Santonic acid is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

containing both

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

and

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

functionality Function or functionality may refer to: Computing * Function key, a type of key on computer keyboards * Function model, a structured representation of processes in a system * Function object or functor or functionoid, a concept of object-oriente ...

. It was synthesized from

santonin Santonin is a drug which was widely used in the past as an anthelminthic. It is an organic compound consisting of colorless flat prisms, turning slightly yellow from the action of light and soluble in alcohol, chloroform and boiling water. Accord ...

by base-mediated

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

of a lactone followed by a multistep rearrangement process by R. B. Woodward.Reusch, William (1999).
Base-catalyzed rearrangements
". In: ''Virtual Textbook of Organic Chemistry''.

Michigan State University Michigan State University (Michigan State, MSU) is a public university, public Land-grant university, land-grant research university in East Lansing, Michigan. It was founded in 1855 as the Agricultural College of the State of Michigan, the fi ...

. Retrieved September 10, 2008. Unusually for a carboxylic acid, santonic acid does not form hydrogen-bonded

dimer Dimer may refer to: * Dimer (chemistry), a chemical structure formed from two similar sub-units ** Protein dimer, a protein quaternary structure ** d-dimer * Dimer model, an item in statistical mechanics, based on ''domino tiling'' * Julius Dimer ( ...

s in the crystalline phase. Rather, it adopts a polymeric structure, with individual santonic acid molecules linked by intermolecular carboxyl-to-ketone hydrogen bonds.

References

Ketones Sesquiterpenes Propionic acids Tricyclic compounds {{ketone-stub