2747-05-9

Basic information

• Product Name: 7-Acetoxy-4-methylcoumarin
• Synonyms: MUB ACETATE;MU-AC;MUACETATE;2H-1-Benzopyran-2-one, 7-(acetyloxy)-4-methyl-;4-Methyl-2-oxo-2H-chromen-7-yl acetate;7-ACETOXY-4-METHYLCOUMARIN;7-(ACETYLOXY)-4-METHYL-2-BENZOPYRONE;ACETIC ACID 4-METHYLUMBELLIFERYL ESTER
• CAS NO: 2747-05-9
• Molecular Formula: C₁₂H₁₀O₄
• Molecular Weight: 218.21
• EINECS: 220-386-6
• Product Categories: Coumarin
• Mol File: 2747-05-9.mol

Chemical Properties

• Melting Point: 149-150 °C(lit.)
• Boiling Point: 278.88°C (rough estimate)
• Flash Point: 191.5°C
• Appearance: /
• Density: 1.1096 (rough estimate)
• Vapor Pressure: 8.68E-06mmHg at 25°C
• Refractive Index: 1.4270 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• BRN: 189667
• CAS DataBase Reference: 7-Acetoxy-4-methylcoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Acetoxy-4-methylcoumarin(2747-05-9)
• EPA Substance Registry System: 7-Acetoxy-4-methylcoumarin(2747-05-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8-10-21
• Hazardous Substances Data: 2747-05-9(Hazardous Substances Data)

Usage

Uses

Used in Enzyme Assays:
7-Acetoxy-4-methylcoumarin is used as a fluorogenic substrate for esterases, particularly for carboxyesterases. It is broadly applied to various types of esterases due to its ability to produce a fluorescent signal upon hydrolysis by these enzymes. This property makes it a valuable tool in the study and analysis of esterase activity in different biological systems.
Used in Intracellular pH Measurement:
In the field of cellular biology, 7-Acetoxy-4-methylcoumarin is utilized as a probe for measuring intracellular pH in specific cell types, such as rat proximal convoluted tubules. The compound's fluorescence properties allow for the accurate determination of pH levels within these cells, providing valuable insights into cellular processes and functions.
Used in Pharmaceutical Research:
Due to its unique chemical properties and reactivity, 7-Acetoxy-4-methylcoumarin may also be used in the development of new pharmaceutical compounds. Its ability to interact with esterases and other biological targets can potentially lead to the discovery of novel drugs with various therapeutic applications.
Used in Chemical Synthesis:
As a versatile chemical building block, 7-Acetoxy-4-methylcoumarin can be employed in the synthesis of a wide range of chemical compounds, including those with potential applications in the fields of materials science, pharmaceuticals, and agrochemicals.

InChI:InChI=1/C12H12O4/c1-7-5-12(15-8(2)13)16-11-6-9(14)3-4-10(7)11/h3-6,12,14H,1-2H3

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 108-46-3 recorcinol 
• 141-97-9 ethyl acetoacetate 
• 4163-60-4 β-D-galactose peracetate 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 604-69-3 β-D-glucose pentaacetate 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 102-29-4 Resorcinol monoacetate 
• 64-19-7 acetic acid 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 

Downstream Products

• 2555-29-5 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one 
• 64309-74-6 3-chloro-4-methyl-2-oxo-2H-chromen-7-ylacetate 
• 2747-04-8 7-acetoxy-4-bromomethyl-2H-1-benzopyran-2-one 
• 6748-68-1 8-acetyl-7-hydroxycoumarin 
• 90104-85-1 8-Benzoyl-7-hydroxycoumarin 
• 20312-83-8 8-Benzoyl-7-hydroxy-4-methylcoumarin 
• 89-74-7 2,4-dimethylacetophenone. 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 64-19-7 acetic acid 
• 1335126-09-4 4-methyl-2-oxo-2H-chromen-7-yl N-(p-chlorophenyl)glycinate 
• 1335126-10-7 4-methyl-2-oxo-2H-chromen-7-yl N-(o-methoxyphenyl)glycinate 
• 1335126-11-8 4-methyl-2-oxo-2H-chromen-7-yl N-(p-methoxyphenyl)glycinate 
• 1335126-12-9 4-methyl-2-oxo-2H-chromen-7-yl N-(o-methylphenyl)glycinate 
• 1335126-13-0 4-methyl-2-oxo-2H-chromen-7-yl N-(m-methylphenyl)glycinate 

Relevant articles and documents

A new method for annulation of the α-pyrone ring

New derivatives of coumarin, containing annulated α-pyrone rings, were obtained by reaction of the borate complexes of three isomeric acyl(hydroxy)coumarins with acid anhydrides. It was shown that the borate complex of 3-acetyl-4-hydroxy-2-pyrone also condenses with acetic anhydride to form a derivative containing a new annulated α-pyrone ring.

