6748-68-1

Usage

Uses

Used in Pharmaceutical Industry:
8-Acetyl-7-hydroxycoumarin is used as an intermediate in the synthesis of various pharmaceutical products due to its potential biological and pharmacological activities. Its anti-inflammatory, anticancer, and antimicrobial properties make it a promising candidate for the development of new drugs.
Used in Agrochemical Industry:
8-Acetyl-7-hydroxycoumarin is also used in the synthesis of agrochemical products, leveraging its antimicrobial properties to protect crops from diseases and pests, thereby enhancing agricultural productivity.
Used in Scientific Research:
8-Acetyl-7-hydroxycoumarin is utilized in various scientific research applications, particularly in the study of its antioxidant and anticoagulant activities. Its potential to modulate several biological pathways makes it a valuable compound for exploring new therapeutic targets and understanding disease mechanisms.
Used in Drug Delivery Systems:
To enhance the efficacy and bioavailability of 8-Acetyl-7-hydroxycoumarin, novel drug delivery systems are being developed. These systems aim to improve the compound's delivery to target tissues, reducing side effects and increasing therapeutic outcomes in various medical applications.

InChI:InChI=1/C11H8O4/c1-6(12)10-8(13)4-2-7-3-5-9(14)15-11(7)10/h2-5,13H,1H3

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 10387-49-2 7-acetyloxycoumarin 
• 66185-72-6 7-(phenylcarbonyl)oxy-4-methyl-2H-1-benzopyran-2-one 
• 2747-05-9 4-methylumbelliferyl acetate 
• 31005-05-7 7-(phenylcarbonyl)oxy-2H-1-benzopyran-2-one 
• 121571-31-1 (S)-3,3-dimethyloxirane-2-carboxaldehyde 
• 112699-36-2 7-acetyloxy-8-iodo-2H-1-benzopyran-2-one 

Downstream Products

• 89019-07-8 7-methoxy-8-coumarinul methyl ketone 
• 65535-49-1 8-acetyl-7-benzyloxycoumarin 
• 1164495-37-7 7-Hydroxy-8-((E)-3-thiophen-2-yl-acryloyl)-chromen-2-one 
• 116611-95-1 (E)-7-hydroxy-8-(3-(4-methoxyphenyl)acryloyl)coumarin 
• 412031-62-0 7-Hydroxy-8-[(E)-3-(3,4,5-trimethoxy-phenyl)-acryloyl]-chromen-2-one 
• 116611-95-1 7-Hydroxy-8-[(E)-3-(4-methoxy-phenyl)-acryloyl]-chromen-2-one 
• 412031-66-4 7-Hydroxy-8-[(E)-3-(4-hydroxy-3-methoxy-phenyl)-acryloyl]-chromen-2-one 
• 412031-61-9 8-[(E)-3-(3,4-Dimethoxy-phenyl)-acryloyl]-7-hydroxy-chromen-2-one 
• 2009-24-7 8-hydroxypsoralen 
• 65535-50-4 7-Benzyloxy-8-hydroxycoumarin 

Relevant academic research and scientific papers

Synthesis of 2,3-dihydro-3-hydroxy-2-hydroxylalkylbenzofurans from epoxy aldehydes. One-step syntheses of brosimacutin G, vaginidiol, vaginol, smyrindiol, xanthoarnol, and avicenol A. Biomimetic syntheses of angelicin and psoralen

(Chemical Equation Presented) We have developed two practical one-step syntheses of 2,3-dihydro-3-hydroxy-2-hydroxyalkylbenzofurans from readily available optically pure α,β-epoxy aldehydes. Electron-deficient resorcinols react with epoxy aldehydes using either Cs2CO3 in DMF or KOH/CaCl2 in MeOH to give adducts 13, 16, 18, 20, 21, and brosimacutin G (6t). Grignard reagents prepared by low-temperature halogen-metal exchange of acetoxy iodocoumarins 35d and 40 and acetoxy bromonaphthalene 41 add to epoxy aldehyde (S)-26 to complete the first syntheses of vaginidiol (7c), vaginol (7t), smyrindiol (8c), xanthoarnol (8t), and avicenol A (9t). Acid-catalyzed fragmentation of vaginidiol or vaginol provides angelicin, while that of smyrindiol or xanthoarnol affords psoralen. In both cases, the trans isomers fragment only twice as fast as the cis isomers, possibly through the intermediacy of a common benzylic cation. This may have implications for the biosynthesis of angelicin and psoralen.

Intermolecular character of the Fris rearrangement in the series of acyloxycoumarins

In the study of the Fris rearrangement in the series of 7-and 4-acyloxycoumarins we obtained certain data indicating intermolecular character of the rearrangement. The Fris rearrangement of a mixture of 7-benzoyloxy-4-metylcoumarin and 7-acetoxycoumarin results in formation of four reaction products in approximately equal molar ratio. Also, four products were obtained in the Fris rearrangement of 7-and 4-acyloxycoumarins in the presence of hydroxycoumarins. The Fris rearrangement of acyloxycoumarins in the presence of m-xylene at acylcoumarin-m-xylene ratio of 1:6 leads to the corresponding hydroxycoumarins and acylated m-xylenes. Intermediate formation of acylium ions was also detected by evolution of carbon monooxide at the Fris rearrangement of 7-pyvaloyloxy-and 7-isobutyryloxy-4-methylcoumarins. A product of intermolecular migration, 3-acetyl-4-hydoxy-6-methylcoumarin, was discovered also in the rearrangement of 4-acetoxycoumarin in the presence of 4-hydoxy-6-methylcoumarin catalyzed by phosphorus oxychloride.