137-16-6

Basic information

• Product Name: Sodium lauroylsarcosinate
• Synonyms: n-methyl-n-(1-oxododecyl)glycine sodium salt;N-LAURYL SARCOSINE, SODIUM SALT;N-LAUROYLSARCOSINE NA-SALT;N-LAUROYLSARCOSINE SODIUM SALT;N-LAUROYLSARCOSINE SODIUM SALT HYDRATE;N-DODECANOYL-N-METHYLGLYCINE SODIUM SALT;N-DODECANOYLSARCOSINE SODIUM SALT HYDRATE;N-DODECANOYLSARCOSINE SODIUM SALT MONOHYDRATE
• CAS NO: 137-16-6
• Molecular Formula: C₁₅H₂₈NO₃*Na
• Molecular Weight: 293.38
• EINECS: 205-281-5
• Product Categories: Hair Care;Oral Care;Skin Care;Amino ACIDS SERIES;Anionic Surfactants;Carboxylate (Surfactants);Functional Materials;Surfactants;Biochemistry;Nonionic Surfactants (for Biochemistry);Surfactants (for Biochemistry);Cosmetic Ingredients & Chemicals;Additional Anionic DetergentsDetergents;Anionic;Detergents;Detergents A to Z;detergent
• Mol File: 137-16-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 46 °C
• Boiling Point: 413.2 °C at 760 mmHg
• Flash Point: 267℃
• Appearance: White/Powder
• Density: 1.033 g/mL at 20 °C
• Vapor Pressure: 0.02 hPa (20 °C)
• Storage Temp.: room temp
• Solubility: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility: Soluble in water (293 g/L).
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,4368
• BRN: 5322974
• CAS DataBase Reference: Sodium lauroylsarcosinate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium lauroylsarcosinate(137-16-6)
• EPA Substance Registry System: Sodium lauroylsarcosinate(137-16-6)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-41-38-23
• Safety Statements: 22-24/25-36/37/39-27-26-45-38-37/39
• RIDADR: UN 2811 6.1 / PGII
• WGK Germany: 3
• RTECS: MC0598960
• F: 3-10
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 137-16-6(Hazardous Substances Data)

Usage

Description

Sodium lauroylsarcosinate, also known as sarkosyl, is an anionic surfactant derived from sarcosine. It is a white powder with an amphiphilic nature due to its hydrophobic 12-carbon chain (lauroyl) and hydrophilic carboxylate. This surfactant is known for its mildness, biodegradability, and ability to denature proteins, making it a versatile compound with various applications in personal care, household, and industrial products.

Uses

Used in Personal Care Products:
Sodium lauroylsarcosinate is used as a co-surfactant in cleanser formulations such as shampoos and body washes for its foaming and cleansing properties. It is also used in oral care applications like toothpaste and syndet and combo bars. The typical usage levels range from 1-5% on an active basis. It enhances the appearance and feel of hair by improving body, suppleness, and sheen, especially in chemically damaged hair. As a modified fatty acid, it is more soluble and has increased crystallinity and acidity compared to its original fatty acid composition.
Used in Household and Industrial Applications:
Sodium lauroylsarcosinate is used as a detergent, foaming agent, and antienzyme in various household and industrial applications. It is known for its high foam, eco-friendly properties, good chlorine stability, and anti-corrosion characteristics.
Used in Biochemical Research:
Sodium lauroylsarcosinate is used for solubilization and separation of membrane proteins and glycoproteins. It is also used in the lysis of cells during the isolation of RNA and has been reported to inhibit hexokinase. It is useful in concentrated salt solutions used in the cell lysis step during RNA purification, as it helps avoid excessive foaming.
Used in Pharmaceutical Formulations:
Due to its microbicidal property, sodium lauroylsarcosinate is being considered as a potent anti-microbicide in topical formulations, especially against sexually transmitted diseases (STDs).
Used in Dentifrices:
Sodium lauroyl sarcosinate is used as a detergent and foaming agent in dentifrices, as mentioned in the patent by King, US 2689170 (1954 to Colgate-Palmolive).
Used in Inhibition of Bacterial Flora:
Sodium lauroylsarcosinate inhibits the bacterial flora of human saliva and gut at a concentration of 0.25% and also acts as a fungistatic agent in aqueous dispersion (1%).

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

N-Lauroylsarcosine is an anionic surfactant which also has protein denaturant potency. In addition, it has been shown as a microbicide for sexually transmitted diseases.

Synthetic route

N-acyl sarcosinate (97-78-9) → sodium N-lauroylsarcosinate (137-16-6)

Conditions	Yield
With sodium hydroxide In ethanol at 50 - 70℃;	99%

n-dodecanoyl chloride (112-16-3) + sarcosine (107-97-1) → sodium N-lauroylsarcosinate (137-16-6)

Conditions	Yield
With sodium hydroxide In water at 15 - 20℃; pH=8 - 10;	97%

n-dodecanoyl chloride (112-16-3) + sodium sarcosinate (4316-73-8) → sodium N-lauroylsarcosinate (137-16-6)

