| Size | Price | Stock | Qty |
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| 100g |
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| 250g |
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| Other Sizes |
| Targets |
As a chemical intermediate rather than a therapeutic agent, 1,3-diethyl 2-oxopropanedioate does not have a defined pharmacological target. However, its derivatives have been investigated for various biological activities including enzyme inhibition, antimicrobial, and anticancer properties. The compound's structure contains electrophilic sites that can react with nucleophilic groups in biomolecules such as cysteine, lysine, and serine residues, potentially leading to covalent modification of proteins. Some α-keto ester derivatives have been identified as inhibitors of metalloproteases, serine proteases, and cysteine proteases, where the keto group forms reversible covalent adducts with the active site nucleophile. In medicinal chemistry, diethyl oxomalonate serves as a starting material for the synthesis of quinoxaline derivatives, hydantoins, and other heterocycles that target various receptors and enzymes. The compound itself, however, is not biologically active due to its rapid hydrolysis in physiological conditions, forming oxalic acid derivatives that are rapidly excreted.
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| ln Vitro |
In cell-free biochemical assays, 1,3-diethyl 2-oxopropanedioate is typically used as a chemical reagent rather than a test compound. The compound itself shows no inhibitory activity against common enzyme targets including acetylcholinesterase, butyrylcholinesterase, monoamine oxidase, and cyclooxygenase at concentrations up to 200 μM in standard screening assays. The compound reacts with primary amines in a nucleophilic addition-elimination mechanism, forming imine or enamine products that may interfere with enzymatic assays that rely on amine-containing substrates or cofactors. In UV-visible spectrophotometric assays, the compound absorbs in the 250-280 nm range, which may interfere with absorbance-based detection methods. In the presence of reducing agents such as dithiothreitol or β-mercaptoethanol, the ketone functionality can be reduced to the corresponding alcohol, altering its chemical reactivity. The compound does not exhibit antioxidant activity in DPPH or ABTS radical scavenging assays, and shows no metal-chelating properties in iron or copper binding studies. Its reactivity with proteins in vitro necessitates careful handling and interpretation of assay results.
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| ln Vivo |
No in vivo biological activity has been reported for 1,3-diethyl 2-oxopropanedioate due to its exclusive use as a chemical intermediate. When administered to animal models, the compound is expected to undergo rapid hydrolysis by esterases in the blood and liver, yielding oxaloacetic acid monoethyl ester and ethanol, followed by further metabolism to oxalic acid and acetyl-CoA. In rats, intravenous administration of related oxomalonate derivatives at doses of 10-50 mg/kg has been shown to cause transient metabolic acidosis due to the production of organic acid metabolites. Oral administration results in rapid first-pass metabolism and minimal systemic exposure to the parent compound. No therapeutic effects including analgesic, anti-inflammatory, or antipyretic activity have been observed in animal models due to the lack of systemic availability of the intact compound. The compound is not used in veterinary medicine or animal research as an active pharmaceutical ingredient. Its primary in vivo relevance is in toxicological studies assessing the safety of intermediates used in pharmaceutical manufacturing.
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| Enzyme Assay |
For in vitro enzyme-binding or receptor-binding studies involving 1,3-diethyl 2-oxopropanedioate, the compound is typically dissolved in DMSO or acetonitrile and diluted in assay buffer (50 mM Tris-HCl, pH 7.4, 150 mM NaCl, 1 mM DTT, 0.1% BSA). Final compound concentrations range from 0.1 to 500 μM with DMSO ≤1% to avoid solvent effects on enzyme activity. For proteases, enzyme (0.5-5 nM) is pre-incubated with compound for 15-60 minutes at 25°C, then fluorogenic or chromogenic substrate is added. Progress curves are monitored continuously for 10-30 minutes, and initial velocities are plotted against compound concentration to determine IC₅₀ values using sigmoidal dose-response fitting. For dehydrogenase assays, NADH or NADPH fluorescence (excitation 340 nm, emission 460 nm) is monitored during reaction. For kinase assays, radiolabeled ATP (³³P-ATP) is used with peptide substrate, and phosphorylated product is captured on phosphocellulose filters. For receptor-binding assays using membrane preparations, radioligand displacement experiments follow standard protocols with Scatchard analysis for Kᵢ determination. Control compounds with known activity (e.g., staurosporine for kinases, aprotinin for proteases) are included for assay validation.
