• Name

  STEAROYL ETHANOLAMIDE

• EINECS 203-883-2
• CAS No. 111-57-9
• Article Data33
• CAS DataBase
• Density 0.905 g/cm³
• Solubility 1mg/L at 20℃
• Melting Point 103-104 °C(Solv: ethanol (64-17-5))
• Formula C₂₀H₄₁NO₂
• Boiling Point 486.034 °C at 760 mmHg
• Molecular Weight 327.551
• Flash Point 247.744 °C
• Transport Information
• Appearance
• Safety 22-24/25
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Monoethanolstearamide;N-(2-Hydroxyethyl)octadecanamide;N-(2-Hydroxyethyl)stearamide;N-Octadecanoylethanolamine;N-Stearoylethanolamine;NSC 3377;Stearic ethanolamide;Stearicethylolamide;Stearic monoethanolamide;Stearic monoethanolamine;Stearoylmonoethanolamide;
• PSA 49.33000
• LogP 5.74730

Synthetic route

141-43-5

ethanolamine

57-11-4

stearic acid

111-57-9

N-stearoylethanolamine

Conditions

Conditions	Yield
Stage #1: stearic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: ethanolamine In dichloromethane for 12h;	96%
Stage #1: stearic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 4h; Stage #2: ethanolamine In ethanol at 20℃; for 0.5h; Inert atmosphere;	95.5%
Stage #1: stearic acid With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Stage #2: ethanolamine In dichloromethane; acetonitrile at 20℃; Inert atmosphere;	90%

111-63-7

vinyl stearate

141-43-5

ethanolamine

111-57-9

N-stearoylethanolamine

Conditions

Conditions	Yield
With sodium methylate at 80℃; for 1h; Neat (no solvent);	95.4%
With sodium methylate at 80℃; for 1h; Concentration; Temperature; Time; Solvent;	95.4%

141-43-5

ethanolamine

112-76-5

Stearoyl chloride

111-57-9

N-stearoylethanolamine

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 4.5h;	95%
In tetrahydrofuran at 0 - 20℃; for 2h;	81%
In tetrahydrofuran at 0 - 20℃; for 2h;	81%

14464-32-5

stearic acid N-hydroxysuccinimide ester

141-43-5

ethanolamine

111-57-9

N-stearoylethanolamine

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 2.5h;	88%

141-43-5

ethanolamine

124-26-5

stearamide

111-57-9

N-stearoylethanolamine

Conditions

Conditions	Yield
Stage #1: stearamide With triethylamine; methyl chloroformate In dichloromethane at 0 - 20℃; for 2h; Stage #2: ethanolamine In dichloromethane at 0 - 20℃; for 20h;	74%

111-63-7

vinyl stearate

141-43-5

ethanolamine

A

10287-60-2

O-stearoylethanolamine

B

111-57-9

N-stearoylethanolamine

Conditions

Conditions	Yield
With Novozym 435 In hexane at 45℃; for 5h; Enzymatic reaction;	A 17.4% B 72.3%
With Candida antarctica lipase for 20h; Concentration; Time; Enzymatic reaction;	A 26.5% B 61.6%

...Expand

10287-60-2

O-stearoylethanolamine

111-57-9

N-stearoylethanolamine

Conditions

Conditions	Yield
at 20℃; Geschwindigkeit der Umlagerung in wss. Loesung vom pH 7.5 und 10;

111-61-5

stearic acid ethyl ester

141-43-5

ethanolamine

111-57-9

N-stearoylethanolamine

Conditions

Conditions	Yield
at 160℃; unter Abdestillieren des gebildeten Wassers;

C20H38O4

141-43-5

ethanolamine

111-57-9

N-stearoylethanolamine

Conditions

Conditions	Yield
In dichloromethane at 20℃; Cooling with ice;

57-11-4

stearic acid

111-57-9

N-stearoylethanolamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid 2: acetonitrile / 24 h View Scheme

112-61-8

Methyl stearate

141-43-5

ethanolamine

111-57-9

N-stearoylethanolamine

Conditions

Conditions	Yield
In acetonitrile for 24h;

141-43-5

ethanolamine

57-11-4

stearic acid

A

111-57-9

N-stearoylethanolamine

B

14351-40-7

stearic acid monoethanolamide stearate

Conditions

Conditions	Yield
With zeolite H-beta-150 In hexane at 180℃; under 15001.5 Torr; for 3h; Reagent/catalyst; Inert atmosphere;	A 104 mg B 38 mg

...Expand

111-57-9

N-stearoylethanolamine

6333-54-6

N-stearoylglycine

Conditions

Conditions	Yield
With 1,3-DIOXOLANE; potassium hypochlorite; TEMPOL; potassium bromide; sodium hydroxide In water for 1h; Industrial scale; Green chemistry;	96.6%

111-57-9

N-stearoylethanolamine

N-(2-oxoethyl)octadecanamide

Conditions

Conditions	Yield
With Dess-Martin periodane In chloroform at 20℃; for 72h;	92%
With Dess-Martin periodane In chloroform at 20℃; for 72h;	92%