(E)-4 - methyl -7 - hydroxyl -8 - (3 - (ferrocenyl) acryloyl) coumarin as well as preparation method and application thereof

The invention discloses (E)-4 - methyl -7 - hydroxyl -8 - (3 - (ferrocenyl) acryloyl) coumarin as well as a preparation method and application thereof, and (E)-4 - methyl -7 - hydroxyl -8 - (3 - (ferrocenyl) acryloyl) coumarin has the following structural formula. The present disclosure uses resorcinol as a raw material and condenses with Knoevenagal. 7 (7) Fries-methyl 8 hydroxyl E (-4 - 3 -8 - (ferrocenyl) acryloyl) coumarin is added into ABTBTBTS?, DPPHPHI and galvinvinvinvinylisopropyl -7 -) coumarin to exhibit excellent antioxidation activity, and the antioxidant performance is E superior -4 - to -7 - the -8 - corresponding 3 - ferrocenyl chalcone and coumarin-based chalcone, and has potential application values and is excellent in anti-oxidation activity and excellent in anti-oxidation performance.

Synthesis and biological evaluation of new coumarin derivatives as cytotoxic agents

New coumarin derivatives 9a–f, 10a–e, and 11a–f were synthesized and evaluated for their cytotoxic activity against a human breast cancer cell line (MCF-7). All compounds exhibited good activity in the nanomolar range, using doxorubicin and erlotinib as positive controls. The most active compound 9d with IC50 of 21 nM was tested against the HCT-116, HepG-2, A549, and SGC-7901 cell lines, with IC50 values of 0.021, 0.170, 0.028, and 0.11 μM, respectively. Compound 9d was further investigated for its ability to suppress the expression of epidermal growth factor receptor (EGFR). Compound 9d decreased the concentration of EGFR by 87%, using erlotinib as a positive control. A docking study revealed similar or higher scores than for erlotinib and similar binding poses providing interactions with the hinge region of the tyrosine kinase (TK). Besides the effect on expression, this in silico investigation predicts the possibility of direct binding between the new coumarin derivatives and the EGFR TK. Moreover, computational calculation for ADME properties for the most active compounds 9d, 9e, 10c, and 11c revealed the expected high gastrointestinal tract absorption, moderate water solubility with no central nervous system toxicity, and druglikeness.

A multi-responsive crown ether-based colorimetric/fluorescent chemosensor for highly selective detection of Al3+, Cu2+ and Mg2+

A novel multi-response chemosensor L based on coumarin-chalcone-crown ether was designed and synthesized, which exhibited a high selectivity for the colorimetric detecting Al3+ and Cu2+ and fluorescent recognizing Al3+ and Mg2+ in ethanol. L can monitor Al3+ and Cu2+ via distinct color changes from a slight yellow to pink and to orange, respectively. The sensor L can also monitor Al3+ and Mg2+ by fluorescence emission responses at 592 nm and 547 nm with low detection limits of 0.31 μM and 0.23 μM, respectively. The selectivity of L toward Al3+, Cu2+ and Mg2+ was not interfered by a large number of coexisting ions and was found to be reversible. By means of spectrometric titration, Job's plot, mass spectrometry, 1H NMR titration and IR spectroscopy analysis, it was unanimously confirmed that the sensor L had a stoichiometric ratio of 1:1 with Cu2+ and Mg2+, and 1:2 with Al3+. The order of the stability of the complexes formed by L and Al3+, Cu2+, Mg2+ was as follows: L-Al3+ > L-Cu2+ > L-Mg2+. At the same time, some possible bonding modes and sensing mechanisms were further proposed, and the optimized structure of the sensor L and its sensing mechanism for Al3+, Cu2+ and Mg2+ were confirmed by the calculations of DFT/B3LYP and TD-DFT methods in a suite of Gaussian 09 programs.

