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Palmitoyl serinol

Cat No.:V50399 Purity: ≥98%
Palmitoyl serinol (N-Palmitoyl serinol) is an analog of the endocannabinoid N-palmitoylethanolamine (PEA).
Palmitoyl serinol
Palmitoyl serinol Chemical Structure CAS No.: 126127-31-9
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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Other Forms of Palmitoyl serinol:

  • Palmitoyl serinol-d5 (N-Palmitoyl serinol-d5)
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Top Publications Citing lnvivochem Products
Product Description
Palmitoyl serinol (N-Palmitoyl serinol) is an analog of the endocannabinoid N-palmitoylethanolamine (PEA). Palmitoyl serinol improves the epidermal permeability barrier of normal and inflamed skin.
Palmitoyl serinol (CAS#: 126127-31-9), also known as N-Palmitoyl serinol, is a synthetic analog of the endocannabinoid N-palmitoyl ethanolamine (PEA). It is a derivative of C-16 ceramide and functions as a GPR119 agonist and CB1-dependent signaling modulator. It is known for its ability to improve the epidermal permeability barrier and stimulate ceramide production in skin models, as well as induce apoptosis in neuroblastoma cells.
Biological Activity I Assay Protocols (From Reference)
Targets
Palmitoyl serinol targets multiple pathways. It is a GPR119 agonist (EC50 = 9 uM), increasing cAMP in cells expressing GPR119. It also acts via a CB1-dependent mechanism to stimulate ceramide production. Additionally, it binds to PKCzeta and induces apoptosis in neuroblastoma cells. It is an analog of C-16 ceramide and mimics its biological functions.
ln Vitro
Through a CB1-dependent mechanism, palmitoylserinol (N-palmitoserinol) increases ceramide synthesis in an in vitro skin inflammation model [2].
It stimulates ceramide production through a CB1-dependent mechanism in an in vitro model of skin inflammation. In neuroblastoma cells, it induces apoptosis with an IC50 of approximately 80 uM via binding to PKCzeta. It reduces IL-4-induced decreases in the levels of long-chain fatty acid-containing ceramides in IL-4-stimulated HaCaT keratinocytes, an effect blocked by the CB1 antagonist AM-251.
ln Vivo
Palmitoyl serinol improves the epidermal permeability barrier in both normal and inflamed skin in vivo models. It is a metabolite of human commensal bacteria and can be used to study skin barrier function and lipid metabolism in animal models. Its ability to influence the endocannabinoid system in vivo makes it relevant for studying skin inflammation and other CB1-mediated processes.
Enzyme Assay
For a cell-free binding assay to assess PKCzeta binding, the purified PKCzeta enzyme (0.1-0.5 ug) is incubated with a fluorescently labeled PKC substrate peptide and varying concentrations of Palmitoyl serinol (0-200 uM) in a kinase buffer containing 100 uM ATP and 100 uM CaCl2. The reaction proceeds for 30 minutes at 30degC. The fluorescence intensity (e.g., at 485/535 nm) is measured to determine the level of substrate phosphorylation. The IC50 for PKCzeta binding is calculated from the inhibition curve, and this effect can be blocked by the PKCzeta inhibitor Gö 6983.
Cell Assay
For in vitro cell assays, HaCaT keratinocytes are cultured in DMEM with 10% FBS. Cells are pre-treated with Palmitoyl serinol (1-50 uM) for 24 hours, then stimulated with IL-4 (10 ng/mL) to induce inflammation and reduce ceramide levels. After 48 hours, cells are harvested, and total lipids are extracted. Ceramide species are analyzed by LC-MS. For apoptosis assays, F-11 neuroblastoma cells are seeded and treated with Palmitoyl serinol (25-200 uM) for 24-48 hours. Cell viability is measured by MTT, and apoptosis is confirmed by Caspase-3/7 activation and flow cytometry.
Animal Protocol
A typical in vivo protocol for skin barrier studies uses hairless mice. Palmitoyl serinol is formulated in a cream or lotion (0.1-1%) and applied topically to the dorsal skin twice daily for 5-7 days. Some groups may be treated with a CB1 antagonist (AM-251) prior to Palmitoyl serinol application. The transepidermal water loss (TEWL) is measured using a Tewameter to assess barrier function. Skin biopsies are taken at the endpoint for histological analysis (H&E staining) and lipid extraction to measure ceramide levels by LC-MS.
ADME/Pharmacokinetics
Palmitoyl serinol (MW: 329.52) is a solid with low water solubility but can be dissolved in DMSO or ethanol for in vitro assays. For in vivo topical applications, it is incorporated into lipid-based creams. It is stable for long-term storage at -20degC. It is a metabolite of human commensal bacteria and plays a role in the entourage effect of endocannabinoid signaling.
Toxicity/Toxicokinetics
Palmitoyl serinol is generally considered safe for topical use in research models. In vitro, it induces apoptosis in neuroblastoma cells at higher concentrations (IC50 ~80 uM), but this is concentration-dependent. No significant systemic toxicity has been reported in standard animal studies at the doses used for skin barrier research. Standard laboratory safety precautions should be followed. It is not for human use.
References

[1]. N-Palmitoyl Serinol Stimulates Ceramide Production through a CB1-Dependent Mechanism in In Vitro Model of Skin Inflammation. Int J Mol Sci. 2021;22(15):8302. Published 2021 Aug 2.

Additional Infomation
Palmitoyl serine is a fatty amide.
Palmitoyl serinol is also an analog of C-16 ceramide, a key structural component of the skin barrier. It is used in research to study skin barrier function, inflammation, and the endocannabinoid system. It is also known as N-palmitoyl serinol and is an important tool in understanding the role of CB1 receptors in ceramide synthesis and skin health.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H39NO3
Molecular Weight
329.51800
Exact Mass
329.292
CAS #
126127-31-9
Related CAS #
Palmitoyl serinol-d5;946524-35-2
PubChem CID
9862307
Appearance
Typically exists as solid at room temperature
Density
1.0±0.1 g/cm3
Boiling Point
525.9±40.0 °C at 760 mmHg
Flash Point
271.9±27.3 °C
Vapour Pressure
0.0±3.1 mmHg at 25°C
Index of Refraction
1.475
LogP
5.68
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
17
Heavy Atom Count
23
Complexity
255
Defined Atom Stereocenter Count
0
SMILES
CCCCCCCCCCCCCCCC(NC(CO)CO)=O
InChi Key
MZUNFYMZKTWADX-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(23)20-18(16-21)17-22/h18,21-22H,2-17H2,1H3,(H,20,23)
Chemical Name
N-(1,3-dihydroxypropan-2-yl)hexadecanamide
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 3.0347 mL 15.1736 mL 30.3472 mL
5 mM 0.6069 mL 3.0347 mL 6.0694 mL
10 mM 0.3035 mL 1.5174 mL 3.0347 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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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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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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