4069-67-4

Basic information

• Product Name: 7-HYDROXY-3-METHYL-2H-CHROMEN-2-ONE
• Synonyms: 7-HYDROXY-3-METHYL-2H-CHROMEN-2-ONE
• CAS NO: 4069-67-4
• Molecular Formula: C₁₀H₈O₃
• Molecular Weight: 176.17
• Mol File: 4069-67-4.mol

Chemical Properties

• Melting Point: 218 °C
• Boiling Point: 377.4±37.0 °C(Predicted)
• Appearance: /
• Density: 1.319±0.06 g/cm3(Predicted)
• PKA: 8.00±0.20(Predicted)
• CAS DataBase Reference: 7-HYDROXY-3-METHYL-2H-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-HYDROXY-3-METHYL-2H-CHROMEN-2-ONE(4069-67-4)
• EPA Substance Registry System: 7-HYDROXY-3-METHYL-2H-CHROMEN-2-ONE(4069-67-4)

Safety Data

• Hazardous Substances Data: 4069-67-4(Hazardous Substances Data)

Upstream product

• 72136-39-1 7-methoxy-3-methyl-2H-chromen-2-one 
• 123-62-6 propionic acid anhydride 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 2605-68-7 methyl 2-(triphenylphosphoranylidene)propionate 
• 105-37-3 Ethyl propionate 
• 108-46-3 recorcinol 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 27772-62-9 ethyl 2-formylpropionate 
• 137-40-6 sodium proprionate 
• 119091-63-3 3-methyl-2-oxo-2H-chromene-7-yl propionate 

Downstream Products

• 156006-09-6 7-(1-methylacetonyloxy)-3-methylcoumarin 
• 245736-80-5 3-methyl-7-(2'-oxocyclohexyloxy)coumarin 
• 141497-65-6 8-acetyl-4-methyl umbelliferone 
• 141497-70-3 3-methyl-6-acetyl-7-hydroxycoumarin 
• 186303-86-6 4-methyl-7-retinoyloxy-coumarin 

Relevant articles and documents

Design, synthesis, and evaluation of 3,7-substituted coumarin derivatives as multifunctional Alzheimer’s disease agents

Multitarget directed ligands (MTDLs) are emerging as promising treatment options for Alzheimer’s disease (AD). Coumarin derivatives serve as a good starting point for designing MTDLs due to their inherent inhibition of monoamine oxidase (MAO) and cholinesterase enzymes, which are complicit in AD’s complex pathophysiology. A preliminary series of 3,7-substituted coumarin derivatives were synthesised and evaluated for enzyme inhibitory activity, cytotoxicity as well as neuroprotective ability. The results indicated that the compounds are weak cholinesterase inhibitors with five compounds demonstrating relatively potent inhibition and selectivity towards MAO-B with IC50 values between 0.014 and 0.498 hx00B5;μM. Significant neuroprotective effects towards MPP+-compromised SH-SY5Y neuroblastoma cells were also observed, with no inherent cytotoxicity at 10 μM for all compounds. The overall results demonstrated that substitution of the phenylethyloxy moiety at the 7-position imparted superior general activity to the derivatives, with the propargylamine substitution at the 3-position, in particular, displaying the best MAO-B selectivity and neuroprotection.

Photocontrolled endogenous reactive oxygen species (ROS) generation

A cell-permeable small molecule for light-triggered generation of endogenous reactive oxygen species (ROS) is reported.

Intracellular enzyme-activatable prodrug for real-time monitoring of chlorambucil delivery and imaging

Carboxylesterase, a necessary enzyme in various mammalian cells, has been employed in various biological applications. Herein, we designed and synthesized a novel carboxylesterase-based prodrug, which can realize simultaneous drug-release imaging and cancer chemotherapy. This prodrug comprises three parts: coumarin as the fluorophore and the cleavable architecture, chlorambucil as the anticancer drug, and acetyl group as the enzyme-responsive unit. The presence of carboxylesterase leads to the activation of coumarin fluorescence, and this fluorescence serves as the reporting signal for assessing the enzyme level and drug release. Moreover, the prodrug was incorporated in liposome for monitoring drug release and chemotherapeutic effect in living cells. Upon internalization by HeLa cells, the prodrug can release chlorambucil and exhibit high cytotoxicity. This approach may provide some helpful insights for enhancing therapeutic effect and tracking the release of prodrug.

