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Camphoric acid



Camphoric acid
IUPAC name (1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid
Identifiers
CAS number
SMILES O=C(O)[C@]1(C)CC[C@H](C(O)=O)C1(C)C
Properties
Molecular formula C10H16O4
Molar mass 200.23 g/mol
Density 1.21 g/cm3
Melting point

183-187 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Camphoric acid, C10H16O4 or in Latin form Acidum camphoricum, is a white crystallisable substance obtained from the oxidation of camphor, it exists in three optically different forms; dextrorotatory one is obtained by the oxidation of dextrorotatory camphor and used in pharmaceuticals.

Additional recommended knowledge

Contents

History

Acidum camphoricum was studied and isolated for the first time by French pharmacist Nicolas Vauquelin in the early 1800s but it wasn't until September of 1874 that Dutch chemist Jacobus H. van 't Hoff proposed the first suggestion for its molecular structure and optical properties. In 1904 Finnish chemist Gustav Komppa became the first to succeed in manufacturing camphor from this acid.

Chemical properties and isolation

Camphoric acid may be prepared by oxidising camphor with nitric acid.

Pharmaceutical uses

This acid has a mild camphor action; it is not very toxic and can be used in very large doses, up to 4 grammes (60 grains), without serious effects; it is supposed to paralyse the nerve-endings in the sweat glands, and is used in the night-sweats of phthisis. It does not affect other secretions as does atropine, nor irritate the stomach like agaric acid. Camphoric acid is also employed in solution, 0.2 to 5.0 percent by weight or volume, with sufficient alcohol, as a local antiseptic to the nose, throat, and bladder, among other uses, is usually administered as a powder, or in cachets, but may also be given in mixtures suspended with compound powder of tragacanth, or dissolved by the addition of diluted alcohol or a flavouring tincture. When used as an antihydrotic the dose should be given two or three hours before bedtime.

References

    • Acidum camphoricum. The British Pharmaceutical Codex. Retrieved on September 4, 2005.
    • Camphoric acid. Science and Technology. Retrieved on September 4, 2005.
    • Camphoric acid. Taiwan Tekho Camphor Co. Retrieved on September 4, 2005.
    • Jacobus Henricus van 't Hoff (1874). "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". Archives neerlandaises des sciences exactes et naturelles 9: 445-454.
     
    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Camphoric_acid". A list of authors is available in Wikipedia.
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