4361-00-6

Basic information

• Product Name: 3-OXO-3H-BENZO[F]CHROMENE-2-CARBOXYLIC ACID
• Synonyms: IFLAB-BB F1018-1512;AKOS BBS-00004750;3-OXO-3H-BENZO[F]CHROMENE-2-CARBOXYLIC ACID;RARECHEM AB KA K018;5,6-Benzocoumarine-3-carboxylic acid;2-Oxo-5,6-[1,3]butadieno-2H-1-benzopyran-3-carboxylic acid;3-Oxo-3H-naphtho[2,1-b]pyran-2-carboxylic acid;5,6-Benzocoumarin-3-carboxylic acid
• CAS NO: 4361-00-6
• Molecular Formula: C₁₄H₈O₄
• Molecular Weight: 240.21
• Mol File: 4361-00-6.mol
• Article Data: 37

Chemical Properties

• Melting Point: 236-239°C
• Boiling Point: 486.2 °C at 760 mmHg
• Flash Point: 194 °C
• Appearance: /
• Density: 1.487 g/cm³
• Vapor Pressure: 2.88E-10mmHg at 25°C
• Refractive Index: 1.719
• PKA: 1.68±0.20(Predicted)
• CAS DataBase Reference: 3-OXO-3H-BENZO[F]CHROMENE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-OXO-3H-BENZO[F]CHROMENE-2-CARBOXYLIC ACID(4361-00-6)
• EPA Substance Registry System: 3-OXO-3H-BENZO[F]CHROMENE-2-CARBOXYLIC ACID(4361-00-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 4361-00-6(Hazardous Substances Data)

Usage

General Description

3-OXO-3H-BENZO[F]CHROMENE-2-CARBOXYLIC ACID is a chemical compound with a molecular formula of C17H10O4. It belongs to the class of benzo[f]chromene carboxylic acids and is characterized by a 3-oxo-3H-benzo[f]chromene moiety and a carboxylic acid functional group. 3-OXO-3H-BENZO[F]CHROMENE-2-CARBOXYLIC ACID has potential biological and pharmaceutical applications as it exhibits various pharmacological activities, including antioxidant, anti-inflammatory, and antimicrobial properties. It is also known to have potential therapeutic effects against certain diseases, making it a subject of interest for researchers in various fields. Additionally, this compound can be used as a building block in the synthesis of other organic compounds and is of interest for further studies in medicinal chemistry and drug development.

InChI:InChI=1/C14H8O4/c15-13(16)11-7-10-9-4-2-1-3-8(9)5-6-12(10)18-14(11)17/h1-7H,(H,15,16)

Upstream product

• 19523-57-0 2-ethoxy-1-naphthaldehyde 
• 141-82-2 malonic acid 
• 4431-57-6 3-oxo-3H-benzo[f]chromene-2-carboxylic acid amide 
• 731-90-8 N-(2-hydroxy-1-naphthalidene)aniline 
• 734-88-3 ethyl 5,6-benzocoumarin-3-carboxylate 
• 860452-66-0 5-(2-hydroxy-[1]naphthylmethylene)-1,3-diphenyl-barbituric acid 
• 303772-50-1 5-(2-hydroxy-[1]naphthylmethylene)-1,3-diphenyl-2-thio-barbituric acid 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 4352-88-9 3-oxo-3H-benzo[f]chromene-2-carbonitrile 
• 2033-24-1 cycl-isopropylidene malonate 
• 55135-70-1 (Z)-1-((phenylamino)methylene)naphthalen-2-one 
• 135-19-3 β-naphthol 
• 71942-38-6 3-oxo-3H-benzo[f]chromene-2-carbonyl chloride 
• 148642-24-4 1-((pyrimidine-2-ylimino)methyl)naphthalene-2-ol 

