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N-Stearoyl Taurine

Cat No.:V89776 Purity: ≥98%
Several different anandamide amino acids have been isolated and characterized from bovine brain, including N-arachidonyl dopamine (NADA) and N-arachidonyl serine (ARA-S).
N-Stearoyl Taurine
N-Stearoyl Taurine Chemical Structure CAS No.: 63155-80-6
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
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Product Description
Several different anandamide amino acids have been isolated and characterized from bovine brain, including N-arachidonyl dopamine (NADA) and N-arachidonyl serine (ARA-S). During mass spectrometry lipidomics analysis of rat brain, a series of fatty amides of a third amino acid, taurine, were discovered. This novel compound is found in the kidney and activates members of the transient receptor potential (TRP) calcium channel family. N-stearoyl taurine is a prominent aminoacyl endocannabinoid isolated from rat brain during lipidomics analysis.
N‑Stearoyl Taurine (CAS 63155‑80‑6) is an endogenous amino‑acyl endocannabinoid and fatty acid‑taurine conjugate derived from stearic acid. It has the molecular formula C20H41NO4S and a molecular weight of 391.61 g/mol. This compound, which is present in kidney and isolated from rat brain during lipidomics profiling, is used as a biochemical assay reagent and research tool in endocannabinoid signaling studies.
Biological Activity I Assay Protocols (From Reference)
Targets
N‑Stearoyl Taurine activates members of the transient receptor potential (TRP) family of calcium channels, acting as an endogenous lipid signaling molecule. It is classified as a mouse metabolite. Its mechanism involves binding to and modulating TRP channels, leading to calcium influx and downstream signaling effects. The compound belongs to the N‑acyl taurine family, which are recognized as a novel class of bioactive lipids.
ln Vitro
In vitro, N‑Stearoyl Taurine is used to study calcium channel activation. It induces calcium influx in cells expressing TRP channels, as measured by fluorescent calcium indicators (e.g., Fluo‑4). The compound has been isolated from rat brain and identified through lipidomics profiling, confirming its presence as an endogenous signaling molecule. It serves as a standard in LC‑MS methods for the detection of N‑acyl taurines in biological samples.
ln Vivo
In vivo, N‑Stearoyl Taurine is an endogenous metabolite present in rat brain and kidney, suggesting a physiological role in these tissues. As a mouse metabolite, it may be involved in local calcium signaling and nociception. It is not administered exogenously as a therapeutic; rather, its levels are measured in rodent models to understand its role in lipid signaling and metabolic regulation.
Enzyme Assay
The interaction of N‑Stearoyl Taurine with TRPV1 channels can be assessed using a calcium flux assay in a cell‑free membrane system. TRPV1‑expressing cell membranes are immobilized on a 96‑well plate. N‑Stearoyl Taurine (0.1-100 uM) is added, and calcium influx is measured using a fluorescent calcium indicator (e.g., Fluo‑4, λ_ex 485 nm, λ_em 525 nm) with a plate reader. The increase in fluorescence relative to control is quantified. Capsaicin (1 uM) is used as a positive control.
Cell Assay
N‑Stearoyl Taurine can be added to cultured neuronal cells (e.g., dorsal root ganglion neurons) at concentrations of 1-50 uM. Intracellular calcium levels are measured using Fluo‑4 AM loading (2 uM, 30 min, 37degC). Fluorescence intensity is recorded in a plate reader or by confocal microscopy. The percentage of cells showing calcium transients is calculated, and the EC₅0 for TRP channel activation is determined. Ruthenium red (10 uM) is used as a TRPV1 antagonist to confirm specificity.
Animal Protocol
N‑Stearoyl Taurine is not administered to animals as a drug, but its endogenous levels are measured in animal models. For a typical study, rats are euthanized, and brain tissue (hippocampus, cortex) or kidney is dissected. Lipids are extracted using chloroform:methanol (2:1) containing internal standards. N‑Stearoyl Taurine is quantified by LC‑MS/MS in multiple reaction monitoring mode. Levels are compared between treatment groups (e.g., pain models, inflammatory models) to assess changes in endogenous N‑acyl taurine metabolism.
ADME/Pharmacokinetics
N‑Stearoyl Taurine is an endogenous metabolite; its pharmacokinetics are defined by its natural biosynthesis and degradation. It is formed by the conjugation of stearic acid with taurine via an amide bond. It circulates in low concentrations and is rapidly hydrolyzed by fatty acid amide hydrolase (FAAH). The half‑life in plasma is estimated to be short (<30 min). It is stored as a solution in methanol at −20degC and protected from light. The compound is stable for up to 2 years under these conditions.
Toxicity/Toxicokinetics
No specific toxicity data are available for N‑Stearoyl Taurine. As an endogenous lipid metabolite, it is expected to have low acute toxicity at physiological concentrations. At high concentrations, it may cause calcium‑mediated cytotoxicity. The compound is for research use only; it is not for human or therapeutic use. Standard laboratory precautions should be used: wear gloves and safety goggles, avoid inhalation, and use in a well‑ventilated area.
References

[1]. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. J. Biol. Chem. 276(46), 42639-42644 (2001).

Additional Infomation
N-Stearyl taurine is a fatty acid-taurine conjugate derived from stearic acid. It plays a metabolic role in mice. Functionally, it is related to octadecanoic acid. It is the conjugate acid of N-stearoyl taurine (1-).
N‑Stearoyl Taurine is not a drug; it is a research biochemical. It is used as a standard in lipidomics for the detection of N‑acyl taurines, and as a tool for studying the role of fatty acid‑taurine conjugates in endocannabinoid signaling and TRP channel activation. It is also used in studies of kidney function and neuronal calcium signaling. The compound is a member of a novel class of endogenous signaling lipids, with potential implications for pain, inflammation, and metabolic regulation.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H41NO4S
Molecular Weight
391.61
Exact Mass
391.275
CAS #
63155-80-6
PubChem CID
168274
Appearance
Colorless to light yellow liquid
Density
1.0±0.1 g/cm3
Index of Refraction
1.480
LogP
5.65
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
19
Heavy Atom Count
26
Complexity
418
Defined Atom Stereocenter Count
0
SMILES
CCCCCCCCCCCCCCCCCC(=O)NCCS(=O)(=O)O
InChi Key
LMIJIHJZVURGQK-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H41NO4S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(22)21-18-19-26(23,24)25/h2-19H2,1H3,(H,21,22)(H,23,24,25)
Chemical Name
2-(octadecanoylamino)ethanesulfonic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.5536 mL 12.7678 mL 25.5356 mL
5 mM 0.5107 mL 2.5536 mL 5.1071 mL
10 mM 0.2554 mL 1.2768 mL 2.5536 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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