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5-SteamDistillEugenol1SS09

5-SteamDistillEugenol1SS09 - Steam Distillation and...

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05/25/09 Steam Distillation and Infrared Spectrometry: Isolation and Identification of the Major Component of Cloves 1 . Reading Assignment: a) Fessenden, R.J., Fessenden, J.S., Feist, P. Organic Laboratory Techniques , 3 rd ed.; Brooks/Cole: Pacific Grove, 2001, pp 107-110. B) Loudon, G.M. Organic Chemistry 4 th ed.; Oxford University Press, 2002, Section 12.3A. Introduction Plants and animals contain a vast array of organic molecules that can be isolated, studied and utilized to improve our quality of life. Many of these natural products are used as flavors, fragrances, dyes and pharmaceuticals. In fact, approximately 1/3 of the 50 anti-cancer drugs on the market today are based on natural products. 2 Some important examples of these gifts from Mother Nature are shown below 3 : Penicillin V (top left) isolated from mold. Brevetoxin A (top right) – a highly potent neurotoxin isolated from the same microorganism responsible for the red tides. Taxol (bottom left), a microtubule stabilizer and potent anti-cancer compound isolated from the bark of the pacific Yew tree. Aspirin (above) is a derivative of the natural product salicin found in the bark of the Willow tree.
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05/25/09 A number of techniques are employed to isolate the natural products: most commonly extraction and distillation. Essential oils, hydrophobic liquids containing volatile aromatic compounds, are isolated from some plants using steam distillation . Some examples of the organic molecules found in these essential oils are limonene, extracted from orange and lemon peels, vanillin from vanilla beans, and ethyl cinnamate, eugenol, cinnamaldehyde, caryophyllene, and estragole all found in the bark of cinnamon trees (figure 1). O O ethyl cinnamate O H cinnamaldehyde major component ~90% CH 3 H H CH 3 H 3 C caryophyllene OCH 3 estragole (R)-limonene Responsible for "orange" smell. Environmentally friendly cleaner. O H OCH 3 OH vanillin Flavoring agent in foods, beverages, pharmaceuticals. OCH 3 OH eugenol Organic compounds found in the oil of cinnamon Figure 1. Some natural products isolated from essential oils. In today’s lab you will isolate the essential oil from cloves. The main constituent of clove oil is also found in the oil of cinnamon and has a pleasant, spicy, clove-like odor and is used in perfumes and flavorings. It also contains medicinal qualities and is useful as a local antiseptic and anesthetic. After isolating the oil you will use infrared (IR) spectrometry and a simple, qualitative test to identify the organic compound common to both oil of cloves and cinnamon. Steam Distillation Distillation, in general, is a separation or purification technique that takes advantage of differences in boiling points of components in a mixture. Simple distillation can be used to separate a relatively low boiling liquid (b.p. < 150 o C) from non-volatile impurities or another liquid with a boiling point that differs by at least 25 o C. Simple distillation is not appropriate for isolating an extremely high boiling compound like today’s compound (bp > 250 o C) because
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05/25/09 heating mixtures at such high temperatures often leads to decomposition.
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