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4-Hydroxycoumarin

CAS# 1076-38-6

4-Hydroxycoumarin

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Quality Control of 4-Hydroxycoumarin

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Chemical structure

4-Hydroxycoumarin

3D structure

Chemical Properties of 4-Hydroxycoumarin

Cas No. 1076-38-6 SDF Download SDF
PubChem ID 15564935 Appearance Powder
Formula C9H6O3 M.Wt 162.14
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility DMSO : 250 mg/mL (1541.88 mM; Need ultrasonic)
Chemical Name 4-oxochromen-2-olate
SMILES C1=CC=C2C(=C1)C(=O)C=C(O2)[O-]
Standard InChIKey OWBBAPRUYLEWRR-UHFFFAOYSA-M
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 4-Hydroxycoumarin

The herbs of Guazuma ulmifolia

Biological Activity of 4-Hydroxycoumarin

Description4-Hydroxycoumarin serves as an immediate precursor of 4-hydroxycoumarin (4HC) type anticoagulants (for example, warfarin).
TargetsAChR
In vitro

Effect of different C3-aryl substituents on the antioxidant activity of 4-hydroxycoumarin derivatives.[Pubmed: 21964183]

Bioorg Med Chem. 2011 Nov 1;19(21):6233-8.

The antioxidant activity of 4-Hydroxycoumarin synthetic derivatives and 4-methylumbelliferone were determined taking 4-Hydroxycoumarin as the reference compound.
METHODS AND RESULTS:
Six 3-aryl-4-Hydroxycoumarin derivatives were synthesized from 4-Hydroxycoumarin as precursor in order to evaluate changes in their antioxidant properties due to C3-aryl substituent nature. Free radical scavenging capacities of these compounds against two different species DPPH(·) and ABTS(·+) and the protecting ability towards the β-carotene-linoleic acid co-oxidation enzymatically induced by lipoxygenase were measured. In addition, the relationship between the activities of these molecules against DPPH radical and the bond dissociation energy of O-H (BDE) calculated using methods of computational chemistry was evaluated.

Larvicidal activity of 4-hydroxycoumarin derivatives against Aedes aegypti.[Pubmed: 21043993]

Pharm Biol. 2011 Feb;49(2):190-3.

During our search for new types of coumarin derivatives possessing a larvicidal activity, we investigated the synthesis of 4-Hydroxycoumarin derivatives.
METHODS AND RESULTS:
The structure analyses were conducted by nuclear magnetic resonance (NMR), and mass (MS) spectroscopy revealed that the coumarin derivatives were obtained in good yields, and the eight coumarin derivatives were 3-{1,2,3,4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyl}-1-naphthalen-1-on (1), 3-{1,2,3,4-tetrahydro-3-[4-(4-trifluoro methylbenzyloxy)phenyl}-1-naphthalen-1-ol (2), brodifacoum (3), difethialone (4), bromadiolone (5), 4-hydroxy-3-(1,2,3,4-tetrahydronaphthalen-1-yl)-2H-chromen-2-one (coumatetralyl) (6), cis-flocoumafen (7) and trans-flocoumafen (8). The compounds were tested against the F(21) laboratory strain of Aedes aegypti L. Brodifacoum and cis-flocoumafen mediated strong activity with an LC(50) values of 8.23 and 9.34 ppm, respectively.
CONCLUSIONS:
The above indicates that brodifacoum may play a more important role in the toxicity of 4-Hydroxycoumarin derivatives.

Protocol of 4-Hydroxycoumarin

Structure Identification
Chem Biol Drug Des. 2015 May 22.

