page_title: Aplysioviolin
section_title: History
hierarchical_section_title: Aplysioviolin / History
caption_attribution_description: English: Rudiger syntheses
context_page_description: Aplysioviolin is a purple-colored molecule secreted by sea hares of the genera Aplysia and Dolabella to deter predators. Aplysioviolin is a chemodeterrent, serving to dispel predators on olfactory and gustatory levels as well as by temporarily blinding predators with the molecule's dark color. Aplysioviolin is an important component of secreted ink and is strongly implicated in the sea hares' predatory escape mechanism. While the ink mixture as a whole may produce dangerous hydrogen peroxide and is relatively acidic, the aplysioviolin component alone has not been shown to produce human toxicity.
context_section_description: Aplysioviolin, along with the other components of sea hare ink, has been utilized as a dye since antiquity. Aplysioviolin in particular has been implicated in classical-age dyeing, and has recently been the subject of investigation as the ancient tekhelet (תְּכֵלֶת) dye of Hebrew and other Mediterranean civilizations, though it remains one of several possible historical contenders. Aplysioviolin was first specifically isolated and characterized as a pH-dependent color-changing zoochrome by Lederer & Huttrer in 1942. A first structure was proposed by Rüdiger in 1967 using a chromic-acid based microdegredation technique. This technique was similarly applied in the years following to characterize the structures of the related compounds phycoerythrobilin and phycocyanobilin. The 1967 proposed structure was later modified to remove an angular hydroxyl group at the 7' position, and the final structure was given by Rüdiger & O'Carra in 1969.
caption: Diagram of Rüdiger's two structureal elucidations of aplysioviolin. Note the difference between the -OH and -H functional groups on the 7' carbon.
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