Camphoric acid

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Camphoric acid

Chemical name	(1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid
Chemical formula	C₁₀H₁₆O₄
Molecular mass	200.23 g/mol
CAS number	[124-83-4]
Density	1.21 g/cm³
Melting point	183-187 °C
Boiling point	unknown °C
SMILES	O=C(O)[C@]1(C)CC[C@H](C(O)=O)C1(C)C
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.

1 History
2 Chemical properties and isolation
3 Pharmaceutical uses
4 References

[edit] 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.

[edit] Chemical properties and isolation

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

[edit] 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.

[edit] 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.