Structural insights into monoamine oxidase inhibitory potency and selectivity of 7-substituted coumarins from ligand- and target-based approaches

A new series of 3-, 4-, 7-polysubstituted coumarins have been designed and evaluated for their monoamine oxidase A and monoamine oxidase B (MAO-A and MAO-B) inhibitory potency. Substituents at position 7 consisted of a bridge of different physicochemical

A dual-channel fluorescence-enhanced sensor for aluminum ions based on photoinduced electron transfer and excimer formation

Sensor 1 was developed as the first example of a fluorescence-enhanced Al3+ sensor with unique dual-channel emissions. The addition of Al3+ to 1 elicits a large fluorescence enhancement by inhibition of a quenching Photoinduced electron-transfer (PET) channel and also a dramatic fluorescence enhancement due to promotion of an emissive excimer channel formation. The dual-channel fluorescence-enhanced response of the sensor contributes to its high sensitivity and selectivity. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

A coumarin-based colorimetric fluorescent probe for hydrogen sulfide

A coumarin-based fluorescent probe for selective detection of hydrogen sulfide (H2S) is presented. This 'off-on' probe exhibited high selectivity towards H2S in aqueous solution with a detection limit of 30 nM. Notably, because of it

A fluorescence-enhanced chemodosimeter for Fe3+ based on hydrolysis of bis(coumarinyl) Schiff base

Bis(coumarinyl) Schiff base 1 was designed and synthesized as a fluorescence turn-on chemodosimeter for Fe3+. The chemodosimeter was readily synthesized in four steps from 2,4-dihydroxybenzaldehyde. The addition of Fe3+ to chemodosimeter 1 induced about a 140-fold enhancement in fluorescence. Furthermore, chemodosimeter 1 was also highly selective to Fe 3+ over other metal ions, and most of the related metals ions exhibited negligible detection interference. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Fluorescent probe for detecting beta-galactosidase as well as preparation method and application of fluorescent probe

The invention relates to a fluorescent probe for detecting beta-galactosidase as well as a preparation method and application of the fluorescent probe. The chemical structural formula of the fluorescent probe is shown as (I). The fluorescent probe provided by the invention is high in sensitivity, low in detection limit (0.168 mU/mL), good in selectivity, quick in response and capable of specifically detecting the activity and content of beta-galactosidase. A fluorescent method for screening a beta-galactosidase inhibitor is established for the first time on the basis of the fluorescent probe,the test result is consistent with the test result of a commercial substrate, and the method is reliable.

Synthesis of 7-Azido-3-Formylcoumarin – A Key Precursor in Bioorthogonally Applicable Fluorogenic Dye Synthesis

Coumarins represent an important group of natural products and a common part of various drugs and fluorescent dyestuffs. Herein, we present the synthesis of a coumarin that can serve as a key starting material in the design and synthesis of bioorthogonally applicable fluorogenic dyes. The synthesis of 7-azido-3-formylcoumarin started from 7-diallylaminocoumarin. This allyl protected aminocoumarin is otherwise hard to obtain by conventional methods but was conveniently accessed in good yields by a sequential, Wittig-reaction–UV isomerization process. This sequential approach was studied in more details and applied for the synthesis of a series of substituted coumarins even in one-pot.

FLUORESCENT COMPOUNDS FOR IMAGING OF BLOOD VESSELS AND BLOOD FLOW, AND AN IN VIVO SCREEN FOR PRO- AND ANTI-ANGIOGENIC AGENTS

The present invention discloses fluorescent compounds and a method for their use for selective imaging of blood vessels and blood flow. By applying these fluorescent compounds and the imaging process to a zebrafish model, the present invention further pro