110-25-8

Basic information

• Product Name: N-OLEOYLSARCOSINE
• Synonyms: N-Methyloleamidoacetic acid;Glycine, N-methyl-N-(1-oxo-9-octadecenyl)-, (Z)-;Hamposyl o;Maprosyl o;Medialanic acid;Nsc96995;Oleic sarcosine;Oleoyl N-methylaminoacetic acid
• CAS NO: 110-25-8
• Molecular Formula: C₂₁H₃₉NO₃
• Molecular Weight: 353.54
• EINECS: 203-749-3
• Product Categories: Efficient oil with antirust additive;Lubricant additive
• Mol File: 110-25-8.mol

Chemical Properties

• Melting Point: 16.1-17.0℃
• Boiling Point: 499.4 °C at 760 mmHg
• Flash Point: 221°C
• Appearance: light yellow liquid
• Density: 0.961
• Vapor Pressure: 2.47E-11mmHg at 25°C
• Refractive Index: 1.481
• PKA: 3.62±0.10(Predicted)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: N-OLEOYLSARCOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-OLEOYLSARCOSINE(110-25-8)
• EPA Substance Registry System: N-OLEOYLSARCOSINE(110-25-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 110-25-8(Hazardous Substances Data)

Usage

Uses

Used in Lubricating Oil and Grease Industry:
N-OLEOYLSARCOSINE is used as an anti-tarnishing sunscreen additive for lubricating oil and grease. Its ability to form complexes with metal ions helps prevent the oxidation and corrosion of metal surfaces, thereby extending the life of the lubricants and protecting the machinery from wear and tear.
Used in Cosmetics Industry:
N-OLEOYLSARCOSINE is used as an emulsifier and solubilizer in cosmetic formulations. Its amphiphilic nature allows it to mix oil and water-based ingredients, creating stable emulsions. It also helps improve the texture and spreadability of the products, providing a smooth and non-greasy feel on the skin.
Used in Pharmaceutical Industry:
N-OLEOYLSARCOSINE is used as a penetration enhancer in transdermal drug delivery systems. Its ability to interact with the skin's lipids and proteins enables the efficient delivery of drugs through the skin, improving the bioavailability and therapeutic effects of the medication.
Used in Food Industry:
N-OLEOYLSARCOSINE is used as a flavor enhancer and emulsifier in the food industry. Its ability to bind with taste receptors and improve the stability of food emulsions contributes to the enhancement of flavor and texture in various food products.

InChI:InChI=1/C21H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20(23)22(2)19-21(24)25/h10-11H,3-9,12-19H2,1-2H3,(H,24,25)/b11-10-

Synthetic route

N-oleoylsarcosine methyl ester → N-oleoylsarcosine (110-25-8)

Conditions	Yield
Stage #1: N-oleoylsarcosine methyl ester With lithium hydroxide In ethanol; water at 20℃; for 12h; Stage #2: With hydrogenchloride In water pH=2;	98%

sodium sarcosinate (4316-73-8) + oleic acid chloride → N-oleoylsarcosine (110-25-8)

Conditions	Yield
With water; sodium hydroxide In toluene at 30℃; for 1h; Solvent;	97.8%

(Z)-9-octadecenoyl chloride (112-77-6) + sarcosine (107-97-1) → N-oleoylsarcosine (110-25-8)

Conditions	Yield
With sodium hydroxide

sarcosine (107-97-1) + cis-Octadecenoic acid (112-80-1) + sodium sarcosinate (4316-73-8) → N-oleoylsarcosine (110-25-8)

Conditions	Yield
In water; isopropyl alcohol

(Z)-9-octadecenoyl chloride (112-77-6) → N-oleoylsarcosine (110-25-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane; methanol / 0 - 20 °C 2.1: lithium hydroxide / ethanol; water / 12 h / 20 °C 2.2: pH 2 View Scheme

N-oleoylsarcosine (110-25-8) + 6-nitroveratryl alcohol (1016-58-6) → 4,5-dimethoxy-2-nitrobenzyl [methyl(oleoyl)amino]acetate (1413644-53-7)

Conditions	Yield
Stage #1: N-oleoylsarcosine With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: 6-nitroveratryl alcohol In dichloromethane at 20℃; Inert atmosphere;	82%

2-Ethylhexyl alcohol (104-76-7) + N-oleoylsarcosine (110-25-8) → 2-ethylhexyl N-oleoylsarcosinate

Conditions	Yield
at 150℃; for 3h; Inert atmosphere; Dean-Stark;
at 150℃; for 3h; Dean-Stark; Inert atmosphere;	421.7 g
at 150℃; for 3h; Dean-Stark; Inert atmosphere;	421.7 g
at 150℃; for 3h; Dean-Stark; Inert atmosphere; Reflux;	421.7 g

2-Ethylhexylamine (104-75-6) + N-oleoylsarcosine (110-25-8) → N'-2-ethylhexyl N-oleoylsarcosinamide

Conditions	Yield
at 130℃; for 3h; Inert atmosphere; Dean-Stark;
at 130℃; for 3h; Dean-Stark; Inert atmosphere;	266.6 g
at 130℃; for 3h; Dean-Stark; Inert atmosphere;	266.6 g
at 130℃; for 3h; Dean-Stark; Inert atmosphere;	266.6 g