Synthesis and anticholinergic activity of 4-hydroxycoumarin derivatives containing substituted benzyl-1,2,3-triazole moiety.[Pubmed: 26010139]


METHODS AND RESULTS:
A series of 4-Hydroxycoumarin-derived compounds 8a-p containing N-benzyl-1,2,3-triazole motif were designed as AChE inhibitors. The title compounds were obtained conveniently using multicomponent click reaction. The in vitro anticholinesterase evaluation of synthesized compounds against AChE and BuChE showed that some of them are potent and selective inhibitors of AChE.
CONCLUSIONS:
Among them, 2-chlorobenzyl derivative 8k showed the most potent activity against AChE (IC50 = 0.18 μm). Its activity was also superior to that of standard drug tacrine. The kinetic study and molecular docking simulation of the most potent compound 8k were also described.

Nat Commun. 2013;4:2603.

Microbial biosynthesis of the anticoagulant precursor 4-hydroxycoumarin.[Pubmed: 24129598]

4-Hydroxycoumarin (4HC) type anticoagulants (for example, warfarin) are known to have a significant role in the treatment of thromboembolic diseases--a leading cause of patient morbidity and mortality worldwide. 4HC serves as an immediate precursor of these synthetic anticoagulants. Although 4HC was initially identified as a naturally occurring product, its biosynthesis has not been fully elucidated.
METHODS AND RESULTS:
Here we present the design, validation, in vitro diagnosis and optimization of an artificial biosynthetic mechanism leading to the microbial biosynthesis of 4HC. Remarkably, function-based enzyme bioprospecting leads to the identification of a characteristic FabH-like quinolone synthase from Pseudomonas aeruginosa with high efficiency on the 4HC-forming reaction, which promotes the high-level de novo biosynthesis of 4HC in Escherichia coli (~500 mg l⁻1 in shake flasks) and further in situ semisynthesis of warfarin.
CONCLUSIONS:
This work has the potential to be scaled-up for microbial production of 4HC and opens up the possibility of biosynthesizing diverse coumarin molecules with pharmaceutical importance.

4-Hydroxycoumarin Dilution Calculator

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4-Hydroxycoumarin Molarity Calculator

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Preparing Stock Solutions of 4-Hydroxycoumarin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.1675 mL 30.8375 mL 61.6751 mL 123.3502 mL 154.1877 mL
5 mM 1.2335 mL 6.1675 mL 12.335 mL 24.67 mL 30.8375 mL
10 mM 0.6168 mL 3.0838 mL 6.1675 mL 12.335 mL 15.4188 mL
50 mM 0.1234 mL 0.6168 mL 1.2335 mL 2.467 mL 3.0838 mL
100 mM 0.0617 mL 0.3084 mL 0.6168 mL 1.2335 mL 1.5419 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 4-Hydroxycoumarin

Microbial biosynthesis of the anticoagulant precursor 4-hydroxycoumarin.[Pubmed:24129598]

Nat Commun. 2013;4:2603.

4-Hydroxycoumarin (4HC) type anticoagulants (for example, warfarin) are known to have a significant role in the treatment of thromboembolic diseases--a leading cause of patient morbidity and mortality worldwide. 4HC serves as an immediate precursor of these synthetic anticoagulants. Although 4HC was initially identified as a naturally occurring product, its biosynthesis has not been fully elucidated. Here we present the design, validation, in vitro diagnosis and optimization of an artificial biosynthetic mechanism leading to the microbial biosynthesis of 4HC. Remarkably, function-based enzyme bioprospecting leads to the identification of a characteristic FabH-like quinolone synthase from Pseudomonas aeruginosa with high efficiency on the 4HC-forming reaction, which promotes the high-level de novo biosynthesis of 4HC in Escherichia coli (~500 mg l(-)(1) in shake flasks) and further in situ semisynthesis of warfarin. This work has the potential to be scaled-up for microbial production of 4HC and opens up the possibility of biosynthesizing diverse coumarin molecules with pharmaceutical importance.

Larvicidal activity of 4-hydroxycoumarin derivatives against Aedes aegypti.[Pubmed:21043993]

Pharm Biol. 2011 Feb;49(2):190-3.

