Ingredient Profile—Ethylhexyl Methoxycinnamate

Feb 1, 2012 | Contact Author | By: Michael J. Fevola, PhD, Johnson & Johnson
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Title: Ingredient Profile—Ethylhexyl Methoxycinnamate
ethylhexyl methoxycinnamatex sunscreenx UV filterx activex
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Keywords: ethylhexyl methoxycinnamate | sunscreen | UV filter | active

Abstract: Ethylhexyl methoxycinnamate (EHMC) is among the most frequently used organic ultraviolet (UV) filters, known primarily for its role as an active ingredient in sunscreen products.

Market Data

  • Awareness among consumers about the harmful effects of UV boosted sun care sales by 6.5% in 2012 in the United States.
  • Sun care marketers are diversifying their product offerings; a common trend emerging is to include tint.
  • Although spray-on sun care products are popular, there are rising concerns associated with the inhalation of nanoparticles.
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Ethylhexyl methoxycinnamate (EHMC) is among the most frequently used organic ultraviolet (UV) filters, known primarily for its role as an active ingredient in sunscreen products.1–3 EHMC also has been used in hair, skin, nail and color cosmetic products to protect substrates, e.g., hair from damage by UVB radiation, and to help stabilize formulations against photodegradation.

Chemistry and Manufacture

EHMC, shown in Figure 1, is the 2-ethylhexyl ester of para-methoxycinnamic acid. Its molecular formula is C18H26O3, corresponding to a molecular weight of 290.4 g/mol.1,4 The compound is often referred to as octyl methoxy-cinnamate (OMC) because it bears a C8 alkyl group; however, this name does not reflect the distinctly branched nature of the 2-ethylhexyl group in EHMC. The previous US Pharmacopeia (USP) name for EHMC was octyl methoxycinnamate; this name was changed to octinoxate in the year 2000 and was adopted as the US over-the-counter (OTC) drug name for EHMC in 2002.2,3

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This is an excerpt of an article from GCI Magazine. The full version can be found here.

 

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Figure 1. Chemical structure of EHMC

Figure 1. Chemical structure of EHMC

Figure 2. Synthesis of 2-EH starting from propylene gas

Figure 2. Synthesis of 2-EH starting from propylene gas

Figure 3. Synthesis of EHMC starting from PA

Figure 3. Synthesis of EHMC starting from PA, a) via direct aldol condensation with 2-ethylhexylacetate, and b) via aldol condensation with methyl acetate to yield methyl para-methoxycinnamate as an intermediate, followed by transesterification with 2-EH

Figure 4. Synthesis of EHMC via the Heck reaction

Figure 4. Synthesis of EHMC via the Heck reaction

Figure 5. Synthesis of EHMC via the ketene route

Figure 5. Synthesis of EHMC via the ketene route

Biography: Michael J. Fevola, PhD, Johnson & Johnson

Michael J. Fevola, PhD, is a manager in the New Technologies group at Johnson & Johnson Consumer and Personal Products Worldwide in Skillman, NJ, where he leads R&D in polymer and surface chemistry. Fevola has authored 12 peer-reviewed articles and book chapters, is an inventor on six US patents, and is a member of the Personal Care Product Council’s International Nomenclature Committee and the Society of Cosmetic Chemists.

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