Physicochemical Properties
| Molecular Formula | C18H37NO2 |
| Molecular Weight | 299.4919 |
| Exact Mass | 299.282 |
| Elemental Analysis | C, 72.19; H, 12.45; N, 4.68; O, 10.68 |
| CAS # | 544-31-0 |
| Related CAS # | Palmitoylethanolamide-d4;1159908-45-8 |
| PubChem CID | 4671 |
| Appearance | White to off-white solid powder |
| Density | 0.9±0.1 g/cm3 |
| Boiling Point | 461.5±28.0 °C at 760 mmHg |
| Melting Point | 99 °C |
| Flash Point | 232.9±24.0 °C |
| Vapour Pressure | 0.0±2.6 mmHg at 25°C |
| Index of Refraction | 1.463 |
| LogP | 5.82 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 16 |
| Heavy Atom Count | 21 |
| Complexity | 219 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])N([H])C([H])([H])C([H])([H])O[H] |
| InChi Key | HXYVTAGFYLMHSO-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h20H,2-17H2,1H3,(H,19,21) |
| Chemical Name | N-(2-Hydroxyethyl)hexadecanamide |
| Synonyms | Palmidrol; NSC 23320; NSC23320; NSC-23320; Palmitoylethanolamide; Palmidrol; 544-31-0; N-(2-Hydroxyethyl)hexadecanamide; Palmitoyl ethanolamide; Palmitamide MEA; Impulsin; N-(2-Hydroxyethyl)palmitamide;Palmitoylethanolamide |
| 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) |
Biological Activity
| Targets | Human Endogenous Metabolite; cannabinoid receptor-inactive eCB-related molecule |
| ln Vitro | Palmitoyl ethanolamide is an N-(long-chain-acyl)ethanolamine that is the ethanolamide of palmitic (hexadecanoic) acid. It has a role as an anti-inflammatory drug, an antihypertensive agent, a neuroprotective agent and an anticonvulsant. It is a N-(long-chain-acyl)ethanolamine, an endocannabinoid and a N-(saturated fatty acyl)ethanolamine. It is functionally related to a hexadecanoic acid. |
| ln Vivo | Interferon production in mice receiving intravenous or topical treatment is not stimulated by palmitoylethanolamide, also known as palmidrol. However, this medication activates macrophages when applied repeatedly, as evidenced by increased interferon production in vitro. The interferon response to ds-RNA is slightly elevated when interferon stimulation is postponed until 4–10 days following the initial dose of palmitoylethanolamide. There is a noticeable drop in interferon production following this period of increased activity. The ability of palmitoylethanolamide to shield mice from a lethal dose of the EMC virus is negligible. The toxicity of ds-RNA is inhibited when this medication is used. There is discussion on a potential mechanism by which palmitoylethanolamide reduced the virulence of the virus in the organism[1]. |
| References |
[1]. Effect of impulsin treatment of interferon production and antiviral resistance of mice. Arch Immunol Ther Exp (Warsz). 1977;25(5):655-61. |
| Additional Infomation |
Palmitoyl ethanolamide is an N-(long-chain-acyl)ethanolamine that is the ethanolamide of palmitic (hexadecanoic) acid. It has a role as an anti-inflammatory drug, an antihypertensive agent, a neuroprotective agent and an anticonvulsant. It is a N-(long-chain-acyl)ethanolamine, an endocannabinoid and a N-(saturated fatty acyl)ethanolamine. It is functionally related to a hexadecanoic acid. A cannabinoid receptor-inactive eCB-related molecule used as prophylactic in helping to prevent respiratory viral infection. Palmidrol is available for human use as a supplement (400 mg capsules) and as food for medical purposes In Italy and Spain (300 mg and 600 mg tablets). Palmitoylethanolamide has been reported in Brassica napus, Saccharomyces cerevisiae, and Caenorhabditis elegans with data available. Palmidrol is a natural fatty acid amide that is both a food component and an endogenously synthesized compound, with potential analgesic and anti-inflammatory activities. Upon administration, palmidrol may inhibit the release of pro-inflammatory mediators from activated mast cells. This may reduce inflammation and pain. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~2.6 mg/mL (~8.68 mM) |
| 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 : PEG300 ：Tween 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). 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 : PEG300：Tween 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). 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 | 3.3390 mL | 16.6950 mL | 33.3901 mL | |
| 5 mM | 0.6678 mL | 3.3390 mL | 6.6780 mL | |
| 10 mM | 0.3339 mL | 1.6695 mL | 3.3390 mL |