Decyl glucoside: A Non-ionic surfactant

Decyl glucoside is a naturally-derived surfactant used in shampoos, body washes, cleansers and liquid soaps. Surfactants are a class of ingredient that helps to lift dirt and oil from the skin, allowing it to be rinsed away. Decyl glucoside also has the ability to produce a nice foam, giving it an enjoyable sensory feel. Given that decyl glucoside is also gentle on the skin, compared to some other surfactants that are used, it makes it a good option for sensitive skin types.

Synthesis of Decyl glucoside

The eutectic solvent is choline chloride and succinic acid (molar ratio 1: 1) as a catalyst for the preparation of alkyl glycosides Adding a round bottom flask equipped with a condenser tube at a molar ratio of glucose to n-nonanol of 1:4, and introducing nitrogen purge for 10 minutes, then stir the mixture of glucose and n-nonanol, and dissolve the mixture of glucose and n-nonanol. The liquid is heated to a temperature of 80 ° C to 90 ° C, and a eutectic solvent having a mass of 1% to 1.5% by mass of glucose. Solution, and the temperature of the reaction solution in the round bottom flask is heated to 90 ° C - 95 ° C, and the reaction is carried out for 4 hours - 5 hours.After cooling, after the temperature of the reaction solution is lowered to room temperature, the reaction solution is extracted with ethyl acetate to separate the low total a molten solvent (ie, a catalyst), and then the extract is subjected to distillation to remove ethyl acetate and n-nonanol to obtain a product which is a thioglycoside. The yield of Decyl glucoside was 74%. The eutectic solvent recovered above can be reused.[1]

Allergic contact dermatitis to Decyl glucoside

In 2017 the American Contact Dermatitis Society named alkyl glucosides “Allergen of the Year.” Decyl glucosides are non-ionic surfactants and cleansing agents formed through the condensation of glucose with a fatty alcohol. Their use in cosmetic products has increased as they are biodegradable and considered less irritant and less allergenic than anionic surfactants. They are found in rinse-off products (cleaning agents, shampoos, and hair dyes) and occasionally in leave-on cosmetics (sunscreens, fragrances, and deodorants).

Our first case highlights the importance of searching for the hidden allergen in the components of facial cream, as nowadays the majority of facial creams contain UV filters. As demonstrated by our two cases, either concomitant or cross-reactivity to several alkyl glucosides in the same patient is frequent. This may be explained by the difficulty in achieving high purity of these chemicals and/or by their chemical similarity. For the patient it is important to know cross-reactivities, given the great number of cosmetics with alkyl glucosides. Furthermore, it should be noted that in both patients other important sensitizations were identified, emphasizing the importance of polysensitization. Most authors believe that alkyl glucosides are an underreported cause of allergic contact dermatitis in cosmetics as demonstrated by the high number of patients found in the European multicenter photopatch test study. Moreover, previous sensitization to alkyl glucosides through cosmetics may favor further reactivity to decyl glucoside in Tinosorb M. Taking into account the diversity of products containing alkyl glucosides, patient guidance might become a challenging issue.[2]

Safety assessment of Decyl glucoside

The Cosmetic Ingredient Review (CIR) Expert Panel assessed the safety of 19 Decyl glucosides as used in cosmetics and concluded that these ingredients are safe in the present practices of use and concentration when formulated to be nonirritating. Most of these Decyl glucosides function as surfactants in cosmetics, but some have additional functions as skin-conditioning agents, hair-conditioning agents, or emulsion stabilizers. The Panel reviewed the available animal and clinical data on these ingredients. Since glucoside hydrolases in human skin are likely to break down these ingredients to release their respective fatty acids and glucose, the Panel also reviewed CIR reports on the safety of fatty alcohols and were able to extrapolate data from those previous reports to support safety.[3]

References

[1] JIANGSU WAN QI BIOTECHNOLOGY - CN109593109, 2019, A

[2] Monteiro AF, Paulino M, Máquina A, Amaro C, Viana I. Allergic contact dermatitis to decyl glucoside: Still an important allergen in Tinosorb M. Contact Dermatitis. 2020 Feb;82(2):126-128.

[3] Fiume MM, Heldreth B, Bergfeld WF, Belsito DV, Hill RA, Klaassen CD, Liebler D, Marks JG Jr, Shank RC, Slaga TJ, Snyder PW, Andersen FA. Safety assessment of decyl glucoside and other alkyl glucosides as used in cosmetics. Int J Toxicol. 2013 Sep-Oct;32(5 Suppl):22S-48S.

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