Benzylideneacetone (trans-Benzylideneacetone) is a metabolite found in gram-negative entomopathogenic bacterium Xenorhabdus nematophila, it is an enzyme inhibitor against phospholipase A2 (PLA2). Benzylideneacetone is an immunosuppressa
Physicochemical Properties
| Molecular Formula | C10H10O |
| Molecular Weight | 146.1858 |
| Exact Mass | 146.073 |
| CAS # | 1896-62-4 |
| Related CAS # | Benzylideneacetone;122-57-6 |
| PubChem CID | 637759 |
| Appearance | Off-white to light yellow <39°C powder,>42°C liquid |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 260.8±9.0 °C at 760 mmHg |
| Melting Point | 38.5-41ºC |
| Flash Point | 65.6±0.0 °C |
| Vapour Pressure | 0.0±0.5 mmHg at 25°C |
| Index of Refraction | 1.563 |
| LogP | 2.17 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 11 |
| Complexity | 152 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(C([H])([H])[H])/C(/[H])=C(\[H])/C1C([H])=C([H])C([H])=C([H])C=1[H] |
| InChi Key | BWHOZHOGCMHOBV-BQYQJAHWSA-N |
| InChi Code | InChI=1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+ |
| Chemical Name | (E)-4-phenylbut-3-en-2-one |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| 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]. |
| References |
[1]. Benzylideneacetone, an immunosuppressant, enhances virulence of Bacillus thuringiensisagainst beet armyworm (Lepidoptera: Noctuidae). J Econ Entomol. 2008 Feb;101(1):36-41. |
| Additional Infomation |
Trans-benzylideneacetone is the trans-isomer of benzylideneacetone. It acts as an inhibitor of the enzyme phospholipase A2 (EC 3.1.1.4) of insects like diamond back moth. It has a role as a flavouring agent, a fragrance, a bacterial metabolite and an EC 3.1.1.4 (phospholipase A2) inhibitor. Benzylideneacetone has been reported in Basella alba and Polygala senega with data available. Benzylideneacetone is a flavouring ingredient. Benzylideneacetone is present in hydrolysed soy protein Benzylideneacetone belongs to the family of Phenylpropenes. These are compounds containing a phenylpropene moeity, which consists of a propene substituent bound to a phenyl group. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~684.04 mM) |
| 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. 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. 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 corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| 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 |