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Acetovanillone

CAS# 498-02-2

Acetovanillone

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Chemical structure

Acetovanillone

3D structure

Chemical Properties of Acetovanillone

Cas No. 498-02-2 SDF Download SDF
PubChem ID 2214 Appearance White powder
Formula C9H10O3 M.Wt 166.2
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms Acetovanillone
Solubility DMSO : ≥ 100 mg/mL (601.79 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name 1-(4-hydroxy-3-methoxyphenyl)ethanone
SMILES CC(=O)C1=CC(=C(C=C1)O)OC
Standard InChIKey DFYRUELUNQRZTB-UHFFFAOYSA-N
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 Acetovanillone

The herbs of Nerium indicum Mill.

Biological Activity of Acetovanillone

DescriptionAcetovanillone is the NADPH oxidase inhibitor, induces oxidative stress.
TargetsNADPH-oxidase
In vitro

The NADPH oxidase inhibitor apocynin (acetovanillone) induces oxidative stress.[Pubmed: 16120450]

Toxicol Appl Pharmacol. 2006 May 1;212(3):179-87. Epub 2005 Aug 24.

Apocynin (Acetovanillone) is often used as a specific inhibitor of NADPH oxidase.
METHODS AND RESULTS:
In N11 glial cells, apocynin induced, in a dose-dependent way, a significant increase of both malonyldialdehyde level (index of lipid peroxidation) and lactate dehydrogenase release (index of a cytotoxic effect). Apocynin evoked also, in a significant way, an increase of H(2)O(2) concentration and a decrease of the intracellular glutathione/glutathione disulfide ratio, accompanied by augmented efflux of glutathione and glutathione disulfide. Apocynin induced the activation of both pentose phosphate pathway and tricarboxylic acid cycle, which was blocked when the cells were incubated with glutathione together with apocynin. The cell incubation with glutathione prevented also the apocynin-induced increase of malonyldialdehyde generation and lactate dehydrogenase leakage. Apocynin exerted an oxidant effect also in a cell-free system: indeed, in aqueous solution, it evoked a faster oxidation of the thiols glutathione and dithiothreitol, and elicited the generation of reactive oxygen species, mainly superoxide anions.
CONCLUSIONS:
Our results suggest that apocynin per se can induce an oxidative stress and exert a cytotoxic effect in N11 cells and other cell types, and that some effects of apocynin in in vitro and in vivo experimental models should be interpreted with caution.

Synergistic effect of laccase mediators on pentachlorophenol removal by Ganoderma lucidum laccase.[Pubmed: 18987855]

Applied Microbiology & Biotechnology, 2008 , 81 (4) :783-90.

Laccases have low redox potentials limiting their environmental and industrial applications. The use of laccase mediators has proven to be an effective approach for overcoming the low redox potentials. However, knowledge about the role played by the mediator cocktails in such a laccase-mediator system (LMS) is scarce.
METHODS AND RESULTS:
Here, we assembled different dual-agent mediator cocktails containing 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS), vanillin, and/or Acetovanillone, and compared their mediating capabilities with those of each individual mediator alone in oxidation of pentachlorophenol (PCP) by Ganoderma lucidum laccase. Cocktails containing ABTS and either vanillin or Acetovanillone strongly promoted PCP removal compared to the use of each mediator alone. The removal enhancement was correlated with mediator molar ratios of the cocktails and incubation times. Analysis of the kinetic constants for each mediator compound showed that G. lucidum laccase was very prone to react with ABTS rather than vanillin and Acetovanillone in the cocktails. Moreover, the presence of the ABTS radical (ABTS+*) and vanillin or Acetovanillone significantly enhanced PCP removal concomitant with electron transfer from vanillin or Acetovanillone to ABTS+*.
CONCLUSIONS:
These results strongly suggest that vanillin and Acetovanillone mediate the reaction between ABTS and PCP via multiple sequential electron transfers among laccase and its mediators.

