| Size | Price | Stock | Qty |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| Targets |
The molecular targets of DCBA are not directly relevant to its biological activity, as it is a metabolite rather than a pharmacologically active compound. However, its parent compound DEET primarily targets insect olfactory receptors, specifically odorant receptor co-receptors (Orco) in mosquitoes and other insects, disrupting their ability to detect host-derived attractants. DCBA itself does not possess significant insect repellent activity and is considered a detoxification product. In mammalian systems, DCBA may interact with organic anion transporters for renal excretion and may undergo further conjugation reactions. As a carboxylic acid metabolite, it has the potential to bind to plasma proteins such as albumin, though with relatively low affinity. The compound's primary utility lies in its role as a exposure biomarker rather than as a therapeutic agent targeting specific biological molecules.
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| ln Vitro |
In vitro activity of DCBA is primarily related to its use as an analytical standard and reference compound in metabolism studies rather than as a biologically active agent with specific pharmacological effects. In enzyme kinetics studies, DCBA can be used as a substrate or product in assays investigating the metabolism of DEET by cytochrome P450 enzymes, particularly CYP2B6 and CYP2C19. The compound may be detected and quantified in in vitro metabolism assays using liver microsomes or recombinant P450 enzymes. In cell-based systems, DCBA is not typically associated with significant cytotoxicity or biological activity at concentrations relevant to biomonitoring. Its primary in vitro application is in the development and validation of analytical methods, including LC-MS/MS and HPLC assays, for the quantification of DEET exposure in biological samples. Specific IC50 or EC50 values for DCBA against biological targets are not applicable.
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| ln Vivo |
In vivo activity of DCBA is characterized by its role as a urinary biomarker of DEET exposure. Following DEET absorption in humans and animals, DCBA is formed through hepatic metabolism and excreted in urine, where its concentration reflects the extent of DEET exposure. In pharmacokinetic studies, the urinary excretion of DCBA has been used to assess the absorption, distribution, metabolism, and elimination of DEET. The compound itself does not exhibit therapeutic effects in vivo but serves as an indicator of metabolic processing. In animal studies, the measurement of DCBA in urine has been employed to evaluate DEET exposure in various species, including rats, mice, and humans. The compound's in vivo half-life is related to the elimination of DEET and its metabolites, typically with a urinary excretion half-life of several hours to days depending on the exposure route and dose.
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| Enzyme Assay |
For in vitro enzyme assays involving DCBA as a metabolite, the following protocol is typically used: Liver microsomes (e.g., human or rat) are incubated with DEET (10-100 μM) in the presence of an NADPH-regenerating system (1 mM NADPH, 5 mM glucose-6-phosphate, 1 U/mL glucose-6-phosphate dehydrogenase) in 100 mM phosphate buffer (pH 7.4) at 37°C for 30-60 minutes. The reaction is terminated by the addition of ice-cold acetonitrile containing an internal standard. After centrifugation, the supernatant is analyzed by LC-MS/MS to quantify the formation of DCBA. For DCBA detection, a C18 column is used with a mobile phase of 0.1% formic acid in water and acetonitrile, with gradient elution. The mass spectrometer is operated in negative ion mode, monitoring the transition m/z 220 → 176 for DCBA. Calibration curves are prepared using authentic DCBA standards. Alternatively, recombinant CYP enzymes can be used to identify specific P450 isoforms responsible for DCBA formation.
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| Cell Assay |
For in vitro cell-based assays with DCBA, the following typical protocol is used: Human hepatocytes (cryopreserved or freshly isolated) are cultured in Williams' E medium supplemented with 10% FBS and antibiotics at 37°C in 5% CO₂. Cells are seeded in 24-well plates at 5 × 10⁵ cells per well and allowed to attach for 4-6 hours. DEET is added to the culture medium at concentrations of 10-100 μM, and cells are incubated for 24 hours. Culture medium and cell lysates are collected at various time points. DCBA is extracted from the medium and cell lysates using protein precipitation with acetonitrile, followed by LC-MS/MS analysis. For cytotoxicity assessment, hepatocytes or other cell lines (e.g., HepG2) are treated with DCBA at concentrations of 0.1-1000 μM for 24-72 hours, and cell viability is assessed using the MTT assay. However, DCBA is typically not used in cell-based functional assays due to its status as a metabolite rather than an active compound.
