Presentation Abstracts CHEM 23201 - Tuesday Fall 2011 Updated: 14 Nov 2011 @ 8:43 am 1 November 2011 11:00 – 11:12 Evan Graham Bromocresol Green pH indicators are chemical compounds that are used to visually determine the pH of a solution. Bromocresol green is a commonly used pH indicator. Bromocresol green is a member of the triphenylmethane family that is characterized by three phenol groups, two alcohol groups and a sulfate group. It can be synthesized from one molecule of 2Sulfobenzoic anhydride for every two molecules of m-Cresol. The final structure of bromocresol green can undergo a chemical change at different pH’s, which in turn alters the color of the compound, in this case from yellow at a lower pH to blue at a higher pH. After searching the literature, I have found that when the pH is increased, the chemical alteration of bromocresol green involves a loss of a proton resulting in the transfer of electrons, creating a resonance stabilized structure. The exact reason why the chemical change results in a color change requires further research. 11:13 – 11:25 John Rieth The Synthesis, Physical Properties, and Uses of Thymol The use of antiseptics and antifungal agents has greatly contributed to the increase of human life expectancy. One chemical that that is both an antiseptic and antifungal agent is thymol, an organic compound which can be isolated from the plant Thymus vulgaris or manufactured synthetically. Thymol has unique physical properties and several uses. The ways by which thymol can be synthesized, identified, and used were found in the literature. Thymol can be synthesized by conducting a hydrogenation reaction with Phenol, 5-methyl-2-(1-methylethenyl)-. This chemical can then be identified by its physical properties. This chemical has many chemical uses, especially as a fungicide. Thymol can easily be synthesized and can be used as an antifungal agent in many circumstances. 11:26 – 11:38 Kelsey Fink Resveratrol: Synthesis and Characterization of a Chemopreventive Agent In 2011, about 571,950 people in America alone are expected to die of cancer. However, resveratrol, found in the skin of red grapes, has been found to prevent cancer and reduce the size of tumors. The general topic of this presentation is to display general information regarding resveratrol such as the synthesis, characterization, and effects it has in preventing cancer. I have reviewed articles found through the Notre Dame library, online journals, and the Internet to learn about the mechanism and characteristics of resveratrol. Resveratrol has been shown to be an effective agent in the cancer prevention. Therefore, further research should be done to give more information on how this works. Also, investigations should be done about how to include resveratrol in our daily diet. 1 November 2011 12:30 – 12:42 Marcel Frenkel Poison Ivy's Poison Poison Ivy is a common roadside plant. Urushiol is the resin from poison ivy that can cause dermatitis. This presentation explores the role of Urushiol in dermatitis as well as its chemical properties and synthesis. To acquire information for this presentation primary, secondary and tertiary resources were used. Urushiol, causes dermatitis by interacting with langerhans’ cells that then recruit T-cells causing pathology. Urushiol is a yellow liquid, with a boiling point of 176 O C, it is composed of many pyrocatechol that can have saturated or unsaturated side chains of 15 carbons. They are synthesized from catechol, the side chains are then extended by an enzyme called chalcone synthases. Understanding the effects of Urushiol might allow for the development of a hyposensitivity agent. 12:43 – 12:55 KC Conley Folic Acid and Modern Medicine Alzheimer’s and Dementia are two illnesses that face many people directly or indirectly. Folic acid helps to produce red blood cells and treat/prevent many diseases including memory loss. I am finding its synthesis, chemical properties, discovering how it replaces needed vitamins and the role it plays in fighting memory loss. To find this, I will be search secondary sources including SciFinder, Reaxys and Web of Science. I found that folic acid replaces vitamin B, which is vital in memory and brain function, how, why it is needed. Due to folic acid being so vital in the retention of memory, future studies could focus on how the addition of more folic acid in a young person’s life would affect their memory loss in the future. 8 November 2011 11:00 – 11:12 Emily Siebert Pyridoxal Phosphate: The Active Form of Vitamin B6 Heart disease has become a huge problem in the United States and has been linked to vitamin deficiencies. Pyridoxal phosphate is the active form of Vitamin B6 and known for its function as a coenzyme in the metabolism of the human body. This presentation will look into the characterization (physical properties and spectra), synthesis, and role of pyridoxal phosphate in the human body to understand its function. I approached this by reading the scientific literature regarding the compound. Pyridoxal phosphate is a complex molecule that is synthesized from pyridoxal and the enzyme pyridoxal kinase and holds an important role as a coenzyme in metabolic reactions. The next step is to consider how much people need to consume of pyridoxal phosphate to prevent a deficiency. 11:13 – 11:25 Andrea Rosado Synthesis of Uric Acid and the Reducing Effects of Allopurinol Americans are often afflicted with medical conditions such as gout and kidney stones, as well as more prevalent conditions including diabetes, cardiovascular diseases, and multiple sclerosis. All of these conditions involve an abnormality in uric acid levels in the blood stream. For example, in gout, excess uric acid in the blood accumulates and precipitates in joints and capillaries. If the compound crystallizes in the kidneys, uric acid stone formation may occur. Through research, I wish to understand both the synthetic reactions and metabolic pathways that lead to the synthesis of this important compound, as well as the chemistry behind medical treatments with serum abnormalities. It is an aromatic acid that does not protonate like carboxylic acids or most other organic acids. Instead of undergoing deprotonation at a carbon-hydrogen site, it is deprotonated at nitrogen sites. Synthesis of uric acid can follow various pathways, some of the more interesting paths including bovine spleen extract and oxygen. The acid is the final product in the metabolism of purine, a compound that is generally found in animal meats. A drug called allopurinol is used to treat gout, high levels of uric acid in the body, and kidney stones. It works to reduce uric acid levels by inhibiting xanthine oxidase, an enzyme involved in the production of uric acid. Uric acid has a unique and complicated role in human life. It is essential to survival, metabolism, and excretion, yet if something goes wrong in these processes then uric acid becomes quite problematic. 