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D1415

Sigma-Aldrich

4,6-Dioxoheptanoic acid

powder

Sinónimos:

Succinylacetone

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About This Item

Fórmula lineal:
CH3COCH2COCH2CH2CO2H
Número de CAS:
51568-18-4
Peso molecular:
158.15
MDL number:
MFCD00002797
UNSPSC Code:
12352211
PubChem Substance ID:
24893433
NACRES:
NA.25

form

powder

Quality Level

200

mp

66-67 °C (lit.)

lipid type

saturated FAs

storage temp.

2-8°C

SMILES string

CC(=O)CC(=O)CCC(O)=O

InChI

1S/C7H10O4/c1-5(8)4-6(9)2-3-7(10)11/h2-4H2,1H3,(H,10,11)

InChI key

WYEPBHZLDUPIOD-UHFFFAOYSA-N

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Application

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)

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.
An inhibitor of heme biosynthesis

related product

Referencia del producto
Descripción
Precios

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000401309
0000356544
0000356545
0000356544
0000356545

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The effects of levulinic acid and 4, 6-dioxoheptanoic acid on the metabolism of etiolated and greening barley leaves
Meller E and Gassman ML
Plant Physiology, 67(4), 728-732 (1981)
Hilde Laeremans et al.
JIMD reports, 53(1), 90-102 (2020-05-13)
Nitisinone is used to treat hereditary tyrosinemia type 1 (HT-1) by preventing accumulation of toxic metabolites, including succinylacetone (SA). Accurate quantification of SA during newborn screening is essential, as is quantification of both SA and nitisinone for disease monitoring and
C M Mak et al.
Hong Kong medical journal = Xianggang yi xue za zhi, 24(4), 340-349 (2018-03-03)
Hereditary channelopathies and cardiomyopathies are potentially lethal and are clinically and genetically heterogeneous, involving at least 90 genes. Genetic testing can provide an accurate diagnosis, guide treatment, and enable cascade screening. The genetic basis among the Hong Kong Chinese population
Naomi Pode-Shakked et al.
European journal of medical genetics, 63(6), 103901-103901 (2020-03-11)
Maple syrup urine disease is a rare autosomal-recessive aminoacidopathy, caused by deficient branched-chain 2-keto acid dehydrogenase (BCKD), with subsequent accumulation of branched-chain amino acids (BCAAs): leucine, isoleucine and valine. While most cases of MSUD are classic, some 20% of cases
Succinylacetone as primary marker to detect tyrosinemia type I in newborns and its measurement by newborn screening programs
De Jesus V, et al.
Molecular Genetics and Metabolism, 113(1-2), 67-75 (2014)
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