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| Other Sizes |
| Targets |
Benzylideneacetone targets phospholipase A2 (PLA2), an enzyme that releases arachidonic acid from membrane phospholipids. By inhibiting PLA2, it reduces the production of arachidonoid (eicosanoid) inflammatory mediators. It also has antibacterial activity against some gram-negative plant-pathogenic bacteria. Its effects on insect PLA2 have been documented.
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| ln Vitro |
In vitro, benzylideneacetone is a phospholipase A2 (PLA2) inhibitor. It has inhibitory effects on arachidonoid biosynthesis. The compound has antibacterial activity against some gram-negative plant-pathogenic bacteria. It enhances baculovirus pathogenicity of Xylaria minor. Its activity is assessed in enzyme inhibition assays and antibacterial susceptibility tests.
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| ln Vivo |
In vivo, benzylideneacetone is used in research to study PLA2 inhibition and its effects on inflammation and immune responses. It enhances baculovirus pathogenicity. As a natural product from Xenorhabdus nematophila, it plays a role in the bacterium's pathogenicity against insects. Further in vivo studies are needed to evaluate its therapeutic potential.
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| Enzyme Assay |
The in vitro enzyme inhibition assay for benzylideneacetone measures its ability to inhibit phospholipase A2 (PLA2) activity. The assay is performed using purified PLA2 enzyme and a fluorescent or radiolabeled phospholipid substrate. The compound's ability to inhibit the release of the labeled product is measured, and IC50 values are calculated.
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| Cell Assay |
In vitro cellular studies are conducted using immune cells or insect cells. Cells are treated with benzylideneacetone at various concentrations. PLA2 activity is measured by assessing arachidonic acid release. Inflammatory mediator production is measured by ELISA. Antibacterial activity is assessed by determining the minimum inhibitory concentration (MIC) against gram-negative bacteria. Cell viability is assessed using standard cytotoxicity assays.
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| Animal Protocol |
In vivo animal experiments with benzylideneacetone are limited. The compound is a natural product from Xenorhabdus nematophila with potential applications in insect pest control. Further in vivo studies are needed to evaluate its efficacy. Animals would be administered benzylideneacetone via various routes, and endpoints would include inflammation reduction and antibacterial effects.
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| ADME/Pharmacokinetics |
Benzylideneacetone has a molecular formula of C10H10O and a molecular weight of 146.19 g/mol. It is an α,β-unsaturated ketone. For storage, it should be kept at -20°C, protected from light and moisture. The compound is supplied with high purity for research purposes. It is a monoterpene produced by Xenorhabdus nematophila.
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| Toxicity/Toxicokinetics |
As a research chemical, benzylideneacetone is not intended for human use. Its toxicological profile is not fully characterized. Standard laboratory safety precautions should be followed when handling it. Its effects are related to its mechanism as a PLA2 inhibitor, which could have anti-inflammatory and antibacterial effects.
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| Additional Infomation |
Trans-benzylacetone is the trans isomer of benzylacetone. It inhibits phospholipase A2 (EC 3.1.1.4) in insects such as the diamondback moth. It can be used as a flavoring agent, spice, bacterial metabolite, and phospholipase A2 (EC 3.1.1.4) inhibitor. Benzylacetone has been reported to be found in Malabar spinach (Basella alba) and Polygala senega, and relevant data exist. Benzylacetone is a flavoring ingredient. Hydrolyzed soy protein also contains benzylacetone. Benzylacetone belongs to the phenylpropene class of compounds. These compounds contain a phenylpropene structural unit consisting of an propylene substituent and a phenyl group.
Benzylideneacetone is also known as trans-benzalacetone and 4-Phenyl-3-buten-2-one. It is a monoterpene produced by the insect pathogenic bacterium Xenorhabdus nematophila. It is a phospholipase A2 (PLA2) inhibitor with inhibitory effects on arachidonoid biosynthesis. The compound has antibacterial activity against some gram-negative plant-pathogenic bacteria. It is used in research on inflammation, immunity, and insect pathology. |
| Molecular Formula |
C10H10O
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|---|---|
| Molecular Weight |
146.1858
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| Exact Mass |
146.073
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| CAS # |
122-57-6
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| Related CAS # |
trans-Benzylideneacetone;1896-62-4
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| PubChem CID |
637759
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| Appearance |
<39°C Powder,>42°C Liquid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
260.8±9.0 °C at 760 mmHg
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| Melting Point |
41.5 °C
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| Flash Point |
65.6±0.0 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.563
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| LogP |
2.17
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
11
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| Complexity |
152
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(C([H])([H])[H])/C(/[H])=C(\[H])/C1C([H])=C([H])C([H])=C([H])C=1[H]
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| InChi Key |
BWHOZHOGCMHOBV-BQYQJAHWSA-N
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| InChi Code |
InChI=1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+
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| Chemical Name |
(E)-4-phenylbut-3-en-2-one
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~684.04 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (17.10 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (17.10 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (17.10 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.8404 mL | 34.2021 mL | 68.4041 mL | |
| 5 mM | 1.3681 mL | 6.8404 mL | 13.6808 mL | |
| 10 mM | 0.6840 mL | 3.4202 mL | 6.8404 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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