Sodium lauroyl sarcosinate

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]

Sodium lauroyl sarcosinate
Names
IUPAC name
Sodium N-(Dodecanoyl)-N-methylglycinate
Systematic IUPAC name
Sodium (N-methyldodecanamido)acetate
Identifiers
3D model (JSmol)
ECHA InfoCard 100.004.801
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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Infobox references

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]

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.
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