Downstream Products

• 64468-31-1 N-(4-Methylphenyl)-3-oxo-3H-naphtho<2,1-b>pyran-2-carboxamid 
• 64468-29-7 2-(N-Phenylcarboxamido)-3(H)-oxonaphtho<2,1-b>pyran 
• 35078-19-4 3-(2-Benzimidazolyl)-5,6-benzocumarin 
• 71942-38-6 3-oxo-3H-benzo[f]chromene-2-carbonyl chloride 
• 1029683-81-5 C₈₃H₈₂N₁₆O₁₆ 
• 1029683-85-9 C₉₇H₁₀₂N₂₀O₂₀ 
• 892298-60-1 5,6-benzo-3-(3-phenyl-1,2,4-oxadiazol-5-yl)coumarin 
• 892296-17-2 5,6-benzo-3-[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]coumarin 
• 1422520-70-4 C₄₂H₃₃N₃O₈S₃ 
• 25816-60-8 3-oxo-3H-naphtho[2,1-b]pyran-2-carboxylic acid methyl ester 
• 734-88-3 ethyl 5,6-benzocoumarin-3-carboxylate 
• 64678-90-6 N-(4-Methoxyphenyl)-3-oxo-3H-naphtho<2,1-b>pyran-2-carboxamid 

Relevant articles and documents

Ionic liquid-mediated synthesis of coumarin-3-carboxylic acids via knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes

A simple, efficient, and green protocol for synthesis of coumarin-3-carboxylic acids is described via Knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes in [Hmim]Tfa ionic liquid, which was found to give better results than other ionic liquids. Furthermore, ionic liquid is easily reused without any appreciable loss in activity. Copyright Taylor & Francis Group, LLC.

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A two-photon benzocoumarin-NBD dyad for highly selective and sensitive ratiometric detection of H2S in biological samples

Hydrogen sulfide (H2S), the third endogenous gas signaling transmitter, plays an important role in the basic signal conduction process of human physiology and pathology. It is critical to monitor the dynamic change of H2S in living organisms. In this article, a two-photon ratiometric fluorescent probe (BCD) based on the benzocoumarin-NBD framework was first designed and synthesized. The probe showed large emission separation (about 115 nm), excellent selectivity, and high sensitivity. Moreover, it could be applied to ratiometric image endogenous H2S biosynthesis in the living cells and zebrafish.

Sodium ion chemosensor of 3-oxo-3h-benzo[f]chromene-2- -carboxylic acid: An experimental and computational study

A fluorescence compound with the typical skeleton of benzocoumarin was synthesized and its interaction with various metal ions was evaluated. The synthesis was performed via Knoevenagel condensation whereas identification of the product was accomplished by various spectroscopic techniques. The chemosensor test against representative metal ions was monitored by fluorescence spectrophotometry. A density functional theory calculation (DFT, functional/basis set; M06/6-31G (d, p)) was also performed to clarify the experimental results and to confirm the mechanism of interaction. 3-Oxo-3H-benzo- [f]chromene-2-carboxylic acid 1 was obtained as a yellow solid in 60 % chemical yield. Melting point; 235.6-236.7 ?C and λmax UV/Vis, λem and Stokes shift (MeOH, nm) of 374, 445 and 71 nm, respectively. The structure of the compound was identified based on spectroscopic data and literature comparison. Compound 1 exhibited a chelation quenched fluorescence (CHQF) phenomenon selectively toward the Na+, with a binding stoichiometry (1:2) and LoD and LoQ of 0.14 and 0.48 mg/L, respectively. Based on DFT calculations, compound 1 chelated Na+ through mechanism of oxidative (1:1 equivalent) and reductive (2:1 equivalent) photoinduced electron transfer (PET), correspondingly.

Synthesis and antioxidant activity of conjugates of hydroxytyrosol and coumarin

Antioxidants have been the subject of intense research interest due to their numerous health benefits. In this work, a series of new conjugates of hydroxytyrosol and coumarin were synthesized and evaluated for their free radical scavenging, toxicity and antioxidant mechanism in vitro. The all target compounds 14a–t exhibited better radical scavenging activity than BHT, hydroxytyrosol, and coumarin in both DPPH radical and ABTS+ radical cation scavenging assays. The structure-activity relationships study indicated that the number and position of hydroxyl groups on the coumarin ring were vital to a good antioxidant capacity. Furthermore, the most promising compound 14q showed less toxicity in hemolysis assay and weaker antiproliferative effects than BHT against normal WI-38 and GES cells, and enhanced viability of H2O2-induced HepG2 cells. Additionally, 14q decreased the apoptotic percentage of HepG2 cells, reduced the ROS produce and LDH release, and improved GSH and SOD levels in H2O2-treated HepG2 cells. Lastly, 14q exhibited more stability than hydroxytyrosol in methanol solution. These results revealed that conjugations of hydroxytyrosol and coumarin show better antioxidant capacity, and are the efficacious approach to finding novel potential antioxidant.