| 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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| 250mg |
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| 500mg |
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| Other Sizes |
Purity: ≥98%
| Targets |
Heme biosynthesis
Succinylacetone targets δ-aminolevulinic acid dehydratase (ALAD), the second enzyme in the heme biosynthesis pathway. By inhibiting ALAD, succinylacetone blocks the conversion of δ-aminolevulinic acid to porphobilinogen, leading to the accumulation of δ-aminolevulinic acid and disruption of heme synthesis. This inhibition is the basis for its use in studying heme metabolism and related disorders. |
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| ln Vitro |
4,6-Dioxoheptanoic acid (succinylacetone, SA) was examined with regard to its ability to a) inhibit the second enzyme of the heme pathway, δ-aminolevulinic acid (ALA) dehydratase, b) lower the heme concentration, and c) inhibit cell growth of murine erythroleukemia (MEL) cells in culture. SA profoundly inhibited ALA dehydratase in broken cell preparations at concentrations as low as 10−7 M. The stimulation of hemoglobin production by DMSO and butyrate in MEL cells was inhibited by the addition of SA to the cell medium. When 1 mM SA was added to the medium, there was a profound inhibition of ALA dehydratase activity, and the heme concentration of cells declined progressively with each cell division. Cell growth was markedly inhibited after two cell divisions [1].
In vitro, succinylacetone is a potent inhibitor of δ-aminolevulinic acid dehydratase. It decreases the growth of murine erythroleukemia cells when used at concentrations of 0.1 mM. The compound's ability to inhibit heme biosynthesis makes it a valuable tool for studying the role of heme in cellular processes. |
| ln Vivo |
In vivo, succinylacetone is used in research to study the pathophysiology of hereditary tyrosinemia type I, a disorder characterized by the accumulation of succinylacetone due to a deficiency of fumarylacetoacetate hydrolase. The compound's ability to inhibit heme biosynthesis and cause the accumulation of δ-aminolevulinic acid is used to model the biochemical abnormalities seen in this disorder.
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| Enzyme Assay |
This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
In vitro enzyme/receptor binding assays for succinylacetone typically involve evaluating its inhibitory activity against purified δ-aminolevulinic acid dehydratase. The enzyme is incubated with varying concentrations of succinylacetone and its substrate, δ-aminolevulinic acid. The reaction is monitored by measuring the formation of porphobilinogen, and the Ki or IC₅₀ is determined. |
| Cell Assay |
For in vitro cell-based assays, succinylacetone is dissolved in DMSO or aqueous buffers and applied to cultured cells such as erythroleukemia cells at concentrations ranging from 0.01-1 mM. The effects on cell proliferation, heme synthesis, and porphyrin accumulation are assessed after 24-72 hours of treatment.
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| Animal Protocol |
In vivo animal studies for succinylacetone are typically conducted in rodent models of hereditary tyrosinemia type I. Succinylacetone is administered orally or intraperitoneally at doses ranging from 1-100 mg/kg. The effects on heme biosynthesis, δ-aminolevulinic acid levels, and liver function are evaluated.
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| ADME/Pharmacokinetics |
Succinylacetone has a molecular formula of C₇H₁₀O₄ and a molecular weight of 158.15 g/mol. It is a white solid with a purity of ≥97%. It is soluble in DMSO and is typically stored as a powder at -20°C.
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| Toxicity/Toxicokinetics |
Health effects: Long-term high levels of succinylacetone are associated with type I tyrosinemia.
Succinylacetone is considered to have a manageable toxicity profile for research use. As a research chemical, it is not intended for human therapeutic use. Appropriate safety precautions, including the use of personal protective equipment, should be followed when handling the compound. |
| References | |
| Additional Infomation |
4,6-Dioxoheptanoic acid is a dioxomonocarboxylic acid, a derivative of heptanoic acid, in which the hydrogen atoms at positions 4 and 6 are replaced by oxo groups. It is an abnormal metabolite of the tyrosine metabolic pathway and a marker of type 1 tyrosinemia. It is a human metabolite. It is a β-diketone and a dioxomonocarboxylic acid. Succinylacetone is a metabolite of tyrosine and a specific marker of type 1 tyrosinemia. Type 1 tyrosinemia is a hereditary metabolic disorder caused by a deficiency of fumaroacetoacetase, the enzyme required to break down tyrosine. (A3530)
Succinylacetone is a potent inhibitor of δ-aminolevulinic acid dehydratase used as a research tool to study heme biosynthesis and related disorders. It is also known as 4,6-dioxoheptanoic acid. Succinylacetone is not approved for clinical use and is intended for research purposes only. It is supplied by various research chemical suppliers for non-human use. |
| Molecular Formula |
C7H10O4
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|---|---|
| Molecular Weight |
158.153
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| Exact Mass |
158.058
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| Elemental Analysis |
C, 53.16; H, 6.37; O, 40.46
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| CAS # |
51568-18-4
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| Related CAS # |
4,6-Dioxoheptanoic acid-13C5; 881835-86-5; 4,6-Dioxoheptanoic acid; 51568-18-4
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| PubChem CID |
5312
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| Appearance |
White to off-white solid powder
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| Density |
1.189 g/cm3
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| Boiling Point |
318.7ºC at 760 mmHg
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| Melting Point |
66-67ºC
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| Flash Point |
160.8ºC
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| Index of Refraction |
1.455
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| Source |
Endogenously produced metabolite
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| LogP |
0.399
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
11
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| Complexity |
183
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(=O)CC(=O)CCC(O)=O
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| InChi Key |
WYEPBHZLDUPIOD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H10O4/c1-5(8)4-6(9)2-3-7(10)11/h2-4H2,1H3,(H,10,11)
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| Chemical Name |
4,6-dioxoheptanoic acid
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| Synonyms |
NSC174804; NSC 174804; 4,6-DIOXOHEPTANOIC ACID; Succinylacetone; 51568-18-4; succinyl acetone; Heptanoic acid, 4,6-dioxo-; NSC 174804; CCRIS 1387; KZ0KV2Q190; NSC-174804
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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 (~632.3 mM; with ultrasonication)
H2O: ~100 mg/mL (~632.3 mM; with ultrasonication) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.81 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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 (15.81 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 DMSO stock solution (25.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (15.81 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 DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.3231 mL | 31.6156 mL | 63.2311 mL | |
| 5 mM | 1.2646 mL | 6.3231 mL | 12.6462 mL | |
| 10 mM | 0.6323 mL | 3.1616 mL | 6.3231 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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