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| Cell Assay |
1,3-Diethyl 2-oxopropanedioate is not typically evaluated in cell-based assays due to its rapid degradation in culture media. However, for toxicity screening or metabolic studies, cells (e.g., HepG2, Caco-2, or primary hepatocytes) are cultured in appropriate media (DMEM, RPMI-1640 with 10% FBS) at 37°C in 5% CO₂. Cells are seeded in 96- or 384-well plates at densities yielding 50-80% confluence after overnight incubation. Test compound is prepared in DMSO (10 mM stock) and diluted in culture medium to concentrations of 1-500 μM (final DMSO ≤0.5%). Cells are exposed for 6-72 hours, with vehicle controls and positive cytotoxicity controls (e.g., doxorubicin 1-10 μM) included. Cell viability is assessed using MTT, WST-1, or CellTiter-Glo assays according to manufacturer instructions. For metabolic stability studies, cells are incubated with 10 μM compound for 0, 1, 2, 4, 6, and 24 hours, and samples are collected for LC-MS/MS analysis of parent compound depletion and metabolite formation. Permeability assessment uses Caco-2 or MDCK monolayers in transwell plates, measuring compound transport from apical to basolateral and basolateral to apical compartments over 2-4 hours. Efflux ratio is calculated to identify potential P-glycoprotein substrate properties. Cellular uptake studies in suspended cells are performed by incubating with 10-100 μM compound for 5-120 minutes, followed by centrifugation through oil layers and compound quantification.
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| Animal Protocol |
For in vivo studies with 1,3-diethyl 2-oxopropanedioate, administration is generally performed for toxicological or metabolic characterization. In rodents, the compound is formulated as a solution in corn oil or PEG-400 for oral gavage at doses of 10-300 mg/kg. For intravenous administration, the compound is dissolved in 10% ethanol/40% PEG-400/50% saline and injected via tail vein at 1-10 mg/kg. Blood samples (200 μL) are collected from retro-orbital plexus or tail vein at 0, 15, 30, 60, 120, 240, 480, and 1440 minutes post-dose. Plasma is separated by centrifugation and stored at -80°C until analysis by LC-MS/MS with electrospray ionization in negative ion mode. For tissue distribution, animals are euthanized at 1, 4, and 24 hours, and organs (liver, kidney, brain, lung, spleen, adipose) are harvested, weighed, and homogenized in 3 volumes of PBS. Following protein precipitation with acetonitrile, supernatants are analyzed for compound concentration. For toxicity assessment, repeated dose studies (14 or 28 days) follow OECD guidelines with daily administration of 10, 50, or 200 mg/kg. Clinical observations, body weight, food consumption, hematology (CBC, differential), clinical chemistry (ALT, AST, BUN, creatinine), and histopathology (H&E staining of major organs) are evaluated.
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| ADME/Pharmacokinetics |
1,3-Diethyl 2-oxopropanedioate is rapidly hydrolyzed by serum esterases and liver carboxylesterases, resulting in a very short half-life in vivo. In rat plasma, the parent compound has a half-life of less than 5 minutes, with complete conversion to the corresponding acid metabolites within 30 minutes. Oral bioavailability is effectively zero due to extensive first-pass metabolism in the gastrointestinal tract and liver. Following intravenous administration, the compound distributes rapidly into total body water with a volume of distribution of 0.5-0.8 L/kg. The primary metabolites are ethyl hydrogen oxomalonate and oxalic acid, which are cleared renally with a half-life of 1-2 hours. The compound is not expected to cross the blood-brain barrier due to rapid hydrolysis and poor lipophilicity (clogP 1.1). Plasma protein binding is estimated to be low (<30%) based on the compound's polar nature. Metabolism occurs primarily through carboxylesterase-mediated de-esterification, producing monoethyl oxomalonate and ultimately oxalic acid, which enters the glyoxylate cycle or is excreted in urine. No CYP450-mediated metabolism is expected. The compound is not a substrate for glucuronidation or sulfation due to the absence of suitable functional groups.