N-oleoylsarcosine (110-25-8) + 2,2'-iminobis[ethanol] (111-42-2) → N',N' bis(2-hydroxyethyl) N-oleoylsarcosinamide

Conditions	Yield
With Amberlyst 15 acidic resin at 150℃; for 3h; Inert atmosphere; Dean-Stark;
With Amberlyst 15 acidic resin at 150℃; for 3h; Dean-Stark; Inert atmosphere;	371.6 g
With Amberlyst 15 acidic resin at 150℃; for 3h; Dean-Stark; Inert atmosphere;	371.6 g
With Amberlyst 15 acidic resin at 150℃; for 3h; Dean-Stark; Inert atmosphere;	371.6 g

N-oleoylsarcosine (110-25-8) + butan-1-ol (71-36-3) → butyl N-oleoylsarcosinate

Conditions	Yield
With Amberlyst 15 acidic resin for 3h; Inert atmosphere; Dean-Stark; Reflux;	310 g
With Amberlyst 15 acidic resin for 3h; Dean-Stark; Reflux; Inert atmosphere;	310 g
With Amberlyst 15 acidic resin for 3h; Dean-Stark; Inert atmosphere; Reflux;	310 g
With Amberlyst 15 acidic resin for 3h; Dean-Stark; Inert atmosphere; Reflux;	310 g

ethanol (64-17-5) + N-oleoylsarcosine (110-25-8) → ethyl N-oleoylsarcosinate

Conditions	Yield
for 3h; Inert atmosphere; Dean-Stark; Reflux;	280 g
for 3h; Dean-Stark; Inert atmosphere; Reflux;	280 g
for 3h; Dean-Stark; Inert atmosphere; Reflux;	280 g
for 3h; Dean-Stark; Inert atmosphere; Reflux;	280 g

N-oleoylsarcosine (110-25-8) + 2-methoxy-ethanol (109-86-4) → 2-methoxyethyl N-oleoylsarcosinate

Conditions	Yield
With Amberlyst 15 acidic resin at 160℃; for 3h; Inert atmosphere; Dean-Stark;
With Amberlyst 15 acidic resin at 160℃; for 3h; Dean-Stark; Inert atmosphere;	273.5 g

N-oleoylsarcosine (110-25-8) + ethylene glycol (107-21-1) → 2-hydroxyethyl N-oleoylsarcosinate

Conditions	Yield
With Amberlyst 15 acidic resin at 160℃; for 3h; Inert atmosphere; Dean-Stark;
With Amberlyst 15 acidic resin at 160℃; for 3h; Dean-Stark; Inert atmosphere;	312.7 g
With Amberlyst 15 acidic resin at 160℃; for 3h; Dean-Stark; Inert atmosphere;	312.7 g
With Amberlyst 15 acidic resin at 160℃; for 3h; Dean-Stark; Inert atmosphere;	312.7 g

N-oleoylsarcosine (110-25-8) + 2-methoxyethylamine (109-85-3) → N'-2-methoxyethyl N-oleoylsarcosinamide

Conditions	Yield
With Amberlyst 15 acidic resin at 150℃; for 3h; Inert atmosphere; Dean-Stark;
With Amberlyst 15 acidic resin at 150℃; for 3h; Dean-Stark; Inert atmosphere;	263.9 g
With Amberlyst 15 acidic resin at 150℃; for 3h; Dean-Stark; Inert atmosphere;	263.9 g
With Amberlyst 15 acidic resin at 150℃; for 3h; Dean-Stark;	263.9 g

N-oleoylsarcosine (110-25-8) + 1-amino-3-(dimethylamino)propane (109-55-7) → N-oleoyl-N'-3-(dimethylamino)propylsarcosinamide

Conditions	Yield
With Amberlyst 15 acidic resin at 150℃; for 3h; Inert atmosphere; Dean-Stark;
With Amberlyst 15 acidic resin at 150℃; for 3h; Dean-Stark; Inert atmosphere;	377.8 g
With Amberlyst 15 acidic resin at 150℃; for 3h; Dean-Stark; Inert atmosphere;	377.8 g
With Amberlyst 15 acidic resin at 150℃; for 3h; Dean-Stark; Inert atmosphere;	377.8 g

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + N-oleoylsarcosine (110-25-8) → 2-methoxyethyl N-oleoylsarcosinate

Conditions	Yield
With Amberlyst 15 acidic resin at 160℃; for 3h; Dean-Stark; Inert atmosphere;	273.5 g
With Amberlyst 15 acidic resin at 160℃; for 3h; Dean-Stark; Inert atmosphere;	273.5 g

Upstream product

• 112-77-6 (Z)-9-octadecenoyl chloride 
• 107-97-1 sarcosine 
• 112-80-1 cis-Octadecenoic acid 
• 4316-73-8 sodium sarcosinate 

Downstream Products

• 1413644-53-7 4,5-dimethoxy-2-nitrobenzyl [methyl(oleoyl)amino]acetate 

Relevant articles and documents

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