2-oxobutanedioic acid

• ChemBase ID: 102212
• Molecular Formular: C4H4O5
• Molecular Mass: 132.07156
• Monoisotopic Mass: 132.00587323
• SMILES: OC(=O)CC(=O)C(=O)O
• Canonical SMILES: OC(=O)CC(=O)C(=O)O
• InChI: InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
• InChIKey: KHPXUQMNIQBQEV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-oxobutanedioic acid
• IUPAC Traditional name: oxaloacetic acid; oxalacetate
• Synonyms: Oxaloacetic acid; Oxobutanedioic acid; 2-Oxosuccinic acid; Ketosuccinic acid; Oxalacetic acid; OXALACETIC ACID; Oxaloacetic acid; Oxosuccinic acid; Oxaloacetic acid; Oxalacetic acid; 2-Ketosuccinic acid; 2-Oxobutanedioic acid; NSC 284205; NSC 77688; OAA; Oxaloethanoic Acid; α-Ketosuccinic Acid; 2-oxobutanedioic acid; 丁酮二酸; 草醋酸; 草酰乙酸; 2-氧代丁二酸; 氧代丁二酸; 草醋酸

Database IDs

• CAS Number: 328-42-7
• EC Number: 206-329-8
• MDL Number: MFCD00002592
• Beilstein Number: 1705475
• Merck Index: 146909
• PubChem SID: 162088653; 24886860; 24897993; 24898047; 24898071
• PubChem CID: 970
• CHEBI ID: 30744
• Chemspider ID: 945
• Wikipedia Title: Oxaloacetic_acid

CALCULATED PROPERTIES

• Acid pKa: 2.4098313
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -4.923712
• LogD (pH = 7.4): -6.9175906
• Log P: -0.041897602
• Molar Refractivity: 24.3338 cm^3
• Polarizability: 9.61056 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear; H2O: soluble100 mg/mL
• Apperance: powder; Powder
• Melting Point: 160°C; 161 - 163°C; 161 °C; 161 °C (dec.)(lit.); 161°C dec.
• Flash Point: 88°C(190°F)
• Density: ? g/cm^3
• Hydrophobicity(logP): -1.112
• Std enthalpy of combustion: -1205.58 kJ/mol
• Std enthalpy of formation: -943.21 kJ/mol

Safety Information

• Storage Condition: 0°C
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 20-26-36/37/39-45; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95.0% (T); ≥97%; ≥98.0% (enzymatic); ≥98.0% (T); 95%; 97%; 98%; 98+%; 98-99%
• Grade: Hybri-Max™; purum
• Suitability: suitable for cell culture; suitable for hybridoma; suitable for insect cell culture
• Impurities: endotoxin, tested
• Product Line: BioReagent
• Linear Formula: HO2CCH2COCO2H; HOOCCH2COCOOH

DETAILS

MP Biomedicals - 02194719

Cell Culture Reagent
Purity: 98-99%

MP Biomedicals - 02100568

Purity: 98-99%
Free of chloride. A superior substrate for use in Malic Dehydrogenase UV assay.

Sigma Aldrich - O4126

Biochem/physiol Actions
Oxaloacetic acid is an intermediate in the TCA Cycle.
Packaging
1, 5, 25, 100 g in poly bottle

Sigma Aldrich - O7753

Application
Use as a TCA (Krebs cycle) intermediate supplement in insect cell culture applications. Enhances insect cell growth and productivity.

Sigma Aldrich - O9504

Application
Use as a TCA (Krebs cycle) intermediate supplement in hybridoma cell culture applications. Enhances hybridoma growth and productivity.
Legal Information
Hybri-Max is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 171255

Packaging
5 g in glass bottle

Sigma Aldrich - 75660

Other Notes
Substrate for citrate synthase1; and malate dehydrogenase2

Toronto Research Chemicals - O845030

A four carbon dicarboxylic acid that is an intermediate in the citric acid cycle and glucogenesis. It has been shown to inhibit succinate dehydrogenase.

REFERENCES

• Zeylemaker, W.P. et al.: Biochim. Biophys. Acta Enzymol., 132, 210 (1967)
• Dalla-Betta, P. et al.: Int. J. Mol. Sci., 10, 2809 (1967)
• Substrate for citrate synthase.