4,6-DIOXOHEPTANOIC ACID

Product Name: 4,6-DIOXOHEPTANOIC ACID
CAS No.: 51568-18-4
Chemical Name: 4,6-DIOXOHEPTANOIC ACID
Synonyms: SUCCINYLACETONE;4,6-dioxoheptanoicaci;[13C7]-Succinylacetone;4,6-DIOXOHEPTANOIC ACID;Succinylacetone in Water;Heptanoic acid, 4,6-dioxo-;Succinylacetone-3,4,5,6,7-13C5;4,6-Dioxoheptanoic acid, 10 mM in DMSO;4,6-Dioxoheptanoic acid-3,4,5,6,7-13C5;4,6-Dioxoheptanoic acid (mixture of isomers)
CBNumber: CB1385063
Molecular Formula: C7H10O4
Formula Weight: 158.15
MOL File: 51568-18-4.mol

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4,6-DIOXOHEPTANOIC ACID Property

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

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: D1415
Product name: 4,6-Dioxoheptanoic acid
Purity: powder
Packaging: 100mg
Price: $322
Updated: 2025/07/31

Sigma-Aldrich

Product number: D1415
Product name: 4,6-Dioxoheptanoic acid
Purity: powder
Packaging: 1g
Price: $1840
Updated: 2025/07/31

TCI Chemical

Product number: U0127
Product name: Succinylacetone
Packaging: 100MG
Price: $234
Updated: 2023/01/07

TCI Chemical

Product number: U0127
Product name: Succinylacetone
Packaging: 25MG
Price: $79
Updated: 2022/04/27

Cayman Chemical

Product number: 25501
Product name: Succinylacetone
Purity: ≥98%
Packaging: 10mg
Price: $32
Updated: 2024/03/01

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4,6-DIOXOHEPTANOIC ACID Chemical Properties,Usage,Production

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

4,6-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)

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

4,6-DIOXOHEPTANOIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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51568-18-4, 4,6-DIOXOHEPTANOIC ACIDRelated Search:

Heptanoic acid prohexadione-calcium 4,6-DIOXOHEPTANOIC ACID 3,5-Dioxocyclohexanecarboxylic acid TRINEXAPAC-ETHYL Trinexapac-ethyl PROHEXADIONE 4-ACETYL-3,5-DIOXO-1-METHYLCYCLOHEXANECARBOXYLIC ACID Ethyl 2,4-dioxoheptanoate ,97% 4-ACETYL-3,5-DIOXO-CHA(1-ME, 1-COOH) 3,5-DIOXO-4-PROPIONYL-CYCLOHEXANECARBOXYLIC ACID CALCIUM SALT 7-(4-Methoxyphenyl)-5,7-dioxoheptanoic acid 7-(4-Chlorophenyl)-5,7-dioxoheptanoic acid 2-Diazo-3,6-dioxoheptanoic acid ethyl ester 7-(4-CHLOROPHENYL)-4,7-DIOXOHEPTANOIC ACID 7-(5-METHYLTHIEN-2-YL)-4,7-DIOXOHEPTANOIC ACID BIS-2,2-SUCCINOYLMETHYLENE-PROPIONIC ACID CHOLESTERYL ESTER 3-(1,2,3,4-Tetrahydro-6-methoxy-1-oxo-2-naphthoyl)propionicacid

4,6-DIOXOHEPTANOIC ACID

SUCCINYLACETONE

Succinylacetone-3,4,5,6,7-13C5

4,6-Dioxoheptanoic acid-3,4,5,6,7-13C5

[13C7]-Succinylacetone

Heptanoic acid, 4,6-dioxo-

4,6-dioxoheptanoicaci

4,6-Dioxoheptanoic acid (mixture of isomers)

Succinylacetone in Water

4,6-Dioxoheptanoic acid, 10 mM in DMSO

51568-18-4

CH3COCH2COCH2CH2CO2H

Biochemicals and Reagents

BioChemical

Saturated fatty acids and derivatives

Lipids

Keto fatty acids

Fatty Acids

Aliphatics

Intermediates & Fine Chemicals

Pharmaceuticals