A FAAH substrate discovered during metabolite profiling
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N-Lignoceroyl Taurine

Item No. 10007286

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[(1-oxotetracosyl)amino]-ethanesulfonic acid
CAS Number
807370-75-8
Molecular Formula
C26H53NO4S
Formula Weight
475.8
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2.5 mg/mlDMSO: 5 mg/mlEthanol: 0.15 mg/mlPBS (pH 7.2): 0.1 mg/ml
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC(NCCS(=O)(O)=O)=O
InChi Code
InChI=1S/C26H53NO4S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-26(28)27-24-25-32(29,30)31/h2-25H2,1H3,(H,27,28)(H,29,30,31)
InChi Key
DDCFSFYOVZMRHL-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $87

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    10 mg

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    Product Description

    Several different arachidonoyl amino acid conjugates, including N-arachidonoyl dopamine and N-arachidonoyl-L-serine, have been isolated and characterized from bovine brain.1 N-lignoceroyl taurine is one of several novel taurine-conjugated fatty acids discovered during mass spectrometry lipidomic analysis of brain and spinal cord from wild-type and fatty acid amide hydrolase (FAAH) knockout mice.2 The levels of N-lignoceroyl taurine were elevated 23-26 fold in FAAH-/- mice compared to wild-type mice, indicating that FAAH utilizes N-lignoceroyl taurine as a substrate. However, in vitro experiments with purified FAAH indicate N-lignoceroyl taurine is hydrolyzed 2,000 times more slowly by FAAH compared to oleoyl ethanolamide.2 N-acyl taurines bearing polyunsaturated acyl chains can activate members of the transient receptor potential (TRP) family of calcium channels, including TRPV1 and TRPV4.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. The Journal of Biological Chemisty 276(46), 42639-42644 (2001).

    2. Saghatelian, A., Trauger, S.A., Want, E.J., et al. Assignment of endogenous substrates to enzymes by global metabolite profiling. Biochemistry 43(45), 14332-14339 (2004).

    3. Saghatelian, A., McKinney, M.K., Bandell, M., et al. A FAAH-regulated class of N-acyl taurines that activates TRP ion channels. Biochemistry 45(30), 9007-9015 (2006).