Palmitoylethanolamide supplier

Name
PALMITOYLETHANOLAMIDE
EINECS 208-867-9
CAS No. 544-31-0
Article Data41
CAS DataBase
Density 0.91 g/cm³
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
Appearance White solid.
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 49.33000
LogP 4.96710

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;

: 57-10-3
1-hexadecylcarboxylic acid

thorium oxide: thorium oxide

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: DCC-DMAP 2: 92 percent / CH2Cl2 / 2 h / Ambient temperature View Scheme

: 112-67-4
n-hexadecanoyl chloride

ent-17-methyl-morphinan-3-ol: ent-17-methyl-morphinan-3-ol

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N 2: 92 percent / CH2Cl2 / 2 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 20 h / Ambient temperature 2: LiAlH4 / tetrahydrofuran / 0.75 h / Ambient temperature View Scheme

: 57-10-3
1-hexadecylcarboxylic acid

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dicyclohexylcarbodiimide 2: 91 percent / CH2Cl2 / 0.33 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid 2: acetonitrile / 24 h View Scheme
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / 3 h View Scheme

: 141-43-5
ethanolamine

: 120246-99-3
palmitoyl ethyl carbonate

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

Conditions

Conditions	Yield
In dichloromethane at 0 - 10℃; Product distribution / selectivity;
In cyclohexane at 0 - 10℃; Product distribution / selectivity;

: C18H34O4

: 141-43-5
ethanolamine

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

Conditions

Conditions	Yield
In dichloromethane at 20℃; Cooling with ice;
In chloroform at 0 - 10℃; Product distribution / selectivity;

: C22H40O4

: 141-43-5
ethanolamine

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

Conditions

Conditions	Yield
In dichloromethane at 0 - 10℃; Product distribution / selectivity;

: 112-39-0
hexadecanoic acid methyl ester

: 141-43-5
ethanolamine

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

Conditions

Conditions	Yield
In acetonitrile for 24h;
In acetonitrile for 24h;
With zeolite H-beta-22 In hexane at 180℃; under 15001.5 Torr; for 3h; Reagent/catalyst; Inert atmosphere;

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

: 2441-41-0
N-palmitoyl glycine

Conditions

Conditions	Yield
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; sodium hydroxide In tetrahydrofuran; water for 1.5h; Reagent/catalyst; Industrial scale; Green chemistry;	98.5%

: 13734-41-3
t-Boc-L-valine

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

: 2-(palmitoylamino)ethyl N-tert-butoxycarbonyl-L-valinate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 23℃; for 12h; Steglich Esterification; Inert atmosphere;	95%

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

: 3173-56-6
benzyl isothiocyanate

: N-[2-(benzylaminocarbonyl)-oxyethyl]-hexadecanamide

Conditions

Conditions	Yield
Stage #1: 2-(palmitoylamino)ethanol With 4 Å molecular sieves In toluene Heating / reflux; Stage #2: benzyl isothiocyanate With 4 Å molecular sieves for 6h; Heating / reflux;	94%

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

: 541-41-3
chloroformic acid ethyl ester

: N-[2-(ethoxycarbonyl)-oxyethyl]-hexadecanamide

Conditions

Conditions	Yield
With 4-methyl-morpholine In tetrahydrofuran at 20 - 45℃; for 3h;	93%

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

: 2495-72-9
1-acetoxy-2-palmitoylamino-ethane

Conditions

Conditions	Yield
With acetic anhydride In pyridine	93%

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

: 2949-22-6
Glycine ethyl ester isocyanate

: N-[[2-(ethoxycarbonylmethyl)-aminocarbonyl]-oxyethyl]-hexadecanamide

Conditions

Conditions	Yield
Stage #1: 2-(palmitoylamino)ethanol With 4 Å molecular sieves In toluene Heating / reflux; Stage #2: Glycine ethyl ester isocyanate With 4 Å molecular sieves for 6h; Heating / reflux;	92%

