Basic information
- CAS
142-58-5- Standard SMILES
CCCCCCCCCCCCCC(=O)NCCO- InChIKey
JHIXEZNTXMFXEK-UHFFFAOYSA-N- Molecular formula
- C16H33NO2
- Average molar mass
- 271.44 g/mol
- Monoisotopic mass
- 271.2511293
Overview
N-(tetradecanoyl)ethanolamine is an N-(long-chain-acyl)ethanolamine resulting from the formal condensation of the carboxy group of tetradecanoic acid (myristic acid) with the amino group of ethanolamine. It is a N-(long-chain-acyl)ethanolamine and a N-(saturated fatty acyl)ethanolamine. It is functionally related to a tetradecanoic acid.
Names & identifiers
- Preferred name
- N-Myristoylethanolamine
- IUPAC
- N-(2-hydroxyethyl)tetradecanamide
- English name
- N-(2-hydroxyethyl)myristamide
- Molecular formula
- C16H33NO2
- Molecular weight
- 271.44
Names & synonyms
142-58-5N-(2-HYDROXYETHYL)TETRADECANAMIDEN-myristoylethanolamineComperlan MMTetradecanamide, N-(2-hydroxyethyl)-Loramine MY 228Schercomid MMEMyristyl monoethanolamideMyristoyl monoethanolamide6CYG57WXZ0Monoethanolamine myristic acid condensateDTXSID0042452
Show more names
AM-3165N-(2-Hydroxyethyl)myristamidN-(tetradecanoyl)ethanolamineMyristic acid monoethanolamideN-(2-Hydroxyethyl)myristic amide
RefChem:825500DTXCID8022452N-(2-Hydroxyethyl)myristamidemyristoyl ethanolamideMyristic monoethanolamideMyristamide MEAMyristoyl-EAMyristoyl-ethanolamine
Database identifiers
- CAS
142-58-5- PubChem CID
- 8890
- DTXSID
DTXSID0042452- ChEMBL
CHEMBL5277451- ChEBI
CHEBI:85262
Properties
Computed structural properties
- XLogP
- 5.1
- Topological polar surface area
- 49.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 14
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 195
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl ethanolamines (endocannabinoids) [FA0804]
Cosmetics
Cosmetic ingredients (Myristamide MEA) -> CIR (Cosmetic Ingredient Review)
Personal care product
Viscosity controlling; Foam boosting; Antistatic
Physical DescriptionOther Solid
Physicochemical properties
- Melting point
- 93 · 93-94 °C
- Boiling point
- 436.3 · 436.3±28.0 °C(Predicted)
- Density
- 0.916 · 0.916±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 20 mg/ml; · DMF: 20 mg/ml; DMSO: 10 mg/ml; Ethanol: 1 mg/ml
- form
- A crystalline solid
- pka
- 14.49 · 14.49±0.10(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
Danger
H318 (66.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Tetradecanamide, N-(2-hydroxyethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Tetradecanamide, 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)
Tetradecanamide, N-(2-hydroxyethyl)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesEye Dam. 1 (66.7%)
Toxicology
Toxicity Summary
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...Myristamide MEA
Safe for use in cosmetics, with qualifications
Safety data
- tsca
- TSCA listed
Chemistry & industry
Uses & manufacturing
Uses
CIR ingredient: Myristamide MEA
Used as foam stabilizer and rinse improver for detergents, an opacifier in cosmetics, a corrosion inhibitor, a mold release agent, and an intermediate for sulfated and ethoxylated derivatives for detergents; [HSDB]
FOAM STABILIZER & RINSE IMPROVER FOR DETERGENT PRODUCTS
CHEM INT FOR SULFATED & ETHOXYLATED DERIVS FOR DETERGENTS
COSMETIC INGREDIENT (ESP AS AN OPACIFIER)
CORROSION INHIBITOR
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) No Data
(1981) No Data
U.S. Production
2023: 75,000 - <500,000 lb
(1979) AT LEAST 9.1X10+6 G-MIXT WITH C12 AMIDE
(1981) AT LEAST 6.8X10+6 G-MIXT WITH C12 AMIDE
Consumer UsesSurfactant (surface active agent)
Industry UsesSurfactant (surface active agent)
Methods of ManufacturingREACTION OF TETRADECANOIC ACID, COCONUT OIL ACIDS, OR THEIR METHYL ESTERS WITH 2-AMINOETHANOL IN A 1:1 RATIO (SODIUM METHYLATE MAY BE USED AS A CATALYST)
Use ClassificationCosmetics -> Viscosity controlling; Foam boosting; Antistatic
General Manufacturing Information
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
Tetradecanamide, N-(2-hydroxyethyl)-: ACTIVE
Applications
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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