CONTEXT: Coumarins are natural substances found in a variety of plants. It is well known that plant-derived natural products are extensively used as biologically active compounds. Among them, coumarins were the first preservatives used by man, originally in their natural state within plant tissues and then as natural materials obtained by water distillation. During our search for new types of coumarin derivatives possessing a larvicidal activity, we investigated the synthesis of 4-Hydroxycoumarin derivatives. OBJECTIVE: The coumarin derivatives were synthesized and the structure determination and larvicidal effects were studied. MATERIALS AND METHODS: The structure analyses were conducted by nuclear magnetic resonance (NMR), and mass (MS) spectroscopy revealed that the coumarin derivatives were obtained in good yields, and the eight coumarin derivatives were 3-{1,2,3,4-tetrahydro-3-[4-(4-trifluoromethylbenzyloxy)phenyl}-1-naphthalen-1-on (1), 3-{1,2,3,4-tetrahydro-3-[4-(4-trifluoro methylbenzyloxy)phenyl}-1-naphthalen-1-ol (2), brodifacoum (3), difethialone (4), bromadiolone (5), 4-hydroxy-3-(1,2,3,4-tetrahydronaphthalen-1-yl)-2H-chromen-2-one (coumatetralyl) (6), cis-flocoumafen (7) and trans-flocoumafen (8). RESULTS: The compounds were tested against the F(21) laboratory strain of Aedes aegypti L. Brodifacoum and cis-flocoumafen mediated strong activity with an LC(50) values of 8.23 and 9.34 ppm, respectively. DISCUSSION AND CONCLUSION: The above indicates that brodifacoum may play a more important role in the toxicity of 4-Hydroxycoumarin derivatives.

Synthesis and anticholinergic activity of 4-hydroxycoumarin derivatives containing substituted benzyl-1,2,3-triazole moiety.[Pubmed:26010139]

Chem Biol Drug Des. 2015 Nov;86(5):1215-20.

A series of 4-Hydroxycoumarin-derived compounds 8a-p containing N-benzyl-1,2,3-triazole motif were designed as AChE inhibitors. The title compounds were obtained conveniently using multicomponent click reaction. The in vitro anticholinesterase evaluation of synthesized compounds against AChE and BuChE showed that some of them are potent and selective inhibitors of AChE. Among them, 2-chlorobenzyl derivative 8k showed the most potent activity against AChE (IC50 = 0.18 mum). Its activity was also superior to that of standard drug tacrine. The kinetic study and molecular docking simulation of the most potent compound 8k were also described.

Effect of different C3-aryl substituents on the antioxidant activity of 4-hydroxycoumarin derivatives.[Pubmed:21964183]

Bioorg Med Chem. 2011 Nov 1;19(21):6233-8.

The antioxidant activity of 4-Hydroxycoumarin synthetic derivatives and 4-methylumbelliferone were determined taking 4-Hydroxycoumarin as the reference compound. Six 3-aryl-4-Hydroxycoumarin derivatives were synthesized from 4-Hydroxycoumarin as precursor in order to evaluate changes in their antioxidant properties due to C3-aryl substituent nature. Free radical scavenging capacities of these compounds against two different species DPPH(.) and ABTS(.+) and the protecting ability towards the beta-carotene-linoleic acid co-oxidation enzymatically induced by lipoxygenase were measured. In addition, the relationship between the activities of these molecules against DPPH radical and the bond dissociation energy of O-H (BDE) calculated using methods of computational chemistry was evaluated.

Description

4-Hydroxycoumarin, a coumarin derivative, is one of the most versatile heterocyclic scaffolds and is frequently applied in the synthesis of various organic compounds. 4-Hydroxycoumarin possesses both electrophilic and nucleophilic properties. 4-Hydroxycoumarin derivatives are employed as the anticoagulant, antibacterial, antifungal, antiviral, antitumor, antiprotozoal, insecticidal, antimycobacterial, antimutagenic, antioxidant, anti-inflammatory agents, HIV protease inhibitors and tyrosine kinase inhibitors.

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