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

: 36919-66-1
2-pentadecyl-2-oxazoline

Conditions

Conditions	Yield
Stage #1: 2-(palmitoylamino)ethanol With thionyl chloride at 0 - 20℃; for 15.5h; Inert atmosphere; Stage #2: With potassium tert-butylate In toluene at 40℃; for 2h;	92%
Multi-step reaction with 2 steps 1: thionyl chloride / 15.5 h / 0 - 20 °C / Inert atmosphere 2: potassium tert-butylate / toluene / 2 h / 40 °C View Scheme

: 1191-99-7
2,3-dihydro-2H-furan

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

: tetrahydrofuranyl ether of N-(2-hydroxyethyl)-hexadecanamide

Conditions

Conditions	Yield
With pyridinium methanesulfonate at 4 - 50℃; for 1h;	90%

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

: 22838-58-0
Boc-D-Val-OH

: 2-(palmitoylamino)ethyl N-tert-butoxycarbonyl-D-valinate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 23℃; for 12h; Steglich Esterification; Inert atmosphere;	89%

: 15761-38-3
L-N-Boc-Ala

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

: 2-(palmitoylamino)ethyl N-tert-butoxycarbonyl-L-alaninate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 23℃; for 12h; Steglich Esterification; Inert atmosphere;	84%

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

: 14000-31-8
pyrophosphoric acid

: 84552-09-0
N-Palmitoylethanolamine phosphate

Conditions

Conditions	Yield
In methanesulfonic acid	83%

: 108-30-5
succinic acid anhydride

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

: 117597-84-9
4-oxo-4-(2-palmitamidoethoxy)butanoic acid

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 18h;	83%
In N,N-dimethyl-formamide at 20℃; for 18h;	83%
In tetrahydrofuran at 50℃;	83%

: 13139-16-7
N-(tert-butyloxycarbonyl)-L-isoleucine

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

: 2-(palmitoylamino)ethyl N-tert-butoxycarbonyl-L-isoleucinate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 23℃; for 12h; Steglich Esterification; Inert atmosphere;	81%

: 108-31-6
maleic anhydride

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

: (E)-4-oxo-4-(2-palmitamidoethoxy)but-2-enoic acid

Conditions

Conditions	Yield
In tetrahydrofuran at 50℃;	80%

: 2564-83-2, 45842-10-2
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

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

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)-N-(2-((triisopropylsilyl)oxy)ethyl)hexadecanamide

Conditions

Conditions	Yield
With pyridine In hexane at 60℃; for 36h; chemoselective reaction;	79%

...Expand

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

: 13139-14-5
Boc-Trp-OH

: 2-(palmitoylamino)ethyl N-tert-butoxycarbonyl-L-tryptophanate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 23℃; for 12h; Steglich Esterification; Inert atmosphere;	77%

: 85-44-9
phthalic anhydride

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

: 31384-20-0
2-[(2-palmitamidoethoxy)carbonyl]benzoic acid

Conditions

Conditions	Yield
In tetrahydrofuran at 50℃;	75%
In 1,4-dioxane at 40℃; for 5h;

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

: 7536-55-2, 142847-17-4, 75647-01-7
N-t-butyloxycarbonyl-D-asparagine

: 2-(palmitoylamino)ethyl N-tert-butoxycarbonyl-D-asparaginate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 23℃; for 12h; Steglich Esterification; Inert atmosphere;	66%

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

: 1192358-13-6
N-(2-azidoethyl)palmitamide

Conditions

Conditions	Yield
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;	66%

: 87-51-4
indole-3-acetic acid

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

: 1363333-30-5
N-palmitoyl-O-(2-(indol-3-yl)-1-oxoethyl)ethanol-2-amine

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform; acetone at 20℃; for 12h;	65.7%

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

: 65260-72-2
2-aminoethyl hexadecanoate

Conditions

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In acetonitrile for 3.5h;	65%

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

Product Name

PALMITOYLETHANOLAMIDE

Synthetic route

Palmitoylethanolamide Specification

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