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Oxaloacetic acid

Alias: Oxaloacetic acid; 2-Oxosuccinic acid
Oxaloacetic acid (2-Oxosuccinic acid, OAA) is a metabolic intermediate that participates in various pathways such as citric acid cycle, gluconeogenesis, urea cycle, glyoxylate cycle, amino acid synthesis and fatty acid synthesis.
Oxaloacetic acid
Oxaloacetic acid Chemical Structure CAS No.: 328-42-7
Product category: Reactive Oxygen Species
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Oxaloacetic acid (2-Oxosuccinic acid, OAA) is a metabolic intermediate that participates in various pathways such as citric acid cycle, gluconeogenesis, urea cycle, glyoxylate cycle, amino acid synthesis and fatty acid synthesis. Oxaloacetic acid can promote reactive oxygen species (ROS) clearance and improve mitochondrial function.
Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
ln Vivo
Oxaloacetic acid (10 mg/kg, once a day, for 3 consecutive days) can significantly reduce the acute lung injury induced by paraquat (50 mg/kg, once) and improve the survival rate of paraquat-poisoned mice[3] .
References

[1]. F. L. Breusch. The fate of oxaloacetic acid in different organs. Biochem J. 1939 Nov; 33(11): 1757-1770.

[2]. Oxaloacetic acid mediates ADP-dependent inhibition of mitochondrial complex II-driven respiration. J Biol Chem. 2018 Dec 21;293(51):19932-19941.

[3]. Oxaloacetate acid ameliorates paraquat-induced acute lung injury by alleviating oxidative stress and mitochondrial dysfunction. Front Pharmacol. 2022 Oct 13;13:1029775.

Additional Infomation
Oxaloacetic acid is an oxodicarboxylic acid that is succinic acid bearing a single oxo group. It has a role as a metabolite and a geroprotector. It is an oxo dicarboxylic acid and a C4-dicarboxylic acid. It is functionally related to a succinic acid. It is a conjugate acid of an oxaloacetate(2-).
Oxalacetic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Oxalacetic acid has been reported in Drosophila melanogaster, Medicago sativa, and other organisms with data available.
Anhydrous Enol-oxaloacetate is the anhydrous form of enol-oxaloacetate, a small molecule blood glutamate scavenger, that can be used to lower glutamate plasma levels, and has potential neuroprotective activity. Upon administration, enol-oxaloacetate targets and binds to glutamate in the bloodstream. This lowers glutamate plasma levels and lowers the free glutamate available to be picked up by cells, such as tumor brain cells, thereby preventing glutamate metabolism and glutamate-mediated signaling. This prevents the proliferation of rapidly growing cells, such as brain tumor cells. And by lowering glutamate plasma levels, a molecular imbalance is formed and glutamate is excreted across the blood-brain barrier, resulting in lower free brain glutamate. This may help protect the brain from excitotoxicity in conditions where there is a surge of glutamate production, such as traumatic brain injury, thereby protecting neuronal cells. Glutamate, a non-essential amino acid and the major excitatory neurotransmitter in the central nervous system (CNS), provides energy and generates building blocks for the production of macromolecules, which are needed for cellular growth and survival.
Oxalacetic acid is a metabolite found in or produced by Saccharomyces cerevisiae.
A dicarboxylic acid ketone that is an important metabolic intermediate of the CITRIC ACID CYCLE. It can be converted to ASPARTIC ACID by ASPARTATE TRANSAMINASE.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H4O5
Molecular Weight
132.07
Exact Mass
132.005
CAS #
328-42-7
PubChem CID
970
Appearance
Solid powder
Density
1.6±0.1 g/cm3
Boiling Point
341.9±25.0 °C at 760 mmHg
Melting Point
161 °C (dec.)(lit.)
Flash Point
174.8±19.7 °C
Vapour Pressure
0.0±1.6 mmHg at 25°C
Index of Refraction
1.498
LogP
-1.6
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
3
Heavy Atom Count
9
Complexity
158
Defined Atom Stereocenter Count
0
SMILES
C(C(=O)C(=O)O)C(=O)O
InChi Key
KHPXUQMNIQBQEV-UHFFFAOYSA-N
InChi Code
InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
Chemical Name
2-oxobutanedioic acid
Synonyms
Oxaloacetic acid; 2-Oxosuccinic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ≥ 100 mg/mL (757.17 mM) DMSO : ≥ 100 mg/mL (757.17 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (757.17 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; sonication assisted. (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 7.5717 mL 37.8587 mL 75.7174 mL
5 mM 1.5143 mL 7.5717 mL 15.1435 mL
10 mM 0.7572 mL 3.7859 mL 7.5717 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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