6093-67-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Hydroxycoumarin is used as a precursor in the synthesis of various pharmaceuticals due to its unique chemical structure and bioactivity. It serves as a starting material for the production of drugs with therapeutic applications, leveraging its inherent properties to enhance the efficacy of the final products.
Used in Perfumery:
In the fragrance industry, 5-Hydroxycoumarin is utilized as a component in the production of perfumes. Its sweet odor makes it a desirable ingredient for creating pleasant and long-lasting scents, contributing to the overall appeal of perfumes and other fragranced products.
Used in Textile Industry:
5-Hydroxycoumarin is employed as a fluorescent whitening agent in the textile industry. Its ability to emit fluorescence under ultraviolet light enhances the whiteness and brightness of fabrics, making it an essential component in the production of textiles with a vibrant and clean appearance.
Used in Cosmetics:
In the cosmetics industry, 5-Hydroxycoumarin is used for its antioxidant, anti-inflammatory, and antimicrobial properties. These attributes make it a valuable ingredient in skincare and beauty products, where it can help protect the skin from oxidative stress, reduce inflammation, and prevent microbial infections.
Used in Research and Analytical Chemistry:
5-Hydroxycoumarin is also used as a reagent and a fluorescent marker in various research and analytical chemistry applications. Its fluorescent properties allow for the detection and quantification of specific compounds or biological molecules, making it a useful tool in scientific research and laboratory settings.

InChI:InChI=1/C9H6O3/c10-7-2-1-3-8-6(7)4-5-9(11)12-8/h1-5,10H

Upstream product

• 51559-36-5 5-methoxycoumarin 
• 91136-61-7 2-oxo-2H-chromen-5-yl acetate 
• 90947-66-3 5-hydroxycoumarin-3-carboxylic acid 
• 86761-34-4 3-(2,6-dimethoxyphenyl)acrylic acid methyl ester 
• 471-25-0 Propiolic acid 
• 108-46-3 recorcinol 
• 873974-01-7 5-methoxy-2-oxo-2H-chromene-3,8-dicarboxylic acid-3-ethyl ester-8-methyl ester 
• 91-64-5 coumarin 
• 154424-13-2 (E)-3-(2,6-dimethoxy-phenyl)-acrylic acid methyl ester 
• 700-44-7 6-methoxysalicylaldehyde 
• 387-46-2 2,6-dihydroxybenzaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 39503-30-5 3-formyl-2-hydroxy-4-methoxy-benzoic acid methyl ester 
• 84632-12-2 5-methoxy-2-oxo-2H-chromene-3,8-dicarboxylic acid 

Downstream Products

• 141234-13-1 5-<(E)-3-(4,5-dihydro-5,5-dimethyl-4-oxo-2-furanyl)-2-butenyloxy>-coumarin 
• 17235-14-2 (Z)-4-(o-hydroxyphenyl)-2-methylbut-3-en-2-ol 
• 184351-95-9 5-Hydroxy-6-iodo-chromen-2-one 
• 1012326-86-1 2,6-dihydroxy-trans-cinnamic acid 
• 126051-06-7 coumarin-5-oxybutyric acid N-hydroxysuccinimide ester 
• 126051-18-1 coumarin-5-oxybutyric acid 
• 150598-44-0 5-[(2-oxo-2H-1-benzopyran-5-yl)oxy]pentanoic acid ethyl ester 
• 150598-37-1 trifluoromethanesulfonic acid 2-oxo-2H-1-benzopyran-5-yl ester 
• 1158849-78-5 5-(4-phenoxybutoxy)-2H-[1]benzopyran-2-one 
• 1370319-68-8 C₁₄H₁₃NO₂ 
• 92190-32-4 5-isopentenyloxycoumarin 
• 1415658-72-8 5-geranyloxycoumarin 
• 1415658-73-9 5-farnesyloxycoumarin 
• 150598-40-6 rac-(E)-5-[2-(3-methoxy-3-oxo-1-propenyl)-3-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenoxy]pentanoic acid ethyl ester 

Relevant academic research and scientific papers

Metal-free, Br?nsted acid-mediated synthesis of coumarin derivatives from phenols and propiolic acids

A novel synthesis of coumarin derivatives by Br?nsted acid-mediated condensation and intramolecular cyclization of phenols and propiolic acids was reported. This transformation requires the use of TfOH in place of a conventional metal mediator, and it occurs under mild conditions and provides rapid access to coumarin derivatives in good yields.

Process for preparing coumarin derivatives using phenol and propiolic acid

Provided is a manufacturing method of coumarin derivative. The manufacturing method of coumarin derivative comprises a step of making a phenol compound react with a propiolic acid compound. According to the present invention, the manufacturing method of coumarin derivative is quick and efficient, and is useful to fields requiring synthesis of coumarin derivatives of various structures.COPYRIGHT KIPO 2016

Synthetic models related to methoxalen and menthofuran-cytochrome P450 (CYP) 2A6 interactions. Benzofuran and coumarin derivatives as potent and selective inhibitors of CYP2A6

Human microsomal cytochrome P450 (CYP) 2A6 contributes extensively to nicotine detoxication but also activates tobacco-specific procarcinogens to mutagenic products. We prepared a series of benzofuran and coumarin derivatives that have inhibitory effects on the activity of human CYP2A6. The reported compounds methoxalen and menthofuran had potent inhibitory effects on the activity of CYP2A6 with IC50 values of 0.47 μM and 1.27 μM, respectively. Synthetic benzofuran (4-methoxybenzofuran: IC50=2.20 μM) and coumarin (5-methoxycoumarin: IC50=0.13 μM and 6-methoxycoumarin: IC50=0.64 μM) derivatives, which have more selective effects than those of methoxalen and menthofuran, exhibited comparable activities against CYP2A6. These compounds can be used as a lead compounds in the design of CYP2A6 inhibitor drugs to reduce smoking and tobacco-related cancers.

Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors

All of the mono isopentenyloxy, -geranyloxy and -farnesyloxy derivatives of coumarin were synthesized and their inhibitory potency against soybean 15-lipoxygenase (SLO) and human 15-lipoxygenase-1 (HLO-1) were determined. Amongst the synthetic analogs, 5-farnesyloxycoumarin showed the most potent inhibitory activity against SLO (IC50 = 0.8 μM) while 6-farnesyloxycoumarin was the strongest HLO-1 inhibitor (IC50 = 1.3 μM). The IC50 variations of the farnesyl derivatives for HLO-1 (1.3 to ～75 μM) were much higher than that observed for SLO (0.8-5.8 μM). SAR studies showed that hydrogen bonding, CH/π, anion-π and S-OC interactions with FeIII-OH, Leu408, Glu357 and Met419 were the distinct intermolecular interactions which can lead to important role of the coumarin substitution site in HLO-1 inhibitory potency, respectively.

Intramolecular conjugate addition of α,β-unsaturated lactones having an alkanenitrile side chain: Stereocontrolled construction of carbocycles with quaternary carbon atoms

An efficient method for constructing carbocycles with all-carbon quaternary stereocenters has been developed on the basis of a stereoselective cyclization reaction of ,-unsaturated lactones having an alkanenitrile side chain. Treatment of the substrate with lithium hexamethyldisilazide (LiHMDS) in the presence of triisopropylsilyl chloride (TIPSCl) led to the generation of the corresponding -cyano carbanion species which readily underwent an intramolecular conjugate addition reaction. It was found that thecombined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine is also effective for the cyclization reaction without using a strong base. Interestingly, different ste-reochemical outcomes were observed in the two cyclization methods. Georg Thieme Verlag Stuttgart - New York.

Design, synthesis, and biological evaluation of coumarin derivatives tethered to an edrophonium-like fragment as highly potent and selective dual binding site acetylcholinesterase inhibitors

A large series of substituted coumarins linked through an appropriate spacer to 3-hydroxy-N,N-dimethylanilino or 3-hydroxy-N,N,N-trialkylbenzaminium moieties were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors. The highest AChE inhibitory potency in the 3-hydroxy-N,N-dimethylanilino series was observed with a 6,7-dimethoxy-3-substituted coumarin derivative, which, along with an outstanding affinity (IC50=0.236 nm) exhibits excellent AChE/BChE selectivity (SI>300 000). Most of the synthesized 3-hydroxy-N,N,N- trialkylbenzaminium salts display an AChE affinity in the sub-nanomolar to picomolar range along with excellent AChE/BChE selectivities (SI values up to 138 333). The combined use of docking and molecular dynamics simulations permitted us to shed light on the observed structure-affinity and structure-selectivity relationships, to detect two possible alternative binding modes, and to assess the critical role of π-π stacking interactions in the AChE peripheral binding site.

4-Phenoxybutoxy-substituted heterocycles - A structure-activity relationship study of blockers of the lymphocyte potassium channel Kv1.3

The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC50 of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC50s of 150 nM to 10 μM in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC50 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers.

Synthesis and biological evaluation of alkoxycoumarins as novel nematicidal constituents

We synthesized all of the monomethoxycoumarins, 5-alkoxycoumarins and their derivatives, and investigated their nematicidal activity against the phytopathogenic nematode, Bursaphelenchus xylophilus. Among the compounds, 5-ethoxycoumarin showed the highest nematicidal activity. Furthermore, 5-ethoxycoumarin was comparatively harmless against both the brine shrimps, Artemia salina, and the Japanese killifish, Oryzias latipes.

Synthesis of photochromic dyes based on annulated coumarin systems

Novel 2H-chromenes derived from hydroxycoumarins were synthesized, and their photochromic behaviour was studied under flash-photolysis conditions, showing a wide absorption range in the visible region. All the compounds exhibit low fluorescence, which apparently has no negative effect on their photochromic properties.

Use of microwave irradiation and solid acid catalysts in an enhanced and environmentally friendly synthesis of coumarin derivatives

Condensation of phenol, 1,3-dihydroxybenzene and 1,3,5- trihydroxybenzene with propynoic and propenoic acids and ethyl acetoacetate using solid acid catalysts and microwave irradiation produces coumarins in excellent yields. The use of heterogeneous catalysts eliminates the production of acidic waste streams associated with conventional (Lewis) acid catalysts. This quick, efficient and environmentally friendly procedure permits the synthesis of substituted coumarins as well as coumarins without 4-alkyl substituents, which are the most difficult to synthesize.