Sodium lauroyl sarcosinate

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Sodium lauroyl sarcosinate
Sodium lauroyl sarcosinate.svg
Names
IUPAC name
Sodium N-(Dodecanoyl)-N-methylglycinate
Systematic IUPAC name
Sodium (N-methyldodecanamido)acetate
Identifiers
3D model (JSmol)
ECHA InfoCard 100.004.801 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C15H29NO3.Na/c1-3-4-5-6-7-8-9-10-11-12-14(17)16(2)13-15(18)19;/h3-13H2,1-2H3,(H,18,19);/q;+1/p-1
  • CCCCCCCCCCCC(=O)N(C)CC(=O)[O-].[Na+]
Properties
C15H28NNaO3
Molar mass 293.383 g·mol−1
Melting point 140 °C (284 °F; 413 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sodium lauroyl sarcosinate (INCI), also known as sarcosyl, is an anionic surfactant derived from sarcosine used as a foaming and cleansing agent in shampoo, shaving foam, toothpaste, and foam wash products. [1]

Contents

This surfactant is amphiphilic due to the hydrophobic 12-carbon chain (lauroyl) and the hydrophilic carboxylate. Since the nitrogen atom is in an amide linkage, the nitrogen is not pH active and is neutrally charged in all aqueous solutions regardless of pH. The carboxylate has a pKa of about 3.6 and is therefore negatively charged in solutions of pH greater than about 5.5.

pH-sensitive vesicles can be prepared using this surfactant with another cationic or water-insoluble amphiphiles such as 1-decanol. [2] [3] [4]

Addition of an mixture of equal parts of sodium lauroyl sarcosinate and the non-ionic surfactant sorbitan monolaurate (S20) to a buffered water:ethanol solution led to the formation of micelle-like aggregates, even though neither surfactant formed micelles when present alone. Such aggregates can help carry other small molecules, such as drugs, through the skin. [5]

In culture

Sodium lauroyl sarcosinate was sold as a special ingredient called "Gardol" in Colgate "Dental Cream", as toothpaste was then called, during the 1950s [6] [7] [8] through the mid-1960s in the US [9] [10] and the mid-1970s in France. [11] Its current use as a preventive dentifrice is in Arm & Hammer Baking Soda Toothpaste, a Church & Dwight product, where it is used as a surfactant. [12]

Related Research Articles

Sodium laureth sulfate (SLES), an accepted contraction of sodium lauryl ether sulfate (SLES), also called sodium alkylethersulfate, is an anionic detergent and surfactant found in many personal care products and for industrial uses. SLES is an inexpensive and very effective foaming agent. SLES, sodium lauryl sulfate (SLS), ammonium lauryl sulfate (ALS), and sodium pareth sulfate are surfactants that are used in many cosmetic products for their cleaning and emulsifying properties. It is derived from palm kernel oil or coconut oil. In herbicides, it is used as a surfactant to improve absorption of the herbicidal chemicals and reduces time the product takes to be rainfast, when enough of the herbicidal agent will be absorbed.

Sodium dodecyl sulfate (SDS) or sodium lauryl sulfate (SLS), sometimes written sodium laurilsulfate, is an organic compound with the formula CH3(CH2)11OSO3Na and structure H3C(CH2)11−O−S(=O)2−ONa+. It is an anionic surfactant used in many cleaning and hygiene products. This compound is the sodium salt of the 12-carbon organosulfate. Its hydrocarbon tail combined with a polar "headgroup" give the compound amphiphilic properties that make it useful as a detergent. SDS is also component of mixtures produced from inexpensive coconut and palm oils. SDS is a common component of many domestic cleaning, personal hygiene and cosmetic, pharmaceutical, and food products, as well as of industrial and commercial cleaning and product formulations.

<span class="mw-page-title-main">Detergent</span> Surfactants with cleansing properties

A detergent is a surfactant or a mixture of surfactants with cleansing properties when in dilute solutions. There are a large variety of detergents, a common family being the alkylbenzene sulfonates, which are soap-like compounds that are more soluble in hard water, because the polar sulfonate is less likely than the polar carboxylate to bind to calcium and other ions found in hard water.

<span class="mw-page-title-main">Surfactant</span> Substance that lowers the surface tension between a liquid and another material

Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. Surfactants may function as emulsifiers, wetting agents, detergents, foaming agents, or dispersants. The word "surfactant" is a blend of surface-active agent, coined c. 1950.

