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328-42-7

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328-42-7 Usage

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; ) 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.

Chemical Properties

off-white crystals

Uses

Different sources of media describe the Uses of 328-42-7 differently. You can refer to the following data:
1. A four carbon dicarboxylic acid that is an intermediate in the citric acid cycle and glucogenesis. It has been shown to inhibit succinate dehydrogenase.
2. Use as a TCA (Krebs cycle) intermediate supplement in hybridoma cell culture applications. Enhances hybridoma growth and productivity.
3. 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.

Definition

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

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.

Flammability and Explosibility

Notclassified

Biological Activity

Oxalacetic acid (Oxaloacetic acid, 2-Oxosuccinic acid, Ketosuccinic acid) is an intermediate of the citric acid cycle, where it reacts with acetyl-CoA to form citrate, catalysed by citrate synthase. It is also involved in gluconeogenesis, urea cycle, glyoxylate cycle, amino acid synthesis, and fatty acid synthesis. Oxaloacetate is also a potent inhibitor of Complex II.

Biochem/physiol Actions

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.

Purification Methods

Crystallise it from boiling EtOAc, or from hot Me2CO/hot *C6H6. [Beilstein 3 IV 1808.]

Check Digit Verification of cas no

The CAS Registry Mumber 328-42-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,2 and 8 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 328-42:
(5*3)+(4*2)+(3*8)+(2*4)+(1*2)=57
57 % 10 = 7
So 328-42-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)/p-2

328-42-7 Well-known Company Product Price

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  • CAS number
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  • Alfa Aesar

  • (A12739)  Oxalacetic acid, 97%   

  • 328-42-7

  • 5g

  • 474.0CNY

  • Detail
  • Alfa Aesar

  • (A12739)  Oxalacetic acid, 97%   

  • 328-42-7

  • 25g

  • 1959.0CNY

  • Detail
  • Alfa Aesar

  • (A12739)  Oxalacetic acid, 97%   

  • 328-42-7

  • 100g

  • 6725.0CNY

  • Detail
  • Alfa Aesar

  • (15789)  Oxalacetic acid, 98+%   

  • 328-42-7

  • 2g

  • 254.0CNY

  • Detail
  • Alfa Aesar

  • (15789)  Oxalacetic acid, 98+%   

  • 328-42-7

  • 10g

  • 1246.0CNY

  • Detail

328-42-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name oxaloacetic acid

1.2 Other means of identification

Product number -
Other names 2-Oxosuccinic acid,Ketosuccinic acid,Oxalacetic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:328-42-7 SDS

328-42-7Relevant articles and documents

Oxalacetic acid as amino group acceptor in transamination.

CAMMARATA,COHEN

, p. 117 - 120 (1953)

-

Structure Elucidation of Phomopsin A, a Novel Cyclic Hexapeptide Mycotoxin produced by Phomopsis leptostromiformis

Culvenor, Claude C. J.,Cockrum, Peter A.,Edgar, John A.,Frahn, John L.,Gorst-Allman, Charles P.,et al.

, p. 1259 - 1262 (1983)

Phomopsin A, the main mycotoxin isolated from cultures of Phomopsis leptostromiformis and the cause of lupinosis disease in animals grazing infected lupins, is a cyclic hexapeptide containing 3-hydroxyisoleucine, 3,4-didehydrovaline, N-methyl-3-(3-chloro-4,5-dihydroxyphenyl)-3-hydroxyalanine, E-2,3-didehydroaspartic acid, E-2,3-didehydroisoleucine, and 3,4-didehydroproline; its 13C n.m.r. spectrum was completely assigned and the amino-acid sequence established unambiguously by extensive heteronuclear 13C- selective population inversion n.m.r. experiments.

Oxaloacetic acid formation in liver mitochondria and its influence on succinate oxidation with the addition of ethylenediaminetetraacetic acid.

KUNZ,MUELLER,STRACK

, p. 204 - 211 (1960)

-

Kritzmann

, p. 603 (1939)

Bacterial flavoprotein monooxygenase YxeK salvages toxic S-(2-succino)-adducts via oxygenolytic C–S bond cleavage

Ellis, Holly R.,Kammerer, Bernd,Lagies, Simon,Matthews, Arne,Sch?nfelder, Julia,Schleicher, Erik,Stull, Frederick,Teufel, Robin

, (2021/10/06)

Thiol-containing nucleophiles such as cysteine react spontaneously with the citric acid cycle intermediate fumarate to form S-(2-succino)-adducts. In Bacillus subtilis, a salvaging pathway encoded by the yxe operon has recently been identified for the detoxification and exploitation of these compounds as sulfur sources. This route involves acetylation of S-(2-succino)cysteine to N-acetyl-2-succinocysteine, which is presumably converted to oxaloacetate and N-acetylcysteine, before a final deacetylation step affords cysteine. The critical oxidative cleavage of the C–S bond of N-acetyl-S-(2-succino)cysteine was proposed to depend on the predicted flavoprotein monooxygenase YxeK. Here, we characterize YxeK and verify its role in S-(2-succino)-adduct detoxification and sulfur metabolism. Detailed biochemical and mechanistic investigation of YxeK including 18O-isotope-labeling experiments, homology modeling, substrate specificity tests, site-directed mutagenesis, and (pre-)steady-state kinetics provides insight into the enzyme’s mechanism of action, which may involve a noncanonical flavin-N5-peroxide species for C–S bond oxygenolysis.

Two-Dimensional Tin Selenide (SnSe) Nanosheets Capable of Mimicking Key Dehydrogenases in Cellular Metabolism

Gao, Meng,Wang, Zhenzhen,Zheng, Huizhen,Wang, Li,Xu, Shujuan,Liu, Xi,Li, Wei,Pan, Yanxia,Wang, Weili,Cai, Xiaoming,Wu, Ren'an,Gao, Xingfa,Li, Ruibin

supporting information, p. 3618 - 3623 (2020/02/13)

While dehydrogenases play crucial roles in tricarboxylic acid (TCA) cycle of cell metabolism, which are extensively explored for biomedical and chemical engineering uses, it is a big challenge to overcome the shortcomings (low stability and high costs) of recombinant dehydrogenases. Herein, it is shown that two-dimensional (2D) SnSe is capable of mimicking native dehydrogenases to efficiently catalyze hydrogen transfer from 1-(R)-2-(R′)-ethanol groups. In contrary to susceptible native dehydrogenases, lactic dehydrogenase (LDH) for instance, SnSe is extremely tolerant to reaction condition changes (pH, temperature, and organic solvents) and displays extraordinary reusable capability. Structure–activity analysis indicates that the single-atom structure, Sn vacancy, and hydrogen binding affinity of SnSe may be responsible for their catalytic activity. Overall, this is the first report of a 2D SnSe nanozyme to mimic key dehydrogenases in cell metabolism.

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