A dicarboxylic acid and byproduct of propionate catabolism
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Labeled Version(s)
35232Methylmalonic Acid-d3
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Methylmalonic Acid

Item No. 14885

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methyl-propanedioic acid
CAS Number
516-05-2
Synonyms
  • Isosuccinic Acid
  • Methylmalonate
  • MMA
  • NSC 25201
Molecular Formula
C4H6O4
Formula Weight
118.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
OC(C(C)C(O)=O)=O
InChi Code
InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)
InChi Key
ZIYVHBGGAOATLY-UHFFFAOYSA-N
Shipping & Storage Information
Storage
Room temperature
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 g

    $22

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    5 g

    $53

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    10 g

    $73

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    25 g

    $128

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    Product Description

    Methylmalonic acid is a dicarboxylic acid and byproduct of propionate catabolism.1 It impairs mitochondrial respiration, increases glucose consumption, and downregulates the transcription of the mature neuronal markers neuron-specific enolase (ENO2) and synaptophysin (SYP) in neuronally differentiated SH-SY5Y cells. Intrastriatal administration of methylmalonic acid (100 mg/ml) induces neuronal loss in rats.2 Methylmalonic acid accumulates in the tissues and body fluids of patients with methylmalonic acidemia, an inborn error of metabolism characterized by a deficiency in the activity of L-methylmalonyl-CoA mutase or its cofactor 5-deoxyadenosylcobalamin and leads to seizures, intellectual disabilities, psychomotor abnormalities, and coma.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. da Costa, R.T., Dos Santos, M.B., Silva, I.C.S., et al. Methylmalonic acid compromises respiration and reduces the expression of differentiation markers of SH-SY5Y human neuroblastoma cells. ACS Chem. Neurosci. 12(14), 2608-2618 (2021).

    2. Narasimhan, P., Sklar, R., Murrell, M., et al. Methylmalonyl-CoA mutase induction by cerebral ischemia and neurotoxicity of the mitochondrial toxin methylmalonic acid. J. Neurosci. 16(22), 7336-7346 (1996).