<span class="mw-page-title-main">Toothpaste</span> Substance to clean and maintain teeth

Toothpaste is a paste or gel dentifrice used with a toothbrush to clean and maintain the aesthetics and health of teeth. Toothpaste is used to promote oral hygiene: it is an abrasive that aids in removing dental plaque and food from the teeth, assists in suppressing halitosis, and delivers active ingredients to help prevent tooth decay and gum disease (gingivitis). Owing to differences in composition and fluoride content, not all toothpastes are equally effective in maintaining oral health. The decline of tooth decay during the 20th century has been attributed to the introduction and regular use of fluoride-containing toothpastes worldwide. Large amounts of swallowed toothpaste can be poisonous. Common colors for toothpaste include white and blue.

<span class="mw-page-title-main">Micelle</span> Group of fatty molecules suspended in liquid by soaps and/or detergents

A micelle or micella is an aggregate of surfactant amphipathic lipid molecules dispersed in a liquid, forming a colloidal suspension. A typical micelle in water forms an aggregate with the hydrophilic "head" regions in contact with surrounding solvent, sequestering the hydrophobic single-tail regions in the micelle centre.

In colloidal and surface chemistry, the critical micelle concentration (CMC) is defined as the concentration of surfactants above which micelles form and all additional surfactants added to the system will form micelles.

<span class="mw-page-title-main">Fluoride therapy</span> Medical use of fluoride

Fluoride therapy is the use of fluoride for medical purposes. Fluoride supplements are recommended to prevent tooth decay in children older than six months in areas where the drinking water is low in fluoride. It is typically used as a liquid, pill, or paste by mouth. Where public water supplies are fluoridated further fluoride by mouth is typically not needed. Fluoride has also been used to treat a number of bone diseases.

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<span class="mw-page-title-main">Amphiphile</span> Hydrophilic and lipophilic chemical compound

An amphiphile, or amphipath, is a chemical compound possessing both hydrophilic and lipophilic (fat-loving) properties. Such a compound is called amphiphilic or amphipathic. Common amphiphilic compound is surfactant, which is a main ingredient of soaps, detergents, and lipoproteins. The phospholipid amphiphiles are the major structural component of cell membranes.

<span class="mw-page-title-main">Polysorbate 80</span> Nonionic surfactant and emulsifier used in food and cosmetics

Polysorbate 80 is a nonionic surfactant and emulsifier often used in pharmaceuticals, foods, and cosmetics. This synthetic compound is a viscous, water-soluble yellow liquid.

<span class="mw-page-title-main">Tin(II) fluoride</span> Chemical compound

Tin(II) fluoride, commonly referred to commercially as stannous fluoride (from Latin stannum, 'tin'), is a chemical compound with the formula SnF2. It is a colourless solid used as an ingredient in toothpastes.

Sensodyne is a brand name of toothpaste and mouthwash targeted at people with sensitive teeth. Sensodyne is owned by Haleon and is marketed under the name Shumitect in Japan.

A hydrotrope is a compound that solubilizes hydrophobic compounds in aqueous solutions by means other than micellar solubilization. Typically, hydrotropes consist of a hydrophilic part and a hydrophobic part, but the hydrophobic part is generally too small to cause spontaneous self-aggregation. Hydrotropes do not have a critical concentration above which self-aggregation spontaneously starts to occur. Instead, some hydrotropes aggregate in a step-wise self-aggregation process, gradually increasing aggregation size. However, many hydrotropes do not seem to self-aggregate at all, unless a solubilizate has been added. Examples of hydrotropes include urea, tosylate, cumenesulfonate and xylenesulfonate.

<span class="mw-page-title-main">Lyotropic liquid crystal</span>

Lyotropic liquid crystals result when fat-loving and water-loving chemical compounds known as amphiphiles dissolve into a solution that behaves both like a liquid and a solid crystal. This liquid crystalline mesophase includes everyday mixtures like soap and water.

Zendium is a brand of toothpaste marketed by Unilever in Austria, Belgium, Croatia, Czech Republic, France, Germany, Hungary, Italy, the Middle East, the Netherlands, Scandinavia, Slovakia and Switzerland.

