23782-85-6

Basic information

• Product Name: 4-HYDROXY-3-PHENYL-2(5H)-FURANONE
• Synonyms: 4-HYDROXY-3-PHENYL-2(5H)-FURANONE;4-HYDROXY-3-PHENYL-5H-FURAN-2-ONE
• CAS NO: 23782-85-6
• Molecular Formula: C₁₀H₈O₃
• Molecular Weight: 176.17
• Mol File: 23782-85-6.mol

Chemical Properties

• Melting Point: 263-265 °C(lit.)
• Boiling Point: 395.3 °C at 760 mmHg
• Flash Point: 183.9 °C
• Appearance: /
• Density: 1.39 g/cm³
• Vapor Pressure: 5.85E-07mmHg at 25°C
• Refractive Index: 1.642
• PKA: 3.42±0.10(Predicted)
• CAS DataBase Reference: 4-HYDROXY-3-PHENYL-2(5H)-FURANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-3-PHENYL-2(5H)-FURANONE(23782-85-6)
• EPA Substance Registry System: 4-HYDROXY-3-PHENYL-2(5H)-FURANONE(23782-85-6)

Safety Data

• Hazardous Substances Data: 23782-85-6(Hazardous Substances Data)

Usage

Uses

Used in Food and Beverage Industry:
4-HYDROXY-3-PHENYL-2(5H)-FURANONE is used as a flavoring agent for its sweet and fruity scent, enhancing the taste and aroma of various food and beverage products.
Used in Perfume and Cosmetic Industry:
In the perfume and cosmetic industry, 4-HYDROXY-3-PHENYL-2(5H)-FURANONE is used as a fragrance ingredient to impart a pleasant and natural scent to products, capitalizing on its sweet caramel-like aroma.
Used in Health and Wellness Applications:
4-HYDROXY-3-PHENYL-2(5H)-FURANONE is studied for its potential health benefits, such as its antioxidant properties that may help protect cells from damage, and its anti-inflammatory effects that could contribute to reducing inflammation in the body.

InChI:InChI=1/C10H8O3/c11-8-6-13-10(12)9(8)7-4-2-1-3-5-7/h1-5,11H,6H2

Upstream product

• 4423-79-4 cyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 16537-09-0 t-butyl phenylacetate 
• 101-41-7 benzeneacetic acid methyl ester 
• 103-82-2 phenylacetic acid 
• 96-35-5 glycolic acid methyl ester 
• 105-36-2 ethyl bromoacetate 
• 114-70-5 sodium phenylacetate 
• 98026-98-3 3-Diazotetrahydrofuran-2,4-dione 
• 71-43-2 benzene 
• 188940-78-5 Methoxycarbonylmethyl phenylacetate 
• 100074-79-1 2,5-dihydro-2-oxo-3-phenyl-5-triphenylphosphoniumfuran-4-olate 
• 91497-39-1 2-ethoxy-2-oxoethyl 2-phenylacetate 

Downstream Products

• 54798-88-8 4-methoxyl-3-phenylfuran-2(5H)-one 
• 178619-02-8 4-bromo-3-phenyl-2(5H)-furanone 
• 1247734-10-6 5-[(6-(benzyloxy)-2-hydroxy-3-methoxyphenyl)(hydroxy)methyl]-4-hydroxy-3-phenylfuran-2(5H)-one 
• 1247734-46-8 5-[(2-(benzyloxy)-6-hydroxy-3-methoxyphenyl)(hydroxy)methyl]-4-hydroxy-3-phenylfuran-2(5H)-one 
• 1514776-24-9 7-(4-(2-(3-phenylfuran-2(5H)-one-4-yloxy)ethyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1514776-33-0 7-(4-(2-(3-phenylfuran-2(5H)-one-4-yloxy)ethyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid 
• 1514776-29-4 7-(4-(2-(3-phenylfuran-2(5H)-one-4-yloxy)ethyl)piperazin-1-yl)-1-(4-fluorophenyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1514776-26-1 7-(4-(2-(3-phenylfuran-2(5H)-one-4-yloxy)ethyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 265643-67-2 5-hydroxymethyl-4-phenyl-1H-pyrazol-3-ol 
• 273940-57-1 2-bromo-5-methoxy-benzoic acid 5-oxo-4-phenyl-2,5-dihydro-furan-3-yl ester 
• 162011-90-7 rofecoxib 
• 5635-16-5 3,4-diphenyl-2(5H)-furanone 
• 1450824-55-1 4-(2-(3,4-dimethoxyphenylacetyloxyl)ethoxy)-3-phenylfuran-2(5H)-one 
• 1450824-52-8 4-(2-(4-fluorophenylacetyloxyl)ethoxy)-3-phenylfuran-2(5H)-one 

