Probing the Dye Chemistry of Genipin-Based Temporary Tattoos Using a Self-Assembled Monolayer Skin Mimic

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Inkbox is a company in Toronto that has commercialized the world's first two-week tattoo. This technology hasornamental applications, as well as exciting potential in medical applications. The key to this technology in anactive ingredient derived from a fruit extract called Genipin, which has previously been explored as a non-toxiccrosslinking reagent for tissue engineering and materials science. When Genipin is applied to the skin, ittransforms into a vibrant blue colour. Although the chemistry behind this transformation is not wellunderstood, it is believed to bind to the skin by reacting with amino acids, and then undergo furtheroligomerization reactions to form the vibrant blue colour of the tattoo. In this proposal, we will use a synthetic"skin mimic" to acquire a better understanding of this reaction process under controlled conditions. Our skinmimic will comprise a layer of molecules adhered to a solid surface that is amenable to advanced spectroscopicanalysis. We will bind Genipin to the skin mimic and study its reactivity, using spectroscopic data to establishthe binding as well as the subsequent reactions that cause the blue colouration of Inkbox tattoos. These studieswill help Inkbox optimize its formulation to enhance skin penetration and increase tattoo longevity, and alsoprovide insight into how intermolecular interactions may be able to alter the colouration of the product.