Design, synthesis, and biological activity of Schiff bases bearing salicyl and 7-hydroxycoumarinyl moieties

Abstract: 18 (11 novel) Schiff bases, derivatives of salicylaldehyde, 2-hydroxyacetophenone, and 6-acetyl-, 8-acetyl-, and 8-formyl-7-hydroxy-4-methylcoumarin were synthesized and characterized by their spectral studies. 6-Acetyl-7-hydroxy-4-methylcoumarin was prepared by novel method under microwave assistance. These Schiff bases were evaluated for antibacterial activities against 12 bacterial and six fungi strains in vitro. N-(3,5-Dichloro-2-hydroxybenzylidene)-4-aminobenzenesulfonic acid sodium salt proved to be the most active against Staphylococcus aureus and MRSA strains (MIC 0.0194?μmol/cm3). The substitution pattern, two chlorine atoms in the salicylidene ring and the SO3Na group, is probably the most beneficial for the activity against Gram-(+) bacteria strains. All Schiff bases were evaluated for cancer efficacy against CFPAC-1 and HeLa cell cultures originating from human pancreas cancer or human cervical cancer. Schiff bases derived from salicylaldehyde are highly effective in pancreas and cervical cancer cells; however, they demonstrate also substantial toxicity towards NIH3T3 cells. Derivatives of coumarin contain three highly selective compounds: 7-hydroxy-8-[(4-methoxyphenylimino)methyl]-4-methyl-2H-chromen-2-one, N-[(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)methylene]-4-aminobenzenesulfonic acid sodium salt, and 7-hydroxy-8-[1-(4-hydroxyphenylimino)ethyl]-4-methyl-2H-chromen-2-one suggesting more promising potential of the second group of substances.

Synthesis and biological evaluation of novel coumarin derivatives as potential antimicrobials agents

Objective: Synthesize new series of 7-hydroxy-4-methylcoumarin and 7-alkoxy-4-methylcoumarin derivatives featuring thiosemicarbazone or thiazolidin-4-one moieties and to evaluate their antimicrobial activity against two strains of Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), two Gram-negative bacteria (Escherichia Coli and Pseudomonas aeruginosa), and Candida albicans. Methods: Preparation of the new coumarin derivatives was done by adopting Pechmann condensation and attaching different isothiocyanates to give coumarin-thiosemicarbazone hybrids. Thiosemicarbazones were cyclized into thiazolidine-4-ones using chloroacetic acid or diethyl bromo malonate. Results: Compounds VIb, Xb, XIVb, and XVc gave the highest inhibition zones (>20 mm) against Staphylococcus aureus. Their MIC (minimum inhibitory concentration) values ranging from 0.19-0.36 μg/ml were better than the reference drug tobramycin with MIC= 2μg/ml. Conclusion: The newly synthesized compounds with the 7-hydroxyl group showed better antimicrobial activity than those with the 7-alkoxy groups.

Synthesis and photooxygenation of linear and angular furocoumarin derivatives as a hydroxyl radical source: Psoralen, pseudopsoralen, isopseudopsoralen, and allopsoralen

Synthesis of linear and angular furocoumarins with new skeleton structure of potential photobiological feature interest was carried out through Williamson reaction of hydroxycoumarins with 3-chloro-2-butanone followed by cyclization with polyphosphoric acid or by heating in a strongly alkaline solution. The photooxygenation reactions of synthesized furocoumarins were performed in chloroform and in the presence of tetraphenylporphyrin as singlet oxygen sensitizer (1O2). The photooxygenation reactions afforded the photocleaved product through [2 + 2] cycloaddition and the photooxygenated products through ene reaction and [4 + 2] cycloaddition. The photoproducts were isolated and fully characterized by spectral analyses.

An improved helferich method for the α/β-stereoselective synthesis of 4-methylumbelliferyl glycosides for the detection of microorganisms

An improved Helferich method is presented. It involves the glycosylation of 4-methyl-umbelliferone with glycosyl acetates in the presence of boron trifluoride etherate combined with triethylamine, pyridine, or 4-dimethylaminopyridine under mild conditions, followed by deprotection to give fluorogenic 4-methylumbelliferyl glycoside substrates. Due to the use of base, the glycosylation reaction proceeds more easily, is uncommonly α- or β-stereoselective, and affords the corresponding products in moderate to excellent yields (51%-94%) under appropriate conditions.

Manganese(III)-mediated direct Csp2-H radical trifluoromethylation of coumarins with sodium trifluoromethanesulfinate

Mn(OAc)3-mediated direct Csp2-H radical trifluoromethylation of coumarins with CF3SO2Na (Langlois reagent) to afford selective 3-trifluoromethyl coumarins in moderate to good yields is described. This methodology can also be applied to the trifluoromethylation of quinolinones and pyrimidinones. The Royal Society of Chemistry 2014.

Tris(pentafluorophenyl)borane catalyzed acylation of alcohols, phenols, amines, and thiophenols under solvent-free condition

The acylation of alcohols, phenols, amines, and thiophenols was accomplished with 0.5 mol % of tris(pentafluorophenyl)borane [B(C 6F5)3] at ambient temperature under solvent-free condition. Major advantages of this method include high yield, short reaction time, simple procedure, compatibility with sensitive protecting groups as well as other functional groups, absence of racemization of optical active compounds, and epimerization of sugars.