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N-OLEOYLSARCOSINE

CAS Number: 110-25-8
EC Number: 203-749-3
Chemical formula: C21H39NO3
Molar mass: 353.547 g·mol−1

N-Oleoylsarcosine (Sarkosyl O) is an amphiphilic oleic acid derivative having a sarcosine head group (N-methylglycine) which is used as a water-in-oil emulsifier and corrosion inhibitor.

N-oleoylsarcosine is a corrosion inhibitor with the chemical formula C21H39NO3 and a molecular weight of 353.54. 
N-Oleoylsarcosine is an oil-soluble surfactant with a variety of groups and has been reported abroad since the 1930s. 
N-Oleoylsarcosine was first used in pure form or as a grain of salt in textile washing, toothpaste, shampoo, etc., but has since been introduced into the field of corrosion and rust inhibition.

Applications of N-Oleoylsarcosine:
N-Oleoylsarcosine is a mild surfactant which irritates skin and eyes comparatively little and is therefore used in personal care products such as skin cleansing agents because of N-Oleoylsarcosine antimicrobial and virucidal properties.
The sarcosine head group of the long-chain amphiphilic N-acylamino acid is responsible for the formation of chelate-like structures in the adsorption on polar and charged surfaces, e.g. on metals.

The molecules form oriented monomolecular films that protect the metal surface from corrosive attack.

N-Oleoylsarcosine possesses already at low concentrations very good rust protection properties (in particularly in combination with the imidazoline derivative 2-(2-heptadec-8-enyl-2-imidazolin-1-yl)ethanol which also acts emulsifying and anticorrosive), also against non-ferrous metals such as aluminum and copper.
Therefore, N-oleoylsarcosine is added as a corrosion inhibitor and emulsifier to rust protection fluids and lubricating greases, fuels and lubricants and refrigerating lubricants such as drilling and cutting oils.

Production of N-Oleoylsarcosine:
A standard method for the preparation of N-acylamino acids is the Schotten-Baumann reaction, in which oleoyl chloride (from oleic acid and, e.g. phosphorus trichloride) is added to an aqueous solution of N-methylglycine at pH 10 (kept constant by the addition of sodium hydroxide solution).

Fatty acid-free N-oleoylsarcosine is obtained as an oil. 
The method is not suitable for industrial surfactant synthesis because of the relatively expensive production of the carboxylic acid chlorides and the expensive disposal of the phosphonic acid obtained as a byproduct.

N-Oleoylsarcosine can be obtained in the reaction of oleic acid, N-methylglycine and N-Oleoylsarcosine sodium salt at 170 °C for 8 to 10 hours upon elimination of water.

More gentle conditions (120 °C) and shorter reaction times (3.5 hours) can be used when methyl oleate is reacted with sodium N-methylglycinate upon the addition of equimolar amounts of sodium methoxide in methanol. 
After absorption in water, acidification with concentrated sulfuric acid and extraction with butanone, N-Oleoylsarcosine is obtained in 92.5% yield.

Properties of N-Oleoylsarcosine:
N-Oleoylsarcosine is a clear, yellow to brown, viscous liquid, which is sparsely soluble in water and acts acidic. 
As long-chain N-acylamino acid, the surfactant is soluble in many organic solvents and in mineral oil. 

In the alkaline N-Oleoylsarcosine dissolves well in water. 
Because of N-Oleoylsarcosine carboxamide structure, Sarkosyl O is chemically stable even at high pH values and strongly foaming as an anionic surfactant. 
N-oleyl sarcosine is only slightly toxic and easily biodegradable.

Identifiers of N-Oleoylsarcosine:
CAS Number: 110-25-8
ChemSpider: 5289148
ECHA InfoCard: 100.003.410
EC Number: 203-749-3
PubChem CID: 6912870
UNII: 4011K1S96Y
CompTox Dashboard (EPA): DTXSID5042243
InChI: InChI=1S/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-
Key: DIOYAVUHUXAUPX-KHPPLWFESA-N
SMILES: CCCCCCCC/C=CCCCCCCCC(=O)N(C)CC(=O)O

Properties of N-Oleoylsarcosine:
Chemical formula: C21H39NO3
Molar mass: 353.547 g·mol−1
Molecular Weight: 353.5
XLogP3-AA: 6.8
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 17
Exact Mass: 353.29299411
Monoisotopic Mass: 353.29299411
Topological Polar Surface Area: 57.6 Ų
Heavy Atom Count: 25
Complexity: 366
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Names of N-Oleoylsarcosine:

Preferred IUPAC name of N-Oleoylsarcosine:
[(9Z)-N-Methyloctadec-9-enamido]acetic acid

Other names of N-Oleoylsarcosine:
Oleyl sarcosine

Synonyms of N-Oleoylsarcosine:
N-Oleoylsarcosine
Sarkosyl O
Oleic sarcosine
Hamposyl O
Maprosyl O
2-[methyl-[(E)-octadec-9-enoyl]amino]acetic acid
Oleyl N-methylglycine
Oleyl methylaminoethanoic acid
N-OLEOYL SARCOSINE
Medialanic acid
NSC-96995
N-Methyl-N-(1-oxo-9-octadecenyl)glycine
Glycine, (Z)-
SCHEMBL220435
SCHEMBL2557574
DTXSID60859192
NSC96995
ZINC59207670
N-Methyl-N-[(9E)-octadec-9-enoyl]glycine
(E)-2-(N-methyloctadec-9-enamido)acetic acid
Glycine, N-methyl-N-[(9E)-1-oxo-9-octadecen-1-yl]-
N-Methyl-N-[(9E)-9-octadecenoyl]glycin
N-Methyl-N-[(9E)-9-octadecenoyl]glycine
N-Méthyl-N-[(9E)-9-octadecenoyl]glycine
N-Oleoyl Sarcosine
[(9E)-N-METHYLOCTADEC-9-ENAMIDO]ACETIC ACID
16693-85-9
2-(N-Methyloleamido)acetic acid
2-[(9E)-N-METHYLOCTADEC-9-ENAMIDO]ACETIC ACID
203-749-3
57368-03-3
Glycine, N-methyl-N-(1-oxo-9-octadecenyl)-
Glycine, N-methyl-N-[(9Z)-1-oxo-9-octadecenyl]-
Hamposyl O
Maprosyl O
Medialanic acid (VAN)
MFCD03936142 [MDL number]
N-Methyl-N-(1-oxo-9-octadecenyl)glycine
Oleoyl N-methylaminoacetic acid
Oleoyl sarcosine
Sarcosine, N-oleoyl-

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