An ω-alkyne derivative of linoleic acid
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Linoleic Acid Alkyne

Item No. 10541

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9Z,12Z-octadecadien-17-ynoic acid
CAS Number
1219038-31-9
Synonyms
  • Click Tag™ Linoleic Acid Alkyne
  • FA 18:4
Molecular Formula
C18H28O2
Formula Weight
276.4
Purity
≥95%
Formulation (Request formulation change)
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.15 M Tris-HCl pH 8.5: 1 mg/mlDMF: 100 mg/mlDMSO: 100 mg/mlEthanol: 100 mg/mlPBS (pH 7.2): 0.025 mg/ml
SMILES
C#CCCC/C=C\C/C=C\CCCCCCCC(O)=O
InChi Code
InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h1,6-7,9-10H,3-5,8,11-17H2,(H,19,20)/b7-6-,10-9-
InChi Key
WPOFIMJJIQUNRW-HZJYTTRNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    100 µg

    $61

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    500 µg

    $242

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    1 mg

    $394

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    5 mg

    $1,513

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    Product Description

    Linoleic acid alkyne is an ω-alkyne derivative of linoleic acid (Item No. 90150). The ω-alkyne moiety allows Cu(I)-catalyzed cycloaddition chemistry with other molecules containing an azide group.1,2 Linoleic acid alkyne has been used in experiments focusing on the biological roles of linoleic acid.3,4 Alternatively, this modified lipid can be used to synthesize other alkyne-containing products, such as glycerophospholipids, for click chemistry.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gaebler, A., Penno, A., Kuerschner, L., et al. A highly sensitive protocol for microscopy of alkyne lipids and fluorescently tagged or immunostained proteins. J. Lipid. Res. 57(10), 1934-1947 (2016).

    2. Grammel, M., and Hang, H.C. Chemical reporters for biological discovery. Nat. Chem. Biol. 9(8), 475-484 (2013).

    3. Beavers, W.N., Serwa, R., Shimozu, Y., et al. ω-Alkynyl lipid surrogates for polyunsaturated fatty acids: Free radical and enzymatic oxidations. J. Am. Chem. Soc. 136(32), 11529-11539 (2014).

    4. Windsor, K., Genaro-Mattos, T.C., Kim, H.-Y.H., et al. Probing lipid-protein adduction with alkynyl surrogates: application to Smith-Lemli-Opitz syndrome. J. Lipid. Res. 54(10), 2842-2850 (2013).

    5. Milne, S.B., Tallman, K.A., Serwa, R., et al. Capture and release of alkyne-derivatized glycerophospholipids using cobalt chemistry. Nat. Chem. Biol. 6(3), 205-207 (2010).