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51568-18-4,MFCD00002797
Catalog No.:AA003KH3

51568-18-4 | 4,6-Dioxoheptanoic acid

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10mg
≥98%
in stock  
$46.00   $32.00
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100mg
97%
in stock  
$62.00   $43.00
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250mg
95%
in stock  
$135.00   $95.00
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1g
95%
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$297.00   $208.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003KH3
Chemical Name:
4,6-Dioxoheptanoic acid
CAS Number:
51568-18-4
Molecular Formula:
C7H10O4
Molecular Weight:
158.1519
MDL Number:
MFCD00002797
SMILES:
OC(=O)CCC(=O)CC(=O)C
NSC Number:
174804
Properties
Properties
 
BP:
318.7°C at 760 mmHg  
Form:
Solid  
MP:
66-67°C  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
183  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
5  
XLogP3:
-0.8  

Literature

Title: Heme and heme biosynthesis intermediates induce heme oxygenase-1 and cytochrome P450 2A5, enzymes with putative sequential roles in heme and bilirubin metabolism: different requirement for transcription factor nuclear factor erythroid- derived 2-like 2.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20121101

Title: Single dose NTBC-treatment of hereditary tyrosinemia type I.

Journal: Journal of inherited metabolic disease 20120901

Title: Evaluation of a novel, commercially available mass spectrometry kit for newborn screening including succinylacetone without hydrazine.

Journal: Clinica chimica acta; international journal of clinical chemistry 20120816

Title: Evaluation of factors influencing accuracy in the analysis of succinylacetone in dried blood spots.

Journal: Clinica chimica acta; international journal of clinical chemistry 20120816

Title: Plant growth regulator daminozide is a selective inhibitor of human KDM2/7 histone demethylases.

Journal: Journal of medicinal chemistry 20120726

Title: Dried blood spot analysis by digital microfluidics coupled to nanoelectrospray ionization mass spectrometry.

Journal: Analytical chemistry 20120417

Title: [Application of succinylacetone levels measurement in the blood and urine in the diagnosis of tyrosinemia type 1].

Journal: Zhonghua er ke za zhi = Chinese journal of pediatrics 20120201

Title: LC-MS/MS method for simultaneous determination on a dried blood spot of multiple analytes relevant for treatment monitoring in patients with tyrosinemia type I.

Journal: Analytical chemistry 20120117

Title: The stability of markers in dried-blood spots for recommended newborn screening disorders in the United States.

Journal: Clinical biochemistry 20111201

Title: Functional significance of the ATP-binding cassette transporter B6 in hepatocellular carcinoma.

Journal: Molecular oncology 20111001

Title: Long-term outcome of living donor liver transplantation in a Thai boy with hereditary tyrosinemia type I: a case report.

Journal: Journal of the Medical Association of Thailand = Chotmaihet thangphaet 20111001

Title: Lon peptidase 1 (LONP1)-dependent breakdown of mitochondrial 5-aminolevulinic acid synthase protein by heme in human liver cells.

Journal: The Journal of biological chemistry 20110729

Title: Newborn screening for Tyr-I: two years' experience of the New York State program.

Journal: Molecular genetics and metabolism 20110601

Title: Improved tandem mass spectrometry (MS/MS) derivatized method for the detection of tyrosinemia type I, amino acids and acylcarnitine disorders using a single extraction process.

Journal: Clinica chimica acta; international journal of clinical chemistry 20110512

Title: Nonactin biosynthesis: unexpected patterns of label incorporation from 4,6-dioxoheptanoate show evidence of a degradation pathway for levulinate through propionate in Streptomyces griseus.

Journal: Journal of natural products 20101227

Title: Hereditary tyrosinemia type 1 metabolites impair DNA excision repair pathways.

Journal: Biochemical and biophysical research communications 20101008

Title: Plastid-associated porphobilinogen synthase from Toxoplasma gondii: kinetic and structural properties validate therapeutic potential.

Journal: The Journal of biological chemistry 20100716

Title: Clinical practice. NTBC therapy for tyrosinemia type 1: how much is enough?

Journal: European journal of pediatrics 20100601

Title: skn-1-Dependent and -independent regulation of aip-1 expression following metabolic stress in Caenorhabditis elegans.

Journal: Molecular and cellular biology 20100601

Title: Assessing the DNA methylation status of single cells with the comet assay.

Journal: Analytical biochemistry 20100515

Title: Significant increase of succinylacetone within the first 12 h of life in hereditary tyrosinemia type 1.

