83769-04-4

Basic information

• Product Name: 3,4-Dihydro-8-hydroxy-3-Methyl-1-oxo-1H-2-benzopyran-7-carboxylic Acid Methyl Ester
• Synonyms: 3,4-Dihydro-8-hydroxy-3-Methyl-1-oxo-1H-2-benzopyran-7-carboxylic Acid Methyl Ester
• CAS NO: 83769-04-4
• Molecular Formula: C12H12O5
• Molecular Weight: 236.22068
• Product Categories: Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 83769-04-4.mol

Chemical Properties

• Appearance: /
• Solubility: DCM, Methanol
• CAS DataBase Reference: 3,4-Dihydro-8-hydroxy-3-Methyl-1-oxo-1H-2-benzopyran-7-carboxylic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dihydro-8-hydroxy-3-Methyl-1-oxo-1H-2-benzopyran-7-carboxylic Acid Methyl Ester(83769-04-4)
• EPA Substance Registry System: 3,4-Dihydro-8-hydroxy-3-Methyl-1-oxo-1H-2-benzopyran-7-carboxylic Acid Methyl Ester(83769-04-4)

Safety Data

• Hazardous Substances Data: 83769-04-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-carboxylic Acid Methyl Ester is used as a research compound for studying the biosynthesis of Ochratoxin A and its potential applications in the development of pharmaceuticals and treatments for related conditions.
Used in Toxicology Research:
3,4-Dihydro-8-hydroxy-3-Methyl-1-oxo-1H-2-benzopyran-7-carboxylic Acid Methyl Ester is also utilized in toxicology research to understand the mechanisms of action and potential health risks associated with Ochratoxin A exposure, which can help in the development of strategies for prevention and mitigation of its toxic effects.

Upstream product

• 1830-54-2 3-oxopentanedioic acid dimethyl ester 
• 75716-69-7 dimethyl 2-hydroxyl-4-methylbenzene-1,3-dicarboxylate 
• 75-07-0 acetaldehyde 
• 885680-13-7 C₁₉H₃₀O₆Si 
• 885680-12-6 tert-butyldimethyl(pent-4-yn-2-yloxy)silane 
• 534-17-8 caesium carbonate 

Downstream Products

• 16281-39-3 5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-(1H)-2-benzopyran-7-carboxylic acid 
• 16281-43-9 (+/-)-3,4-dihydro-8-hydroxy-3-methyl-7-isocoumarincarboxylic acid 
• 344348-28-3 methyl 5-chloro-8-hydroxy-3-methyl-1-oxoisochromane-7-carboxylate 

Relevant articles and documents

Method for the efficient synthesis of highly-substituted oxetan- and azetidin-, dihydrofuran- and pyrrolidin-3-ones and its application to the synthesis of (±)-pseudodeflectusin

Highly substituted four- and five-membered heterocycles were prepared starting with O,P- and N,P-acetals by using a one-pot method involving base induced cyclization and a Horner-Wadsworth-Emmons (HWE) olefination reaction. Divergent synthesis of various heterocycles was achieved by using this method and transformations of the alkenyl group in the products of these processes were exemplified. Finally, a short and efficient synthesis of (±)- pseudodeflectusin based on the new methodology was achieved.

Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers

The mycotoxin ochratoxin A is a potent inhibitor of the protein biosynthesis and known to be cytotoxic in nanomolar concentrations. In order to investigate the relationship between stereochemistry and cytotoxicity of this compound, all four ochratoxin A stereoisomers have been synthesized. Using the liver cell line Hep G2, the compounds were tested for cytotoxic and apoptotic potential. It could be shown, that the l-configuration of the phenylalanine moiety of the molecule is mostly responsible for the high cytotoxicity of ochratoxin A while the stereocenter at the dihydroisocoumarine structure is of less importance.

A new and expedient total synthesis of ochratoxin A and d 5-ochratoxin A

A new total synthesis of the mycotoxin ochratoxin A (OTA) is presented, in which it is prepared in 9% overall yield from commercially available substrates. The key step consists of the condensation reaction between protected L-phenylalanine and 5-chloro-8-hydroxy-3-methyl-1-oxoisochromane-7-carboxylic acid (ochratoxin α, OTα). The same strategy could be successfully applied to L-d5-phenylalanine, leading to the first total synthesis of d5-OTA, a molecular tracer for the detection and analytical quantification of the natural mycotoxin in food samples by means of stable isotope dilution assay (SIDA). Georg Thieme Verlag Stuttgart.

COMPOUNDS AND COMPOSITIONS USEFUL IN THE TREATMENT OF NEOPLASIA

There is described compounds for use in therapy, said compounds being defined by Formula (1): There is also described an anti-proliferative composition comprising one or more compounds according to Formula (1), and a method of treatment of neoplasia comprising the administration of such a compound or composition.

SYNTHESES OF (+)- AND (-)-MELLEIN UTILIZING AN ANNELATION REACTION OF ISOXAZOLES WITH DIMETHYL 3-OXOGLUTARATE

Naturally occurring dihydroisocoumarins, (+)- and (-)-mellein (2 and 3), metabolites of fungals, Cercospora sp. and Aspergillus sp., etc., were synthesized from the isoxazoles (32) and (33) by the annelation reactions with dimethyl 3-oxoglutarate.