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

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

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

Downstream Products

• 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 
• 314742-04-6 3,4-dimethyl-7-(2-oxo-2-phenyl-ethoxy)-chromen-2-one 
• 91406-11-0 3,4-dimethyl-2-oxo-2H-1-benzopyran-7-yl ethanesulfonate 
• 1592003-37-6 3,4-dimethyl-7-hydroxy-8-phenylazo-2H-1-benzopyran-2-one 
• 1592003-66-1 7-(5-phenylamino-1,3,4-thiadiazol-2-yl)methoxy-3,4-dimethyl-2H-1-benzopyran-2-one 
• 1592003-67-2 7-(4-ethyl-5-thioxo-1,2,4-triazol-3-yl)methoxy-3,4-dimethyl-2H-1-benzopyran-2-one 
• 1592003-68-3 7-(4-phenyl-5-thioxo-1,2,4-triazol-3-yl)methoxy-3,4-dimethyl-2H-1-benzopyran-2-one 
• 1592003-46-7 4-benzyl-1-(3,4-dimethyl-2-oxo-2H-1-benzopyran-7-yloxyacetyl)semicarbazide 
• 1592003-69-4 3-benzyl-1-(3,4-dimethyl-2-oxo-2H-1-benzopyran-7-yloxy)acetamidoimidazolidin-2,4,5-trione 
• 1592003-70-7 2-(3,4-dimethyl-2-oxo-2H-1-benzopyran-7-yloxy)-N'-(4-methoxybenzylidene)acetohydrazide 
• 1592003-40-1 1-(3,4-dimethyl-7-hydroxy-2-oxo-2H-1-benzopyran-8-yl)-3-phenylurea 
• 1592003-51-4 2-benzylamino-6,7-dimethyl-5H-pyrano[6,5-e]benzoxazol-5-one 
• 1592003-52-5 7,8-dimethyl-3-phenyl-2,6-dihydropyrano[6,5-f]-1,4-benzoxazin-6-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.

Synthesis, characterization, and determination of photophysicochemical properties of peripheral and nonperipheral tetra-7-oxy-3,4-dimethylcoumarin substituted zinc, indium phthalocyanines

The photochemical and photophysical properties of peripheral and nonperipheral zinc and indium phthalocyanines containing 7-oxy-3,4-dimethylcoumarin synthesized were investigated in this study. 7-Hydroxy-3,4-dimethylcoumarin (1) was synthesized via Pechma

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.

Umbelliferyloxymethyl phosphonate compounds-weakly binding zinc ionophores with neuroprotective properties

Umbelliferone is a member of the coumarin family of compounds which are known for diverse pharmacological activity including in targets relevant to Alzheimers disease, AD. The toxicity associated with some forms of the amyloid protein, Aβ, and the role of Zn2+ (and other biometals) dyshomeostasis in this, are of great interest in AD and make metal ionophore capability desirable in so called multi target drug ligands MTDLs. A new series of umbelliferyloxymethyl phosphonic acid diethylester compounds (umbelliferyloxymethyl phosphonates) bearing a phosphonate at the 7-position (compounds 1, 3-6), hydrolysis products 2, 2a and 2b from 1 and analogues 7 and 8 of 1 with 7-O to 7-S and 1-O to 1-NH substitutions, are reported. Single crystal X-ray structures of compounds 1, 2 and 2a were determined. In terms of neuroprotective properties, the compounds 1, 2, 3, 4, 5 and 6 at 1 μM concentration, inhibited the toxicity of Aβ1-42 (Aβ42) in both toxic Amyloid Derived Diffusible Ligand (ADDL) and fibrillar (fibril) forms towards rat hippocampal cells. Compound 7 displayed cytotoxicity and 8 failed to inhibit Aβ42 toxicity. Concerning compound-metal ionophore activity (assessed using chemical experiments), despite weak binding to Zn2+ determined from 31P NMR titration of 1 and 2 by ZnCl2, compounds 1, 3, 4, 5 and 6 demonstrated ionophore assisted partition of Zn2+ from water to octanol at micromolar concentrations with efficacy on a par with or better than the chelator MTDL clioquinol (5-chloro-7-iodo-8-hydroxyquinoline). Partition was assessed using furnace Atomic Absorption Spectroscopy (AAS). In further experiments interaction of compound 1 with Zn2+ or it's pathways was inferred by (i) delayed fluorescence response with added Zn2+ in cells treated with FluoZin-3 and (ii) by suppression of Zn2+ promoted aggregation of Aβ42.

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.

Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer's disease: Design, synthesis and biological evaluation

A series of new coumarin-dithiocarbamate hybrids were designed and synthesized as multitarget agents for the treatment of Alzheimer's disease. Most of them showed potent and clearly selective inhibition towards AChE and MAO-B. Among these compounds, compound 8f demonstrated the most potent inhibition to AChE with IC50 values of 0.0068 μM and 0.0089 μM for eeAChE and hAChE, respectively. Compound 8g was identified as the most potent inhibitor to hMAO-B, and it is also a good and balanced inhibitor to both hAChE and hMAO-B (0.114 μM for hAChE; 0.101 μM for hMAO-B). Kinetic and molecular modeling studies revealed that 8g was a dual binding site inhibitor for AChE and a competitive inhibitor for MAO-B. Further studies indicated that 8g could penetrate the BBB and exhibit no toxicity on SH-SY5Y neuroblastoma cells. More importantly, 8g did not display any acute toxicity in mice at doses up to 2500 mg/kg and could reverse the cognitive dysfunction of scopolamine-induced AD mice. Overall, these results highlighted 8g as a potential multitarget agent for AD treatment and offered a starting point for design of new multitarget AChE/MAO-B inhibitors based on dithiocarbamate scaffold.

Synthesis of Novel Anti-inflammatory Psoralen Derivatives?-?Structures?with?Distinct?Anti-Inflammatory?Activities

As a continuum to our work with coumarins, 12 psoralens were synthesized and evaluated for their anti-inflammatory activity. Psoralens were prepared in three steps; at first, 7-hydroxycoumarins were synthesized by von Pechmann condensation and then converted to 7-(2-oxopropoxy)coumarins. In the final step, a fused furan ring was introduced in an intramolecular ring-formation reaction. Based on a SciFinder search, two out of the 12 synthesized psoralen derivatives (compounds 9 and 12) were found to be novel. The derivatives displayed anti-inflammatory activity by suppressing iNOS and IL-6 expression, but their mechanism of action seemed to be dependent on the substitution. Compound 6 with propyl side chain inhibited NF-κB mediated transcription, while compound 10 with a phenyl substituent down-regulated iNOS expression in a posttranscriptional manner. The results introduce psoralen derivatives as promising anti-inflammatory compounds with potential for treatment of conditions involving iNOS and/or IL-6-mediated adverse responses.

Neuroprotective effects of benzyloxy substituted small molecule monoamine oxidase B inhibitors in Parkinson's disease

The benzyloxy substituted small molecules are well-known highly potent monoamine oxidase B inhibitors, but their therapeutic potential against Parkinson's disease have not been investigated in detail. In this paper, a series of representative benzyloxy substituted derivatives were synthesized and evaluated for MAO-A/B inhibition. In addition, their neuroprotective effects were investigated in 6-OHDA- and rotenone-treated PC12 cells. It was observed that most of the compounds exhibited a marked increase in survival of PC12 cells which treated with the neurotoxins. Among them, 13 exhibited remarkable and balanced neuroprotective potency. The protective effects of 13 against neurotoxins-induced apoptosis were confirmed with flow cytometry and staining methods. Furthermore, 13 also showed good BBB permeability and low toxicity according to in vitro BBB prediction and in vivo acute toxicity test. The results indicated that 13 is an effective and promising candidate to be further developed as disease-modifying drug for Parkinson's disease therapy.

Design, synthesis and cytotoxicity of novel dihydroartemisinin-coumarin hybrids via click chemistry

In order to develop novel chemotherapeutic agents with potent anticancer activities, we designed four series of novel compounds employing hybridization strategy. Twenty novel dihydroartemisinin-coumarin hybrids, 10a-e, 11a-e, 12a-e, 13a-e, were synthesized via click chemistry in this study and their structures were characterized by HRMS and NMR. The cytotoxic activities were measured by MTT assay against three cancer cell lines (HCT-116, MDA-MB-231, and HT-29) under normoxic or anoxic conditions, respectively. The target compounds exhibited moderate activity with IC50 values in the 0.05-125.40 μM range, and these compounds exhibited better activity against HT-29 cell line under anoxic condition. The cytotoxic activities of most compounds under anoxic condition displayed one- to 10-fold greater activity than under normoxic condition. Compounds 10a - e showed better selectivity against the HT-29 cell line than the other two cell lines. These results indicated that our design of CA IX inhibitors does correspond with its action mode to some degree and deserves further investigation.

p27 PROTEIN INDUCER

The present invention provides a p27 protein inducing agent comprising a compound represented by general formula (11) below or pharmaceutically acceptable salt thereof as an active ingredient: wherein G 1 , G 2 , G 3 and G 8 are each independently selected from -N= etc., Ring G 6 is selected from divalent aryl etc., A is selected from amino etc., G 4 is selected from oxygen etc., G 5 is selected from oxygen etc., G 7 is selected from -CH 2 - etc., and R 2 is selected from C 1-6 alkyl etc.