15074-18-7

Usage

Uses

Used in Perfume and Cosmetics Industry:
4-Hydroxy-3-benzylcoumarin is used as a fragrance ingredient for its pleasant odor, enhancing the sensory experience of perfumes and cosmetics.
Used in Chemical Research:
4-Hydroxy-3-benzylcoumarin serves as a fluorescent pH indicator, aiding in the visualization and measurement of pH levels in various chemical studies.
Used in Food Industry:
As a flavoring agent, 4-Hydroxy-3-benzylcoumarin contributes to the taste and aroma profiles of food products, enhancing consumer appeal.
Used in Pharmaceutical Applications:
4-Hydroxy-3-benzylcoumarin is studied for its potential therapeutic properties, including anti-inflammatory, antioxidant, and anti-tumor effects, indicating its use as a pharmaceutical agent for various health-related treatments.

InChI:InChI=1/C16H12O3/c17-15-12-8-4-5-9-14(12)19-16(18)13(15)10-11-6-2-1-3-7-11/h1-9,18H,10H2

Upstream product

• 1821-19-8 3,3'-phenylmethylene-bis-4-hydroxycoumarin 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 100-51-6 benzyl alcohol 
• 5186-54-9 3-diazobenzopyran-2,4(3H)-dione 
• 108-88-3 toluene 
• 4438-85-1 3H-chromene-2,4-dione 
• 66-76-2 dicoumarol 
• 1330776-87-8 4-hydroxy-3-(phenyl(pyrrolidin-1-yl)methyl)-2H-chromen-2-one 
• 86795-49-5 3-(phenyl-λ³-iodanylidene)chromane-2,4-dione 
• 53317-09-2 9-benzyl-9-borabicyclo[3.3.1]nonane 

Downstream Products

• 110229-42-0 3-Benzyl-4-chlor-cumarin 
• 110229-45-3 4-Azido-3-benzyl-cumarin 
• 64555-96-0 3-benzyl-4-(2-morpholin-4-yl-ethoxy)-chromen-2-one 
• 473876-51-6 (4-Hydroxy-2-oxo-2H-chromen-3-yl)-phenyl-acetic acid 

Relevant academic research and scientific papers

β-Chain Hydrogen-Bonding in 4-Hydroxycoumarins

Abstract: In the solid state, some 3-substituted 4-hydroxycoumarins β-ketoester enols form infinite translational hydrogen-bonded β-chains with varying degrees of alignment between adjacent delocalized systems. Nine related structures have been studied. A

Microwave assisted benzylation of naphthols and 4-hydroxycoumarin under catalyst & solvent free conditions

An expeditious and highly practical, microwave assisted benzylation of naphthols and 4-hydroxycoumarin has been developed under catalyst-free & solvent-free conditions. Alcohols undergo heat induced dehydration to form ethers, which collapse reversibly to form the carbocation which was captured immediately by a suitable nucleophile to furnish the benzylated compounds.

3-Methylene-2,4-chromandione in situ trapping: Introducing molecular diversity on 4-hydroxycoumarin

3-Methylene-2,4-chromandione trapped in a solid-state stable Mannich adduct, is released in solution. In the presence of different nucleophiles, this highly reactive intermediate allows the introduction of molecular diversity on C-3 position of 4-hydroxycoumarin.

Pd/C-catalyzed alkylation of heterocyclic nucleophiles with alcohols through the "borrowing hydrogen" process

The alkylation of heterocyclic compounds is important for the synthesis of various biologically active compounds. In this paper, we present the development of a Pd/C-catalyzed alkylation of heterocyclic compounds using alcohols as the alkylating agents. T

Efficient C-3 reductive alkylation of 4-hydroxycoumarin by dehydrogenative oxidation of benzylic alcohols through ruthenium catalysis

A practical route to prepare 4-hydroxycoumarin derivatives functionalized at the C-3 position is described through a catalytic coupling reaction between 4-hydroxycoumarin and a series of substituted benzylic alcohols. The reaction is conducted in the pres

Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1,5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions

A practical and sustainable chemical process for the synthesis of highly substituted tetrahydro-isobenzofuran-1,5-diones was achieved for the first time through asymmetric cascade Michael-aldol reaction of 4-hydroxy-3-alkyl-5H-furan- 2-ones with alkyl vinyl ketones in the presence of a catalytic amount of l-proline or 9-amino-9-deoxyepiquinine/TCA. In this article, we discovered for the first time the asymmetric synthesis of privileged bicyclic lactones through kinetic resolution and show the synthetic application to pharmaceuticals and natural products synthesis.

Iridium catalysed alkylation of 4-hydroxy coumarin, 4-hydroxy-2-quinolones and quinolin-4(1H)-one with alcohols under solvent free thermal conditions

Ir catalysed alkylation of 4-hydroxy coumarin, 4-hydroxy-2-quinolones and quinolin-4(1H)-one with a range of substituted benzyl and aliphatic alcohols under solvent free thermal conditions afforded the corresponding monoalkylated products in high to excel

Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: Quinone oxidoreductase-1 (NQO1)

The synthesis is reported here of two novel series of inhibitors of human NAD(P)H quinone oxidoreductase-1 (NQO1), an enzyme overexpressed in several types of tumor cell. The first series comprises substituted symmetric dicoumarol analogues; the second series contains hybrid compounds where one 4-hydroxycoumarin systemis replaced by a different aromatic moiety. Several compounds show equivalent or improved NQO1 inhibition over dicoumarol, both in the presence and in the absence of added protein. Further, correlation is demonstrated between the ability of these agents to inhibit NQO1 and computed binding affinity. We have solved the crystal structure of NQO1 complexed to a hybrid compound and find good agreement with the in silico model. For both MIA PaCa-2 pancreatic tumor cells and HCT116 colon cancer cells, dicoumarol shows the greatest toxicity of all compounds. Thus, we provide a computational, synthetic, and biological platform to generate competitive NQO1 inhibitors with superior pharmacological properties to dicoumarol. This will allow a more definitive study of NQO1 activity in cells, in particular, its drug activating/detoxifying properties and ability to modulate oncoprotein stability. 2009 American Chemical Society.

The rhodium carbenoid route to 3-aryl-4-hydroxycoumarins: Synthesis of derrusnin

3-Aryl-4-hydroxycoumarins have been obtained in satisfactory yields and selectivity through a Rh(II)-mediated arylation of diazocoumarin. The utility of this approach is demonstrated by synthesis of the natural product derrusnin.

Materials and methods for treating coagulation disorders

This invention is drawn to compounds which are more easily metabolized by the metabolic drug detoxification systems. Particularly, warfarin analogs which have been designed to include esters within the structure of the compounds are taught. The invention