| Size | Price | Stock | Qty |
|---|---|---|---|
| 25g |
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| Other Sizes |
| Targets |
2,4-Dihydroxypyrimidine-5-carboxylic Acid is an endogenous metabolite with no established high-affinity drug target. The compound is functionally related to uracil and is a conjugate acid of uracil-5-carboxylate. It is used in medicinal chemistry as a building block to prepare 1-aromatic aldoxime uracil derivatives, which are thymidine phosphorylase (TP) inhibitors of potential utility in cancer therapy. TP is often upregulated in solid tumors and catalyzes the phosphorolysis of nucleosides.
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| ln Vitro |
In vitro, 2,4-Dihydroxypyrimidine-5-carboxylic Acid is used as a starting material for the synthesis of uracil derivatives that inhibit thymidine phosphorylase (TP). Thymidine phosphorylase is involved in tumor angiogenesis and the activation of fluoropyrimidine prodrugs. The uracil-5-carboxylate scaffold has been incorporated into compounds with submicromolar IC50 values against TP. The parent compound itself does not have reported IC50 values against TP.
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| ln Vivo |
In vivo, 2,4-Dihydroxypyrimidine-5-carboxylic Acid itself has no reported pharmacological activity. However, it is a key synthetic intermediate for the preparation of thymidine phosphorylase inhibitors, which have potential in vivo anti-angiogenic and anti-tumor activities. The compound is used in prodrug strategies for delivering uracil-based therapeutics. No direct animal efficacy studies have been reported for the parent compound.
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| Enzyme Assay |
For in vitro chemical synthesis reactions, 2,4-Dihydroxypyrimidine-5-carboxylic Acid is weighed out and dissolved in an appropriate organic solvent (e.g., DMSO, DMF, or methanol) to prepare stock solutions (e.g., 100 mM). The compound is then used as a starting material in multi-step synthetic reactions: coupling reactions, amide bond formation, or esterification to generate uracil-based derivatives for biological evaluation. Typical reaction conditions include room temperature to reflux for 1-24 hours.
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| Cell Assay |
For cell-based studies of thymidine phosphorylase inhibitors derived from 2,4-Dihydroxypyrimidine-5-carboxylic Acid, the synthesized uracil derivatives are tested in cancer cell lines. Cells (e.g., HT-29, MCF-7, HeLa) are cultured in standard medium (RPMI-1640 or DMEM with 10% FBS). Cells are seeded in 96-well plates at 5,000-10,000 cells/well and treated with test compounds (0-100 microM) for 48-72 hours. Cytotoxicity (MTT assay), thymidine phosphorylase enzyme activity (cell lysates), and anti-proliferative effects are measured. IC50 values are calculated by dose-response curves.
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| Animal Protocol |
For in vivo studies of thymidine phosphorylase inhibitors derived from 2,4-Dihydroxypyrimidine-5-carboxylic Acid, synthesized uracil derivatives are typically evaluated in rodent xenograft models of cancer. Tumor-bearing mice (e.g., HT-29 colon cancer xenografts) are treated with test compounds via oral gavage or intraperitoneal injection daily for 2-4 weeks. Tumor volume is measured every 2-3 days with calipers. At study termination, tumors are excised for TP enzyme activity assays, histology, and immunohistochemistry. No standard protocol exists for the parent compound itself.
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| ADME/Pharmacokinetics |
2,4-Dihydroxypyrimidine-5-carboxylic Acid is a small, polar molecule (MW 156.10, logP -1.43) with high water solubility at pH>7. It has two hydrogen bond donors and four acceptors. As a synthetic intermediate, it is not a drug and no PK studies have been reported for this specific compound. If administered systemically, it would be expected to have low oral bioavailability, high renal clearance, and limited tissue penetration due to its low lipophilicity.
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| Toxicity/Toxicokinetics |
2,4-Dihydroxypyrimidine-5-carboxylic Acid is an endogenous metabolite with low expected toxicity. The compound has a melting point of 283degC (dec.). It is a white to light yellow solid powder. No specific LD50 data is reported. The compound may cause eye and skin irritation. Standard laboratory safety precautions (gloves, safety glasses, fume hood) are recommended. The compound is not intended for human consumption. No reproductive or developmental toxicity data is available.
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| Additional Infomation |
Uracil-5-carboxylic acid is a pyrimidine monocarboxylic acid, a compound in which uracil is linked to a carboxyl group at the 5-position. It is functionally related to uracil. It is the conjugate acid of uracil-5-carboxylic acid ester and a tautomer of 2,4-dihydroxypyrimidine-5-carboxylic acid. 2,4-Dihydroxypyrimidine-5-carboxylic acid has been reported in stevia, and relevant data are available. See also: Uracil-5-carboxylic acid ester (note moved here).
2,4-Dihydroxypyrimidine-5-carboxylic Acid is not a drug but a research-use biochemical and synthetic building block. It has no approved therapeutic status, no clinical trial history, and is not intended for human consumption. It is used in the preparation of 1-aromatic aldoxime uracil derivatives as thymidine phosphorylase inhibitors for cancer research. The compound also serves as an endogenous metabolite standard for LC-MS applications and is a tautomer of uracil-5-carboxylic acid. Available with >97% purity from chemical suppliers. |
| Molecular Formula |
C5H4N2O4
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|---|---|
| Molecular Weight |
156.10
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| Exact Mass |
156.017
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| CAS # |
23945-44-0
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| PubChem CID |
90301
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| Appearance |
White to light yellow solid powder
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| Density |
1.8±0.1 g/cm3
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| Boiling Point |
564.9±60.0 °C at 760 mmHg
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| Melting Point |
283 °C (dec.)(lit.)
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| Flash Point |
295.4±32.9 °C
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| Vapour Pressure |
0.0±1.6 mmHg at 25°C
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| Index of Refraction |
1.705
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| LogP |
-1.43
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
268
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=C(C(=O)NC(=O)N1)C(=O)O
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| InChi Key |
ZXYAAVBXHKCJJB-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H4N2O4/c8-3-2(4(9)10)1-6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
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| Chemical Name |
2,4-dioxo-1H-pyrimidine-5-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: 27.5 mg/mL (176.17 mM)
H2O: < 0.1 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.75 mg/mL (17.62 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 27.5 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: ≥ 2.75 mg/mL (17.62 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 27.5 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 | 6.4061 mL | 32.0307 mL | 64.0615 mL | |
| 5 mM | 1.2812 mL | 6.4061 mL | 12.8123 mL | |
| 10 mM | 0.6406 mL | 3.2031 mL | 6.4061 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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