Palmitoylethanolamide

HCID 4671
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Basic information

CAS
544-31-0
Standard SMILES
CCCCCCCCCCCCCCCC(=O)NCCO
InChIKey
HXYVTAGFYLMHSO-UHFFFAOYSA-N
Molecular formula
C18H37NO2
Average molar mass
299.5 g/mol
Monoisotopic mass
299.28242942

Overview

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 anticonvulsant, an antihypertensive agent and a neuroprotective agent. 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.

Names & identifiers

Preferred name
Palmitoylethanolamide
IUPAC
N-(2-hydroxyethyl)hexadecanamide
English name
Palmitoylethanolamide
Molecular formula
C18H37NO2
Molecular weight
299.49

Names & synonyms

PalmitoylethanolamidePalmidrol544-31-0N-(2-Hydroxyethyl)hexadecanamidePalmitoyl ethanolamidePalmitic acid monoethanolamideHydroxyethylpalmitamideLoramine P 256palmitylethanolamidePalmidrolumLevagenPalmdrol prodes
Show more names
N-palmitoylethanolaminePALMITAMIDE MEAN-(2-Hydroxyethyl)palmitamidePEA MicroPEA PALMIDROL2-(palmitoylamino)ethanol
Monoethanolamine palmitic acid amidepalmitic monoethanolamidePalmitinsaeure-beta-hydroxyethylamidAnandamide (16:0)hexadecanoyl ethanolamideN(2-hydroxyethyl)palmitide6R8T1UDM3VN(2-hydroxyethyl) palmitide

Database identifiers

CAS
544-31-0
PubChem CID
4671
DTXSID
DTXSID4042254
ChEMBL
CHEMBL417675
ChEBI
CHEBI:71464
UNII
6R8T1UDM3V
EC Number
208-867-9
Nikkaji
J6.414I

Properties

Computed structural properties

XLogP
6.2
Topological polar surface area
49.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
16
Heavy atoms
21

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Lipids · 2 items

Lipids -> Unambiguous Lipids

Fatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl ethanolamines (endocannabinoids) [FA0804]

Cosmetics · 3 items

Cosmetic ingredients (Palmitamide MEA) -> CIR (Cosmetic Ingredient Review)

Foam boosting; Viscosity controlling; Antistatic

Personal care product

Melting Point98.5 °C
Physical Description · 2 items

Other Solid

Solid

Collision Cross Section · 2 items

189.0 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Unambiguous Lipids]

189.87 Ų [M+H]+ [CCS Type: TIMS; Method: single field calibrated]

Physicochemical properties

Melting point
97 · 97-98℃
Boiling point
461.5 · 461.5±28.0 °C(Predicted)
Density
0.91 · 0.910±0.06 g/cm3(Predicted)
vapor pressure
0.45 Pa · 0.45Pa at 20℃
RTECS
8950000 · ML8950000
storage temp.
-20 °C · -20°C

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 2.5% (4 of 162) of reports.

Danger

H315 (97.5%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P273, P280, P302+P352, P305+P354+P338, P317, P321, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 162 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Hexadecanamide, N-(2-hydroxyethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexadecanamide, N-(2-hydroxyethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 12-01-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/23420

Hazard Classes and CategoriesSkin Irrit. 2 (97.5%)

Toxicology

Toxicity Summary · 2 items

The CIR Expert Panel concluded that the ethanolamides listed subsequently are safe in the present practices of use and concentration described in this safety assessment when formulated to be non-irritating. The Expert Panel cautioned that these ingredients should not be used in cosmetic products in which N-nitroso compounds may be formed...Palmitamide MEA...

Safe for use in cosmetics, with qualifications

Safety data

wgk
2
tsca
TSCA listed
ridadr
UN3077
hs_code
2934.99.4400
Signal word
Danger
Symbol(GHS)
GHS05,GHS09

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 4 items

Compounds capable of relieving pain without the loss of CONSCIOUSNESS.

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.

Compounds that interact with and stimulate the activity of CANNABINOID RECEPTORS.

Tissue LocationsPlacenta
Cellular LocationsExtracellular

Uses & manufacturing

UsesCIR ingredient: Palmitamide MEA
U.S. Production2023: 75,000 - <500,000 lb
Consumer UsesSurfactant (surface active agent)
Industry UsesSurfactant (surface active agent)
Use ClassificationCosmetics -> Foam boosting; Viscosity controlling; Antistatic
General Manufacturing Information · 2 items

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

Hexadecanamide, N-(2-hydroxyethyl)-: ACTIVE

Applications · 2 items

DescriptionPalmitoylethanolamide (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.

UsesPalmitoylethanolamide 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

Upstream & downstream products

Downstream products

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
山东天微医药科技有限公司+86-18653895227 · [email protected]
苏州申拓医药科技有限公司13911244683 18151949202
Additional notes · 1 item

DefinitionChEBI: Palmitoylethanolamide 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.

Related reactions

6 records
New reaction record

Compound notes

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