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| Other Sizes |
| Targets |
IC50: 13.10 μg/mL (Botrytis cinerea); MIC: 32 μg/mL (B. cinerea)[1]
trans,trans-Dibenzylideneacetone (DBA) targets chitinase, an enzyme produced by the fungal pathogen Botrytis cinerea that degrades chitin, a key component of fungal cell walls. By inhibiting chitinase, DBA disrupts fungal cell wall remodeling and hyphal growth, leading to antifungal effects. DBA does not have a defined target in mammalian cells; in organic synthesis, it acts as a ligand for palladium(0) in catalytic reactions (Pd2(dba)3 and Pd(dba)2), stabilizing the metal center and facilitating oxidative addition and transmetalation steps. |
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| ln Vitro |
In vitro, trans,trans-Dibenzylideneacetone inhibits Botrytis cinerea chitinase with an IC50 of 13.10 microg/mL. The minimum inhibitory concentration (MIC) against B. cinerea is 32 microg/mL. The EC50 values for inhibition of mycelial growth and spore germination are 16.29 and 14.64 microg/mL, respectively. DBA can control B. cinerea infection in cherry tomatoes by inhibiting chitinase activity. In palladium-catalyzed cross-coupling reactions, DBA acts as a ligand, stabilizing Pd(0) and facilitating C-C and C-N bond formation.
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| ln Vivo |
In vivo, trans,trans-Dibenzylideneacetone has been shown to control gray mold (Botrytis cinerea) infection in cherry tomatoes (a post-harvest fruit model) by inhibiting chitinase activity. This suggests potential as a post-harvest fungicide for fruit preservation. No in vivo studies in mammals have been reported. DBA is not developed as a systemic antifungal drug for human use due to potential toxicity and lack of selectivity for fungal vs. mammalian targets. It remains primarily a research chemical.
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| Enzyme Assay |
Generic enzyme inhibition assay for chitinase: Recombinant Botrytis cinerea chitinase is incubated with various concentrations of trans,trans-Dibenzylideneacetone (0.1-100 microg/mL) in assay buffer (50 mM sodium acetate, pH 5.5). The chitinase substrate (e.g., 4-methylumbelliferyl N,N‘,N“-triacetylchitotriose, 4-MU-(GlcNAc)3, 100 microM) is added. The mixture is incubated at 37degC for 30-60 minutes. The reaction is stopped with 0.1 M Na2CO3. Fluorescence is measured at excitation 360 nm and emission 450 nm. IC50 values are calculated from dose-response curves. For DBA, IC50 = 13.10 microg/mL. Pd coordination assays: UV-Vis spectrophotometry monitors the formation of Pd2(dba)3 complexes.
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| Cell Assay |
Antifungal cell-based assay: Botrytis cinerea is cultured on potato dextrose agar (PDA) plates at 25degC. Spores are harvested and resuspended in potato dextrose broth (PDB). For mycelial growth inhibition: fungal plugs (5 mm diameter) are placed on PDA plates containing various concentrations of DBA (0-100 microg/mL). After 3-5 days of incubation at 25degC, colony diameters are measured, and EC50 values are calculated. For spore germination inhibition: spores are incubated in PDB with DBA (0-100 microg/mL) for 24-48 hours. Germination percentage is determined microscopically. For DBA, EC50 values for mycelial growth and spore germination are 16.29 and 14.64 microg/mL, respectively. MIC is 32 microg/mL. Cytotoxicity in mammalian cells (e.g., HeLa, NIH3T3) can also be assessed by MTT assay.
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| Animal Protocol |
In vivo protocol for post-harvest fruit antifungal activity: Cherry tomatoes (Solanum lycopersicum) are surface-sterilized with 70% ethanol. Using a sterile needle, a wound (2 mm depth, 3 mm diameter) is made on the equator of each fruit. B. cinerea spore suspension (10 microL of 1×10⁶ spores/mL) is inoculated into the wound. After 1-2 hours, trans,trans-Dibenzylideneacetone is applied as an aqueous suspension (0.5-5 mg/mL) either by spraying or by injecting 10-20 microL into the wound site. Fruits are incubated in humid chambers at 25degC. Lesion diameter is measured daily for 5-7 days. The percentage of infection inhibition is calculated compared to untreated control. For DBA, effective control of B. cinerea infection was demonstrated.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for DBA in animals are not available. As a hydrophobic compound (logP 4.87), DBA has low water solubility. For in vitro assays, it is dissolved in DMSO or ethanol. For in vivo formulation (if needed for animal studies), a vehicle of 5% DMSO, 30% PEG300, 5% Tween 80, 60% saline is recommended for intraperitoneal administration. Powder stored at -20degC for 3 years, in solvent at -80degC for 6 months. Melting point: 107-113degC. Density: 1.1+/-0.1 g/cm3.
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| Toxicity/Toxicokinetics |
Comprehensive toxicology data are not publicly available. As an unsaturated ketone with potential electrophilic reactivity, DBA may be a skin and eye irritant. Standard laboratory precautions apply: use gloves, goggles, and lab coat; avoid inhalation and skin contact. DBA may cause allergic skin reactions. No acute toxicity data (LD50) or repeat-dose toxicity studies are available. In mammalian cell assays (e.g., HeLa, NIH3T3), DBA exhibits concentration-dependent cytotoxicity at high concentrations (>50 microg/mL) but is generally well tolerated at lower concentrations (<25 microg/mL).
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| References | |
| Additional Infomation |
GHS hazard classification: not specifically classified. DBA is a fruit antifungal agent used primarily in agricultural post-harvest research to control gray mold (Botrytis cinerea). It also serves as a ligand in palladium-catalyzed cross-coupling reactions (e.g., Buchwald-Hartwig amination). The trans,trans isomer (E,E) is the most common and stable isomer; cis isomers are less stable. The compound is also known as (E,E)-1,5-diphenyl-1,4-pentadien-3-one. No clinical trials or drug approvals exist.
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| Molecular Formula |
C17H14O
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|---|---|
| Molecular Weight |
234.30
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| CAS # |
35225-79-7
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| Appearance |
Typically exists as solids at room temperature
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
400.7±34.0 °C at 760 mmHg
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| Melting Point |
107-113 °C
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| Flash Point |
176.1±20.6 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.65
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| LogP |
4.87
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| SMILES |
O=C(/C(/[H])=C(\[H])/C1C([H])=C([H])C([H])=C([H])C=1[H])/C(/[H])=C(\[H])/C1C([H])=C([H])C([H])=C([H])C=1[H]
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| Synonyms |
(E,E)-Dibenzylideneacetone; (E,E)-Dibenzylideneacetone; trans,trans-Dibenzalacetone
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.2680 mL | 21.3402 mL | 42.6803 mL | |
| 5 mM | 0.8536 mL | 4.2680 mL | 8.5361 mL | |
| 10 mM | 0.4268 mL | 2.1340 mL | 4.2680 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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