| Size | Price | Stock | Qty |
|---|---|---|---|
| 5g |
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| 10g |
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| Other Sizes |
| Targets |
Phospholipase A2 (PLA2) (EC 3.1.1.4), glucocorticoid receptor (NR3C1), glutathione S-transferase Mu 1 (GSTM1).
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|---|---|
| ln Vitro |
Benzylideneacetone (trans-Benzylideneacetone; 0.005, 0.05, 0.5, 5, 50, 500, 5000 μM) prevents S. exigua larval hemocytes from propagating their hemocytes. Bacillus thuringiensis exhibits increased virulence against Spodoptera exigua when exposed to benzolidene acetone [1].
In vitro studies demonstrate that benzylideneacetone acts as an enzyme inhibitor against phospholipase A2 (PLA2) in insects such as the diamondback moth, inhibiting the enzyme with an IC50 value in the micromolar range. The compound exhibits antimicrobial effects against various microorganisms and has been reported to have immunosuppressant properties. It also shows activity as a bacterial metabolite and has been identified as a ligand for the glucocorticoid receptor (NR3C1) and glutathione S-transferase Mu 1 (GSTM1). The α,β-unsaturated carbonyl moiety is responsible for its biological activity through Michael addition reactions with nucleophilic residues in target proteins. |
| ln Vivo |
In vivo studies have demonstrated that benzylideneacetone functions as an immunosuppressant and enhances the virulence of Bacillus thuringiensis against agricultural pests such as the beet armyworm (Lepidoptera: Noctuidae). The compound's ability to inhibit phospholipase A2 in insects contributes to its effects on insect physiology and immune function. In the context of entomopathogenic bacteria, benzylideneacetone is produced by Xenorhabdus nematophila to suppress the host insect's immune response, facilitating bacterial colonization and subsequent host death. These properties make it a compound of interest in agricultural pest control research.
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| Enzyme Assay |
Phospholipase A2 (PLA2) inhibition assays are conducted using purified PLA2 enzyme and a fluorescent or radioactive substrate. The enzyme is incubated with varying concentrations of benzylideneacetone and the substrate, and enzymatic activity is measured by detecting the release of reaction products. The IC50 value is calculated from dose-response curves. For receptor binding studies, competitive binding assays using radiolabeled ligands and receptor-containing membranes are performed to assess affinity for targets such as the glucocorticoid receptor (NR3C1). Antimicrobial activity is evaluated using standard broth microdilution methods against bacterial and fungal strains.
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| Cell Assay |
In vitro cellular assays for benzylideneacetone typically involve assessing its effects on immune cell function. For immunosuppressant activity, assays using macrophage or lymphocyte cell lines are conducted to measure cytokine production, cell proliferation, and other immune parameters following compound treatment. Antimicrobial activity is assessed using standard susceptibility testing methods against various bacterial and fungal strains. Cytotoxicity against mammalian cell lines is evaluated using MTT or similar cell viability assays to determine the compound's selectivity and safety profile.
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| Animal Protocol |
In vivo efficacy of benzylideneacetone is evaluated in insect models to study its role as a bacterial metabolite and immunosuppressant. For agricultural applications, insects such as beet armyworm (Spodoptera exigua) are treated with the compound in combination with Bacillus thuringiensis, and mortality rates are monitored. The compound's ability to suppress insect immune responses and enhance bacterial virulence is assessed by measuring bacterial load, hemocyte counts, and phenoloxidase activity in treated insects. These studies provide insights into the compound's potential as a biocontrol agent.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of benzylideneacetone have been studied in the context of its role as a bacterial metabolite and flavoring agent. As a small lipophilic molecule with a molecular weight of 146.19, the compound is expected to be readily absorbed and distributed in biological systems. It is metabolized through pathways involving conjugation and oxidation, with excretion occurring primarily via renal and hepatic routes. The compound's volatility and lipophilicity influence its bioavailability and tissue distribution. Detailed PK parameters are typically determined using GC-MS or LC-MS/MS analysis of biological samples.
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| Toxicity/Toxicokinetics |
Toxicological evaluation of benzylideneacetone has been conducted in the context of its use as a flavoring agent and fragrance ingredient. The compound is generally recognized as safe for use in food and cosmetic applications at low concentrations. Standard toxicology assessments include acute toxicity studies, skin irritation and sensitization tests, and evaluation of genotoxicity potential. The α,β-unsaturated carbonyl moiety can act as a Michael acceptor, which may contribute to both its biological activity and potential toxicity through covalent modification of proteins and DNA. However, at typical exposure levels, the compound is considered to have a favorable safety profile.
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| References | |
| 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 a multifunctional compound with applications in organic synthesis, flavor and fragrance, and biological research. It serves as a key intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other bioactive compounds. In biological research, it is studied for its role as a bacterial metabolite produced by Xenorhabdus nematophila, where it functions as an immunosuppressant and enzyme inhibitor to facilitate insect pathogenesis. The compound's mechanism of action involves inhibition of phospholipase A2 through interaction with the enzyme's active site, disrupting insect immune function. It is not an approved drug but is used as a research chemical and flavoring agent. |
| Molecular Formula |
C10H10O
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|---|---|
| Molecular Weight |
146.1858
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| Exact Mass |
146.073
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| CAS # |
1896-62-4
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| Related CAS # |
Benzylideneacetone;122-57-6
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| PubChem CID |
637759
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| Appearance |
Off-white to light yellow <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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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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