An internal standard for the quantification of N-arachidonoyl taurine
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Unlabeled Version(s)
10005537N-Arachidonoyl Taurine
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N-Arachidonoyl Taurine-d4

Item No. 26323

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamido)ethane-1-sulfonic-1,1,2,2-d4 acid
Molecular Formula
C22H33D4NO4S
Formula Weight
415.6
Purity
≥99% deuterated forms (d1-d4)
Formulation
A 1 mg/ml solution 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(NC([2H])([2H])C([2H])([2H])S(=O)(O)=O)=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-/i20D2,21D2
InChi Key
YUNYSWCRLRYOPO-KALLKTRHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    100 µg

    $42

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    Product Description

    N-Arachidonoyl taurine-d4 is intended for use as an internal standard for the quantification of N-arachidonoyl taurine (Item No. 10005537) by GC- or LC-MS. 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).