An essential ω-6 PUFA
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Linoleic Acid

Item No. 90150

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9Z,12Z-octadecadienoic acid
CAS Number
60-33-3
Synonyms
  • C18:2(9Z,12Z)
  • C18:2 n-6
  • FA 18:2
  • 9,12-Octadecadienoic Acid
  • Telfairic Acid
Molecular Formula
C18H32O2
Formula Weight
280.5
Purity
≥98%
Formulation (Request formulation change)
A neat oil
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 1 mg/mlDMF: 100 mg/mlDMSO: 100 mg/mlEthanol: Miscible
SMILES
CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
InChi Code
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
InChi Key
OYHQOLUKZRVURQ-HZJYTTRNSA-N
Side Chain Carbon Sum
18:2
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    50 mg

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    500 mg

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    Product Description

    Linoleic acid is an essential ω-6 polyunsaturated fatty acid (PUFA).1 It is the most abundant PUFA in a variety of foods, and dietary sources of linoleic acid include vegetable oils, meats, nuts, seeds, and eggs. Linoleic acid (30 μM) increases migration of IEC-6 rat intestinal epithelial cells in a wound healing assay.2 Rats fed a linoleate-deficient diet exhibit decreased body weight and an increased ratio of eicosatrienoate to arachidonate in liver and serum phospholipids compared with rats fed a control diet, as well as mild scaling of forepaw skin.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Whelan, J., and Fritsche, K. Linoleic acid. Adv. Nutr. 4(3), 311-312 (2013).

    2. Ruthig, D.J., and Meckling-Gill, K.A. Both (n-3) and (n-6) fatty acids stimulate wound healing in the rat intestinal epithelial cell line, IEC-6. J. Nutr. 129(10), 1791-1798 (1999).

    3. Cunnane, S.C., and Anderson, M.J. Pure linoleate deficiency in the rat: Influence on growth, accumulation of n-6 polyunsaturates, and [1-14C]linoleate oxidation. J. Lipid Res. 38(4), 805-812 (1997).

    Product Citations

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. The FASEB Journal 35(6), e21666 (2021).

    Liu, F., Zuo, X., Liu, Y., et al. Suppression of membranous LRP5 recyling, Wnt/β-catenin signaling, and colon carcinogenesis by 15-LOX-1 peroxidation of linoleic acid in PI3P. Cell Rep. 32(7), 108049 (2020).

    Zou, Y., Li, H., Graham, E.T., et al. Cytochrome P450 oxidoreductase contributes to phospholipid peroxidation in ferroptosis. Nat. Chem. Biol. 16(3), 302-309 (2020).

    Fuchs, D., Tang, X., Johnsson, A.-K., et al. Eosinophils synthesize trihydroxyoctadecenoic acids (TriHOMEs) via a 15-lipoxygenase dependent process. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1865(4), 158611 (2020).

    Ubellacker, J.M., Tasdogan, A., Ramesh, V., et al. Lymph protects metastasizing melanoma cells from ferroptosis. Nature 585(7823), 113-118 (2020).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites. medRxiv (2020).

    Yan, B., Chu, H., Yang, D., et al. Characterization of the lipidomic profile of human coronavirus-infected cells: Implications for lipid metabolism remodeling upon coronavirus replication. Viruses 11(1), 73 (2019).

    Magtanong, L., Ko, P.-J., To, M., et al. Exogenous monounsaturated fatty acids promote a ferroptosis-resistant cell state. Cell Chem. Biol. 26(3), 420-432 (2019).

    Lahvic, J.L., Ammerman, M., Li, P., et al. Specific oxylipins enhance vertebrate hematopoiesis via the receptor GPR132. PNAS 115(37), 9252-9257 (2018).

    Yuan, C., Sidhu, R.S., Kuklev, D.V., et al. Cyclooxygenase allosterism, fatty acid-mediated cross-talk between monomers of cyclooxygenase homodimers. The Journal of Biological Chemisty 284(15), 10046-10055 (2009).