Sodium lauroyl sarcosinate

Sodium lauroyl sarcosinate

Names
IUPAC name Sodium [dodecanoyl(methyl)amino]acetate
Identifiers
CAS Number	137-16-6
Jmol interactive 3D	Image
PubChem	23668817
InChI 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
SMILES CCCCCCCCCCCC(=O)N(C)CC(=O)[O-].[Na+]
Properties
Chemical formula	C15H28NNaO3
Molar mass	293.38 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

Sodium lauroyl sarcosinate (INCI), also known as sarkosyl, is an ionic surfactant derived from sarcosine used as a foaming and cleansing agent in shampoo, shaving foam, toothpaste, and foam wash products.^[1] In molecular biology experiments, sarkosyl is used to inhibit the initiation of DNA transcription.

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]

Addition of an mixture of equal parts of sodium lauroyl sarcosinate and the non-ionic surfactant sorbitan monolaurate (S20) to water 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.^[3]

In culture

Sodium lauroyl sarcosinate was sold as a special ingredient called 'Gardol' in Colgate Dental Cream (toothpaste) during the 1950s^[4][5][6] through the mid-1960s in the US^[7][8] and the mid-1970s in France.^[9] Current use as a preventive dentifrice is in Arm & Hammer toothpaste.

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. doi:10.1038/srep00071.
3. 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: 1–7.
4. Do you remember Gardol? by Olga Werby, May 7, 2013
5. 1956 Colgate Toothpaste with Gardol Original Advertisement
6. Colgate Dental Cream Gardol Father Kids On Sled 1959 Antique Advertisement
7. Colgate Dental Cream with Gardol advertisement in Life Magazine, May 29, 1963 page 4.
8. "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
9. Colgate Dental Cream with Gardol advertisement in a TV spot, November 17, 1975.

• Ambühl, F; Bangerter, P.L. Luisi, P. Skrobal and H.J.Watzke (1993). Langmuir 9: 36–38. doi:10.1021/la00025a011. Cite uses deprecated parameter |coauthors= (help); Missing or empty |title= (help)
• Ghosh, S; J.Dey (2011). J. Colloid and Interface Sci. 358: 208–216. Missing or empty |title= (help)

External links

• "Occupational Allergic Contact Dermatitis From Sodium Lauroyl Sarcosinate in Liquid Soap," Zemtsov, Alexander MD, MSC; Fett, Deborah MD, Dermatitis, June 2005, Volume 16, Issue 2, p. 97