Santonic acid

Santonic acid

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
PubChem	283654
ChemSpider	249878^Y
Jmol-3D images	Image 1
SMILES O=C(O)C(C31C(=O)C2C(C(=O)CC1C2(CC3)C)C)C
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)^Y Key: UNPYYTKZOHYHMZ-UHFFFAOYSA-N^Y 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
Properties
Molecular formula	C₁₅H₂₀O₄
Molar mass	264.32 g mol⁻¹
Density	1.184 g cm⁻³^[1]
Melting point	173 °C^[1]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.^[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

^ ^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 Cryst. C55 (4): 566–568. doi:10.1107/S0108270198014231.
^ Reusch, William (1999). "Base-catalyzed rearrangements". In: Virtual Textbook of Organic Chemistry. Michigan State University. Retrieved September 10, 2008.