Journal: European journal of pediatrics 20100501

Title: Identification of a neonate with hepatorenal tyrosinemia by combined routine newborn screening for succinylacetone, acylcarnitines and amino acids.

Journal: Clinical biochemistry 20100501

Title: Lack of hemodynamic effects after extended heme synthesis inhibition by succinylacetone in rats.

Journal: The Journal of pharmacology and experimental therapeutics 20100401

Title: Preliminary proficiency testing results for succinylacetone in dried blood spots for newborn screening for tyrosinemia type I.

Journal: Clinical chemistry 20091201

Title: The successful inclusion of succinylacetone as a marker of tyrosinemia type I in Tuscany newborn screening program.

Journal: Rapid communications in mass spectrometry : RCM 20091201

Title: Solution structure of succinylacetone, an unsymmetrical beta-diketone, as studied by 13C NMR and GIAO-DFT calculations.

Journal: The Journal of organic chemistry 20091120

Title: 2-Oxoglutarate analogue inhibitors of prolyl hydroxylase domain 2.

Journal: Bioorganic & medicinal chemistry letters 20091101

Title: Improved MS/MS analysis of succinylacetone extracted from dried blood spots when combined with amino acids and acylcarnitine butyl esters.

Journal: Clinica chimica acta; international journal of clinical chemistry 20090901

Title: Post-transcriptional regulation of the expression of ferrochelatase by its variant mRNA.

Journal: Journal of biochemistry 20090601

Title: Clinical, biochemical, and genetic analysis of a Korean neonate with hereditary tyrosinemia type 1.

Journal: Clinical chemistry and laboratory medicine 20090101

Title: A novel mutation causing mild, atypical fumarylacetoacetase deficiency (Tyrosinemia type I): a case report.

Journal: Orphanet journal of rare diseases 20090101

Title: Improved method to determine succinylacetone in dried blood spots for diagnosis of tyrosinemia type 1 using UPLC-MS/MS.

Journal: Biomedical chromatography : BMC 20081101

Title: Acute depletion of heme by succinylacetone alters vascular responses but does not induce hypertension.

Journal: Canadian journal of physiology and pharmacology 20080901

Title: The effect of haem biosynthesis inhibitors and inducers on intestinal iron absorption and liver haem biosynthetic enzyme activities.

Journal: Toxicology and applied pharmacology 20080615

Title: Combined newborn screening for succinylacetone, amino acids, and acylcarnitines in dried blood spots.

Journal: Clinical chemistry 20080401

Title: Enhancing newborn screening for tyrosinemia type I.

Journal: Clinical chemistry 20080401

Title: The inclusion of succinylacetone as marker for tyrosinemia type I in expanded newborn screening programs.

Journal: Rapid communications in mass spectrometry : RCM 20080101

Title: Tandem mass spectrometric determination of succinylacetone in dried blood spots enables presymptomatic detection in a case of hepatorenal tyrosinaemia.

Journal: Journal of inherited metabolic disease 20070801

Title: Analysis of succinylacetone, as a Girard T derivative, in urine and dried bloodspots by flow injection electrospray ionization tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20070101

Title: Porphobilinogen synthase from the butterfly, Pieris brassicae: purification and comparative characterization.

Journal: Journal of insect science (Online) 20070101

Title: Increased mutant frequencies in the HPRT gene locus of leukemia HL-60 cells treated with succinylacetone.

Journal: Cell biology and toxicology 20060901

Title: A GC-MS/MS method for the quantitative analysis of low levels of the tyrosine metabolites maleylacetone, succinylacetone, and the tyrosine metabolism inhibitor dichloroacetate in biological fluids and tissues.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060606

Title: Quantitative determination of succinylacetone in dried blood spots for newborn screening of tyrosinemia type I.

Journal: Molecular genetics and metabolism 20060501

Title: Quantification of succinylacetone in urine of hepatorenal tyrosinemia patients by HPLC with fluorescence detection.

Journal: Clinica chimica acta; international journal of clinical chemistry 20060301

Title: Newborn screening for hepatorenal tyrosinemia: Tandem mass spectrometric quantification of succinylacetone.

Journal: Clinical chemistry 20060301

Title: A GC/MS validated method for the nanomolar range determination of succinylacetone in amniotic fluid and plasma: an analytical tool for tyrosinemia type I.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060217

Title: Determination of succinylacetone in dried blood spots and liquid urine as a dansylhydrazone by liquid chromatography tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060202

Title: Haem repression of the housekeeping 5-aminolaevulinic acid synthase gene in the hepatoma cell line LMH.