Acetovanillone Dilution Calculator

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Preparing Stock Solutions of Acetovanillone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.0168 mL 30.0842 mL 60.1685 mL 120.3369 mL 150.4212 mL
5 mM 1.2034 mL 6.0168 mL 12.0337 mL 24.0674 mL 30.0842 mL
10 mM 0.6017 mL 3.0084 mL 6.0168 mL 12.0337 mL 15.0421 mL
50 mM 0.1203 mL 0.6017 mL 1.2034 mL 2.4067 mL 3.0084 mL
100 mM 0.0602 mL 0.3008 mL 0.6017 mL 1.2034 mL 1.5042 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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Background on Acetovanillone

Apocynin is a selective NADPH-oxidase inhibitor with IC50 of 10 μM. apocynin is an intracellular inhibitor of the assembly of NADPH oxidase in neutrophils and eosinophils and that apocynin requires conversion by peroxidases to exert its inhibitory effec [1] Apocynin can decrease the production of superoxide (O(2)(-)) from activated neutrophils and macrophages. Apocynin, after metabolic conversion, inhibits the assembly of NADPH-oxidase that is responsible for reactive oxygen species (ROS) production.[2] NADPH-oxidase is an enzyme responsible for reactive oxygen species production (ROS) and inhibition of this enzyme represents an attractive therapeutic target for the treatment of many diseases. [3]

References:
[1]. Stolk J,et al. Am J Respir Cell Mol Biol, 1994, 11(1), 95-102. [2]. Stefanska J, et al. Mediators Inflamm, 2008, 106507. [3]. Impellizzeri D et al. Effect of apocynin, a NADPH oxidase inhibitor, on acute lung inflammation. Biochem Pharmacol. 2011 Mar 1;81(5):636-48.

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References on Acetovanillone

Synergistic effect of laccase mediators on pentachlorophenol removal by Ganoderma lucidum laccase.[Pubmed:18987855]

Appl Microbiol Biotechnol. 2008 Dec;81(4):783-90.

Laccases have low redox potentials limiting their environmental and industrial applications. The use of laccase mediators has proven to be an effective approach for overcoming the low redox potentials. However, knowledge about the role played by the mediator cocktails in such a laccase-mediator system (LMS) is scarce. Here, we assembled different dual-agent mediator cocktails containing 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS), vanillin, and/or Acetovanillone, and compared their mediating capabilities with those of each individual mediator alone in oxidation of pentachlorophenol (PCP) by Ganoderma lucidum laccase. Cocktails containing ABTS and either vanillin or Acetovanillone strongly promoted PCP removal compared to the use of each mediator alone. The removal enhancement was correlated with mediator molar ratios of the cocktails and incubation times. Analysis of the kinetic constants for each mediator compound showed that G. lucidum laccase was very prone to react with ABTS rather than vanillin and Acetovanillone in the cocktails. Moreover, the presence of the ABTS radical (ABTS+*) and vanillin or Acetovanillone significantly enhanced PCP removal concomitant with electron transfer from vanillin or Acetovanillone to ABTS+*. These results strongly suggest that vanillin and Acetovanillone mediate the reaction between ABTS and PCP via multiple sequential electron transfers among laccase and its mediators.

The NADPH oxidase inhibitor apocynin (acetovanillone) induces oxidative stress.[Pubmed:16120450]

Toxicol Appl Pharmacol. 2006 May 1;212(3):179-87.

Apocynin (Acetovanillone) is often used as a specific inhibitor of NADPH oxidase. In N11 glial cells, apocynin induced, in a dose-dependent way, a significant increase of both malonyldialdehyde level (index of lipid peroxidation) and lactate dehydrogenase release (index of a cytotoxic effect). Apocynin evoked also, in a significant way, an increase of H(2)O(2) concentration and a decrease of the intracellular glutathione/glutathione disulfide ratio, accompanied by augmented efflux of glutathione and glutathione disulfide. Apocynin induced the activation of both pentose phosphate pathway and tricarboxylic acid cycle, which was blocked when the cells were incubated with glutathione together with apocynin. The cell incubation with glutathione prevented also the apocynin-induced increase of malonyldialdehyde generation and lactate dehydrogenase leakage. Apocynin exerted an oxidant effect also in a cell-free system: indeed, in aqueous solution, it evoked a faster oxidation of the thiols glutathione and dithiothreitol, and elicited the generation of reactive oxygen species, mainly superoxide anions. Our results suggest that apocynin per se can induce an oxidative stress and exert a cytotoxic effect in N11 cells and other cell types, and that some effects of apocynin in in vitro and in vivo experimental models should be interpreted with caution.

Description

Apocynin is a selective NADPH-oxidase inhibitor with an IC50 of 10 μM.

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