| Identification | Back Directory | [Name]
PALMITOYLETHANOLAMIDE | [CAS]
544-31-0 | [Synonyms]
AM 3112
Impulsin
Palmidrol
PEA PALMIDROL
Loramine P 256
PALMITAMIDE MEA
Mackpeart DR 14V
Cetylamide ethanol
PALMITOYLETHANOLIDE
PALMITYLETHANOLAMIDE
Hexadecamide ethanol
PALMITOYLETHANOLAMIDE
N-palmitoylethanolamine
2-(palmitoylamino)ethanol
Palmitoylethanolamide(PEA)
N-HEXADECANOYLETHANOLAMINE
Palmidrol (Palmitamide MEA)
N-(2-Hydroxyethyl)palmitamide
Palmitic acid monoethanolamide
N-(2-Hydroxyethyl)palmitic amide
n-(2-hydroxyethyl)-hexadecanamid
N-(2-HYDROXYETHYL)HEXADECANAMIDE
Palmitoylethanolamide/Pea Powder
HexadecanaMide,N-(2-hydroxyethyl)-
Palmitoylethanolamide micro
(PEA Micro)
Palmitoylethanolamide 544-31-0 Palmidrol
PALMITOYLETHANOLAMIDE ISO 9001：2015 REACH
High quality Blue Lotus Leaf Extract 200:1
Palmitoylethanolamide - CAS 544-31-0 - Calbiochem
N-(2-Hydroxyethyl)hexadecanamide, Palmidrol, PEA
Palmidrol 544-31-0 N-(2-Hydroxyethyl)hexadecanamide
PALMITOYLETHANOLAMIDE N-(2-HYDROXYETHYL)HEXADECANAMIDE | [EINECS(EC#)]
208-867-9 | [Molecular Formula]
C18H37NO2 | [MDL Number]
MFCD00020562 | [MOL File]
544-31-0.mol | [Molecular Weight]
299.49 |
| Chemical Properties | Back Directory | [Melting point ]
97-98℃ | [Boiling point ]
461.5±28.0 °C(Predicted) | [density ]
0.910±0.06 g/cm3(Predicted) | [vapor pressure ]
0.45Pa at 20℃ | [RTECS ]
ML8950000 | [storage temp. ]
−20°C
| [solubility ]
Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml). | [form ]
White solid | [pka]
14.49±0.10(Predicted) | [color ]
White | [Water Solubility ]
4.01mg/L at 20℃ | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. | [InChIKey]
HXYVTAGFYLMHSO-UHFFFAOYSA-N | [LogP]
3.989 at 20℃ | [CAS DataBase Reference]
544-31-0 | [EPA Substance Registry System]
Palmitoylethanolamide (544-31-0) |
| Hazard Information | Back Directory | [Description]
Palmitoylethanolamide (PEA,544-31-0) 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.
| [Chemical Properties]
white powder | [Uses]
antiinflammatory | [Definition]
ChEBI: An N-(long-chain-acyl)ethanolamine that is the ethanolamide of palmitic (hexadecanoic) acid. | [Biological Functions]
Palmitoylethanolamide (PEA,544-31-0) 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.
| [Flammability and Explosibility]
Notclassified | [Biological Activity]
Endogenous lipid that acts as a selective GPR55 agonist (EC 50 values are 4, 19 800 and > 30 000 nM at GPR55, CB 2 and CB 1 receptors respectively). Substrate for fatty acid amide hydrolase (FAAH) and PEA-preferring acid amidase (PAA) and exhibits antinociceptive and anticonvulsant in vivo . Directly activates PPAR α (EC 50 = 3 μ M) producing robust anti-inflammatory actions. | [Biochem/physiol Actions]
Palmitoylethanolamide (PEA,544-31-0) is a natural fatty acid amide of ethanolamine and palmitic acid. It is found in soybeans, egg yolk, and many other food sources. PEA is an endogenous cannabinoid receptor agonist. It is a peroxisome proliferator-activated receptor α (PPAR-α) ligand. PEA possesses anti-inflammatory, anti-allergic, neuroprotective, and analgesic activities. It belongs to the class of lipid mediators and the N-acylethanolamine family. PEA blocks the release of pro-inflammatory mediators from activated mast cells and prevents the recruitment of activated mast cells at the site of nerve injury.
| [Side effects]
There are no known problematic side-effects. PEA can be taken together with any other substance. It enhances the pain-relieving effect of classic analgesics and anti-inflammatories.
Palmitoylethanolamide can be used in combination with other substances without any side effects. | [Synthesis]
1) Under nitrogen protection, triethylamine (2 mL) was slowly added dropwise to a reaction vessel containing mercaptomethyl resin (2 g, MATRIX-INN), N-hydroxymaleimide (1.1 g, 9.7 mmol) and DMF (40 mL). After stirring at room temperature for 24 hours, the temperature was raised to 55°C and stirring was continued for 4 hours. The reaction mixture was cooled to room temperature and filtered, and the resulting NHS resin was washed twice each with DMF, distilled water and isopropanol sequentially, and dried under vacuum.
2) Palmitic acid (1.465 g, 5.72 mmol), NHS resin (1.50 g) prepared above, DIC (diisopropylcarbodiimide, 0.72 g, 5.72 mmol) and triethylamine (2 mL) were suspended in dichloromethane (15 mL). After stirring for 4 h at room temperature, the filtrate was filtered and retained for subsequent reactions (the amount of palmitic acid, DIC and solvent in the filtrate was detected by HPLC). The resin was washed twice each with DMF, water, isopropanol and dichloromethane sequentially, and dried under vacuum to obtain 1.70 g of dried resin with a loading of 1.0 mmol/g of immobilized palmitic acid active ester.
3) Ethanolamine (93.2 mg, 1.58 mmol) was added to a flask containing the activated ester (1.75 g) and 50 mL of ethanol, and suspended and stirred for 0.5 hr. The solid resin was removed by centrifugation and the resin was washed twice with ethanol (the resin was vacuum dried after washing). The liquid phases were combined and concentrated under reduced pressure to give 453 mg of palmitic acid monoethanolamide in 96.6% yield and >99.5% purity (HPLC detection). | [storage]
Store at RT | [References]
1) De Filippis et al. (2011), Palmitoylethanolamide reduces granuloma-induced hyperalgesia by modulation of mast cell activation in rats; Mol. Pain, 7 3
2) Re et al. (2007), Palmitoylethanolamide, endocannabinoids and related cannabimimetic compounds in protection against tissue inflammation and pain: potential use in companion animals; Vet J., 173 21
3) Lambert et al. (2002), The palmitoylethanolamide family: a new class of anti-inflammatory agents?; Curr. Med. Chem., 9 663 |
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