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Ružicka, Leopold

rule isoprene compounds terpenes

[rougi tch ka] (1887–1976) Croatian–Swiss organic chemist: devised the isoprene rule.

Ružicka grew up in Croatia when it was part of Austria-Hungary and, after an education in Germany and Switzerland, he finally became professor in Zürich. In 1916 he began work on perfumes; one famous study concerned the costly perfume fixatives in musk (from a Himalayan deer) and civet (from an African wildcat). He found that the key compounds, muscone and civetone, are cyclic ketones. What was remarkable is that both contain large rings of carbon atoms (16- and 17-membered respectively). It had been thought that such large rings could not exist. In fact, Ružicka’s work showed them to be stable, and he devised methods of synthesis. He also worked on steroids, specially the male sex hormones; his synthesis of testosterone made him rich and he became a major collector of early Dutch paintings. His work on terpenes led to the isoprene rule, which proposes that terpenes have structures based on units of the five-carbon isoprene molecule, joined head-to-tail (1920). In this form, or in its later version (which proposes the biogenesis of these compounds from isopentenyl pyrophosphate) the rule has proved a valuable guide to structure. Ružicka shared a Nobel Prize in 1939.

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