Camphoric acid

Last updated
Camphoric acid
Camphoric acid.png
Camphoric acid 3D ball.png
Names
IUPAC name
(1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.241.243 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 811-021-7
PubChem CID
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) Yes check.svgY
    Key: LSPHULWDVZXLIL-UHFFFAOYSA-N Yes check.svgY
  • 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 183–187 °C (361–369 °F; 456–460 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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Camphoric acid, C 10 H 16 O 4[ 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.

Contents

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.

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References

  1. "Nicolas-Louis Vauquelin | Discoverer, Elements, Chemistry | Britannica". www.britannica.com. Retrieved 2023-11-10.