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| Animal Protocol |
For in vivo animal studies involving DCBA as a biomarker, the following general protocol is used: Male Sprague-Dawley rats (8-10 weeks old, 200-250 g) are administered DEET orally by gavage at doses of 10, 50, and 100 mg/kg in corn oil or a suitable vehicle. Blood samples are collected from the tail vein at predetermined time points (0, 1, 2, 4, 6, 8, 12, 24, 48 hours post-dose). Urine samples are collected using metabolic cages over 24-hour intervals for up to 72 hours. Plasma and urine samples are analyzed for DEET and DCBA concentrations by LC-MS/MS. For human biomonitoring studies, urine samples are collected from volunteers after topical application of DEET-containing repellents, and DCBA concentrations are measured to assess DEET exposure. The study design includes appropriate control groups and ethical approvals for human participation. Pharmacokinetic parameters are calculated using non-compartmental analysis.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of DCBA are derived from its role as the primary metabolite of DEET. After DEET absorption, DCBA is formed primarily through hepatic CYP450-mediated oxidation, with CYP2B6 and CYP2C19 identified as major isoforms involved in its formation. DCBA is highly water-soluble compared to its parent compound and is readily excreted in urine. In humans, following topical application of DEET, urinary DCBA concentrations peak within 6-12 hours and decline with a half-life of approximately 10-20 hours. The compound exhibits minimal plasma protein binding due to its hydrophilic carboxylic acid group. DCBA is not extensively metabolized further but may undergo glucuronidation or glycine conjugation to a limited extent. Renal clearance is the primary elimination pathway, with the compound excreted unchanged in urine. The urinary excretion of DCBA accounts for approximately 5-20% of the administered DEET dose, depending on the route of administration and species.
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| Toxicity/Toxicokinetics |
The toxicity profile of DCBA is not extensively characterized, as it is a metabolite rather than a therapeutic agent. However, DCBA is generally considered to have low toxicity, consistent with its status as a detoxification product of DEET. In toxicological studies, DCBA has not been associated with significant adverse effects at concentrations typically observed in biomonitoring studies. The compound is not genotoxic or mutagenic in standard assays. Acute toxicity studies in rodents have not been specifically conducted for DCBA, but the parent compound DEET has an oral LD50 of approximately 2000-3000 mg/kg in rats, indicating low acute toxicity. DCBA is not classified as a carcinogen or reproductive toxicant. As a research chemical, DCBA should be handled with standard laboratory safety precautions, including the use of appropriate personal protective equipment. The compound is stable under recommended storage conditions and does not pose significant handling hazards.
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| References |
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| Additional Infomation |
DCBA (CAS# 72236-23-8) is a drug metabolite of the insect repellent DEET, with a molecular formula of C12H15NO3 and a molecular weight of 221.25 g/mol. It is also known as DEET ω-carboxylic acid and N,N-diethyl-meta-toluamide metabolite. The concentration of DCBA in urine serves as a reliable biomarker for assessing DEET exposure in humans and animals. DCBA is used in analytical method development, environmental monitoring, and pharmacokinetic studies. Future research could focus on developing more sensitive analytical methods for DCBA detection, investigating its potential as a biomarker for DEET exposure in vulnerable populations, and exploring its environmental fate and persistence.
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| Molecular Formula |
C12H15NO3
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| Molecular Weight |
221.2524
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| Exact Mass |
221.105
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| Elemental Analysis |
C, 65.14; H, 6.83; N, 6.33; O, 21.69
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| CAS # |
72236-23-8
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| PubChem CID |
155713
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| Appearance |
White to off-white solid powder
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| Density |
1.162g/cm3
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| Boiling Point |
418.9ºC at 760 mmHg
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| Flash Point |
207.2ºC
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| Index of Refraction |
1.552
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| LogP |
1.866
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
16
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| Complexity |
261
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCN(CC)C(=O)c1cccc(c1)C(=O)O
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| InChi Key |
PXXLQQDIFVPNMP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H15NO3/c1-3-13(4-2)11(14)9-6-5-7-10(8-9)12(15)16/h5-8H,3-4H2,1-2H3,(H,15,16)
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| Chemical Name |
3-(diethylcarbamoyl)benzoic acid
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| Synonyms |
DCBA; DEET ω-Carboxylic Acid; DEET-Carboxylic Acid;
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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) |
DMSO : ~100 mg/mL (~451.98 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.30 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 (11.30 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 (11.30 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 | 4.5198 mL | 22.5989 mL | 45.1977 mL | |
| 5 mM | 0.9040 mL | 4.5198 mL | 9.0395 mL | |
| 10 mM | 0.4520 mL | 2.2599 mL | 4.5198 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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