| Size | Price | Stock | Qty |
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| 250mg |
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| 500mg |
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| 1g |
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| Other Sizes |
Purity: ≥98%
| Targets |
4-Diethylaminobenzaldehyde targets aldehyde dehydrogenase (ALDH) enzymes, specifically the ALDH1A1 and ALDH3A1 isoforms. It acts as a competitive inhibitor by binding to the active site and competing with the substrate aldehyde. This inhibition blocks the conversion of aldehydes to carboxylic acids, which is crucial for retinoic acid biosynthesis and the detoxification of reactive aldehydes. ALDH1A1 is a marker for cancer stem cells, and its inhibition can sensitize these cells to chemotherapy and reduce their tumor-initiating capacity.
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| ln Vitro |
4-Diethylaminobenzaldehyde (DEAB) forms a persistent covalent acetylase species, which irreversibly inactivates ALDH7A1, and is a reversible competitor (competes with the aldehyde substrate) for ALDH1 with a Ki value of 4 nM[1]. TMZ and 4-diethylaminobenzaldehyde were applied to the introduced cell line LN18 for ten days. The clonogenic potential of LN18 cells was significantly disrupted by TMZ in combination with 4-diethylaminobenzaldehyde (DEAB), according to the colony assay [3].
In vitro, 4-diethylaminobenzaldehyde is used to inhibit ALDH activity in cell-based assays, such as the ALDEFLUOR assay, to identify and isolate ALDH-bright (ALDHbr) stem cell populations. It exhibits an IC₅₀ of approximately 10-50 µM for ALDH1A1. The compound has been shown to reduce the ALDHbr population in various cancer cell lines, including breast, ovarian, and lung cancer cells, and to decrease their proliferation, clonogenicity, and resistance to chemotherapeutics. It also induces apoptosis in ALDH-positive cancer cells. |
| ln Vivo |
In vivo, 4-diethylaminobenzaldehyde has been used in animal models to evaluate the effect of ALDH inhibition on tumor growth. Intraperitoneal administration of the compound (e.g., 5-20 mg/kg) has been shown to reduce tumor burden and enhance the efficacy of chemotherapy in xenograft models. However, its in vivo use is limited by its moderate potency, rapid metabolism, and potential off-target effects. It serves as a proof-of-concept tool for validating ALDH as a therapeutic target in oncology.
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| Enzyme Assay |
In vitro enzyme inhibition assays for 4-diethylaminobenzaldehyde are performed using recombinant ALDH1A1 or ALDH3A1 enzymes. The enzyme is incubated with the substrate (e.g., propionaldehyde or acetaldehyde) and NAD⁺ in a buffer, and the formation of NADH is measured spectrophotometrically at 340 nm. The compound is tested at varying concentrations, and the IC₅₀ is calculated. The mechanism of inhibition (competitive, non-competitive) is determined by analyzing the kinetic parameters (Km, Vmax) in the presence and absence of the inhibitor.
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| Cell Assay |
In vitro cellular experiments for 4-diethylaminobenzaldehyde are carried out using cell lines with high ALDH activity. The ALDEFLUOR assay is a standard method: cells are incubated with the ALDH substrate BODIPY-aminoacetaldehyde and the inhibitor (4-DEAB) as a control. The ALDHbr population is quantified by flow cytometry. Additionally, cell viability, apoptosis, and gene expression changes (e.g., ALDH1A1, NANOG) are assessed. The compound's effect on chemosensitivity is determined by co-treating cells with cytotoxic drugs and measuring the combination index.
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| Animal Protocol |
In vivo animal studies for 4-diethylaminobenzaldehyde involve mouse xenograft models of human cancers. The compound is administered via IP injection, either alone or in combination with standard chemotherapy (e.g., cisplatin, paclitaxel). Tumor growth, animal survival, and histopathological changes are monitored. The ALDH activity in tumor tissue is measured using the ALDEFLUOR assay ex vivo. Pharmacokinetic parameters are partially studied, but the compound's short half-life and rapid clearance limit its utility for sustained in vivo inhibition.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of 4-diethylaminobenzaldehyde are characterized by rapid absorption and distribution. It has a short half-life (approximately 1 hour) in mice due to extensive metabolism by aldehyde oxidase and CYP450 enzymes. The compound is metabolized to its corresponding carboxylic acid, which is excreted renally. Its bioavailability after oral administration is low, and it is typically given intraperitoneally in research studies. Due to its rapid clearance, continuous infusion or multiple dosing may be required for sustained ALDH inhibition in vivo.
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| Toxicity/Toxicokinetics |
The toxicity profile of 4-diethylaminobenzaldehyde is moderate. In cell culture, it shows cytotoxicity at high concentrations (IC₅₀ > 100 µM in most normal cell lines). In animals, acute toxicity studies have reported an LD₅₀ of approximately 200 mg/kg (IP in rodents). Common adverse effects include mild sedation, respiratory depression, and liver enzyme elevation at high doses. The compound is not considered highly toxic for research use, but appropriate safety precautions are necessary.
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| References | |
| Additional Infomation |
4-(diethylamino)benzaldehyde is a member of the benzaldehyde family with a diethylamino substituent at the 4-position. It is an EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor. It belongs to the benzaldehyde family, tertiary amines, and aromatic amines.
4-Diethylaminobenzaldehyde is a widely used ALDH inhibitor and a chemical reagent in organic synthesis. Its primary application is in cancer research to identify and target ALDH-positive cancer stem cells. It serves as a tool to study aldehyde metabolism and the role of ALDH in drug resistance and tumor progression. However, its low potency and poor pharmacokinetics limit its therapeutic development; it is primarily used as a reference compound or a screening hit for more advanced ALDH inhibitors. It is also a precursor for the synthesis of various dyes and pharmaceutical intermediates. |
| Molecular Formula |
C₁₁H₁₅NO
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|---|---|
| Molecular Weight |
177.24
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| Exact Mass |
177.115
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| CAS # |
120-21-8
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| PubChem CID |
67114
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| Appearance |
Yellow to brown solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
329.6±0.0 °C at 760 mmHg
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| Melting Point |
37-41 °C(lit.)
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| Flash Point |
110.2±12.0 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.571
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| LogP |
2.87
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
13
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| Complexity |
146
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
MNFZZNNFORDXSV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H15NO/c1-3-12(4-2)11-7-5-10(9-13)6-8-11/h5-9H,3-4H2,1-2H3
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| Chemical Name |
4-(diethylamino)benzaldehyde
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| Synonyms |
4Diethylaminobenzaldehyde; 4 Diethylaminobenzaldehyde
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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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 (~564.21 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3.25 mg/mL (18.34 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 32.5 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.6421 mL | 28.2103 mL | 56.4207 mL | |
| 5 mM | 1.1284 mL | 5.6421 mL | 11.2841 mL | |
| 10 mM | 0.5642 mL | 2.8210 mL | 5.6421 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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