Santonic acid

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IUPACName= (−)-2,3,3a,4,5,6,7,7a-octahydro-α,3a,5-trimethyl-6,8-dioxo-1,4-methano-1"H"-indene-1-acetic acid
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Formula= C₁₅H₂₀O₄
MolarMass= 264.32 g mol⁻¹
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Density= 1.184 g cm⁻³ cite journal | journal = Acta Cryst. | volume = C55 | issue = 4 | month = April | year = 1999 | pages = 566-568 | doi = 10.1107/S0108270198014231 | title = Santonic acid: catemeric hydrogen bonding in a γ,ε-diketo carboxylic acid | author = A. P. J. Brunskill, H. W. Thompson and R. A. Lalancette ]
MeltingPt=173 °C
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Santonic acid is an organic compound containing both carboxylic acid and ketone functionality.

It can be synthesised by based-catalyzed hydrolysis of santonin followed by a multistep rearrangement process. [Reusch, William (1999). " [http://www.cem.msu.edu/~reusch/VirtualText/rearang2.htm Base-catalyzed rearrangements] ". In: "Virtual Textbook of Organic Chemistry". Michigan State University. Retrieved September 10, 2008.]

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.

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