Magic Bullets: Chemistry vs. Cancer

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    Separating Cherry Cola
    A Simulation

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    General Safety Guidelines
    Teacher Notes
    Conducting the Activity
    Advanced Preparation
    Completed Observations Sheet
    Questions
    Conclusions
      For more information, at
      other Web sites...

      Relevant National Science
      Education Standards

      Relevant New Jersey State
      Science Education Standards

    In many of the biographical readings in Pharmaceutical Achievers the story relates the discovery of a new cancer drug. Often, the chemical that is the active ingredient in the new drug existed in a plant or other naturally occuring organism. Taxol® in the Pacific yew tree and vinblastine in the Madagascar periwinkle are just two examples. In many cases, the natural product is later modified in the laboratory, but before that can happen, the natural substance must be isolated from its plant source. This lab is included to acquaint students with often-used methods of separation in chemistry.

    In the lab, a sample of cherry-flavored cola is tested for the presence of carbon dioxide and then heated. As a result of the heating, the compound that gives the cola its distinctive odor is evaporated off. Water, which makes up most of the mixture, is also boiled off, but this component is condensed and recovered. Four components--carbon dioxide, water, coloring agent and the substance responsible for the cherry odor--can be identified.

    Teacher Notes

    1. This experiment is offered as a simulation of the process of extracting specific compounds from plant or animal resources. Although it is actually a distillation experiment the students are doing, the focus in this lab is on the variety of substances separated from the original mixture, rather than the purification of those substances. Mention can be made, however, that this process not only separates the components, but also purifies them, although several repetitions of the process would be necessary for actual purification.

    2. For further information on extraction methods, consult SourceBook Version 2.1 (Orna, Mary Virginia, Schreck, James O., and Heikkinen, Henry, editors. New Rochelle, NY: ChemSource, 1998. See chapter "Separations," Volume 4.)

    3. The lab activity can be completed in one 45-minute period.

    4. The actual amount of soda in the original flask is unimportant. The volume of 80 ml was chosen simply because a 12-oz. can holds 355 ml, so that four student lab groups can be satisfied with one can of soda, leaving enough for a 35-ml sample for comparisons at the end of the experiment.

    5. A sidearm flask simplifies the apparatus, but availability may be a problem.

    6. The procedure denotes in bold print the specific items that need to be recorded on the observation sheet. The bold notes correspond to the appropriate place to put observations on the data sheet.

    Conducting the Activity

    1. The experiment fits best in the discussion of the discoveries of cancer treatments using "natural" products.

    2. Assign your students to read the Student version as homework the day before to the experiment, and ask students to study the procedure. You may want them to prepare their own data table or use the printable observation sheet. If you wish to alter the observation sheet, use the Microsoft® Word version of the observation sheet. Click here for the completed observation sheet.

    3. Have a supply of ice ready. Each lab group probably needs the equivalent of one tray of ice cubes.

    4. Oversee the pouring of the soda and the lime water to minimize waste.

    5. Check each lab group's apparatus prior to their beginning to heat with the Bunsen burner.

    6. The lime water will turn cloudy as carbon dioxide reacts with the calcium hydroxide to produce calcium carbonate, with low solubility in water.

    7. The odor of cherry will waft out of the flask as the distillation process continues. It might not be too noticeable until the distillate begins condensing in the distillate flask. Be sure students don't miss the odor.

    8. Remind students to pull the tubing out of the flask in the ice water before turning off the burner. This is recommended to prevent sucking purified liquid back into the original sample.

    Advanced Preparation

    Prior to this experiment you will need to:

    1. Prepare a saturated solution of calcium hydroxide (lime water) several days before the lab to allow it to reach saturation. Mass 4.0 g per liter of solution. Allow time to reach saturation and decant or filter.

    2. Prepare one right-angle bent piece of glass tubing per lab group.

    3. You might want to place the angle bends into the stoppers before students get to lab. If you have students do this, show them how to properly use glycerin as a lubricant and how to protect themselves from getting cut on a broken piece of tubing.

