An α-hydroxy very long chain fatty acid
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Product Type

Biochemicals
Lipids
Fatty Acids

Research Area

Lipid Biochemistry
Neuroscience

2-hydroxy Lignoceric Acid

Item No. 22680

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-hydroxy-tetracosanoic acid
CAS Number
544-57-0
Synonyms
  • Cerebronic Acid
  • FA 24:0;O
Molecular Formula
C24H48O3
Formula Weight
384.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (5:1): soluble
SMILES
CCCCCCCCCCCCCCCCCCCCCCC(O)C(O)=O
InChi Code
InChI=1S/C24H48O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23(25)24(26)27/h23,25H,2-22H2,1H3,(H,26,27)
InChi Key
MSUOLNSQHLHDAS-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $295

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    Product Description

    2-hydroxy Lignoceric acid is an α-hydroxy very long chain fatty acid that is normally present in the mammalian nervous system.1 In the brain, 2-hydroxy lignoceric acid is derived from lignoceric acid (Item No. 13353) and further converted to ceramides and cerebrosides during the process of nerve sheath myelination.1,2,3 2-hydroxy Lignoceric acid is produced by the α-oxidation of lignoceric acid in the peroxisome and defects in this pathway are associated with disorders such as Zellweger syndrome.4,5 [Matreya, LLC. Catalog No. 1715]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hoshi, M., and Kishimoto, Y. Synthesis of cerebronic acid from lignoceric acid by rat brain preparation. Some properties and distribution of the α-hydroxylation system. The Journal of Biological Chemisty 248(11), 4123-4130 (1973).

    2. Bourre, J.M., Paturneau-Jouas, M.Y., Daudu, O.L., et al. Lignoceric acid biosynthesis in the developing brain. Activities of mitochondrial acetyl-CoA-dependent synthesis and microsomal malonyl-CoA chain-elongating system in relation to myelination. Eur. J. Biochem. 72(1), 41-47 (1977).

    3. Murad, S., and Kishimoto, Y. α hydroxylation of lignoceric acid to cerebronic acid during brain development. Diminished hydroxylase activity in myelin-deficient mouse mutants. The Journal of Biological Chemisty 250(15), 5841-5846 (1975).

    4. Singh, I., Moser, A.E., Goldfischer, S., et al. Lignoceric acid is oxidized in the peroxisome: Implications for the Zellweger cerebro-hepato-renal syndrome and adrenoleukodystrophy. Proc. Natl. Acad. Sci. USA 81(13), 4203-4207 (1984).

    5. Jung, K., Reszka, R., Kamlage, B., et al. Tissue metabolite profiling identifies differentiating and prognostic biomarkers for prostate carcinoma. Int. J. Cancer 133(12), 2914-2924 (2013).