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O4126

Sigma-Aldrich

Oxaloacetic acid

≥97% (HPLC)

Synonyme(s) :

2-Oxosuccinic acid, Ketosuccinic acid, Oxalacetic acid, Oxobutanedioic acid

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About This Item

Formule linéaire :
HOOCCH2COCOOH
Numéro CAS:
328-42-7
Poids moléculaire :
132.07
Numéro Beilstein :
1705475
Numéro CE :
206-329-8
Numéro MDL:
MFCD00002592
Code UNSPSC :
12352204
ID de substance PubChem :
24897993
Nomenclature NACRES :
NA.32

Niveau de qualité

200

Pureté

≥97% (HPLC)

Forme

powder

Solubilité

H2O: 100 mg/mL, clear to slightly hazy, colorless to light yellow

Température de stockage

−20°C

Chaîne SMILES 

OC(=O)CC(=O)C(O)=O

InChI

1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)

Clé InChI

KHPXUQMNIQBQEV-UHFFFAOYSA-N

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Description générale

Oxaloacetic acid is a dicarboxylic acid. It is an intermediate in the citric acid cycle. It is highly soluble in water and is present ubiquitously. It is produced in the mitochondria by the action of pyruvate carboxylase on pyruvate. Breakdown products of oxaloacetate includes malate, pyruvate and aspartic acid.

Application

Oxaloacetic acid has been used as a substrate for measuring citrate synthase activity in cybrids and neuroblastoma cells. It has also been used for measuring malate dehydrogenase reactivation.

Actions biochimiques/physiologiques

Oxaloacetic acid being an intermediate in the tri carboxylic cycle is central to metabolism. It is part of gluconeogenesis pathway. Mutation in pyruvate carboxylase leads to decreased production of oxaloacetate. It inhibits succinate dehydrogenase and is a key regulator of mitochondrial metabolism.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H319

Classification des risques

Eye Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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MitoTALEN: a general approach to reduce mutant mtDNA loads and restore oxidative phosphorylation function in mitochondrial diseases
Hashimoto M, et al.
Molecular Therapy, 23(10), 15921599-15921599 (2015)
Oxaloacetic acid supplementation as a mimic of calorie restriction
Cash A
Open Longevity Science, 3, 2227-2227 (2009)
Synergistic coordination of polyethylene glycol with ClpB/DnaKJE bichaperone for refolding of heat-denatured malate dehydrogenase
Nian R, et al.
Biotechnology Progress, 25(4), 10781085-10781085 (2009)
Improved mitochondrial and methylglyoxal-related metabolisms support hyperproliferation induced by 50 Hz magnetic field in neuroblastoma cells
Falone S, et al.
Journal of Cellular Physiology, 231(9), 20142025-20142025 (2016)
Oxaloacetic acid mediates ADP-dependent inhibition of mitochondrial complex IIdriven respiration
Fink BD, et al.
The Journal of Biological Chemistry, 293(51), 1993219941-1993219941 (2018)
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