Semi-Permanent Tattoos - Transforming a Canadian Start-Up Company's Product Through Fundamental Chemistry

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Dyes which are either sourced directly or derived from naturally-occurring products are of growing interest in the cosmetics industry. Sourcing chemical dyes or their close precursors from natural products can significantly reduce the environmental impact of manufacture by reducing the number of derivatization and purification steps. The industrial partner, Inkbox Ink, currently uses genipin, a dye precursor derived primarily from extracts of the gardenia fruit, in their semi-permanent tattoo technologies. The general mechanism of action involves the reaction of genipin with primary amines, in this case amino acids in the skin. The mechanism by which a colourless fruit extract becomes a brilliant blue dye is poorly understood, with numerous reports providing contradictory hypotheses. The rare ability of genipin to rapidly form non-permanent skin dyes suggests a number of potential applications. In order to develop new target dyes and facilitate new dermal technologies, the mechanism of action must be better understood. This collaborative research program endeavours to elucidate the mechanism and discover new molecules through systematic synthetic modifications and analytical experiments. The knowledge gained from these studies will be applied to the development of new dyes and skin-binding technologies for Inkbox to commercialize, allowing for rapid growth of a Canadian start-up company.