574-84-5

Usage

Uses

Used in Pharmaceutical Industry:
7,8-DIHYDROXY-6-METHOXYCOUMARIN is used as a therapeutic agent for its antioxidant and anti-inflammatory properties, which can help in the treatment of various diseases and conditions. Its protective effects against hyperuricemia and renal dysfunction also make it a potential candidate for the development of drugs targeting these specific health issues.
Used in Nutraceutical Industry:
7,8-DIHYDROXY-6-METHOXYCOUMARIN can be used as an additive in the nutraceutical industry, where its antioxidant properties can contribute to the development of dietary supplements and functional foods. These products can help consumers maintain a healthy lifestyle and prevent the onset of various diseases.
Used in Cosmetic Industry:
In the cosmetic industry, 7,8-DIHYDROXY-6-METHOXYCOUMARIN can be utilized for its anti-inflammatory and antioxidant properties. It can be incorporated into skincare products, such as creams, lotions, and serums, to help reduce inflammation, protect the skin from oxidative stress, and promote overall skin health.
Used in Agricultural Industry:
7,8-DIHYDROXY-6-METHOXYCOUMARIN can also be applied in the agricultural industry as a natural pesticide or growth promoter. Its antioxidant and anti-inflammatory properties can help protect crops from various diseases and pests, while also promoting healthy growth and development.

InChI:InChI=1/C10H8O5/c1-14-6-4-5-2-3-7(11)15-10(5)9(13)8(6)12/h2-4,12-13H,1H3

Upstream product

• 64-17-5 ethanol 
• 87997-30-6 1-methoxy-2,3,4-trihydroxybenzene 
• 77084-21-0 7-hydroxy-6-methoxy-8-acetyl-2H-<1>-benzopyran-2-one 
• 524-30-1 8-β-D-glucopyranosyloxy-7-hydroxy-6-methoxy-coumarin 
• 77369-04-1 obtusicin 
• 524-30-1 fraxin 
• 24778-11-8 7-β-D-glucopyranosyloxy-8-hydroxy-6-methoxycoumarin 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 7722-84-1 dihydrogen peroxide 
• 73815-12-0 fraxetin diacetate 
• 202288-19-5 8-acetyl-6-hydroxy-7-methoxycoumarin 
• 92-61-5 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one 
• 895127-79-4 fraxetin-7-O-sulfate 
• 667876-16-6 2,3-di[(isopropyl)oxy]-4-methoxybenzaldehyde 

Downstream Products

• 486-21-5 isofraxidin 
• 525-21-3 fraxidin 
• 6035-49-0 6,7,8-trimethoxy-2H-chromen-2-one 
• 71765-80-5 6-methoxy-7-(3',3'-dimethylallyloxy)-8-hydroxycoumarin 
• 28843-40-5 6-methoxy-7,8-methylenedioxycoumarin 
• 90475-47-1 propacin 
• 76948-72-6 cleomiscosin A 
• 76948-72-6 cleomiscosin A 
• 76985-93-8 cleomiscosin B 
• 76985-93-8 (2S,3R)-3-(4-Hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-10-methoxy-2,3-dihydro-1,4,5-trioxa-phenanthren-6-one 
• 95055-94-0 7-O-(3,4-Dimethoxy-α-methylphenacyl)fraxetin 
• 99442-72-5 3-(4-Benzyloxy-3-methoxy-phenyl)-2-(8-hydroxy-6-methoxy-2-oxo-2H-chromen-7-yloxy)-3-oxo-propionic acid ethyl ester 
• 99430-18-9 3-(4-Benzyloxy-3-methoxy-phenyl)-2-(7-hydroxy-6-methoxy-2-oxo-2H-chromen-8-yloxy)-3-oxo-propionic acid ethyl ester 
• 90475-47-1 propacin 

Relevant academic research and scientific papers

Metabolic fate of fraxin administered orally to rats

Naturally occurring fraxin (1) was administered orally to rats to investigate its metabolism. Urinary metabolites were analyzed by three-dimensional HPLC, and fraxetin-7-O-sulfate (2), fraxetin-7-O-β- glucuronide (3), fraxetin (4), 6,7,8-trihydroxycoumarin (5), and fraxidin (6) were isolated. Fraxin (1) was extensively metabolized to 4, which was partly metabolized to 5 in a rat fecal suspension after incubation for 24 h. Urinary excretion of 4 and 5 in rats administered orally with 1 was substantially reduced when the rats were treated with antibiotics to suppress their intestinal flora. Incubation of 1 with a rat liver S-9 mixture yielded 6. These results suggest that hydrolysis and demethylation of 1 are performed by intestinal microflora, while methylation occurs in the liver.

Benzopyranones and Their Sulfate Esters from Pelargonium sidoides

Investigation of the benzopyranones from the roots of Pelargonium sidoides led to the identification of 15 benzopyranones, among them the novel compounds 12 and 14. Furthermore, benzopyranones 4 and 15 were detected in Pelargonium sidoides for the first time. Structure determinations were performed by one- and two-dimensional NMR spectroscopy. An HPLC system for the discrimination of these benzopyranones has been developed. Georg Thieme Verlag KG Stuttgart New York.

Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-influenza Activities

Different catechol and pyrogallol derivatives have been synthesized by oxidation of coumarins with 2-iodoxybenzoic acid (IBX) in DMSO at 25 °C. A high regioselectivity was observed in accordance with the stability order of the incipient carbocation or radical benzylic-like intermediate. The oxidation was also effective in water under heterogeneous conditions by using IBX supported on polystyrene. The new derivatives showed improved antioxidant effects in the DPPH test and inhibitory activity against the influenza A/PR8/H1N1 virus. These data represent a new entry for highly oxidized coumarins showing an antiviral activity possibly based on the control of the intracellular redox value.

Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry

The title natural products (1 and 2, respectively) have been synthesized by Au(I)-catalyzed intramolecular hydroarylation (IMHA) of the relevant aryl propiolate esters (e.g., 13), which were themselves formed by reaction of the corresponding phenols with either 3-(trimethylsilyl)propiolic acid or propiolic acid and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride or dicyclohexylcarbodiimide. (±)-Purpurasol (3) was readily derived from fraxetin (2) by established procedures.

Novel Fe3+-based 1H MRI β-galactosidase reporter molecules

There is increasing interest in the development of reporter agents to reveal enzyme activity in vivo using imaging in small animals. We have previously demonstrated the feasibility of detecting lacZ gene activity using the commercially available 3,4-cyclohexenoesculetin-β-D-galactopyranoside (S-Gal) as a 1H MRI reporter. Specifically, β-galactosidase (β-gal) releases the aglycone, which forms a magnetic resonance contrast-inducing paramagnetic precipitate in the presence of Fe3+. Contrast was primarily T2-weighted signal loss, but T1 effects were also observed. Since T1-contrast generally provides signal enhancement as opposed to loss, it appeared attractive to explore whether analogues could be generated with enhanced characteristics. We now report the design and synthesis of novel analogues together with characterization of 1H MRI contrast based on both T1 and T2 response to b-gal activity in vitro for the lead agent.

A mild, highly selective and remarkably easy procedure for deprotection of aromatic acetates using ammonium acetate as a neutral catalyst in aqueous medium

Ammonium acetate was found to catalyze efficiently the selective deprotection of aromatic acetates in the presence of various sensitive functionalities in aqueous methanol under neutral conditions at room temperature to yield the corresponding phenols in excellent yields. The method has been utilized for deprotection of acetates of several naturally occurring bioactive phenolic compounds and for preparation of venkatasin, a natural coumarino-lignan, from the anticancer compound cleomiscosin A.

Enzymatically amplified voltammetric sensor for microliter sample volumes of salicylate

A new voltammetric sensing strategy for salicylate employing two enzymes and applicable to microliter sample volumes is demonstrated. The method involves the use of the enzyme salicylate hydroxylase to convert salicylate to catechol, which is oxidized at a carbon electrode. The product of this oxidation reaction, o-quinone, is then reduced by a second enzyme, glucose oxidase, to regenerate catechol. Reoxidation of catechol results in a signal that is amplified due to repeated cycling of catechol molecules between the oxidized and reduced states. This chemistry is implemented in two configurations. (i) A paper disk into which both enzymes have been absorbed is mounted on a coplanar three-electrode assembly for aqueous experiments. Determination of salicylate in a nonprescription dermatological product is demonstrated. (ii) A small solution volume confined directly on the coplanar electrodes is used for determination of salicylate in whole blood. The advantages of the use of two enzymes and of monitoring steady-state catalytic currents are discussed.

COUMARINS OF Haplophyllum obtusifolium. STRUCTURES OF TWO NEW COUMARIN GLYCOSIDES

Two coumarin glycosides have been isolated from an aqueous ethanolic extract of the epigeal part of Haplophyllum obtusifolium: (I) - C16H16O10, mp 164-166 deg C, D -52.4 deg (dimethylformamide); and (II) - C26H26O12, mp 206-208 deg C, D -110.5 deg (pyridine).It has been established on the basis of chemical transformations and spectral characteristics that (I) has the structure of fraxetin 7-O-β-D-glucopyranoside and (II) that of scopoletin 7-O-(6'-O-feruloyl-β-D-glucopyranoside).

NEW COUMARINS OF Haplophyllum obtusifolium

Two coumarins have been isolated from an ethanolic extract of the epigeal part of Haplophyllum obtusifolium Lebed.: capensin (I) and the new coumarin obtusicin, C5H16O6, (II), mp 81-91 deg C (CH3OH).The acid hydrolysis of (I) and (II) leads to fraxetin.On the basis of the results of a study of acetylation products and the spectral characteristics (IR, UV, PMR, and mass spectra) it has been established that obtusician has the structure of 8-hydroxy-7-(4'-hydroxy-3'-methyl-but-2'-enyloxy)-6-methoxycoumarin.