38210-27-4

Basic information

• Product Name: Frutinone A
• Synonyms: Frutinone A;6H,7H-[1]Benzopyrano[4,3-b][1]benzopyran-6,7-dione;Chromonocoumarin
• CAS NO: 38210-27-4
• Molecular Formula: C6H14O4
• Molecular Weight: 264.2323
• Product Categories: Aromatics;Heterocycles;Aromatics, Heterocycles
• Mol File: 38210-27-4.mol

Chemical Properties

• Melting Point: 235-236 °C
• Boiling Point: 461.2°Cat760mmHg
• Flash Point: 208.8°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 1.1E-08mmHg at 25°C
• Refractive Index: 1.708
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: Frutinone A(CAS DataBase Reference)
• NIST Chemistry Reference: Frutinone A(38210-27-4)
• EPA Substance Registry System: Frutinone A(38210-27-4)

Safety Data

• Hazardous Substances Data: 38210-27-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Frutinone A is used as a key component in the new synthesis of coumarino(3,4:3',2')chromones, which are important for the development of pharmaceuticals. Its antioxidant properties contribute to the stability and effectiveness of these synthesized compounds.
Used in Chemical Synthesis:
Frutinone A is utilized as an antioxidant in the synthesis of coumarino(3,4:3'',2'')chromones, a class of compounds with potential applications in various industries. Its antioxidant characteristics play a crucial role in ensuring the successful synthesis of these compounds, enhancing their overall quality and performance.

Synthesis Reference(s)

Synthesis, p. 511, 1974 DOI: 10.1055/s-1974-23363

InChI:InChI=1/C16H8O4/c17-14-9-5-1-3-7-11(9)19-15-10-6-2-4-8-12(10)20-16(18)13(14)15/h1-8H

Upstream product

• 533-58-4 2-Iodophenol 
• 5533-04-0 2-(methoxymethoxy)benzaldehyde 
• 1607814-74-3 2-{3-[2-(methoxymethoxy)phenyl]prop-2-ynoyl}phenyl methyl carbonate 
• 1607814-77-6 methyl 2-[2-(methoxymethoxy)phenyl]-4-oxo-4H-chromene-3-carboxylate 
• 1607814-72-1 2-iodophenyl methyl carbonate 
• 634153-24-5 1-ethynyl-2-(methoxymethoxy)benzene 
• 90-02-8 salicylaldehyde 
• 491-38-3 1-benzopyran-4(4H)-one 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 609-65-4 o-chlorobenzoyl chloride 
• 60121-60-0 1-(2-hydroxyphenyl)-3-(2-chlorophenyl)propane-1,3-dione 
• 181938-56-7 3-(2-chlorobenzoyl)-4-hydroxycoumarin 
• 118-91-2 ortho-chlorobenzoic acid 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 

Relevant articles and documents

Synthesis method of Frutinone compound

The invention discloses a synthesis method of a Frutinone compound, which comprises the following steps: (1) under the action of Cs2CO3 and a base, substituted ethyl benzoylacetate and substituted 2-chlorobenzoyl chloride react to obtain intermediate 1; (

Construction of trisubstituted chromone skeletons carrying electron-withdrawing groups via PhIO-mediated dehydrogenation and its application to the synthesis of frutinone A

The construction of the biologically interesting chromone skeleton was realized by PhIO-mediated dehydrogenation of chromanones under mild conditions. Interestingly, this method also found application in the synthesis of the naturally occurring frutinone A.

Flavonoid compound Frutinones A, B and C synthetic method

The invention relates to a synthesis method of flavonoid natural compounds Frutinones A, B and C. The synthesis method comprises the following steps: synthesizing an intermediate 3-benzoyl-4-hydroxycoumarin derivative from the raw materials including cheap 4-hydroxycoumarin and analogues thereof; and performing a key step of nucleophilic substitution on a benzene ring to obtain target products Frutinones A, B and C. The synthesis method can overcome the shortcomings of the prior art and is an atom economic synthesis route. The synthesis method provided by the invention has the characteristics of simple and convenient synthesis route, simplicity in operation, cheap raw materials and safety and practicability and particularly high yield, good stability and relatively wide applicability.

A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives

A new protocol for total synthesis of natural product frutinone A was accomplished in three steps by using inexpensive 2′-hydroxyacetophenone as starting material. The key intermediate 3-(2-chlorobenzoyl)-4-hydroxycoumarin was synthesized in one pot through Baker-Venkataraman rearrangement of 2-acetylphenyl 2-chlorobenzoate followed by introduction of methyl chloroformate under basic conditions. Then, base-promoted intramolecular nucleophilic substitution reaction of 3-(2-chlorobenzoyl)-4-hydroxycoumarin provided frutinone A in excellent yield. The synthetic route features good yield, transition metal-free and mild reaction conditions, and high tolerance for functionality, thereby allowing easy substitutions around the frutinone A core.

Efficient synthesis of frutinone A and its derivatives through palladium-catalyzed C-H activation/carbonylation

Frutinone A, a biologically active ingredient of an antimicrobial herbal extract, demonstrates potent inhibitory activity towards the CYP1A2 enzyme. A three-step total synthesis of frutinone A with an overall yield of 44 is presented. The construction of

A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization

A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu3) efficiently induced the tandem acyl transfer-cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c).