page_title: Tropolone
section_title: Natural occurrence
hierarchical_section_title: Tropolone / Natural occurrence
caption_attribution_description: chemical structure of gamma-thujaplicin
context_page_description: Tropolone is an organic compound with the formula C₇H₅O. It is a pale yellow solid that is soluble in organic solvents. The compound has been of interest to research chemists because of its unusual electronic structure and its role as a ligand precursor. Although not usually prepared from tropone, it can be viewed as its derivative with a hydroxyl group in the 2-position.
context_section_description: Many natural products contain the tropolone skeleton.  Among the simplest, and the first to be made synthetically, were α-, β- and γ-thujaplicins, by Ralph Raphael and colleagues. Others include  puberulic acid, stipitatonic acid, stipitatic acid, puberulonic acid, sepedonin, and theaflavins of black tea. It arises via a polyketide pathway, which affords a phenolic intermediate that undergoes ring expansion.
caption: Hinokitiol (β-thujaplicin) is a naturally-occurring tropolone.[5]
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