Santonic acid
Organic compound / From Wikipedia, the free encyclopedia
Santonic acid is an organic compound containing both carboxylic acid and ketone functionality.
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IUPAC name
(−)-2,3,3a,4,5,6,7,7a-octahydro-α,3a,5-trimethyl-6,8-dioxo-1,4-methano-1H-indene-1-acetic acid | |||
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Properties | |||
C15H20O4 | |||
Molar mass | 264.32 g mol−1 | ||
Density | 1.184 g cm−3[1] | ||
Melting point | 173 °C (343 °F; 446 K)[1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It was synthesized from santonin by base-mediated hydrolysis of a lactone followed by a multistep rearrangement process by R. B. Woodward.[2]
Unusually for a carboxylic acid, santonic acid does not form hydrogen-bonded dimers in the crystalline phase. Rather, it adopts a polymeric structure, with individual santonic acid molecules linked by intermolecular carboxyl-to-ketone hydrogen bonds.[1]