santonic acid

{{Short description|Organic compound}}

{{chembox

| Watchedfields = changed

| verifiedrevid = 464387054

| ImageFileL1 = Santonic-acid-2D-skeletal.png

| ImageFileR1 = Santonic-acid-from-xtal-3D-balls.png

| IUPACName = (−)-2,3,3a,4,5,6,7,7a-octahydro-α,3a,5-trimethyl-6,8-dioxo-1,4-methano-1H-indene-1-acetic acid

| OtherNames =

|Section1={{Chembox Identifiers

| ChEMBL = 1992757

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 249878

| 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)

| InChIKey = UNPYYTKZOHYHMZ-UHFFFAOYAW

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UNPYYTKZOHYHMZ-UHFFFAOYSA-N

| CASNo = 510-35-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII =0735572T0M

| CASNo_Ref = {{Cascite|correct|CAS}}

| PubChem = 283654

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

}}

|Section2={{Chembox Properties

| Formula = C₁₅H₂₀O₄

| MolarMass = 264.32 g mol⁻¹

| Appearance =

| Density = 1.184 g cm⁻³{{ cite journal | journal = Acta Crystallogr. C | volume = 55 | issue = 4 |date=April 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 }}

| MeltingPtC = 173

| MeltingPt_ref =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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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.Reusch, William (1999). "[http://www.cem.msu.edu/~reusch/VirtualText/rearang2.htm Base-catalyzed rearrangements] {{webarchive|url=https://web.archive.org/web/20090207013929/http://www.cem.msu.edu/~reusch/VirtualText/rearang2.htm |date=2009-02-07 }}". 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.