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Structure Database (LMSD)

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Common Name

DL-Cerebronic acid

Systematic Name

2-hydroxy-tetracosanoic acid

Synonyms

Phrenosinic acid
Phrenosic acid

LM ID

LMFA01050080

Formula

C₂₄H₄₈O₃

Exact Mass

Calculate m/z

384.360346

Sum Composition

FA 24:0;O

Status

Curated

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Classification

Biological Context

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 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]

This information has been provided by Cayman Chemical

References

1. 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).

2. 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).

4. 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).

3. 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).

5. 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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

Synthesis of cerebronic acid from lignoceric acid by rat brain preparation. Some properties and distribution of the -hydroxylation system.,
J Biol Chem, 1973

Pubmed ID: 4145326