy-8-[(3-methyl-2-butenyl)oxy]-2H-1-benzopyran-2-one 
• 486-35-1 daphnetin 

Relevant academic research and scientific papers

COUMARINS IN ARTEMISIA CARUIFOLIA

Isolation of daphnetin 7-methyl ether, daphnetin dimethyl ether, daphnetin methylene ether, daphnetin 7-methyl-8(3,3-dimethylallyl) ether and 3,4-dimethoxy-2-hydroxycinnamic acid from Artemisia caruifolia is reperted. - Key Word Index: Artemisia caruifolia; Compositae; coumarins; daphnetin derivatives; 3,4-dimethoxy-2-hydroxycinnamic acid.

Rare benzonaphthoxanthenones from Chinese folk herbal medicine Polytrichum commune and their anti-neuroinflammatory activities in vitro

Two new (1–2) as well as five known (3–7) compounds were isolated from Polytrichum commune, a folk herbal medicine in China, and three of them (2, 4, 5) belong to benzonaphthoxanthenones that are rarely found in nature. Their structures were elucidated by the approach to 1D and 2D NMR spectra. The absolute configuration of 2 was assigned by comparing its experimental and calculated ECD data. 1–5 were investigated for their anti-neuroinflammatory activity against LPS-induced BV-2 cells. 1 and 3 exhibited well protective effect at a concentration of 2.5 μmol/mL. Molecular docking studies were adopted to further investigate the possible mechanism, whose results suggested that 1 might exert anti-neuroinflammatory effect by inhibiting activity of p38α, JNK2 and TAK1 to reduce the liberation of pro-inflammatory cytokines.

5-Phenylcoumarin Derivatives: Design, Synthesis, and Vasodilatory Activity

In continuation of our previous efforts towards the development of coumarin derivatives with potential vasodilatory activity, 5-phenylcoumarin derivatives were designed and synthesized. Target compounds and their precursors exhibited moderately vasodilato

High-selectivity preparation method for 7-methoxy-6/8-hydroxy coumarin

The invention provides a high-selectivity preparation method for 7-methoxy-6/8-hydroxy coumarin and belongs to the field of synthesis of natural medicines. The method comprises the steps of subjecting a catechol coumarin compound to a high-selectivity methylation reaction with a methylation reagent in a proper base catalyst added organic reaction system, so as to obtain a 7-hydroxyl mono-methylate, wherein the mole ratio of a base to the catechol coumarin compound is (2.0 to 7.0): 1, the mole ratio of the methylation reagent to the catechol coumarin compound is (1.0 to 3.0): 1, the temperature of the organic reaction system is 0 DEG C to 30 DEG C, and the reaction time is 1.0 to 5.0 hours. The method has the characteristics of simplicity in operation, moderate conditions, good selectivity, high yield and the like and can be applied to the preparation of mono-methylates of coumarin catechols with different types of substituents.

Ytterbium triflate promoted coupling of phenols and propiolic acids: Synthesis of coumarins

Coumarins are a well-known class of natural occurring and semi-synthetic products with reported important and effective pharmacological activities. In this Letter an improved method for the chemical synthesis of such compounds is described. Coumarins have been obtained in good to excellent yields under microwave irradiation and solvent-free conditions in a short time from differently substituted phenols and propiolic acids used as starting materials in the presence of Yb(OTf)3 hydrate 10% mol as the catalyst.

Synthesis and evaluation of antibacterial and anti-inflammatory properties of naturally occurring coumarins

Coumarins are a group of heterocyclic compounds naturally present in a large variety of plant families. Nevertheless, oxyprenylated coumarins have been only recently seen as valuable and promising biologically active phytochemicals. In this study, we synthesized three naturally occurring O-prenylcoumarins (1), (2), and (3), and evaluated their antibacterial and anti-inflammatory properties in view of their therapeutic potential against periodontal disease. The three O-prenylcoumarins were synthesized using well-known schemes leading to the chromen-2-one nucleus. The periodontal pathogen Porphyromonas gingivalis was found to be highly susceptible to all three O-prenylcoumarins with minimal inhibitory concentration values in the range of 12.5-25 mg/ml; the non-prenylated forms of the coumarins did not show any activity. The antibacterial activity of (1), (2), and (3) appeared to result from its ability to permeate the cell membrane. Using the U937-3xkB-LUC human monocytic cell line, compounds (2) and (3) dose-dependently inhibited lipopolysaccharide-induced NF-kB activation, while (1) did not. The non-prenylated forms of the coumarins were either inactive or much less potent. In conclusion, O-prenylcoumarins (2) and (3) by exhibiting a dual mode of action including antibacterial and anti-inflammatory activities may represent promising targeted therapeutic agents for localized treatment of periodontal diseases.

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

Revision of the structure of a new coumarin isolated from Artemisia carviforia wall

Four coumarins (1-4) were synthesized by the routes shown in Schemes 2-5, respectively. The previously proposed structure for a new coumarin isolated from Artemisia carviforia was incorrect; the structure of the coumarin is represented by formula (3).

Natural Product Chemistry. Part 121. Synthesis of Dicoumarinyl Ethers with the Structures Proposed for Fatagarine and Oreojasmine

Synthesis of the 7,8'-dicoumarinyl ethers: 7-methoxy-7',8-oxydicoumarin and 6,7-dimethoxy-7',8-oxydicoumarin, established that the structures of fatagarine and oreojasmine for which these two structures have been proposed, have to be revised.Synthesis of 7-methoxy-5,7'-oxydicoumarin and 8-methoxy-7,7'-oxydicoumarin exclude the possibility of these dicoumarinyl ether structures for fatagarine. - Keywords: Dicoumarinyl ethers; 6,7-Dimethoxy-7',8-oxydicoumarin; Fatagarine; 7-Methoxy-5,7'-oxydicoumarin; 8-Methoxy-7,7'-oxydicoumarin; 7-Methoxy-7',8-oxydicoumarin; Oreojasmine; Ruta oreojasme

CLAISEN REARRANGEMENTS-XV STRUCTURE REVISION OF THE COUMARIN, CELERIN, BY SYNTHESIS

The four possible structures, 9,12,17 and 26 for celerin have been synthesised and the structure of the natural product revised to 8-hydroxy-7-methoxy-5-(1,1-dimethylallyl)coumarin 26.Efficient alternative synthetic routes to sibiricol 5, coumurrayin 6 and pinnarin 13 have been established.