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
• Article Data: 40

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

Description

7-Acetoxy-4-methylcoumarin, also known as an acetate ester of umbelliferone carrying a 7-O-acetyl group, is a beige crystalline compound with a molecular structure that features a coumarin core and an acetate ester group. It is a derivative of the naturally occurring compound coumarin, which is found in various plants and has been widely studied for its diverse applications in different fields.

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

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 
• 16555-98-9 6-acetyl-7-hydroxy-4-methylcoumarin 
• 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 
• 125733-78-0 8-[(E)-3-(4-Dimethylamino-phenyl)-acryloyl]-7-hydroxy-4-methyl-chromen-2-one 
• 125733-75-7 4-methyl-(4'-methyl-7'-hydroxycoumarin-8-yl)chalcone 
• 125758-33-0 8-[(E)-3-(4-Chloro-phenyl)-acryloyl]-7-hydroxy-4-methyl-chromen-2-one 
• 125758-32-9 8-[(E)-3-(4-Ethoxy-3-methoxy-phenyl)-acryloyl]-7-hydroxy-4-methyl-chromen-2-one 

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.

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.

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.