Camphoric acid

Chemical compound From Wikipedia, the free encyclopedia

Camphoric acid, C10H16O4[citation needed] 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.

Quick facts Names, Identifiers ...
Camphoric acid
Skeletal formula of camphoric acid
Ball-and-stick model of the camphoric acid molecule
Names
IUPAC name
(1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.024.004 Edit this at Wikidata
EC Number
  • 811-021-7
UNII
  • 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) checkY
    Key: LSPHULWDVZXLIL-UHFFFAOYSA-N checkY
  • InChI=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
    Key: LSPHULWDVZXLIL-QUBYGPBYBH
  • InChI=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)
    Key: LSPHULWDVZXLIL-UHFFFAOYAD
  • O=C(O)[C@]1(CC[C@@H](C(=O)O)C1(C)C)C
  • O=C(O)C1CCC(C(=O)O)(C)C1(C)C
Properties
C10H16O4
Molar mass 200.234 g·mol−1
Density 1.21 g/cm3
Melting point 183 to 187 °C (361 to 369 °F; 456 to 460 K)
−129.0·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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,[1] 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

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