111-57-9

N-stearoylethanolamine

24041-12-1

2-heptadecyl-2-oxazoline

Conditions

Conditions	Yield
Stage #1: N-stearoylethanolamine With thionyl chloride at 0 - 20℃; for 15.5h; Inert atmosphere; Stage #2: With potassium tert-butylate In toluene at 40℃; for 2h;	90%
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

111-57-9

N-stearoylethanolamine

15516-43-5

(2-methylphenoxy)acetyl chloride

C29H49NO4

Conditions

Conditions	Yield
With triethylamine In chloroform at 20℃; for 12h;	75%

87-51-4

indole-3-acetic acid

111-57-9

N-stearoylethanolamine

1363333-31-6

N-stearoyl-O-(2-(indol-3-yl)-1-oxoethyl)ethanol-2-amine

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform; acetone at 20℃; for 12h;	71.6%

111-57-9

N-stearoylethanolamine

152252-37-4

(2S,3S,4R,5S,6R)-3,4-Diacetoxy-5-acetylamino-6-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-fluoro-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4R,5S,6R)-3,4-Diacetoxy-5-acetylamino-6-[(2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-(2-octadecanoylamino-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With zirconocene dichloride; silver perchlorate In dichloromethane	64%

77-77-0

Divinyl sulfone

111-57-9

N-stearoylethanolamine

1226976-07-3

C24H47NO4S

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.333333h; Aza-Michael type addition;	56%

111-57-9

N-stearoylethanolamine

15516-47-9

2-(4-methylphenoxy)acetyl chloride

C29H49NO4

Conditions

Conditions	Yield
With triethylamine In chloroform at 20℃; for 12h;	55%

830-96-6

Indole-3-propionic acid

111-57-9

N-stearoylethanolamine

1363333-35-0

N-stearoyl-O-(3-(indol-3-yl)-1-oxopropyl)ethanol-2-amine

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform; acetone at 20℃; for 12h;	52.5%

111-57-9

N-stearoylethanolamine

459-57-4

4-fluorobenzaldehyde

N-(2-(4-formylphenoxy)ethyl)octadecanamide

Conditions

Conditions	Yield
Stage #1: N-stearoylethanolamine With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.75h; Stage #2: 4-fluorobenzaldehyde In tetrahydrofuran at 70℃; for 5h;	48%
Stage #1: N-stearoylethanolamine With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.75h; Stage #2: 4-fluorobenzaldehyde In tetrahydrofuran for 5h;	48%

111-57-9

N-stearoylethanolamine

4122-68-3

4-chlorophenyloxyacetyl chloride

C28H46NO4Cl

Conditions

Conditions	Yield
With triethylamine In chloroform at 20℃; for 12h;	46%

4167-02-6

2-bromoethylphosphoric acid dichloride

111-57-9

N-stearoylethanolamine

131933-62-5

2-octadecanamidoethyl 2'-bromoethyl phosphate

Conditions

Conditions	Yield
With pyridine In diethyl ether; water 1.) 0 deg C, 30 min, 2.) reflux, 4 h;	40%

111-57-9

N-stearoylethanolamine

106967-74-2

2-(3-methoxyphenoxy)acetyl chloride

C29H49NO5

Conditions

Conditions	Yield
With triethylamine In chloroform at 20℃; for 12h;	40%

111-57-9

N-stearoylethanolamine

774-74-3

2-(2,4-dichlorophenoxy)acetyl chloride

C28H45NO4Cl2

Conditions

Conditions	Yield
With triethylamine In chloroform at 20℃; for 12h;	37%

111-57-9

N-stearoylethanolamine

163725-46-0

2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranosyl bromide

A

1-(2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranosyl)-N-octadecanoyl-2-aminoethanol

B

1-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-N-octadecanoyl-2-aminoethanol

C

1,3,4,6-tetra-O-pivaloyl-α-D-galactopyranose

Conditions

Conditions	Yield
at 60℃; under 77574.3 Torr; Molecular sieve; Autoclave; Supercritical conditions; Green chemistry; diastereoselective reaction;	A n/a B n/a C 22%

...Expand

111-57-9

N-stearoylethanolamine

110531-17-4

N-(2-nitryloxy-ethyl)-stearamide

Conditions

Conditions	Yield
With nitric acid; acetic anhydride

111-57-9

N-stearoylethanolamine

17495-17-9

2-heptadecyl-4,5-dihydro-oxazole; hydrochloride

Conditions

Conditions	Yield
With thionyl chloride

111-57-9

N-stearoylethanolamine

22024-22-2

O-(stearoyl)ethanolamine hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at 50℃; durch Hydrolyse des Reaktionsprodukts mit seidendem Wasser;

111-57-9

N-stearoylethanolamine

108-24-7

acetic anhydride

1-acetoxy-2-stearoylamino-ethane

111-57-9

N-stearoylethanolamine

10287-60-2

O-stearoylethanolamine

Conditions

Conditions	Yield
With thionyl chloride

111-57-9

N-stearoylethanolamine

14351-40-7

stearic acid monoethanolamide stearate

Conditions

Conditions	Yield
In water at 220 - 230℃;

N-(2-Hydroxyethyl)stearamide Chemical Properties

N-(2-Hydroxyethyl)stearamide Safety Profile