| Identification | Back Directory | [Name]
4,6-DIOXOHEPTANOIC ACID | [CAS]
51568-18-4 | [Synonyms]
SUCCINYLACETONE
4,6-dioxoheptanoicaci
[13C7]-Succinylacetone
4,6-DIOXOHEPTANOIC ACID
Heptanoic acid, 4,6-dioxo-
Succinylacetone-3,4,5,6,7-13C5
4,6-Dioxoheptanoic acid-3,4,5,6,7-13C5 | [Molecular Formula]
C7H10O4 | [MDL Number]
MFCD00002797 | [MOL File]
51568-18-4.mol | [Molecular Weight]
158.15 |
| Questions And Answer | Back Directory | [Synthesis]
4,6-Dioxoheptanoic acid (DOHA): Ethyl acetal (240 mg, 1.2 mmol) was dissolved in AcOH/H₂O (20 mL, 3:1, v/v) solution and stirred at 50 °C for 4 h under Ar protection. The reaction progress was monitored by TLC (CH₂Cl₂/CH₃OH 10:1). Once the reaction was complete, the solvent was removed by rotary evaporation to give crude 4,6-dioxoheptanoic acid (172.7 mg, 1.09 mmol, 91%). |
| Chemical Properties | Back Directory | [Melting point ]
66-67 °C(lit.)
| [Boiling point ]
318.7±17.0 °C(Predicted) | [density ]
1.189±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
powder
| [pka]
4.54±0.17(Predicted) | [color ]
White to Off-White | [Appearance]
white solid | [InChI]
InChI=1S/C7H10O4/c1-5(8)4-6(9)2-3-7(10)11/h2-4H2,1H3,(H,10,11) | [InChIKey]
WYEPBHZLDUPIOD-UHFFFAOYSA-N | [SMILES]
C(O)(=O)CCC(=O)CC(=O)C | [CAS DataBase Reference]
51568-18-4 |
| Hazard Information | Back Directory | [Description]
Succinylacetone (4,6-dioxoheptanoic acid), is a result of tyrosine metabolism disorder. The synthesis of this medium-chain keto acid in the body is due to the reduced activity of the enzyme fumarylacetoacetate hydrolase. Succinylacetone is an acidogen, its high concentrations can lead to metabolic acidosis, which leads to damage to the liver, kidneys, heart, and nervous system. Succinylacetone appears to be an oncometabolite because patients with high levels of this compound often develop hepatocellular carcinoma.
Succinylacetone is widely used in research as an inhibitor of the enzyme 5-aminolevulinic acid dehydratase (ALAD), which plays a key role in heme biosynthesis.
The product is used primarily as a control for MS/MS. | [Chemical Properties]
White Solid | [Uses]
Succinylacetone (SA) is a specific marker for the inherited metabolic disease, hepatorenal tyrosinemia. It was developed a stable-isotope
quid urine using a 13C4-SA as internal standard. | [Definition]
ChEBI: A dioxo monocarboxylic acid that is heptanoic acid in which oxo groups replace the hydrogens at positions 4 and 6. It is an abnormal metabolite of the tyrosine metabolic pathway and a marker for type 1 tyrosinaemia. | [Biochem/physiol Actions]
4,6-Dioxoheptanoic acid is an inhibitor of heme biosynthesis. It is a catabolic byproduct of tyrosine breakdown and inhibits δ-aminolevulinic acid (ALA) dehydratase enzyme. It is a potential marker for detecting tyrosinemia type I and is measured in dried blood spot of new borns. | [IC 50]
Human Endogenous Metabolite | [storage]
Store at -20°C |
|
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