4-Hydroxycoumarin
4-Hydroxycoumarin serves as an immediate precursor of 4-hydroxycoumarin (4HC) type anticoagulants (for example, warfarin).
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Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to
24 months(2-8C).
Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.
Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Bioorg Med Chem. 2011 Nov 1;19(21):6233-8.
Effect of different C3-aryl substituents on the antioxidant activity of 4-hydroxycoumarin derivatives.[Pubmed:
21964183]
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.
Pharm Biol. 2011 Feb;49(2):190-3.
Larvicidal activity of 4-hydroxycoumarin derivatives against Aedes aegypti.[Pubmed:
21043993]
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.
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.
