Basic information
- CAS
51568-18-4- Standard SMILES
CC(=O)CC(=O)CCC(=O)O- InChIKey
WYEPBHZLDUPIOD-UHFFFAOYSA-N- Molecular formula
- C7H10O4
- Average molar mass
- 158.15 g/mol
- Monoisotopic mass
- 158.0579088
Overview
4,6-dioxoheptanoic acid is 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. It has a role as a human metabolite. It is a dioxo monocarboxylic acid and a beta-diketone.
Names & identifiers
- Preferred name
- Succinylacetone
- IUPAC
- 4,6-dioxoheptanoic acid
- English name
- 4,6-DIOXOHEPTANOIC ACID
- Molecular formula
- C7H10O4
- Molecular weight
- 158.15
Names & synonyms
4,6-DIOXOHEPTANOIC ACIDSuccinylacetone51568-18-4Heptanoic acid, 4,6-dioxo-KZ0KV2Q190NSC-174804DTXSID50199519CHEBI:87897RefChem:186374DTXCID60122010624-726-8NSC 174804
Show more names
4,6-dioxoheptanoicaci[13C7]-SuccinylacetoneSuccinylacetone in WaterSuccinylacetone-3,4,5,6,7-13C54,6-Dioxoheptanoic acid, 10 mM in DMSO4,6-Dioxoheptanoic acid-3,4,5,6,7-13C54,6-Dioxoheptanoic acid (mixture of isomers)
4,6-DioxoheptanoateMFCD00002797SpecPlus_000704Spectrum3_000763Spectrum4_001249DivK1c_006800KBio2_005133KBio2_007701
Database identifiers
- CAS
51568-18-4- PubChem CID
- 5312
- DTXSID
DTXSID50199519- ChEMBL
CHEMBL222824- ChEBI
CHEBI:87897- UNII
Properties
Computed structural properties
- XLogP
- -0.8
- Topological polar surface area
- 71.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 183
Experimental & physicochemical properties
Melting Point66 - 67 °C
Physical DescriptionSolid
Collision Cross Section131.44 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
Physicochemical properties
- Melting point
- 66 · 66-67 °C(lit.)
- Boiling point
- 318.7 · 318.7±17.0 °C(Predicted)
- Density
- 1.189 · 1.189±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- form
- powder
- pka
- 4.54 · 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)
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Health EffectsChronically high levels of succinylacetone are associated with Tyrosinemia Type I.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Cellular LocationsCytoplasm
Uses & manufacturing
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Applications
DescriptionSuccinylacetone (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.
Uses4,6-Dioxoheptanoic acid has been used:as component of dendritic cell conditioning medium and in the inhibition of ALA dehydratase (ALAD) in dendritic cells(50)as an inhibitor of heme biosynthesis in human mononuclear cells(51) and HeLa cells(52)as a standard for the quantification of succinylacetone from Plasmodium falciparum cultures(53)
UsesSuccinylacetone (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.
Suppliers90 total
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…