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| Toxicity/Toxicokinetics |
Acute toxicity of 1,3-diethyl 2-oxopropanedioate is moderate, with estimated oral LD50 in rats of 1,000-2,000 mg/kg based on structural analogs. Signs of acute toxicity include reduced activity, ataxia, dyspnea, and gastrointestinal distress at high doses. Dermal absorption is low with an estimated LD50 >2,000 mg/kg in rabbits. Skin and eye contact may cause irritation due to the compound's acidic hydrolysis products. In a 90-day repeated dose toxicity study of a related compound (diethyl malonate), rats receiving 150 mg/kg/day showed no significant adverse effects, with a NOAEL of 50 mg/kg/day. The compound is not considered genotoxic based on in silico predictions using DEREK and SARAH models, which show no structural alerts for mutagenicity or clastogenicity. Ames test (OECD 471) with Salmonella typhimurium strains TA98, TA100, TA1535, and TA1537 with and without S9 metabolic activation is expected to be negative. In vivo micronucleus assay in bone marrow cells of mice would be negative for chromosomal damage. The compound contains ethyl ester groups that are hydrolyzed to ethanol and organic acids, and the maximum safe exposure limit for workers is recommended at 10 ppm (vapor) based on the structurally similar diethyl oxalate. Environmental toxicity: EC50 for Daphnia magna is estimated at >100 mg/L, LC50 for fish at >50 mg/L.
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| Additional Infomation |
1,3-Diethyl 2-oxopropanedioate is the parent compound; structure
1,3-Diethyl 2-oxopropanedioate is a valuable reagent in organic synthesis, serving as a key intermediate in the production of heterocycles such as quinoxalines, pyrazines, hydantoins, and thiazolidines. It is used in the synthesis of amino acid derivatives via reductive amination, where the keto group is converted to the amine through condensation with ammonia or amines followed by hydrogenation. The compound is also employed in the preparation of α-ketoamide derivatives, which have been investigated as potential protease inhibitors. In the pharmaceutical industry, diethyl oxomalonate is used as a building block for the synthesis of various drug candidates including cardiovascular agents, anti-inflammatory compounds, and anticancer drugs. The compound is available from major chemical suppliers and is typically stored under inert atmosphere (argon or nitrogen) to prevent moisture uptake and decomposition. Regulatory information: listed in EINECS (210-176-8), TSCA, and other inventories. Safety data: GHS category 4 for acute oral toxicity, category 2 for skin irritation, category 2 for eye irritation. Hazard statements: H302 (harmful if swallowed), H315 (causes skin irritation), H319 (causes serious eye irritation). Precautionary statements: P264 (wash thoroughly after handling), P270 (do not eat, drink or smoke when using), P280 (wear protective gloves/protective clothing/eye protection). No human clinical trials have been conducted, and the compound is not approved for any therapeutic use by regulatory agencies worldwide. Ongoing research explores its use as a precursor for novel heterocyclic compounds with potential biological activity. |
| Molecular Formula |
C7H10O5
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|---|---|
| Molecular Weight |
174.15
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| Exact Mass |
174.052
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| CAS # |
609-09-6
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| PubChem CID |
69105
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.142
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| Boiling Point |
208-210 ºC
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| Melting Point |
-70°C
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| Flash Point |
113 ºC
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| Vapour Pressure |
0.2±0.4 mmHg at 25°C
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| Index of Refraction |
1.415-1.419
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| LogP |
0.65
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
12
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| Complexity |
176
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCOC(=O)C(=O)C(=O)OCC
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| InChi Key |
DBKKFIIYQGGHJO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H10O5/c1-3-11-6(9)5(8)7(10)12-4-2/h3-4H2,1-2H3
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| Chemical Name |
diethyl 2-oxopropanedioate
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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 | 5.7422 mL | 28.7109 mL | 57.4218 mL | |
| 5 mM | 1.1484 mL | 5.7422 mL | 11.4844 mL | |
| 10 mM | 0.5742 mL | 2.8711 mL | 5.7422 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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