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Santonic acid

Summary

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

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
  • 510-35-0 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1992757
ChemSpider
  • 249878 checkY
  • 283654
UNII
  • 0735572T0M checkY
  • DTXSID3046871 Edit this at Wikidata
  • 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) checkY
    Key: UNPYYTKZOHYHMZ-UHFFFAOYSA-N checkY
  • 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
  • O=C(O)C(C31C(=O)C2C(C(=O)CC1C2(CC3)C)C)C
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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Infobox references

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]

References edit

  1. ^ a b c 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.