<span class="mw-page-title-main">Peptide amphiphile</span>

Peptide amphiphiles (PAs) are peptide-based molecules that self-assemble into supramolecular nanostructures including; spherical micelles, twisted ribbons, and high-aspect-ratio nanofibers. A peptide amphiphile typically comprises a hydrophilic peptide sequence attached to a lipid tail, i.e. a hydrophobic alkyl chain with 10 to 16 carbons. Therefore, they can be considered a type of lipopeptide. A special type of PA, is constituted by alternating charged and neutral residues, in a repeated pattern, such as RADA16-I. The PAs were developed in the 1990s and the early 2000s and could be used in various medical areas including: nanocarriers, nanodrugs, and imaging agents. However, perhaps their main potential is in regenerative medicine to culture and deliver cells and growth factors.

In colloidal chemistry, the surfactant’s critical micelle concentration (CMC) plays a factor in Gibbs free energy of micellization. The exact concentration of the surfactants that yield the aggregates being thermodynamically soluble is the CMC. The Krafft temperature determines the solubility of the surfactants which in turn is the temperature that CMC is achieved. There are many parameters that affect the CMC. The interaction between the hydrophilic heads and the hydrophobic tails play a part, as well as the concentration of salt within the solution and surfactants.

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<span class="mw-page-title-main">Taurates</span>

Taurates (or taurides) are a group of mild anionic surfactants. They are composed of a hydrophilic head group, consisting of N-methyltaurine (2-methylaminoethanesulfonic acid) and a lipophilic residue, consisting of a long-chain carboxylic acid (fatty acid), both linked via an amide bond. The fatty acids used could be lauric (C12), myristic (C14), palmitic (C16) or stearic acid (C18), but mainly mixtures of oleic acid (C18:1) and coconut fatty acid (C8 – C18) are used. Besides sodium, no other counterions play a relevant role (these could be e. g. ammonium or other alkali or alkaline earth metals).

References

  1. Wallach, D.F.H; R. Mathur; G.J.M. Redziniak; J.F. Tranchant (1992). "Some properties of N-acyl sarcosinate lipid vesicles". J. Soc.Cosmetic Chemists. 43: 113–118.
  2. Akter, N; S. Radiman; F. Mohamed; I.A. Rahman; M.I.H. Reza (2011). "Ternary phase behaviour and vesicle formation of a sodium N-lauroylsarcosinate hydrate/1-decanol/water system". Scientific Reports. 1: 71. Bibcode:2011NatSR...1E..71A. doi:10.1038/srep00071. PMC   3216558 . PMID   22355590.
  3. Ambühl, M; F. Bangerter; P.L. Luisi; P. Skrobal; H.J. Watzke (1993). "Configurational changes accompanying vesiculation of mixed single-chain amphiphiles". Langmuir. 9: 36–38. doi:10.1021/la00025a011.
  4. Ghosh, S; J.Dey (2011). "Interaction of sodium N-lauroylsarcosinate with N-alkylpyridinium chloride surfactants: Spontaneous formation of pH-responsive, stable vesicles in aqueous mixtures". J. Colloid Interface Sci. 358 (1): 208–216. Bibcode:2011JCIS..358..208G. doi:10.1016/j.jcis.2011.02.054. PMID   21420688.
  5. Karande, P; A.Jain; A. Arora; M.J.Ho; S. Mitragotri (2007). "Synergistic effects of chemical enhancers on skin permeability: a case study of sodium lauroylsarcosinate and sorbitan monolaurate". Eur. J. Pharm. Sci. 31 (1): 1–7. doi:10.1016/j.ejps.2007.01.004. PMID   17368869.
  6. Do you remember Gardol? by Olga Werby, May 7, 2013
  7. 1956 Colgate Toothpaste with Gardol Original Advertisement
  8. Colgate Dental Cream Gardol Father Kids On Sled 1959 Antique Advertisement
  9. Colgate Dental Cream with Gardol advertisement in Life Magazine, May 29, 1963 page 4.
  10. "Clinical Test Confirms Colgate a Leader in Reducing New Cavities! Read what happened when Colgate with Gardol was clinically tested against the most widely accepted fluoride dentifrice." Ebony, June 1963, Vol. 18, No. 8, Colgate with Gardol ad
  11. Colgate Dental Cream with Gardol advertisement in a TV spot, November 17, 1975.
  12. "C&D Corporate - Ingredient Disclosure". churchdwight.com. Church & Dwight Co., Inc. Retrieved November 24, 2021.