Camphor Reduction
Chinese Drug, Saved or Poisoned?
Introduction:
Borneol (FIGURE-1), first reported and published in the Tang Bencao in 659 A.D., is often used in drug treatment, especially in Chinese drugs. It is helpful in opening obstruction of orifices, heat syndromes and pain releasing (Dharmananda). Nowadays artificially synthesized borneol, a mixture of borneol and isoborneol (FIGURE-2), becomes more popular than pure natural borneol because of the lower cost in drug production. However, isoborneol is more toxic than borneol and thus is not favored regarding the safety issue of drugs. But how can we synthesize borneol in a way that gives more borneol than toxic isoborneol? An experiment of making borneol from camphor (FIGURE-3) is performed in two different methods, Sodium Borohydride Reduction and Meerwein-Ponndorf-Verley Reduction, to compare the relative product ratio of borneol to isoborneol. The concept of reduction and also oxidation, the opposite procedure of reduction, deals mostly with electron transfer between atoms. It will not be elaborated here, but the reduction procedure involved in this experiment is basically adding hydrogens and losing the carbon-oxygen double bond. (See FIGURE-4) (FIGURE-4)
In order to tell how much borneol is formed during reactions, both qualitatively and quantitatively, infrared spectroscopy and gas chromatography are executed on the products formed from Sodium Borohydride Reduction and Meerwein-Ponndorf-Verley Reduction (MPV).
Infrared (IR) spectroscopy shows the relative absorption of specific chemical bonds in a molecule to the induced infrared radioactive energy. Thus from looking at the peaks on IR spectrum, possible functional groups in a compound can be analyzed (Mohrig, Hammond, & Schartz, 2010). Functional groups are the spesific groups of atoms in a molecule that undergo chemical reactions. These atom groups characterize the molecule. It is improtant to see the particular functional groups after the reaction
Introduction:
Borneol (FIGURE-1), first reported and published in the Tang Bencao in 659 A.D., is often used in drug treatment, especially in Chinese drugs. It is helpful in opening obstruction of orifices, heat syndromes and pain releasing (Dharmananda). Nowadays artificially synthesized borneol, a mixture of borneol and isoborneol (FIGURE-2), becomes more popular than pure natural borneol because of the lower cost in drug production. However, isoborneol is more toxic than borneol and thus is not favored regarding the safety issue of drugs. But how can we synthesize borneol in a way that gives more borneol than toxic isoborneol? An experiment of making borneol from camphor (FIGURE-3) is performed in two different methods, Sodium Borohydride Reduction and Meerwein-Ponndorf-Verley Reduction, to compare the relative product ratio of borneol to isoborneol. The concept of reduction and also oxidation, the opposite procedure of reduction, deals mostly with electron transfer between atoms. It will not be elaborated here, but the reduction procedure involved in this experiment is basically adding hydrogens and losing the carbon-oxygen double bond. (See FIGURE-4) (FIGURE-4)
In order to tell how much borneol is formed during reactions, both qualitatively and quantitatively, infrared spectroscopy and gas chromatography are executed on the products formed from Sodium Borohydride Reduction and Meerwein-Ponndorf-Verley Reduction (MPV).
Infrared (IR) spectroscopy shows the relative absorption of specific chemical bonds in a molecule to the induced infrared radioactive energy. Thus from looking at the peaks on IR spectrum, possible functional groups in a compound can be analyzed (Mohrig, Hammond, & Schartz, 2010). Functional groups are the spesific groups of atoms in a molecule that undergo chemical reactions. These atom groups characterize the molecule. It is improtant to see the particular functional groups after the reaction
Cited: Dharmananda, S. (n.d.). BORNEOL, ARTEMISIA, and MOXA. Retrieved MAR 3, 2011, from Index of /arts: http://www.itmonline.org/arts/borneol.htm Mohrig, J. R., Hammond, C. N., & Schartz, P. F. (2010). Techniques in Organic Chemistry 3rd edition. New York: W. H. Freeman and Company.