    4. Gather glassware needed for experiment.

    5. Cut rubber/Tygon tubing to proper lengths. Beware: Tygon becomes permanently clouded during distillation.

    6. Get ice.

    7. Provide (or have students provide) soda for the experiment. Cherry cola is not an absolute necessity; Surge® or Mountain Dew® work well for color differences due to concentration of the color in the residue (as do cherry colas). Dr. Pepper® or Mr. Pibb® would probably be a fine substitute for cherry colas for the purposes of odor detection.

    Questions

    1. What can you infer from the lime water test?

        Answer: The lime water turned cloudy due to the release of carbon dioxide (bubbles or froth) early in the distillation process, before boiling began. This infusion of CO2 into the lime water resulted in the production of calcium carbonate, a low solubility compound.

    2. Why was the collecting flask placed in an ice bath?

        Answer: The distilled vapors traveling through the flask, tube, and tubing was hot. The ice was needed to cool the vapors until they could condense into droplets that collected in the receiving flask.

    3. Why did the size of the bubbles change so dramatically part way through the extraction?

        Answer: After the early release of carbon dioxide, the solution heated to a higher temperature where actual boiling of the solution, primarily water, could begin. When boiling occurred, the bubbles produced were huge in comparison to those of CO2 It was at this point that students should have observed condensation beginning in the tubing, the tube, and finally, in the flask in the ice bath. This showed that gas (vapor) was produced and then cooled down and condensed in the tube and flask.

    4. Explain the differences in your observations of the liquid in the boiling flask and the liquid in the receiving flask.

        Answer: The liquid in the boiling flask still contained all the coloring material of the original soda. Students know this because none of that color was transferred to the liquid in the receiving flask. The odor is almost completely gone from the boiled liquid, and lingers only slightly in the distillate.

    5. Explain the differences in your observations of the liquid in the boiling flask and the beaker of original cherry cola.

        Answer: The liquid in the boiling flask is darker in color than the original soda because much of the solvent was removed by boiling and distilling the soda. This increased the concentration of the coloring agent, resulting in a darker color. Also, the odor is much reduced in the boiled liquid, but the student can still easily detect the odor in the original soda.

    6. What do the properties of the distillate (the liquid in the small flask) signify?

        Answer: The distillate is clear, colorless, and (almost) odorless. The color was left behind in the boiling flask. Most of the odor was released as the vapors condensed in the receiving flask. These observations indicate the relative purity of this constituent of the mixture.

    7. List the components of the cherry cola, as shown in your extraction experiment. Explain how your lab showed that each component is/was present.

        Answer: Students should have listed the following:

        1. carbon dioxide: gas bubbles turned the lime water cloudy
        2. cherry odor: smell emanated from collection flask
        3. water (or just a clear, colorless liquid): colorless liquid collected in the collection flask
        4. the rest of the liquid left behind in the boiling flask: residue left in the boiling flask

    Conclusions

    1. How does this experiment compare/relate to the work done by chemists in trying to prepare compounds for use in chemotherapy?

        Answer: The process of distillation can be used to separate (extract) pure substances from mixtures, as occurs in plant and animal extractions.

    For more information, at other Web sites...

      The Anti-Cancer Agent Collection — color photomicrographs of anticancer drugs, from Florida State University.

      Semisynthetic Taxol® (paclitaxel) injection — drug information and history from the Bristol-Myers Squibb Company.

      Taxol — scientific overview from the University of Bristol.

      Taxol: A Brief Insight — from chemistry student Victoria Farmer, Imperial College of Science, Technology and Medicine.

    Relevant National Science Education Standards

      Physical Science — The activity explores the nature of a soda as a mixture of many compounds, which, with some work, may be separated.

      Science and Technology — The activity explores the technology of separating mixtures, which is applied in the real world to extracting medicinal compounds from plants.

    Relevant New Jersey State Science Education Standards

      5.` In this activity students must conduct systematic observations, interpret and analyze data, draw conclusions, and communicate their results.
      5.4 The students should learn that scientific knowledge of mixtures and pure substances helps overcome the practical problem of isolating useful compounds from plants.
      5.6 The students will realize that many things are mixtures of many compounds, which can be separated into their various components.

     

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