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| Other Sizes |
| Targets |
The primary target of trans-Benzylideneacetone is phospholipase A2 (PLA2), for which it acts as an enzyme inhibitor. PLA2 is involved in the release of arachidonic acid and subsequent production of inflammatory mediators. The compound also targets cancer cells, demonstrating cytotoxicity against various human cell lines including K562, KB, KB-VCR, and A549. As an immunosuppressant, it may target immune cell pathways. These targets make it relevant for inflammation, immunology, and cancer research.
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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, trans-Benzylideneacetone demonstrates PLA2 inhibitory activity. It exhibits cell growth inhibitory activity against the K562 human chronic myelogenous leukemia cell line with an IC50 of 17000.0 nM. The compound shows cytotoxicity against various human cell lines, including KB, KB-VCR, and A549. As an immunosuppressant, it modulates immune responses in cell-based assays. These in vitro activities support its use in cancer, inflammation, and immunology research. |
| ln Vivo |
In vivo, trans-Benzylideneacetone has potential applications as an immunosuppressant based on its in vitro PLA2 inhibitory and immunosuppressive activities. Its cytotoxicity against cancer cells suggests potential anticancer applications. However, detailed in vivo efficacy data are limited. The compound is a bacterial metabolite and is used in research on inflammation, immunity, and cancer. Further studies are needed to evaluate its therapeutic potential in animal models.
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| Enzyme Assay |
In vitro enzyme assays for trans-Benzylideneacetone involve measuring PLA2 inhibition. The compound is incubated with PLA2 enzyme at concentrations ranging from 0.1-1000 μM, and enzyme activity is measured using fluorescent or radiolabeled substrates. IC50 values are determined. Cytotoxicity assays are conducted using various human cancer cell lines (K562, KB, KB-VCR, A549) with compound concentrations ranging from 0.1-1000 μM for 24-72 hours. Cell viability is assessed using MTT or sulforhodamine B assays. All assays include appropriate controls and reference compounds.
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| Cell Assay |
In vitro cell-based assays for trans-Benzylideneacetone are conducted using cancer cell lines including K562 (chronic myelogenous leukemia), KB, KB-VCR, and A549. Cells are treated with compound concentrations ranging from 0.1-1000 μM for 24-72 hours. Cell viability is assessed using MTT or CellTiter-Glo assays. IC50 values are determined. Immunosuppressive activity is assessed using immune cell proliferation assays. Apoptosis is evaluated by annexin V/PI staining. Experiments include vehicle controls and positive controls (e.g., known PLA2 inhibitors or anticancer agents).
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| Animal Protocol |
In vivo animal studies with trans-Benzylideneacetone are limited, as the compound is primarily used as a research tool. Immunosuppression studies may be conducted in models of immune-mediated diseases. Anticancer studies may be conducted in mouse xenograft models. The compound is administered via intraperitoneal or oral routes at doses ranging from 1-50 mg/kg. Immune parameters or tumor growth are measured. Each group consists of 6-10 animals with vehicle-treated controls. Further studies are needed for comprehensive characterization.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of trans-Benzylideneacetone have not been extensively characterized. As a small, lipophilic molecule, it is expected to have moderate oral bioavailability and reasonable tissue distribution. The compound is a bacterial metabolite and likely undergoes hepatic metabolism through oxidation and conjugation, with elimination via biliary and renal excretion. Detailed PK parameters such as half-life, Cmax, and AUC require further investigation.
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| Toxicity/Toxicokinetics |
Toxicological data for trans-Benzylideneacetone are limited, as the compound is a research tool. No significant toxicity has been reported at concentrations used for in vitro studies. As a bacterial metabolite, it may have a reasonable safety profile. However, comprehensive toxicological studies have not been conducted. As with all research chemicals, appropriate safety precautions should be taken during handling, and the compound should be used only for research purposes.
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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.
trans-Benzylideneacetone is a bacterial metabolite with PLA2 inhibitory, immunosuppressive, and anticancer activities. It exhibits cytotoxicity against various human cancer cell lines including K562, KB, KB-VCR, and A549. The compound is used in research on inflammation, immunology, and cancer. It can also be used as a flavoring agent and spice. Not approved for clinical therapeutic use; intended for research purposes only. |
| 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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| Synonyms |
transBenzylideneacetone; trans Benzylideneacetone
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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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