A dicarboxylic acid and metabolite of L-isoleucine and L-alloisoleucine
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Isomer(s)
44091Ethylmalonic Acid
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Methylsuccinic Acid

Item No. 36430

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methyl-butanedioic acid
CAS Number
498-21-5
Synonyms
  • 2-Methylsuccinic Acid
  • NSC 5276
Molecular Formula
C5H8O4
Formula Weight
132.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
O=C(CC(C)C(O)=O)O
InChi Code
InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)
InChi Key
WXUAQHNMJWJLTG-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $30

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    10 g

    $53

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    25 g

    $103

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    50 g

    $191

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Methylsuccinic acid is a dicarboxylic acid and metabolite of the essential amino acid L-isoleucine and branched-chain amino acid L-alloisoleucine (Item No. 34904).1 It is formed from L-isoleucine and L-alloisoleucine via an R-2-oxo-3-methylvaleric acid intermediate. Urinary levels of methylsuccinic acid are increased in patients with ethylmalonic encephalopathy, an inborn error of metabolism characterized by developmental delay, hypotonia, vascular instability, petechiae, acrocyanosis, chronic diarrhea, and lactic acidemia. Urinary levels of methylsuccinic acid are also increased in patients with short-chain acyl-CoA dehydrogenase deficiency or type 2 diabetes.2,3 It has been found in urban and industrial aerosols of fine particulate matter less than 2.5 µm (PM2.5).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nowaczyk, M.J.M., Lehotay, D.C., Platt, B.-A., et al. Ethylmalonic and methylsuccinic aciduria in ethylmalonic encephalopathy arise from abnormal isoleucine metabolism. Metabolism 47(7), 836-839 (1998).

    2. Gallant, N.M., Leydiker, K., Tang, H., et al. Biochemical, molecular, and clinical characteristics of children with short chain acyl-CoA dehydrogenase deficiency detected by newborn screening in California. Mol. Genet. Metab. 106(1), 55-61 (2012).

    3. Urpi-Sarda, M., Almanza-Aguilera, E., Llorach, R., et al. Non-targeted metabolomic biomarkers and metabotypes of type 2 diabetes: A cross-sectional study of PREDIMED trial participants. Diabetes Metab. 45(2), 167-174 (2019).

    4. Crenn, V., Fronval, I., Petitprez, D., et al. Fine particles sampled at an urban background site and an industrialized coastal site in Northern France - Part 1: Seasonal variations and chemical characterization. Sci. Total Environ. 578, 203-218 (2017).