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C2510_Column_Spearmint_F_2008 - Chemistry 2510 Introduction...

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Chemistry 2510 Introduction to Experimental Organic Chemistry Fall 2008 Experiment #5 Isolation of L-(-) Carvone from Spearmint Oil: An Exercise in Column and Thin-Layer Chromatography Laboratory Notebook : You need to summarize your experimental plan in your lab notebook. Be sure to include a table of all reagents and compounds that will be used in this experiment. Laboratory Observations: Be sure to record any observations during the laboratory. You must record exactly how much of the starting materials you started with and the weight of the isolated product. Results and Conclusions : Separate the components of spearmint oil, evaluate the effectiveness of the separation, and ascertain purity of the components. Relevant Reading: Technique 5, Simple Distillation, pp 77-92, Technique 11, Column Chromatography, pp 119-131, Technique 12, Thin-Layer Chromatography, pp 133—140, and Technique 15, IR Spectroscopy, pp 163-178. Background: Spearmint oil is the natural product isolated from the flowering tops of menta spicata through steam distillation. The familiar oil is used as a flavoring agent in toothpaste, chewing gum, mouth fresheners, and cosmetics. In addition, there are some claims among naturopathic practitioners that spearmint oil may have therapeutic value in treating asthma, exhaustion, fever, flatulence, headache, nausea, and vertigo. The astute scientist must view the therapeutic use of spearmint oil with much skepticism until further scientific research can verify or dispel such claims. Spearmint oil is composed of many volatile organic compounds, but the three main components present are L-(-)-carvone, (+)- limonene, and (1R, 2R, 4R)-dihydrocarveol, shown below: CH 3 CH 3 O CH 3 OH (R)-Carvone (R)-Limonene (1R, 2R, 4R)-Dihydrocarveol
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Procedure: Begin by taking a TLC of the spearmint oil Dissolve a drop of spearmint oil in 1 mL of hexane, and then spot a small TLC plate with the solution. Develop the plate using 10% ethyl acetate/hexane. After the plate is developed,
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C2510_Column_Spearmint_F_2008 - Chemistry 2510 Introduction...

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