Oxaloacetic Acid
OXALACETIC ACID · OXALOACETIC ACID · 2-OXOSUCCINIC ACID · OAA · OXOBUTANEDIOIC ACID · oxalacetic · NSC 77688 · NSC 284205
Identifiers & Physical Properties
| CAS No. | 328-42-7 |
|---|---|
| Molecular formula | C4H4O5 |
| Average molar mass | 132.07 g/mol |
| Monoisotopic mass | 132.00587323 g/mol |
| SMILES | O=C(O)CC(=O)C(=O)O |
| InChIKey | KHPXUQMNIQBQEV-UHFFFAOYSA-N |
| PubChem CID | 970 |
| ChEMBL | CHEMBL1794791 |
| ChEBI | CHEBI:30744 |
| EC No. | 206-329-8 |
| DTXSID | DTXSID8021646 |
Chemical & Physical Properties
| XLogP | -0.6 |
|---|---|
| Topological polar surface area | 91.7 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 5 |
| Rotatable bonds | 3 |
| Heavy atoms | 9 |
| Formal charge | 0 |
| Complexity | 158 |
| Chemical classes | Other Classes -> Organic Acids |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Lipids | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117] |
| Solubility | 134 mg/mLH2O: 100 mg/mLsoluble |
| Melting point | 161 °C161 °C (dec.)(lit.) |
| Physical Description | Off-white powder[Alfa Aesar MSDS]Solid |
| Collision Cross Section | 139.45 Ų [M+H]+ [CCS Type: DTMethod: stepped-field] |
| Boiling point | 163.94°C (rough estimate) |
| Density | 1.3067 (rough estimate) |
| Vapor pressure | 0.003Pa at 20℃ |
| Refractive index | 1.4000 (estimate) |
| Flash point | 88°C |
| Storage conditions | -20°C |
| Physical state | powder |
| pKa (acidity coefficient) | 2.22(at 25℃) |
| Color | White to off-white |
| pH | 3.05(1 mM solution)2.29(10 mM solution)1.68(100 mM solution) |
| Biological source | synthetic (organic) |
| Merck | 14,6909 |
| BRN | 1705475 |
| Stability | Stable. Incompatible with strong oxidizing agents. Keep refrigerated. |
| InChI | 1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9) |
| InChIKey | KHPXUQMNIQBQEV-UHFFFAOYSA-N |
| SMILES | OC(=O)CC(=O)C(O)=O |
| LogP (partition coefficient) | -1.04 at 20℃ |
| CAS DataBase Reference | 328-42-7(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 2F399MM81J |
| NIST Chemistry Reference | Oxalacetic acid(328-42-7) |
| EPA Substance Registry System | Oxalacetic acetic (328-42-7) |
| UNSPSC Code | 12352205 |
| NACRES | NA.75 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H319 |
| GHS precautionary statements | P264-P280-P305+P351+P338-P337+P313 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Hazard symbols | C |
| Risk statements (R) | 34 |
| Safety statements (S) | 26-36/37/39-45 |
| UN transport number | UN 3261 8/PG 2 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Eye Irrit. 2 |
| Packing group | II |
| Customs code | 29183000 |
| Storage class | 11 - Combustible Solids |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | DangerH314 (88.5%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P321, P337+P317, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 61 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Butanedioic acid, oxo-Status: Active Update: 14-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/22927Butanedioic acid, oxo-: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Hazards summary | Causes convulsions in acute intraperitoneal studies of mice[RTECS] Causes burnsInhalation may cause corrosive injuries to upper respiratory tract and lungs[Alfa Aesar MSDS] See Oxalic acid and Acetic acid. |
| Hazard Classes and Categories | Skin Corr. 1B (88.5%) |
| Adverse effects | Dermatotoxin - Skin burns. |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 3261 8/PG 2 |
| Customs code | 29183000 |
| Risk statements (R) | 34 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | C |
| Safety statements (S) | 26-36/37/39-45 |
| Hazard class | 8Eye Irrit. 2 |
| Storage class | 11 - Combustible Solids |
| Packing group | II |
| GHS hazard statements | H319 |
| REACH registrations | Active |
| GHS precautionary statements | P264-P280-P305+P351+P338-P337+P313 |
Applications & Uses
Description
Oxaloacetic acid, also known as oxalacetic acid, is is an α-keto acid and a key component of cellular metabolism in its conjugate base form, oxaloacetate. Oxaloacetate reacts with acetyl-coenzyme A (acetyl-CoA; ) and water to form citrate in the first step of the citric acid cycle and is regenerated by oxidation of L-malate in the final step. It is an intermediate in gluconeogenesis that is formed in mitochondria via carboxylation of pyruvate and subsequently decarboxylated and phosphorylated to form phosphoenolpyruvate. It can be converted to aspartate via addition of an amino group from glutamate. Oxaloacetate (30 μmol/min per 100 g for 30 minutes, i.v.) reduces blood glutamate levels, severity of neurological dysfunction, and brain edema in a rat model of closed head injury.
Uses
Use as a TCA (Krebs cycle) intermediate supplement in hybridoma cell culture applications. Enhances hybridoma growth and productivity.
Uses
Oxaloacetic acid is a substrate for malate dehydrogenase and oxaloacetate decarboxylase. It is an inhibitor of succinic dehydrogenase. It is four carbon dicarboxylic acid that is an intermediate in the citric acid cycle and glucogenesis.
General Description
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.