| Revision as of 13:39, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 421120630 of page Santonic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 20:59, 25 February 2022 edit Fswitzer4 (talk | contribs)Extended confirmed users10,572 editsm Added/Verified UNII and Verified CAS |
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{{Short description|Organic compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 401049719 |
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| verifiedrevid = 464387054 |
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|ImageFileL1=Santonic-acid-2D-skeletal.png |
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| ImageFileL1 = Santonic-acid-2D-skeletal.png |
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|ImageSizeL1=150px |
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|ImageFileR1 = Santonic-acid-from-xtal-3D-balls.png |
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| ImageFileR1 = Santonic-acid-from-xtal-3D-balls.png |
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| IUPACName = (−)-2,3,3a,4,5,6,7,7a-octahydro-α,3a,5-trimethyl-6,8-dioxo-1,4-methano-1''H''-indene-1-acetic acid |
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| OtherNames = |
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|IUPACName= (−)-2,3,3a,4,5,6,7,7a-octahydro-α,3a,5-trimethyl-6,8-dioxo-1,4-methano-1''H''-indene-1-acetic acid |
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|OtherNames= |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChEMBL = 1992757 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 249878 |
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| ChemSpiderID = 249878 |
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| 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) |
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| 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) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = UNPYYTKZOHYHMZ-UHFFFAOYSA-N |
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| StdInChIKey = UNPYYTKZOHYHMZ-UHFFFAOYSA-N |
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| CASNo = 510-35-0 |
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| PubChem = 283654 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = O=C(O)C(C31C(=O)C2C(C(=O)CC1C2(CC3)C)C)C |
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| UNII =0735572T0M |
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| CASNo_Ref = {{Cascite|correct|CAS}} |
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| PubChem = 283654 |
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| SMILES = O=C(O)C(C31C(=O)C2C(C(=O)CC1C2(CC3)C)C)C |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula= C<sub>15</sub>H<sub>20</sub>O<sub>4</sub> |
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| Formula = C<sub>15</sub>H<sub>20</sub>O<sub>4</sub> |
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| MolarMass= 264.32 g mol<sup>−1</sup> |
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| MolarMass = 264.32 g mol<sup>−1</sup> |
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| Appearance= |
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| Appearance = |
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| Density= 1.184 g cm<sup>−3</sup><ref name="Brunskill">{{ cite journal | journal = Acta Cryst. | volume = C55 | issue = 4 | month = April | year = 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 }}</ref> |
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| Density = 1.184 g cm<sup>−3</sup><ref name="Brunskill">{{ 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 }}</ref> |
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| MeltingPtC = 173 |
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| MeltingPt=173 °C<ref name="Brunskill" /> |
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| MeltingPt_ref = <ref name="Brunskill" /> |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Santonic acid''' is an ] containing both ] and ] ]. |
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It was synthesized from ] by base-mediated ] of a lactone followed by a multistep rearrangement process by ].<ref>Reusch, William (1999). " {{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''. ]. Retrieved September 10, 2008.</ref> |
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Unusually for a carboxylic acid, santonic acid does not form ] ]s in the ]. Rather, it adopts a polymeric structure, with individual santonic acid molecules linked by intermolecular carboxyl-to-ketone hydrogen bonds.<ref name="Brunskill" /> |
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==References== |
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{{reflist}} |
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{{ketone-stub}} |