A racemic mixture of (S)-(+)- and (R)-(–)-3-methyl-2-oxovaleric acid
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(±)-3-Methyl-2-oxovaleric Acid (sodium salt)

Item No. 43920

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-methyl-2-oxo-pentanoic acid, monosodium salt
CAS Number
3715-31-9
Synonyms
  • (±)-2-keto-3-Methylpentanoic Acid
  • (±)-2-keto-3-Methylvalerate
  • (±)-3-methyl-2-Oxopentanoic Acid
  • DL-α-keto β-Methylvaleric Acid
  • DL-KMV
Molecular Formula
C6H9O3 • Na
Formula Weight
152.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly Soluble: 1-10 mg/mlPBS (pH 7.2): Soluble: ≥10 mg/ml
SMILES
CCC(C(C([O-])=O)=O)C.[Na+]
InChi Code
InChI=1S/C6H10O3.Na/c1-3-4(2)5(7)6(8)9;/h4H,3H2,1-2H3,(H,8,9);/q;+1/p-1
InChi Key
SMDJDLCNOXJGKC-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 mg

    $65

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    1 g

    $124

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    Product Description

    (±)-3-Methyl-2-oxovaleric acid is a racemic mixture of (S)-(+)- and (R)-(–)-3-methyl-2-oxovaleric acid. (S)- and (R)-3-Methyl-2-oxovaleric acid are products of L-leucine (Item No. 34342) and L-alloisoleucine (Item No. 34904) catabolism, respectively.1,2 Dietary supplementation of (±)-3-methyl-2-oxovaleric acid leads to lower food consumption and weight gain compared with isoleucine supplementation.3 (±)-3-Methyl-2-oxovaleric acid accumulates in the tissues and body fluids of patients with maple syrup urine disease (MSUD), an inborn error of metabolism characterized by branched-chain α-keto acid dehydrogenase (BCKAD) deficiency that leads to progressive ketoacidosis, failure to thrive, neurological dysfunction, and, potentially, death.4,5 (±)-3-Methyl-2-oxovaleric Acid is the cause of the characteristic maple syrup odor that appears in the urine, sweat, and ear wax of infants with MSUD.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sewell, A.C., Heil, M., Podebrad, F., et al. Chiral compounds in metabolism: A look in the molecular mirror. Eur. J. Pediatr. 157(3), 185-191 (1998).

    2. Podebrad, F., Heil, M., Leib, S., et al. Analytical approach in diagnosis of inherited metabolic diseases: Maple syrup urine disease (MSUD) – simultaneous analysis of metabolites in urine by enantioselective multidimensional capillary gas chromatography-mass spectrometry (enantio-MDGC-MS). J. High Resol. Chromatogr. 20(7), 355-362 (1997).

    3. Funk, M.A., Lowry, K.R., and Baker, D.H. Utilization of the L- and DL-isomers of alpha-keto-beta-methylvaleric acid by rats and comparative efficacy of the keto analogs of branched-chain amino acids provided as ornithine, lysine and histidine salts. J. Nutr. 117(9), 1550-1555 (1987).

    4. Matsumoto, I., and Kuhara, T. Inborn Errors of Amino Acid and Organic Acid Metabolism. Mass Spectrometry. Modern Analytical Chemistry 1, 259-298 (1992).

    5. Farias, H.R., Gabriel, J.R., Cecconi, M.L., et al. The metabolic effect of α-ketoisocaproic acid: In vivo and in vitro studies. Metab. Brain Dis. 36(1), 185-192 (2021).