N-Stearoylethanolamine

HCID 27902
NotesReactions
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Basic information

CAS
111-57-9
Standard SMILES
CCCCCCCCCCCCCCCCCC(=O)NCCO
InChIKey
OTGQIQQTPXJQRG-UHFFFAOYSA-N
Molecular formula
C20H41NO2
Average molar mass
327.5 g/mol
Monoisotopic mass
327.31372955

Names & identifiers

Preferred name
N-Stearoylethanolamine
IUPAC
N-(2-hydroxyethyl)octadecanamide
English name
Stearoyl ethanolamide
Molecular formula
C20H41NO2
Molecular weight
327.55

Names & synonyms

N-(2-Hydroxyethyl)octadecanamide111-57-9N-stearoylethanolamineStearic ethanolamideN-(Hydroxyethyl)stearamideOCTADECANAMIDE, N-(2-HYDROXYETHYL)-Monoethanolamine stearic acid amide03XV449Q24DTXSID9042178RefChem:825493DTXCID7022178Stearoyl ethanolamide
Show more names
SEACERAMIDN-StearoylethanolamideAM-1105Stearyl monoethanolamide
N-(2-Hydroxyethyl)stearamideStearoylethanolamideStearamide MEAStearic monoethanolamideStearic acid monoethanolamideStearamylStearoyl-ethanolamineCycloamide SM

Database identifiers

CAS
111-57-9
PubChem CID
27902
DTXSID
DTXSID9042178
ChEMBL
CHEMBL171447
ChEBI
CHEBI:85299
UNII
03XV449Q24
EC Number
203-883-2
Nikkaji
J115.317J

Properties

Computed structural properties

XLogP
7.3
Topological polar surface area
49.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
18
Heavy atoms
23

Experimental & physicochemical properties

Melting Point98.5 °C
Physical Description · 2 items

Large Crystals; Other Solid; Dry Powder

Solid

Kovats Retention Index2347.1
Collision Cross Section198.93 Ų [M+H]+ [CCS Type: TIMS; Method: single field calibrated]

Physicochemical properties

Melting point
103 · 103-104 °C(Solv: ethanol (64-17-5))
Boiling point
486 · 486.0±28.0 °C(Predicted)
Density
0.904 · 0.904±0.06 g/cm3(Predicted)
vapor pressure
0 Pa · 0Pa at 20℃
storage temp.
20 °C · −20°C
solubility
2 mg/ml; · DMF: >2 mg/ml; DMSO: >100 μg/ml; Ethanol: >2 mg/ml; PBS pH 7.2: >100 μg/ml

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 4.3% (12 of 281) of reports.

Danger

H315 (88.3%): Causes skin irritation [Warning Skin corrosion/irritation]；H318 (95.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H411 (37.4%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]；H412 (50.2%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

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 281 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 12 of 281 reports by companies.；There are 5 notifications provided by 269 of 281 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 4 items

Chemical: Octadecanamide, N-(2-hydroxyethyl)-

Octadecanamide, N-(2-hydroxyethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Octadecanamide, 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: 17-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14395；Status: Active Update: 07-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/32501

Octadecanamide, N-(2-hydroxyethyl)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (88.3%)；Eye Dam. 1 (95.7%)；Aquatic Chronic 2 (37.4%)；Aquatic Chronic 3 (50.2%)

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...Stearamide MEA

Safe for use in cosmetics, with qualifications

Regulatory information

Regulatory Information · 4 items

Chemical: Octadecanamide, N-(2-hydroxyethyl)-

Octadecanamide, N-(2-hydroxyethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Octadecanamide, 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: 17-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14395；Status: Active Update: 07-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/32501

Octadecanamide, N-(2-hydroxyethyl)-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
tsca
TSCA listed
Signal word
Danger
Symbol(GHS)
GHS05
safety_code
22-24/25

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular；Membrane

Uses & manufacturing

UsesCIR ingredient: Stearamide MEA
U.S. Production2023: 1,000,000 - <5,000,000 lb；2022: 5,000,000 - <10,000,000 lb；2021: 1,000,000 - <5,000,000 lb；2020: 1,000,000 - <5,000,000 lb
Consumer UsesSurfactant (surface active agent)
Industry UsesStabilizing agent；Flow promoter；Emulsifier；Not Known or Reasonably Ascertainable；Surface modifier；Processing aids not otherwise specified；Surfactant (surface active agent)；Opacifer
Household ProductsInformation on 2 consumer products that contain Stearamide MEA in the following categories is provided:；• Inside the Home
Use ClassificationCosmetics -> Antistatic; Viscosity controlling; Foam boosting
Applications · 1 item

UsesStearoyl Ethanolamide is a prolific fatty acid ethanolamide produced by PLD hydrolysis of membrane phospholipids. Stearoyl Ethanolamide is also used for studying the effect on endocannabinoid signalling and BBB integrity in systemic inflammation.

Preparation methods · 1 item

PreparationIn the stirred state, fatty acids (1.0 mmol, 1.0 equiv) were added to CH2Cl2 (5 mL), followed by CDI (0.178 g, 1.1 mmol, 1.1 equiv). After 30 min, the amine (1.1 mmol, 1.1equiv.)was added. Added CH2Cl2 (25ml) and saturated NH4Cl aqueous solution after 12 h. HCl was added to the mixture to adjusted pH=2. After the organic phase was separated, the aqueous layer was further extracted with CH2Cl2 (3 × 10 mL). The organic phase was collected and placed on Na2SO4 to dried, and filtered. Finally, the product (STEAROYL ETHANOLAMIDE) was obtained by vacuum concentration.

Upstream & downstream products

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
江西益众化工有限公司15307925109 15350027073 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]

Additional notes

DefinitionChEBI: An N-(long-chain-acyl)ethanolamine that is the ethanolamide of octadecanoic acid.

Related reactions

7 records
New reaction record

Compound notes

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