A very long chain fatty acid abundant in sphingomyelin
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Nervonic Acid

Item No. 13940

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
15Z-tetracosenoic acid
CAS Number
506-37-6
Synonyms
  • FA 24:1
  • Selacholeic Acid
Molecular Formula
C24H46O2
Formula Weight
366.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/ml
SMILES
CCCCCCCC/C=C\CCCCCCCCCCCCCC(O)=O
InChi Code
InChI=1S/C24H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9-
InChi Key
GWHCXVQVJPWHRF-KTKRTIGZSA-N
Side Chain Carbon Sum
24:1
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 mg

    $49

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    250 mg

    $102

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    500 mg

    $167

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    Product Description

    Nervonic acid (24:1n-9) is a very long chain fatty acid produced by elongation of oleic acid (18:1n-9) (Item No. 90260) and derived from erucic acid (22:1n-9) (Item No. 90175).1 It is enriched in nervous tissue and is particularly abundant in sphingolipids, such as sphingomyelin in the myelin sheath of nerve fibers.2 Nervonic acid is poorly produced in demyelinating disorders, including multiple sclerosis and adrenoleukodystrophy, suggesting that dietary supplementation may be beneficial.3 In addition, it is deficient in mice which are homozygous for the quaking mutation, a model of Parkinson’s disease.4,5 Nervonic acid also binds and inhibits DNA polymerase β (Ki = 4.0 uM) and HIV-1 reverse transcriptase (Ki = 1.2 µM).6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Taylor, D.C., Francis, T., Guo, Y., et al. Molecular cloning and characterization of a KCS gene from Cardamine graeca and its heterologous expression in Brassica oilseeds to engineer high nervonic acid oils for potential medical and industrial use. Plant Biotechnol. J. 7(9), 925-938 (2009).

    2. Hirvisalo, E.L., and Renkonen, O. Composition of human serum sphingomyelins. J. Lipid Res. 11(1), 54-59 (1970).

    3. Sargent, J.R., Coupland, K., and Wilson, R. Nervonic acid and demyelinating disease. Med. Hypotheses 42(4), 237-242 (1994).

    4. Baumann, N.A., Jacque, C.M., Pollet, S.A., et al. Fatty acid and lipid composition of the brain of a myelin deficient mutant, the "quaking" mouse. Eur. J. Biochem. 4(3), 340-344 (1968).

    5. Cook, C., Barnett, J., Coupland, K., et al. Effects of feeding Lunaria oil rich in nervonic and erucic acids on the fatty acid compositions of sphingomyelins from erythrocytes, liver, and brain of the quaking mouse mutant. Lipids 33(10), 993-1000 (1998).

    6. Kasai, N., Mizushina, Y., Sugawara, F., et al. Three-dimensional structural model analysis of the binding site of an inhibitor, nervonic acid, of both DNA polymerase β and HIV-1 reverse transcriptase. J. Biochem. 132(5), 819-828 (2002).