An arachidonoyl amino acid
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Labeled Version(s)
26323N-Arachidonoyl Taurine-d4
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N-Arachidonoyl Taurine

Item No. 10005537

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[(1-oxo-5Z,8Z,11Z,14Z-eicosatetraenyl)amino]-ethane sulfonic acid
CAS Number
119959-65-8
Molecular Formula
C22H37NO4S
Formula Weight
411.6
Purity
≥98%
Formulation
A 5 mg/ml in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 20 mg/mlPBS (pH 7.2): 1.5 mg/ml
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(N(CCS(=O)(O)=O)[H])=O
InChi Code
InChI=1S/C22H37NO4S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)23-20-21-28(25,26)27/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)(H,25,26,27)/b7-6-,10-9-,13-12-,16-15-
InChi Key
YUNYSWCRLRYOPO-DOFZRALJSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $61

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    1 mg

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    5 mg

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    10 mg

    $726

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    Product Description

    N-Arachidonoyl taurine is an arachidonoyl amino acid.1 It is oxygenated by 12(S)- and 15(S)-lipoxygenase and is converted to 12-HETE-taurine (12-HETE-T) in murine resident peritoneal macrophages.2 N-Arachidonoyl taurine is an activator of the transient receptor potential vanilloid (TRPV) channels TRPV1 and TRPV4 (EC50s = 28 and 21 µM, respectively).1 It increases calcium flux in HIT-T15 pancreatic β-cells and INS-1 rat islet cells when used at a concentration of 10 µM and increases insulin secretion from 832/13 INS-1 pancreatic β-cells.3 The levels of N-arachidonoyl taurine are changed in mouse brain following administration of Δ9-tetrahydrocannabinol (Δ9-THC).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Turman, M.V., Kingsley, P.J., Rouzer, C.A., et al. Oxidative metabolism of a fatty acid amide hydrolase-regulated lipid, arachidonoyltaurine. Biochemistry 47(12), 3917-3925 (2008).

    3. Waluk, D.P., Vielfort, K., Derakhshan, S., et al. N-Acyl taurines trigger insulin secretion by increasing calcium flux in pancreatic β-cells. Biochem. Biophys. Res. Commun. 430(1), 54-59 (2013).

    4. Leishman, E., Murphy, M., Mackie, K., et al. Δ9-Tetrahydrocannabinol changes the brain lipidome and transcriptome differentially in the adolescent and the adult. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1863(5), 479-492 (2018).

    Product Citations

    Wei, W., Lyu, X., Markhard, A.L., et al. PTER is a N-acetyltaurine hydrolase that regulates feeding and obesity. Nature 633(8028), 182-188 (2023).