| Identification | Back Directory | [Name]
2-[(1-OXO-5Z,8Z,11Z,14Z-EICOSATETRAENYL)AMINO]-ETHANE SULFONIC ACID | [CAS]
119959-65-8 | [Synonyms]
N-ARACHIDONOYL TAURINE
N-Arachidonoyl Taurine Exclusive
2-[(1-OXO-5Z,8Z,11Z,14Z-EICOSATETRAENYL)AMINO]-ETHANE SULFONIC ACID
Ethanesulfonic acid, 2-[[(5Z,8Z,11Z,14Z)-1-oxo-5,8,11,14-eicosatetraen-1-yl]amino]- | [Molecular Formula]
C22H37NO4S | [MDL Number]
MFCD08062154 | [MOL File]
119959-65-8.mol | [Molecular Weight]
411.6 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 10 mg/ml; DMSO: 20 mg/ml; PBS (pH 7.2): 1.5 mg/ml | [form ]
A crystalline solid | [color ]
Light yellow to brown |
| Hazard Information | Back Directory | [Description]
N-Arachidonoyl taurine is an arachidonoyl amino acid. 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. N-Arachidonoyl taurine is an activator of the transient receptor potential vanilloid (TRPV) channels TRPV1 and TRPV4 (EC50s = 28 and 21 μM, respectively). 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. The levels of N-arachidonoyl taurine are changed in mouse brain following administration of Δ9-tetrahydrocannabinol (Δ9-THC). | [Uses]
N-Arachidonoyltaurine is a polyunsaturated lipid that inhibits the Cav3.3 current in T-type calcium channels. | [Definition]
ChEBI: A fatty acid-taurine conjugate derived from arachidonic acid. | [IC 50]
TRPV1: 28 μM (EC50); TRPV4: 21 μM (Ki) | [References]
[1] MELISSA V. TURMAN. Oxidative Metabolism of a Fatty Acid Amide Hydrolase-Regulated Lipid, Arachidonoyltaurine?[J]. Biochemistry Biochemistry, 2008, 47 12: 3917-3925. DOI: 10.1021/bi702530z
[2] DOMINIK P. WALUK . N-Acyl taurines trigger insulin secretion by increasing calcium flux in pancreatic β-cells[J]. Biochemical and biophysical research communications, 2013, 430 1: Pages 54-59. DOI: 10.1016/j.bbrc.2012.11.026
[3] EMMA LEISHMAN . Δ9-Tetrahydrocannabinol changes the brain lipidome and transcriptome differentially in the adolescent and the adult[J]. Biochimica et biophysica acta. Molecular and cell biology of lipids, 2018, 1863 5: Pages 479-492. DOI: 10.1016/j.bbalip.2018.02.001 |
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