2107-78-0

Basic information

• Product Name: 3,4-DIMETHYLUMBELLIFERONE
• Synonyms: 7-HYDROXY-3,4-DIMETHYL-CHROMEN-2-ONE;3,4-DIMETHYLUMBELLIFERONE;3,4-DIMETHYL-7-HYDROXYCOUMARIN;DIMETHYLUMBELLIFERONE,3,4-;3,4-DIMETHYLUMBELLIFERONE, FOR FLUORESCE NCE;DIMETHYLUMBELLIFERONE,3,4-(RG);3,4-Dimethylumbelliferone ,98%;3,4-Dimethyl-7-hydroxy-2H-1-benzopyran-2-one
• CAS NO: 2107-78-0
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.2
• Mol File: 2107-78-0.mol
• Article Data: 34

Chemical Properties

• Melting Point: 256℃
• Boiling Point: 377.1 °C at 760 mmHg
• Flash Point: 170.2 °C
• Appearance: /
• Density: 1.255 g/cm³
• Vapor Pressure: 3.19E-06mmHg at 25°C
• Refractive Index: 1.589
• Solubility: alcohols: soluble
• PKA: 8.11±0.20(Predicted)
• CAS DataBase Reference: 3,4-DIMETHYLUMBELLIFERONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHYLUMBELLIFERONE(2107-78-0)
• EPA Substance Registry System: 3,4-DIMETHYLUMBELLIFERONE(2107-78-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8
• HazardClass: IRRITANT
• Hazardous Substances Data: 2107-78-0(Hazardous Substances Data)

Usage

Description

3,4-Dimethylumbelliferone, with the CAS number 2107-78-0, is a white crystalline compound that is primarily utilized in organic synthesis. It serves as an essential intermediate for the production of various organic compounds and has a wide range of applications across different industries.

Uses

Used in Organic Synthesis:
3,4-Dimethylumbelliferone is used as a synthetic intermediate for the production of various organic compounds. Its unique chemical structure allows it to be a versatile building block in the synthesis of a wide array of molecules, making it a valuable asset in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4-dimethylumbelliferone is used as a key component in the development of new drugs. Its chemical properties make it suitable for the synthesis of various pharmaceutical compounds, contributing to the advancement of drug discovery and development.
Used in Chemical Research:
3,4-Dimethylumbelliferone is also employed in chemical research as a reagent and a reference compound. Its distinct properties and reactivity make it an ideal candidate for studying various chemical reactions and mechanisms, furthering our understanding of organic chemistry.
Used in Analytical Chemistry:
In the field of analytical chemistry, 3,4-dimethylumbelliferone is used as a colorimetric reagent for the detection and quantification of various substances. Its ability to form colored complexes with specific analytes makes it a valuable tool for analytical applications.
Used in Biochemical Research:
3,4-Dimethylumbelliferone is also utilized in biochemical research as a substrate for enzymes such as esterases and lipases. Its unique structure allows it to be hydrolyzed by these enzymes, making it a useful tool for studying enzyme activity and inhibition.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 41, p. 1068, 1998 DOI: 10.1021/jm970527v

InChI:InChI=1/C11H10O3/c1-6-7(2)11(13)14-10-5-8(12)3-4-9(6)10/h3-5,12H,1-2H3

Upstream product

• 5852-10-8 (7-hydroxy-4-methyl-2-oxochromen-3-yl)acetic acid 
• 108171-18-2 7-hydroxy-3,4-dimethyl-2-oxo-2H-chromene-6-carboxylic acid 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 108-46-3 recorcinol 
• 17094-21-2 2-methyl-acetoacetic acid methyl ester 
• 10034-85-2 hydrogen iodide 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 2150-47-2 methyl 2,4-dihydroxybenzoate 
• 314044-86-5 7-hydroxy-3,4-dimethyl-2-oxo-2H-chromene-6-carboxylic acid methyl ester 

Downstream Products

• 64309-70-2 3,4-dimethyl-7-acetoxycoumarin 
• 117376-52-0 7-(2-oxocyclohexyloxy)-3,4-dimethylcoumarin 
• 39577-20-3 3,4-dimethyl-7-<4-(4-chlorobenzyl)piperazin-1-yl>propoxycoumarin dihydrochloride 
• 156006-10-9 7-acetonyloxy-3,4-dimethylcoumarin 
• 39577-15-6 3,4-dimethyl-7-[3-(4-phenyl-piperazin-1-yl)-propoxy]-chromen-2-one 
• 54917-82-7 2,4-dihydroxy-3,5-dinitroacetophenone 
• 320350-87-6 7-(3-methoxy-benzyloxy)-3,4-dimethyl-chromen-2-one 

Relevant articles and documents

Development and preclinical studies of broad-spectrum anti-HIV agent (3′R,4′R)-3-cyanomethyl-4-methyl-3′,4′-di-O-(S) -camphanoyl-(+)-cis-khellactone (3-cyanomethyl-4-methyl-DCK)

In prior investigation, we discovered that (3′R,4′R)-3- cyanomethyl-4-methyl-3′,4′-di-O-(S)-camphanoyl-(+)-cis-khellactone (4, 3-cyanomethyl-4-methyl-DCK) showed promising anti-HIV activity. In these current studies, we developed and optimized successfully a practical 10-step synthesis for scale-up preparation to increase the overall yield of 4 from 7.8% to 32%. Furthermore, compound 4 exhibited broad-spectrum anti-HIV activity against wild-type and drug-resistant viral infection of CD4+ T cell lines as well as peripheral blood mononuclear cells by both laboratory-adapted and primary HIV-1 isolates with distinct subtypes and tropisms. Compound 4 was further subjected to in vitro and in vivo pharmacokinetic studies. These studies indicated that 4 has moderate cell permeability, moderate oral bioavailability, and low systemic clearance. These results suggest that 4 should be developed as a promising anti-HIV agent for development as a clinical trial candidate.

2-Aminobenzoxazole-appended coumarins as potent and selective inhibitors of tumour-associated carbonic anhydrases

We have carried out the design, synthesis, and evaluation of a small library of 2-aminobenzoxazole-appended coumarins as novel inhibitors of tumour-related CAs IX and XII. Substituents on C-3 and/or C-4 positions of the coumarin scaffold, and on the benzoxazole moiety, together with the length of the linker connecting both units were modified to obtain useful structure-activity relationships. CA inhibition studies revealed a good selectivity towards tumour-associated CAs IX and XII (K i within the mid-nanomolar range in most of the cases) in comparison with CAs I, II, IV, and VII (K i > 10 μM); CA IX was found to be slightly more sensitive towards structural changes. Docking calculations suggested that the coumarin scaffold might act as a prodrug, binding to the CAs in its hydrolysed form, which is in turn obtained due to the esterase activity of CAs. An increase of the tether length and of the substituents steric hindrance was found to be detrimental to in?vitro antiproliferative activities. Incorporation of a chlorine atom on C-3 of the coumarin moiety achieved the strongest antiproliferative agent, with activities within the low micromolar range for the panel of tumour cell lines tested.

Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents

To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G0/G1 phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis.