N-Docosanoyl Taurine

• CAT Number: R016793
• CAS Number: 783284-48-0
• Molecular Formula: C24H49NO4S
• Molecular Weight: 447.719
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: 2-(docosanoylamino)ethanesulfonic acid
• InChI: InChI=1S/C24H49NO4S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(26)25-22-23-30(27,28)29/h2-23H2,1H3,(H,25,26)(H,27,28,29)
• InChIKey: SAIMYQVCHHQQMU-UHFFFAOYSA-N
• SMILES: CCCCCCCCCCCCCCCCCCCCCC(=O)NCCS(=O)(=O)O

Several different arachidonoyl amino acid conjugates, including N-<wbr></wbr>arachidonoyl dopamine and N-<wbr></wbr>arachidonoyl-<wbr></wbr>L-<wbr></wbr>serine, have been isolated and characterized from bovine brain. N-<wbr></wbr>Docosanoyl taurine is one of several novel taurine-<wbr></wbr>conjugated fatty acids discovered during mass spectrometry lipidomic analysis of brain and spinal cord from wild-<wbr></wbr>type and fatty acid amide hydrolase (FAAH) knockout mice. The levels of N-<wbr></wbr>docosanoyl taurine were elevated ~12 fold in FAAH-<wbr></wbr>/-<wbr></wbr> mice compared to wild-<wbr></wbr>type mice, indicating that FAAH utilizes N-<wbr></wbr>docosanoyl taurine as a substrate. However, in vitro experiments with purified FAAH indicate that related N-<wbr></wbr>fatty acyl taurines and ethanolamines of similar chain length are hydrolyzed 2,000-<wbr></wbr>50,000 times more slowly by FAAH compared to oleoyl ethanolamide. N-<wbr></wbr>acyl taurines bearing polyunsaturated acyl chains can activate members of the transient receptor potential (TRP) family of calcium channels, including TRPV1 and TRPV4.

Reference

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).