Encyclopedia / Organic Acid / Vitamins, Amino Acids and Coenzymes / Organic Intermediate

Oxobutanedioic acid

CAS：328-42-7
MW:132.07156
MF：C4H4O5

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

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Names and ldentifier
Properties
Use and Manufacturing
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Oxobutanedioic acid

1.2 Synonyms: 2-oxobutanedioic acid; 2-OXOSUCCINIC; 2-Oxosuccinic acid; 2-Oxosuccinic acid,Ketosuccinic acid,Oxalacetic acid; a-Ketosuccinic acid; Butanedioic acid, 2-oxo-; cis-Oxaloacetic acid; EINECS 206-329-8; ketosuccinic acid; MFCD00002592; OAA; oxalacetic; Oxalacetic acetic; OXALACETIC ACID; OXALEACETIC ACID; OXALOACETIC ACID; OXLACETIC ACID; OXOBUTANEDIOTIC ACID; OXOSUCCINIC ACID;

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1.3 CAS No.: 328-42-7

1.4 CID: 970

1.5 EINECS: 206-329-8

1.6 Molecular Formula: C4H4O5

1.7 Inchi: InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)

1.8 InChkey: KHPXUQMNIQBQEV-UHFFFAOYSA-N

1.9 Canonical Smiles: C(C(=O)C(=O)O)C(=O)O

1.10 Isomers Smiles: C(C(=O)C(=O)O)C(=O)O

2. Properties

2.1 Solubility: H2O: 100?mg/mL

2.2 Appearance: Solid

2.3 Storage: Store at -20°C.

2.4 Chemical Properties: off-white crystals

2.5 Color/Form: White to off-white

2.6 pKa: 2.22(at 25℃)

2.7 Water Solubility: soluble

2.8 Stability: Stable. Incompatible with strong oxidizing agents. Keep refrigerated.

2.9 StorageTemp: -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: An oxodicarboxylic acid that is succinic acid bearing a single oxo group.

3.2 Description

off-white crystals

Solid

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 derives from a succinic acid. It is a conjugate acid of an oxaloacetate(2-).|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.

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3.3 Purification Methods: Crystallise it from boiling EtOAc, or from hot Me2CO/hot *C6H6. [Beilstein 3 IV 1808.] Oxobutanedioic acid Preparation Products And Raw materials Preparation Products

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

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin corrosion, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H314 Causes severe skin burns and eye damage
Precautionary statement(s)
Prevention	P260 Do not breathe dust/fume/gas/mist/vapours/spray. P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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5. NMR Spectrum

IR : KBr disc

IR : nujol mull

Mass

6. Synthesis Route

328-42-7Total: 37 Synthesis Route

56-41-7 624 Suppliers

328-42-7 93 Suppliers

97-67-6 339 Suppliers

328-42-7 93 Suppliers

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7. Precursor and Product

precursor:

142-45-0

56-41-7

77-92-9

97-65-4

138-09-0

97-67-6

110-17-8

70-47-3

product:

617-45-8

141-82-2

636-61-3

119-18-6

513-85-9

56-84-8

97-67-6

2866-87-7

7580-59-8

513-86-0

8. Computed Properties

Molecular Weight：132.07156g/mol
Molecular Formula：C₄H₄O₅
Compound Is Canonicalized：True
Exact Mass：-0.6
XLogP3-AA：132.00587322
Monoisotopic Mass：132.00587322
Complexity：158
Rotatable Bond Count：3
Hydrogen Bond Donor Count：2
Hydrogen Bond Acceptor Count：5
Topological Polar Surface Area：91.7
Heavy Atom Count：：9
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADcYBgOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACASAgAAACAAAAgAIAICQCAIAAAAAAAAAAAFAAAAAABQIAAAAQAAEIAAAAABDAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

9.Other Information

Usage: Oxalacetic acid is used as a metabolic intermediate in many processes that occur in animals and citric acid cycle. It is a used to converted to aspartic acid by aspartate transaminase.

Usage: Oxaloacetic acid is a substrate for malate dehydrogenase and oxaloacetate decarboxylase. It is an inhibitor of succinic dehydrogenase. It is an intermediate in the citric acid cycle and glucogenesis.

Merck: 14,6909

BRN: 1705475

Description: Oxaloacetic acid 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; Item No. 16160) 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.

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Chemical Properties: off-white crystals

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

Uses: Use as a TCA (Krebs cycle) intermediate supplement in hybridoma cell culture applications. Enhances hybridoma growth and productivity.

Collision Cross Section: 139.45 ?2 [M+H]+ [CCS Type: DT, Method: stepped-field]

Mesh Entry Terms: 2 Ketosuccinic Acid

Manufacturing Info: Butanedioic acid, 2-oxo-: ACTIVE

Use Classification: Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]

10. Toltal 85 Suppliers View more

Hebei Crovell Biotech Co. Ltd

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Baoji Guokang Healthchem co.,ltd

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Dayang Chem (Hangzhou) Co., Ltd.

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Henan Tianfu Chemical Co.,Ltd

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11. Related Questions

: Can Oxobutanedioic acid be used as a radical polarizing agent in dDNP technology?Oxobutanedioic acid is a crucial metabolite that participates in various metabolic processes including the TCA cycle, aspartate synthesis pathway, and glycogen synthesis pathway. It serves as an impor..; What is the first stable product of the C4 carbon fixation cycle?The first stable product of the C4 carbon fixation cycle is oxaloacetate (OAA). In C4 plants, such as maize, sugarcane, and many types of grasses, carbon dioxide is initially fixed into a four-carbon ..; What is Oxobutanedioic Acid and its Biological Functions?Oxobutanedioic acid, also known as malonic acid, is a crystalline organic compound with the chemical formula HO2CC(O)CH2CO2H. It is a common intermediate in many metabolic processes in living organism..

12. Realated Product Infomation