Camphoric acid
{{noinline|date=January 2012}}
{{chembox
| Verifiedfields = changed
| verifiedrevid = 410988013
| Name = Camphoric acid
| ImageFile = Camphoric_acid.png
| ImageSize = 200px
| ImageAlt = Skeletal formula of camphoric acid
| ImageFile1 = Camphoric acid 3D ball.png
| ImageAlt1 = Ball-and-stick model of the camphoric acid molecule
| IUPACName = (1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 20198
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1205405
| EINECS = 811-021-7
| InChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1S/C10H16O4/c1-9(2)6(7(11)12)4-5-10(9,3)8(13)14/h6H,4-5H2,1-3H3,(H,11,12)(H,13,14)
| InChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = LSPHULWDVZXLIL-UHFFFAOYSA-N
| InChI1 = 1/C10H16O4/c1-9(2)6(7(11)12)4-5-10(9,3)8(13)14/h6H,4-5H2,1-3H3,(H,11,12)(H,13,14)/t6-,10+/m0/s1
| SMILES1 = O=C(O)[C@]1(CC[C@@H](C(=O)O)C1(C)C)C
| InChIKey1 = LSPHULWDVZXLIL-QUBYGPBYBH
| PubChem1 = 21491
| InChI2 = 1/C10H16O4/c1-9(2)6(7(11)12)4-5-10(9,3)8(13)14/h6H,4-5H2,1-3H3,(H,11,12)(H,13,14)
| InChIKey2 = LSPHULWDVZXLIL-UHFFFAOYAD
| SMILES2 = O=C(O)C1CCC(C(=O)O)(C)C1(C)C
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 560-09-8
| CASNo_Comment = (1S,3R)
| CASNo2 = 124-83-4
| CASNo2_Comment = (+) i.e., (1R,3S) D-Camphoric acid
| CASNo2_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 62F72U898F
| UNII_Comment = (1S,3R)
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = W77RM1CSD5
| UNII2_Comment = (+) i.e., (1R,3S) D-Camphoric acid
}}
| Section2 = {{Chembox Properties
| C=10|H=16|O=4
| Density = 1.21 g/cm3
| MeltingPtC = 183 to 187
| BoilingPt =
| SolubleOther =
| Solvent =
| MagSus = −129.0·10−6 cm3/mol
}}
}}
Camphoric acid, C10H16O4{{citation needed|date=October 2022}} or in Latin form Acidum camphoricum, is a white crystallisable substance obtained from the oxidation of camphor. It exists in three optically different forms; the dextrorotatory one is obtained by the oxidation of dextrorotatory camphor and is used in pharmaceuticals.
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History
Acidum camphoricum was studied and isolated for the first time by French pharmacist Nicolas Vauquelin in the early 19th century,{{Cite web |title=Nicolas-Louis Vauquelin {{!}} Discoverer, Elements, Chemistry {{!}} Britannica |url=https://www.britannica.com/biography/Nicolas-Louis-Vauquelin |access-date=2023-11-10 |website=www.britannica.com |date=10 November 2023 |language=en}} but it wasn't until September 1874 that Dutch chemist Jacobus H. van 't Hoff proposed the first suggestion for its molecular structure and optical properties. Haller and Blanc synthesized camphor from camphoric acid. In 1904, Finnish chemist Gustav Komppa became the first to succeed in manufacturing synthetic camphoric acid from diethyl oxalate and 3,3-dimethylpentanoic acid, and thus proving the structure of camphor.
Chemical properties and isolation
Camphoric acid may be prepared by oxidising camphor with nitric acid.
References
- {{cite web|title=Acidum camphoricum|work=British Pharmaceutical Codex|url=http://www.henriettesherbal.com/eclectic/bpc1911/acidum-camp.html|accessdate=September 4, 2005 }}
- {{cite web|title=Camphoric acid|work=Science and Technology|url=http://www.probertencyclopaedia.com/cgi-bin/res.pl?keyword=Camphoric+Acid&offset=0|accessdate=September 4, 2005|archive-date=November 13, 2006|archive-url=https://web.archive.org/web/20061113220157/http://www.probertencyclopaedia.com/cgi-bin/res.pl?keyword=Camphoric+Acid&offset=0|url-status=dead}}
- {{cite web|title=Camphoric acid|work=Taiwan Tekho Camphor Co|url=http://www.camphor.com.tw/t-list.htm|accessdate=September 4, 2005 }}
- {{cite journal|author=Jacobus Henricus van 't Hoff|year=1874|title=A suggestion looking to the extension into space of the structural formulas at present used in chemistry. And a note upon the relation between the optical activity and the chemical constitution of organic compounds|journal=Archives Neerlandaises des Sciences Exactes et Naturelles|volume=9|pages=445–454}}
{{DEFAULTSORT:Camphoric Acid}}