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

3D model (Jmol)

249878^Y

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

SMILES

O=C(O)C(C31C(=O)C2C(C(=O)CC1C2(CC3)C)C)C

Properties

C₁₅H₂₀O₄

264.32 g mol⁻¹

1.184 g cm⁻³^[1]

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

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

1 2 3 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.
↑ Reusch, William (1999). "Base-catalyzed rearrangements". In: Virtual Textbook of Organic Chemistry. Michigan State University. Retrieved September 10, 2008.

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