Palmitoylethanolamide

Base Information

• Chemical Name: Palmitoylethanolamide
• CAS No.: 544-31-0
• Deprecated CAS: 1451152-25-2
• Molecular Formula: C18H37NO2
• Molecular Weight: 299.497
• Hs Code.: 2924199090
• European Community (EC) Number: 208-867-9
• NSC Number: 760371,23320
• UNII: 6R8T1UDM3V
• DSSTox Substance ID: DTXSID4042254
• Nikkaji Number: J6.414I
• Wikipedia: Palmitoylethanolamide
• Wikidata: Q2159860
• NCI Thesaurus Code: C66294
• Pharos Ligand ID: 987VFM1WDRKR
• Metabolomics Workbench ID: 4659
• ChEMBL ID: CHEMBL417675
• Mol file: 544-31-0.mol

Synonyms:Impulsin;MimyX;N-(2-hydroxyethyl)palmitate;N-palmitoylethanolamine;palmidrol;palmitoylethanolamide;palmitylethanolamide

Chemical Property of Palmitoylethanolamide

Chemical Property:

• Appearance/Colour: White solid.
• Vapor Pressure: 1.87E-10mmHg at 25°C
• Melting Point: 97-98℃
• Refractive Index: 1.462
• Boiling Point: 461.5 °C at 760 mmHg
• PKA: 14.49±0.10(Predicted)
• Flash Point: 232.9 °C
• PSA: 49.33000
• Density: 0.91 g/cm³
• LogP: 4.96710
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• Water Solubility.: 4.01mg/L at 20℃
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 299.282429423
• Heavy Atom Count: 21
• Complexity: 219

Purity/Quality:

98% up ^*data from raw suppliers

Palmitoylethanolamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NCCO
• Recent ClinicalTrials: PEA for the Relief of Chemotherapy-Induced Peripheral Neuropathy
• Recent EU Clinical Trials: A Randomized, Double-Blind, Placebo Controlled Proof of Concept Study to Evaluate the Safety, Tolerability and Efficacy of Daily Oral THX-110 in Treating Adults with Tourette Syndrome (“ENTOURAGE”)
• Description: Palmitoylethanolamide (PEA) is a fatty acid amide produced in the body that binds to and activates the peroxisome proliferator-activated receptor alpha (PPAR-α). It was initially described as an agonist to the type 2 cannabinoid receptor (CB2), though it is now recognized that PEA does not bind to cannabinoid receptors. PEA is known to have anti-inflammatory, analgesic, and neuroprotective properties. PEA supplements have been used by people with chronic pain as well as those with neuropathic pain.
• Uses: Palmitoylethanolamide is a natural substance produced by the body and it is very effective and safe to use as a supplement for pain and reduce inflammation.PEA can be synthesized within the human body from the abundant fatty acid palmitic acid, but it is not dependent or influenced by dietary consumption of fatty acids. Palmitic acid in the diet is derived from dairy products such as cheese and butter, palm tree oil, and animal meat products. However, increasing palmitic acid in the hope of increasing endogenous PEA synthesis will not be effective.The anti-inflammatory properties of PEA are due to its ability to inhibit inflammation-causing proteins called cytokines. Cytokines are released during periods of inflammation. PEA can suppress the secretion of tumor necrosis factor alpha (TNF alpha), a cytokine, while also inhibiting the release of interleukins. Interleukins are a specific class of cytokines which belong in the immunological system and are activated during the process of inflammation.Chronic Pain and the Use of Palmitoylethanolamide: An Update
• Biological Functions: Palmitoylethanolamide (PEA) is a fatty acid amide molecule involved in a variety of cellular functions in chronic pain and inflammation. It has been shown to have neuroprotective, anti-inflammatory, anti-nociceptive (antipain) and anti-convulsant properties. Often in people with chronic disorders, the body does not produce enough PEA, which causes problems.Taking PEA to supplement the body’s shortage is may be beneficial if you have chronic and neuropathic pain and inflammation, as has been demonstrated in clinical trials. These include peripheral neuropathies such as diabetic neuropathy, chemotherapy-induced peripheral neuropathy, carpal tunnel syndrome, sciatic pain, osteoarthritis, low-back pain, failed back surgery syndrome, dental pains, neuropathic pain in stroke and multiple sclerosis, chronic regional pain syndrome, chronic pelvic pain, postherpetic neuralgia, and vaginal pains.

Technology Process of Palmitoylethanolamide

There total 18 articles about Palmitoylethanolamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.2%

ethanolamine (141-43-5) + 1-hexadecylcarboxylic acid (57-10-3) → 2-(palmitoylamino)ethanol (544-31-0)

Guidance literature:

1-hexadecylcarboxylic acid; In water; at 100 ℃; for 2h;

ethanolamine; In water; at 100 - 200 ℃; for 22h;

Reference yield: 97.5%

hexadecanoic acid ethyl ester (628-97-7) + ethanolamine (141-43-5) → 2-(palmitoylamino)ethanol (544-31-0)

Guidance literature:

With Novozym 435; In 1,4-dioxane; for 0.0666667h; chemoselective reaction; Microwave irradiation; Enzymatic reaction;

DOI:10.3762/bjoc.5.10

Reference yield: 97.0%

ethanolamine (141-43-5) + n-hexadecanoyl chloride (112-67-4) → 2-(palmitoylamino)ethanol (544-31-0)

Guidance literature:

With triethylamine; In dichloromethane; a) 0 deg C, 30 min, b) RT, 2 h;

upstream raw materials:

ethanolamine

n-hexadecanoyl chloride

N-hexadecanoyl glycine methyl ester

1-(2-Thioxo-thiazolidin-3-yl)-hexadecan-1-one

Downstream raw materials:

ethanolamine

1-hexadecylcarboxylic acid

N-palmitoyl glycine

2-[(2-palmitamidoethoxy)carbonyl]benzoic acid

Refernces

• 1、 -. "Green aqueous-phase solvent-free high-purity synthesis method of palmitoylethanolamide". Paragraph 0033. . Retrieved 2021/05/12.
• 2、 Johansson, Silje J. R.,Johannessen, Tonje,Ellefsen, Christiane F.,Ristun, Mali S.,Antonsen, Simen,Hansen, Trond V.,Stenstrom, Yngve,Nolsoe, Jens M. J.. "A Convenient Protocol for the Synthesis of Fatty Acid Amides". supporting information. p. 213 - 217. Retrieved 2019/01/14.