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Cas Database

Name	Palmitoylethanolamide	EINECS	208-867-9
CAS No.	544-31-0	Density	0.91 g/cm³
PSA	49.33000	LogP	4.96710
Solubility	4.01mg/L at 20℃	Melting Point	97-98℃
Formula	C₁₈H₃₇NO₂	Boiling Point	461.5 °C at 760 mmHg
Molecular Weight	299.497	Flash Point	232.9 °C
Transport Information	N/A	Appearance	White solid.
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	(Hydroxyethyl)palmitamide;2-(Palmitoylamino)ethanol;2-Palmitamidoethanol;AM 3112;Impulsin;Loramine P256;N-(2-Hydroxyethyl)hexadecanamide;N-(2-Hydroxyethyl)palmitamide;N-Hexadecanoylethanolamine;N-Palmitoylethanolamine;NSC 23320;Palmidrol;Palmitic acid monoethanolamide;Palmitic monoethanolamide;Palmitoylethanolamide;	Article Data	41

Palmitoylethanolamide Synthetic route

: 141-43-5
ethanolamine

: 57-10-3
1-hexadecylcarboxylic acid

: 544-31-0
2-(palmitoylamino)ethanol

Conditions

Conditions	Yield
Stage #1: 1-hexadecylcarboxylic acid In water at 100℃; for 2h; Stage #2: ethanolamine In water at 100 - 200℃; for 22h;	98.2%
With Novozym 435 In 1,4-dioxane for 0.0666667h; Microwave irradiation; Enzymatic reaction; chemoselective reaction;	97.3%
Stage #1: 1-hexadecylcarboxylic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: ethanolamine In dichloromethane for 12h;	96%

: 628-97-7
hexadecanoic acid ethyl ester

: 141-43-5
ethanolamine

: 544-31-0
2-(palmitoylamino)ethanol

Conditions

Conditions	Yield
With Novozym 435 In 1,4-dioxane for 0.0666667h; Microwave irradiation; Enzymatic reaction; chemoselective reaction;	97.5%

: 141-43-5
ethanolamine

: 112-67-4
n-hexadecanoyl chloride

: 544-31-0
2-(palmitoylamino)ethanol

Conditions

Conditions	Yield
With triethylamine In dichloromethane a) 0 deg C, 30 min, b) RT, 2 h;	97%
With magnesium oxide In tetrahydrofuran; water at 20℃; for 2h;	92%
With sodium carbonate In diethyl ether

: 693-38-9
vinyl palmitate

: 141-43-5
ethanolamine

: 544-31-0
2-(palmitoylamino)ethanol

Conditions

Conditions	Yield
With sodium methylate at 60℃; for 1.5h; Neat (no solvent);	96.5%
With sodium methylate at 60℃; for 1.5h; Concentration; Temperature; Time;
With potassium methanolate In methanol at 65℃; for 3h;

: 555-44-2
glyceroltripalmitate

: 141-43-5
ethanolamine

: 544-31-0
2-(palmitoylamino)ethanol

Conditions

Conditions	Yield
at 50 - 60℃; for 8h;	95.4%

: 141-43-5
ethanolamine

: 112-76-5
Stearoyl chloride

: 544-31-0
2-(palmitoylamino)ethanol

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h; Cooling with ice;	95%

: 141-43-5
ethanolamine

: 100663-86-3
C28H40N2O2

: 544-31-0
2-(palmitoylamino)ethanol

Conditions

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	92%

: 74058-64-3
1-(2-Thioxo-thiazolidin-3-yl)-hexadecan-1-one

: 141-43-5
ethanolamine

: 544-31-0
2-(palmitoylamino)ethanol

Conditions

Conditions	Yield
In dichloromethane for 0.333333h; Ambient temperature;	91%
In dichloromethane for 0.333333h; Product distribution; Ambient temperature; other aminoalcohols and aminophenols in further solvents;	91%

: 142-91-6
palmitic acid isopropyl ester

: 141-43-5
ethanolamine

: 544-31-0
2-(palmitoylamino)ethanol

Conditions

Conditions	Yield
With sodium ethanolate In methanol; ethanol at 60℃; for 4h; Inert atmosphere;	89%

: 214706-34-0
N-hexadecanoyl glycine methyl ester

: 544-31-0
2-(palmitoylamino)ethanol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 0.75h; Ambient temperature;

Palmitoylethanolamide Specification

The Hexadecanamide,N-(2-hydroxyethyl)-, with the CAS registry number 544-31-0, is also known as N-Palmitoylethanolamine. It belongs to the product categories of Cannabinoid Receptor; Cannabinoid. Its EINECS registry number is 208-867-9. This chemical's molecular formula is C₁₈H₃₇NO₂ and molecular weight is 299.49. Its IUPAC name is called N-(2-hydroxyethyl)hexadecanamide. This chemical's classification codes are Analgesics; Analgesics, Non-Narcotic; Anti-Infective Agents; Anti-Inflammatory Agents; Anti-inflammatory agents, non-steroidal; Antirheumatic Agents' Antiviral agents; Central Nervous System Agents; Peripheral Nervous System Agents; Sensory System Agents.

Physical properties of Hexadecanamide,N-(2-hydroxyethyl)-: (1)ACD/LogP: 5.82; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.82; (4)ACD/LogD (pH 7.4): 5.82; (5)ACD/BCF (pH 5.5): 15479.24; (6)ACD/BCF (pH 7.4): 15479.24; (7)ACD/KOC (pH 5.5): 34722.45; (8)ACD/KOC (pH 7.4): 34722.45; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 17; (12)Index of Refraction: 1.462; (13)Molar Refractivity: 90.59 cm³; (14)Molar Volume: 329 cm³; (15)Surface Tension: 34.5 dyne/cm; (16)Density: 0.91 g/cm³; (17)Flash Point: 232.9 °C; (18)Enthalpy of Vaporization: 83.31 kJ/mol; (19)Boiling Point: 461.5 °C at 760 mmHg; (20)Vapour Pressure: 1.87E-10 mmHg at 25°C.

Preparation: this chemical can be prepared by 2-amino-ethanol and hexadecanoyl chloride. This reaction will need reagent MgO and solvent H₂O, tetrahydrofuran. The reaction time is 2 hours with reaction temperature of 20 °C. The yield is about 92%.

Uses of Hexadecanamide,N-(2-hydroxyethyl)-: it can be used to produce palmitic acid-(2-amino-ethyl ester). This reaction will need reagent CBr₄, PPh₃ and solvent acetonitrile with reaction time of 3.5 hours. The yield is about 65%.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NCCO
(2)InChI: InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h20H,2-17H2,1H3,(H,19,21)
(3)InChIKey: HXYVTAGFYLMHSO-UHFFFAOYSA-N

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