D1415
4,6-Dioxoheptanoic acid
powder
Synonym(s):
Succinylacetone
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About This Item
Linear Formula:
CH3COCH2COCH2CH2CO2H
CAS Number:
Molecular Weight:
158.15
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
Product Name
4,6-Dioxoheptanoic acid, powder
InChI key
WYEPBHZLDUPIOD-UHFFFAOYSA-N
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)
form
powder
mp
66-67 °C (lit.)
lipid type
saturated FAs
storage temp.
2-8°C
Quality Level
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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
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
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
lonp1-dependent Breakdown Of Mitochondrial 5-aminolevulinic Acid Synthase Protein By Heme In Human Liver Cells: 904
Tian Q, et al.
Hepatology, 54(4), 785A-785A (2011)
Amy Bergmann et al.
PLoS pathogens, 16(5), e1008499-e1008499 (2020-05-15)
Heme, an iron-containing organic ring, is essential for virtually all living organisms by serving as a prosthetic group in proteins that function in diverse cellular activities ranging from diatomic gas transport and sensing, to mitochondrial respiration, to detoxification. Cellular heme
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