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Santonic acid

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Organic compound
Santonic acid
Names
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
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H20O4/c1-7-9(16)6-10-14(3)4-5-15(10,8(2)13(18)19)12(17)11(7)14/h7-8,10-11H,4-6H2,1-3H3,(H,18,19)Key: UNPYYTKZOHYHMZ-UHFFFAOYSA-N
  • InChI=1/C15H20O4/c1-7-9(16)6-10-14(3)4-5-15(10,8(2)13(18)19)12(17)11(7)14/h7-8,10-11H,4-6H2,1-3H3,(H,18,19)Key: UNPYYTKZOHYHMZ-UHFFFAOYAW
SMILES
  • O=C(O)C(C31C(=O)C2C(C(=O)CC1C2(CC3)C)C)C
Properties
Chemical formula C15H20O4
Molar mass 264.32 g mol
Density 1.184 g cm
Melting point 173 °C (343 °F; 446 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Santonic acid is an organic compound containing both carboxylic acid and ketone functionality.

It was synthesized from santonin by base-mediated hydrolysis of a lactone followed by a multistep rearrangement process by R. B. Woodward.

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.

References

  1. ^ A. P. J. Brunskill, H. W. Thompson and R. A. Lalancette (April 1999). "Santonic acid: catemeric hydrogen bonding in a γ,ε-diketo carboxylic acid". Acta Crystallogr. C. 55 (4): 566–568. doi:10.1107/S0108270198014231.
  2. Reusch, William (1999). "Base-catalyzed rearrangements Archived 2009-02-07 at the Wayback Machine". In: Virtual Textbook of Organic Chemistry. Michigan State University. Retrieved September 10, 2008.


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