Relevant articles and documents

Compound, as well as preparation method and application thereof

The application discloses a compound of which the structure is represented as the following formula, wherein R1 is selected from any one of F, Cl, Br, C1-C5 alkyl group, and a group having the structure as the formula (1), n = 0, 1, 2, 3, 4 or 5; the R2 is selected from any one of a group having the structure as the formula (1), a group having the structure as the formula (2), and a group having the structure as the formula (3). The compound has simple preparation method, can be used as a neuraminidase inhibitor, and has excellent antivirus activity.

Synthesis and bio-evaluation of natural butenolides-acrylate conjugates

A series of novel 3-aryl-4-hydroxy-2(5H) furanone-acrylate hybrids were designed and synthesized based on the natural butenolides and acrylates scaffolds. The structures of the prepared compounds were characterized by 1H-NMR, 13C-NMR and electrospray ionization mass spectrometry (ESI-MS), and the bioactivity of the target compounds against twelve phytopathogenic fungi was investigated. The preliminary in vitro antifungal activity screening showed that most of the target compounds had moderate inhibition on various pathogenic fungi at the concentration of 100 mg·L?1, and presented broad-spectrum antifungal activities. Further studies also indicated that compounds 7e and 7k still showed some inhibitory activity against Pestallozzia theae, Sclerotinia sclerotiorum and Gibberella zeae on rape plants at lower concentrations, which could be optimized as a secondary lead for further research.

Catalytic Undirected Intermolecular C-H Functionalization of Arenes with 3-Diazofuran-2,4-dione: Synthesis of 3-Aryl Tetronic Acids, Vulpinic Acid, Pinastric Acid, and Methyl Isoxerocomate

A variety of 3-aryl tetronic acids have been synthesized by an undirected, intermolecular C-H functionalization of arenes with 3-diazofuran-2,4-dione. This methodology featured as a key step in the synthesis of a series of naturally occurring 3-aryl-5-arylidene tetronic acids (pulvinates) from commercially available tetronic acid. Salient features of the pulvinic acid synthesis include a one-step, stereoselective synthesis of the C5 arylidene group and a single step introduction of the C3 aryl substituent.

Synthesis, molecular docking and biological evaluation of 3-arylfuran-2(5H)-ones as anti-gastric ulcer agent

3-Arylfuran-2(5H)-one derivatives show good antibacterial activity and were determined as tyrosyl-tRNA synthetase (TyrRS) inhibitors. In a systematic medicinal chemistry exploration, we demonstrated chemical opportunities to treat infections caused by Hel

Novel 3-arylfuran-2(5H)-one-fluoroquinolone hybrid: Design, synthesis and evaluation as antibacterial agent

3-Arylfuran-2(5H)-one, a novel antibacterial pharmacophore targeting tyrosyl-tRNA synthetase (TyrRS), was hybridized with the clinically used fluoroquinolones to give a series of novel multi-target antimicrobial agents. Thus, twenty seven 3-arylfuran-2(5H)-one-fluoroquinolone hybrids were synthesized and evaluated for their antimicrobial activities. Some of the hybrids exhibited merits from both parents, displaying a broad spectrum of activity against resistant strains including both Gram-negative and Gram-positive bacteria. The most potent compound (11) in antibacterial assay shows MIC50 of 0.11 μg/mL against Multiple drug resistant Escherichia coli, being about 51-fold more potent than ciprofloxacin. The enzyme assays reveal that 11 is a potent multi-target inhibitor with IC50 of 1.15 ± 0.07 μM against DNA gyrase and 0.12 ± 0.04 μM against TyrRS, respectively. Its excellent inhibitory activities against isolated enzymes and intact cells strongly suggest that 11 deserves to further research as a novel antibiotic.