Conditions	Yield
In water at 10 - 30℃; for 5h; pH=10.3 - 10.6; Schotten-Baumann Reaction; Inert atmosphere;
With sodium hydroxide In water at 10 - 30℃; for 5h; pH=10.3 - 10.6; Inert atmosphere;

lauric acid (143-07-7) → sodium N-lauroylsarcosinate (137-16-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium dodecanoylglycinate; thionyl chloride / 6 h / 25 °C / Inert atmosphere 2: water / 5 h / 10 - 30 °C / pH 10.3 - 10.6 / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride; N-lauroyl glycenic lauric anhydride / 6 h / 25 °C / 760.05 Torr / Inert atmosphere 2: sodium hydroxide / water / 5 h / 10 - 30 °C / pH 10.3 - 10.6 / Inert atmosphere View Scheme

2,2,2-trichloroethyl (2-(tert-butylcarbamoyl)phenyl)sulfamate + sodium N-lauroylsarcosinate (137-16-6) → N-(tert-butyl)-2-(2-(N-methyldodecanamido)acetamido)benzamide

Conditions	Yield
In chlorobenzene at 120℃; for 10h;	72%

Upstream product

• 97-78-9 N-acyl sarcosinate 
• 107-97-1 sarcosine 
• 1120-16-7 lauric acid amide 
• 112-16-3 n-dodecanoyl chloride 
• 143-07-7 lauric acid 
• 4316-73-8 sodium sarcosinate 

Related news

Synergistic effects of chemical enhancers on skin permeability: A case study of Sodium lauroylsarcosinate (cas 137-16-6) and sorbitan monolaurate09/29/2019

Certain mixtures of chemicals are known to synergistically enhance skin permeability to drugs. Here, we report on the transport enhancing properties of mixtures of an anionic surfactant, sodium lauroylsarcosinate (NLS) and a non-ionic surfactant, sorbitan monolaurate (S20) in 1:1 phosphate buffe...detailed

Relevant articles and documents

Synthesis method of N-lauroyl amino acid salt

The invention provides a synthesis method of N-lauroyl amino acid salt, which comprises the following steps: mixing amino acid, alkali and water according to a certain molar ratio to completely dissolve the amino acid, the alkali and the water, and carrying out reduced pressure distillation at 100-120 DEG C to remove water, so as to obtain amino acid salt; mixing amino acid salt and lauramide into a reaction container provided with a tail gas receiving device according to a certain proportion; stirring and reacting for a certain time at a certain temperature; after the reaction is finished, acidifying the reaction mixture by using a hydrochloric acid solution to precipitate the product, filtering and collecting the precipitate to obtain a purified product; carrying out forced air drying on the purified product to remove moisture, so as to obtain a dried product; and dissolving the product with ethanol, adding an alkali solution at a certain temperature, stirring to react for a period of time, cooling to crystallize, and carrying out suction filtration to obtain the lauroyl amino acid salt. Other substances are not used as solvents, so that the problems of over-high production and waste treatment cost and environmental pollution caused by the use of a large amount of solvents at present are solved, and the method has wide market prospects and social benefits.

A laurel acyl amino acid synthetic method of sodium

The invention relates to a synthetic method of lauric acyl amino acid sodium, particularly to a synthetic method which uses lauric acid and phosgene as raw materials. The synthetic method comprises the following steps: ensuring that the reaction lasts for 1 to 20 hours at a temperature of 60 to 100 DEG C with the effect of organic amide catalyst; obtaining acyl chloride through vacuum distillation after the reaction is finished; dripping lauric acyl chloride obtained according to the phosgene method into amino acids alkaline solution for reaction; controlling and ensuring the pH value to be within the range of 8 to 10, the reaction temperature to be 15 to 20 DEG C, and the reaction time to be 4 to 5 hours; carrying out cooling after the reaction is finished; acidizing the reaction solution to pH 1 to 2 with hydrochloric acid solution; filtering, washing and drying white sediment to obtain lauric acyl amino acid; dissolving the prepared lauric acyl amino acid with alcohol; adding alcohol solution with sodium hydroxide of equal molar amount; and crystallizing, sucking, filtering and drying after cooling to obtain the lauric acyl amino acid sodium. According to the invention, the synthetic method is reasonable in process, high in reaction efficiency and good in product quality; the three wastes are seldom generated; and no residual phosphorus and sulfur are contained in the product. Therefore, the synthetic method can be widely used in the production of high-end surface active agents, and has significant utility value and social and economic benefits.

METHOD TO PRODUCE N-ACYL AMINO ACID SURFACTANTS USING N-ACYL AMINO ACID SURFACTANTS OR THE CORRESPONDING ANHYDRIDES AS CATALYSTS

A process of producing N-acyl amino acid based surfactants of Formula (I), wherein, R is selected from C6 to C22 alkyl group, R1 is selected from H, C1 to C4 alkyl, R2 is selected from all groups on a carbon of natural amino acids, R3 is selected from COOX, CH2-SO3X, X is selected from Li+, Na+ or K+; said process comprising steps of A) preparing fatty acid chlorides by halogenating fatty acids with either phosgene or thionyl chloride in the presence of catalytic amount of same or other N-acyl amino acid surfactant of Formula (I) or anhydrides of same surfactant, Formula (II), wherein, R = C6 to C22 alkyl group, R1 = H, C1 to C4 alkyl, R2 = all groups on α carbon of natural amino acids, n = 0 to 4, X = C, SO and B) reacting fatty acid chloride of step (A) with an amino acid in the presence of a base under typical aqueous Schotten Baumann conditions such that said process does not employ a step of purification.