574-84-5

Basic information

• Product Name: 7,8-DIHYDROXY-6-METHOXYCOUMARIN
• Synonyms: 7,8-Dihydroxy-6-MethoxycouMarin 98%;Fraxetin (6-OMe, 7,8-OH);2H-1-Benzopyran-2-one, 7,8-dihydroxy-6-methoxy-;7,8-Dihydroxy-6-methoxy-2H-chromen-2-one;7,8-DIHYDROXY-6-METHOXYCOUMARIN;FRAXETIN;7,8-dihydroxy-6-methoxy-2-benzopyrone;Fratexin
• CAS NO: 574-84-5
• Molecular Formula: C₁₀H₈O₅
• Molecular Weight: 208.17
• EINECS: 209-376-2
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Coumarins
• Mol File: 574-84-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 230-232°C
• Boiling Point: 307.35°C (rough estimate)
• Flash Point: 196 °C
• Appearance: Light yellow crystalline flakes
• Density: 1.3844 (rough estimate)
• Vapor Pressure: 1.56E-09mmHg at 25°C
• Refractive Index: 1.4717 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.22±0.20(Predicted)
• Merck: 13,4288
• CAS DataBase Reference: 7,8-DIHYDROXY-6-METHOXYCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 7,8-DIHYDROXY-6-METHOXYCOUMARIN(574-84-5)
• EPA Substance Registry System: 7,8-DIHYDROXY-6-METHOXYCOUMARIN(574-84-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 574-84-5(Hazardous Substances Data)

Usage

Uses

Fraxetin is a coumarin compound with anti-oxidant and anti-inflammatory activity. Also acts as a protective agent against hyperuricemia and renal dysfunction.

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

• 92-61-5 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one 
• 1413790-91-6 7,8-di-O-(β-D-galactopyranosyl)-6-methoxycoumarin 
• 1413790-17-6 7-O-(β-D-galactopyranosyl)-8-hydroxy-6-methoxycoumarin 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 667876-16-6 2,3-di[(isopropyl)oxy]-4-methoxybenzaldehyde 
• 895127-79-4 fraxetin-7-O-sulfate 
• 483-66-9 sphondin 
• 263271-48-3 8-acetyl-6,7-dimethoxycoumarin 
• 202288-19-5 8-acetyl-6-hydroxy-7-methoxycoumarin 
• 89019-07-8 7-methoxy-8-coumarinul methyl ketone 
• 4055-69-0 2,3-dihydroxy-4-methoxybenzaldehyde 
• 73815-12-0 fraxetin diacetate 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 77084-21-0 7-hydroxy-6-methoxy-8-acetyl-2H-<1>-benzopyran-2-one 

Downstream Products

• 637037-43-5 (Ru(CO)2(P(C₆H₅)3)2(C₉H₃O₂(OCH₃)O₂)) 
• 95055-95-1 7-[2-(3,4-Dimethoxy-phenyl)-2-hydroxy-1-methyl-ethoxy]-8-hydroxy-6-methoxy-chromen-2-one 
• 95055-96-2 3-(3,4-Dimethoxy-phenyl)-10-methoxy-2-methyl-2,3-dihydro-1,4,5-trioxa-phenanthren-6-one 
• 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 
• 90706-59-5 cleomiscosin A diacetate 
• 102070-25-7 8-[(1R,2S)-2-(4-Benzyloxy-3-methoxy-phenyl)-2-hydroxy-1-hydroxymethyl-ethoxy]-7-hydroxy-6-methoxy-chromen-2-one 
• 102070-25-7 8-[(1R,2R)-2-(4-Benzyloxy-3-methoxy-phenyl)-2-hydroxy-1-hydroxymethyl-ethoxy]-7-hydroxy-6-methoxy-chromen-2-one 
• 76948-72-6 cleomiscosin A 
• 102070-27-9 Acetic acid 8-[(1R,2S)-2-acetoxy-1-acetoxymethyl-2-(4-benzyloxy-3-methoxy-phenyl)-ethoxy]-6-methoxy-2-oxo-2H-chromen-7-yl ester 
• 102070-27-9 Acetic acid 8-[(1R,2R)-2-acetoxy-1-acetoxymethyl-2-(4-benzyloxy-3-methoxy-phenyl)-ethoxy]-6-methoxy-2-oxo-2H-chromen-7-yl ester 
• 102070-24-6 3-(4-Benzyloxy-3-methoxy-phenyl)-2-(6-methoxy-7-methoxymethoxy-2-oxo-2H-chromen-8-yloxy)-3-oxo-propionic acid ethyl ester 
• 102070-29-1 cleomiscosin A monoacetate 
• 76985-93-8 cleomiscosin B 
• 99430-21-4 Acetic acid 7-[(1R,2S)-2-acetoxy-1-acetoxymethyl-2-(4-benzyloxy-3-methoxy-phenyl)-ethoxy]-6-methoxy-2-oxo-2H-chromen-8-yl ester 

Relevant articles and documents

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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.

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.