A facile synthesis, antibacterial activity of pulvinone and its derivatives

Pulvinone and several 3-fluoro-4-morpholino substituted pulvinone derivatives were synthesized in five steps from a common precursor, phenyl acetic acid. Most of synthetic morpholine substituted pulvinones showed inhibitory activity against Esherichia col

3-Aryl-4-acyloxyethoxyfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation

Thirty-eight 3-aryl-4-acyloxyethoxyfuran-2(5H)-ones were designed, prepared and tested for antibacterial activities. Some of them showed significant antibacterial activity against Gram-positive organism, Gram-negative organism and fungus. Out of these compounds, 4-(2-(3-chlorophenylformyloxy)ethoxy)-3-(4- chlorophenyl)furan-2(5H)-one (d40) showed the widest spectrum of activity with MIC50 of 2.0 μg/mL against Staphylococcus aureus, 4.3 μg/mL against Escherichia coli, 1.5 μg/mL against Pseudomonas aeruginosa and 1.2 μg/mL against Candida albicans. Our data disclosed that MIC50 values against whole cell bacteria are positive correlation with MIC 50 values against tyrosyl-tRNA synthetase. Meanwhile, molecular docking of d40 into S. aureus tyrosyl-tRNA synthetase active site was also performed, and the inhibitor tightly fitting the active site might be an important reason why it has high antimicrobial activity.

Synthesis, structure, molecular docking, and structure-activity relationship analysis of enamines: 3-Aryl-4-alkylaminofuran-2(5H)-ones as potential antibacterials

Thirty-one 3-aryl-4-alkylaminofuran-2(5H)-ones were designed, prepared and tested for their antibacterial activity. Some of them showed significant antibacterial activity against Gram-positive organisms, especially against Staphylococcus aureus ATCC 25923, but all were inactive against Gram-negative organisms. Out of these compounds, 3-(4-bromophenyl)-4-(2-(4-nitrophenyl) hydrazinyl)furan-2(5H)-one (4a11) showed the most potent antibacterial activity against S. aureus ATCC 25923 with MIC50 of 0.42 μg/mL. The enzyme assay revealed that the possible antibacterial mechanism of the synthetic compounds might be due to their inhibitory activity against tyrosyl-tRNA synthetase. Molecular dockings of 4a11 into S. aureus tyrosyl-tRNA synthetase active site were also performed. This inhibitor snugly fitting the active site might well explain its excellent inhibitory activity. Meanwhile, this modeling disclosed that a more suitable optimization strategy might be to modify the benzene ring at 3-position of furanone with hydrophilic groups.

4-Alkoxy-3-arylfuran-2(5H)-ones as inhibitors of tyrosyl-tRNA synthetase: Synthesis, molecular docking and antibacterial evaluation

A series of novel 4-alkoxy-3-arylfuran-2(5H)-ones as tyrosyl-tRNA synthetase inhibitors were synthesized. Of these compounds, 3-(4-hydroxyphenyl)- 4-(2-morpholinoethoxy)furan-2(5H)-one (27) was the most potent. The binding model and structure-activity rel

Tyrosyl-tRNA synthetase inhibitors as antibacterial agents: Synthesis, molecular docking and structure-activity relationship analysis of 3-aryl-4-arylaminofuran-2(5H)-ones

Thirty-five 3-aryl-4-arylaminofuran-2(5H)-one derivatives were designed, prepared and tested for their inhibitory activity against tyrosyl-tRNA synthetase. Out of these compounds, 3-(3-bromophenyl)-4-(3,5- dichlorophenylamino)furan-2(5H)-one (35) was the most active with IC 50 of 0.09 ± 0.02 μM. The structure-activity relationship revealed that introduction of chlorine atoms at both meta positions of aniline moiety significantly increased the enzyme inhibitory activity. The results of antibacterial assay revealed that the tested compounds showed good activity against Gram-positive bacteria, with 35 being the most potent with MIC 50 of 0.06 μg/mL against Staphylococcus aureus ATCC 25923. Molecular docking of 35 into S. aureus tyrosyl-tRNA synthetase active site was also performed. The inhibitor snugly fitting the active site may well explain its excellent inhibitory activity.