Journal: The Biochemical journal 20051115

Title: Heme deficiency suppresses the expression of key neuronal genes and causes neuronal cell death.

Journal: Brain research. Molecular brain research 20050613

Title: Determination of urinary succinylacetone by capillary electrophoresis for the diagnosis of tyrosinemia type I.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050425

Title: Tandem mass spectrometric assay of succinylacetone in urine for the diagnosis of hepatorenal tyrosinemia.

Journal: Analytical biochemistry 20050415

Title: Renal function in tyrosinaemia type I after liver transplantation: a long-term follow-up.

Journal: Journal of inherited metabolic disease 20050101

Title: Heme-dependent up-regulation of the alpha-globin gene expression by transcriptional repressor Bach1 in erythroid cells.

Journal: Biochemical and biophysical research communications 20041105

Title: Newborn screening for hepatorenal tyrosinemia by tandem mass spectrometry: analysis of succinylacetone extracted from dried blood spots.

Journal: Clinical biochemistry 20041101

Title: Mice deficient in glutathione transferase zeta/maleylacetoacetate isomerase exhibit a range of pathological changes and elevated expression of alpha, mu, and pi class glutathione transferases.

Journal: The American journal of pathology 20040801

Title: Heme deficiency causes apoptosis but does not increase ROS generation in HeLa cells.

Journal: Biochemical and biophysical research communications 20040709

Title: Succinylacetone oxidation by oxygen/peroxynitrite: a possible source of reactive intermediates in hereditary tyrosinemia type I.

Journal: Chemical research in toxicology 20040501

Title: Heme controls the expression of cell cycle regulators and cell growth in HeLa cells.

Journal: Biochemical and biophysical research communications 20040312

Title: Delta-aminolevulinic acid dehydratase from Plasmodium falciparum: indigenous versus imported.

Journal: The Journal of biological chemistry 20040220

Title: Heme positively regulates the expression of beta-globin at the locus control region via the transcriptional factor Bach1 in erythroid cells.

Journal: The Journal of biological chemistry 20040213

Title: Synthesis and immunosuppressive activity of novel succinylacetone analogues.

Journal: Archives of pharmacal research 20030301

Title: CYP2E1 overexpression up-regulates both non-specific delta-aminolevulinate synthase and heme oxygenase-1 in the human hepatoma cell line HLE/2E1.

Journal: International journal of molecular medicine 20030101

Title: The role of endogenous heme synthesis and degradation domain cysteines in cellular iron-dependent degradation of IRP2.

Journal: Blood cells, molecules & diseases 20030101

Title: Heme deficiency interferes with the Ras-mitogen-activated protein kinase signaling pathway and expression of a subset of neuronal genes.

Journal: Cell growth & differentiation : the molecular biology journal of the American Association for Cancer Research 20020901

Title: An examination of heme action in gene expression: heme and heme deficiency affect the expression of diverse genes in erythroid k562 and neuronal PC12 cells.

Journal: DNA and cell biology 20020401

Title: The x-ray structure of yeast 5-aminolaevulinic acid dehydratase complexed with substrate and three inhibitors.

Journal: Journal of molecular biology 20010907

Title: Spectrophotometric microassay for delta-aminolevulinate dehydratase in dried-blood spots as confirmation for hereditary tyrosinemia type I.

Journal: Clinical chemistry 20010801

Title: [Liver failure with coagulopathy in an infant with tyrosinemia].

Journal: Harefuah 20010701

Title: Characterization of a human plasma membrane heme transporter in intestinal and hepatocyte cell lines.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20010601

Title: Heme biosynthesis and oogenesis in the blood-sucking bug, Rhodnius prolixus.

Journal: Insect biochemistry and molecular biology 20010315

Title: Erythropoietin induction in Hep3B cells is not affected by inhibition of heme biosynthesis.

Journal: Biochimica et biophysica acta 20000227

Title: Hypoxic regulation of endothelial glyceraldehyde-3-phosphate dehydrogenase.

Journal: The American journal of physiology 19980201

Title: Ebert PS, et al. Succinylacetone, a potent inhibitor of heme biosynthesis: effect on cell growth, heme contentand delta-aminolevulinic acid dehydratase activity of malignant murine erythroleukemia cells. Biochem Biophys Res Commun. 1979 Jun 27;88(4):1382-90.

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Tags:51568-18-4 Molecular Formula|51568-18-4 MDL|51568-18-4 SMILES|51568-18-4 4,6-Dioxoheptanoic acid