An ω-alkynylated form of palmitic acid
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Unmodified Version(s)
10006627Palmitic Acid 43561Palmitic Acid (sodium salt)
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Palmitic Acid Alkyne

Item No. 13266

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
15-hexadecynoic acid
CAS Number
99208-90-9
Synonyms
  • Alk-14
  • Click Tag™ Palmitic Acid Alkyne
  • FA 16:2
Molecular Formula
C16H28O2
Formula Weight
252.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:5): 0.15 mg/ml
SMILES
C#CCCCCCCCCCCCCCC(O)=O
InChi Code
InChI=1S/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h1H,3-15H2,(H,17,18)
InChi Key
PUZGUNYANHPRKM-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $70

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    1 mg

    $123

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    5 mg

    $436

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    10 mg

    $602

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    Product Description

    Protein S-palmitoylation is the post-translational acylation of proteins and serves to regulate localization, stability, and interaction with associates and substrates.1 Palmitic acid alkyne is a form of palmitic acid (Item No. 10006627) with an ω-terminal alkyne. The terminal alkyne group can be used in linking reactions, known as click chemistry; this chemistry is characterized by high dependability and specificity of the azide-alkyne bioconjugation reactions.2,3 The use of palmitic acid alkyne and related lipids in isolating palmitoylated proteins has been described.4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Aicart-Ramos, C., Valero, R.A., and Rodriguez-Crespo, I. Protein palmitoylation and subcellular trafficking. Biochim. Biophys. Acta 1808(12), 2981-2994 (2011).

    2. Kolb, H.C., and Sharpless, K.B. The growing impact of click chemistry on drug discovery. Drug Discov. Today 8(24), 1128-1137 (2003).

    3. Lutz, J.-F., and Zarafshani, Z. Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-alkyne "click" chemistry. Adv. Drug Deliv. Rev. 60(9), 958-970 (2008).

    4. Martin, B.R., and Cravatt, B.F. Large-scale profiling of protein palmitoylation in mammalian cells. Nat. Methods 6(2), 135-138 (2009).

    5. Yap, M.C., Kostiuk, M.A., Martin, D.D.O., et al. Rapid and selective detection of fatty acylated proteins using ω-alkynyl-fatty acids and click chemistry. J. Lipid Res. 51(6), 1566-1580 (2010).

    6. Jiang, H., Khan, S., Wang, Y., et al. SIRT6 regulates TNF-α secretion through hydrolysis of long-chain fatty acyl lysine. Nature 496(7443), 110-113 (2013).