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Safety Information

O4126

Sigma-Aldrich

Oxaloacetic acid

≥97% (HPLC)

Synonym(s):

2-Oxosuccinic acid, Ketosuccinic acid, Oxalacetic acid, Oxobutanedioic acid

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25 G
₩204,218

₩204,218


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25 G
₩204,218

About This Item

Linear Formula:
HOOCCH2COCOOH
CAS Number:
Molecular Weight:
132.07
Beilstein:
1705475
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

₩204,218


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Quality Level

Assay

≥97% (HPLC)

form

powder

solubility

H2O: 100 mg/mL, clear to slightly hazy, colorless to light yellow

storage temp.

−20°C

SMILES string

OC(=O)CC(=O)C(O)=O

InChI

1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)

InChI key

KHPXUQMNIQBQEV-UHFFFAOYSA-N

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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.[1]

Application

Oxaloacetic acid has been used as a substrate for measuring citrate synthase activity in cybrids[2] and neuroblastoma cells.[3] It has also been used for measuring malate dehydrogenase reactivation.[4]

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.[1] It inhibits succinate dehydrogenase and is a key regulator of mitochondrial metabolism.[5]

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

O4126-1G:
O4126-10MG:
O4126-5G:
O4126-BULK:
O4126-100G:
O4126-25G:
O4126-60KG:
2540122:
O4126-VAR:
O4126-10MG-KC:


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    Oxaloacetic acid mediates ADP-dependent inhibition of mitochondrial complex IIdriven respiration
    Fink BD, et al.
    The Journal of Biological Chemistry, 293(51), 1993219941-1993219941 (2018)
    Synergistic coordination of polyethylene glycol with ClpB/DnaKJE bichaperone for refolding of heat-denatured malate dehydrogenase
    Nian R, et al.
    Biotechnology Progress, 25(4), 10781085-10781085 (2009)
    Oxaloacetic acid supplementation as a mimic of calorie restriction
    Cash A
    Open Longevity Science, 3, 2227-2227 (2009)
    Alexander K H Weiss et al.
    Bioscience reports, 40(3) (2020-02-19)
    FAH domain containing protein 1 (FAHD1) is a mammalian mitochondrial protein, displaying bifunctionality as acylpyruvate hydrolase (ApH) and oxaloacetate decarboxylase (ODx) activity. We report the crystal structure of mouse FAHD1 and structural mapping of the active site of mouse FAHD1.
    Improved mitochondrial and methylglyoxal-related metabolisms support hyperproliferation induced by 50 Hz magnetic field in neuroblastoma cells
    Falone S, et al.
    Journal of Cellular Physiology, 231(9), 20142025-20142025 (2016)

    Articles

    Sigma article discusses tumor cell metabolic pathways, focusing on aerobic glycolysis and mitochondrial activity.

    Fatty acid synthesis supports cancer cell proliferation, essential for membrane generation, protein modification, and bioenergetics.

    Protocols

    Spectrophotometric assay evaluates malic dehydrogenase activity using bovine heart enzyme with critical histidine residue at active site.

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