11:26 – 11:38 Kevin Kho Sunscreen may be Carcinogenic Some sunscreens have been thought to cause cancer. One of the culprits of the carcinogenic sunscreen is a compound known as oxybenzone. Oxybenzone is often found in sunscreens because of its ability to absorb UVB and UVA rays. However, there have been some studies that show that this compound may actually be harmful in large enough doses. Oxybenzone could be absorbed by the skin in large enough quantities and act as a photocarcinogen. By studying the synthesis and the characteristics of this molecule through text and internet sources we may be able to find out how it reflects the UV rays as well as affect the body in a harmful way. 8 November 2011 12:30 – 12:42 Maureen Martin Peppers, especially black peppers, are very nutritional. This is because they contain piperine. Piperine is a bioavailability enhancer. It increases the gastrointestinal absorption of various nutrients. I will discover how piperine is extracted from peppers and how the compound is characterized in addition to the chemistry behind piperine’s health benefits. I will learn about piperine by reviewing the literature that has been compiled about the compound including spectra and reaction mechanisms. In its pure form, piperine is a pale yellow powder. It is separated from the rest of the pepper oils by alcohol and then isolated through precipitation and distillation. It can also be formed synthetically. Piperine’s bioavailability enhancing effect also increases the amounts of medications absorbed by the body, making the effects of the medication last longer. 12:43 – 12:55 Mimi Huang Taxol: The Synthesis, Characterization, and Properties of an Anticancer Workhorse Various methods have been studied to cure cancer, a disease that takes millions of lives each year. Often administered during chemotherapy, taxol has been shown to be a highly effective antitumor agent. In discussing the properties, characteristics, and synthesis of taxol using journal articles, papers, and online database sources, we can begin to explain why it is effective as an anticancer drug. Being a complex molecule, taxol has been synthesized organically but with limited yield. Taxol can be extracted from Pacific yew or synthesized using microorganisms. It affects the growth rate of cell structure components, inhibiting tumor cells from reproducing. Though its specific interaction with the cell is not completely understood, it can be concluded that taxol is a compound of interest in pharmaceutical research. 12:56 – 1:08 Justin Hintz Capsaicin: Beyond your taste buds Well known as the irritant found in chili peppers, there must be many other uses for this potent compound. Capsaicin is being studied and experimented with concerning nerve-related biological issues. The synthesis of capsaicin can be boiled down to a two-reactant process involving vanilylamine and an acylic substance in diethyl ether. It is colorless and odorless, and causes a burning sensation when coming into contact with skin. By using a variety of resources including web searches, journal entries, and online databases, several unique utilizations and characterizations of capsaicin have been found. Capsaicin has multiple medicinal uses, can abate appetite, and can be used as an active irritant. It has an acute ability to stimulate neuron activity. Chemically, this is most likely linked to its low pH and acidic characteristics. 15 November 2011 11:00 – 11:12 Hoang Ho-Pham Tyramine activity in migraines About 29.5 million Americans suffer from migraines triggered from factors such as stress or diet. Cheese can cause migraines from its tyramine concentrations or the “cheese affect”. Tyramine is an amine found in a variety of food. It is synthesized from tyrosine by tyrosine decarboxylase and characterized by NMR, IR, UV/VIS and MS. This project evaluates the relation between tyramine and migraines through searching the literature such as journal articles and books. Intake of tyramine along with monoamine oxidase inhibitors causes a drug-food interaction. With MAO inhibited, tyramine is absorbed and neurotransmitters are released into the synapse, leading to migraines. The project demonstrated that tyramine in cheese is associated to migraines. 11:13 – 11:25 Elizabeth Nuter Nearly one in ten adults display some degree of depression, according to the CDC. Ketamine is a pharmaceutical drug that has been around since the 1960’s, but it’s anti-depressant effects are just beginning to be utilized. Ketamine is different from other anti-depressant drugs because it works in as little as a few hours as compared to months. This presentation will explore the physical properties and spectra, synthesis, and its antidepressant effects. It is synthesized only in the laboratory, using a process that includes a Grignard. The anti-depressant effects are just beginning to be tapped into, and are still in the early stages but appear to be very promising. 11:26 – 11:38 Kevin Nguyen Soap and Water Kill More than Germs Antibacterial agents are used in many everyday chemicals, including deodorants, shaving creams, soaps and toothpastes. One common antibacterial agent is triclosan, which is used in household chemicals and plastics. However, triclosan may also form dangerous byproducts. Triclosan may generate dioxins or react with chlorinated tap water to generate chloroform, a carcinogen. The literature will be searched in order to find out what byproducts triclosan forms and whether or not they are harmful. It has been found that triclosan does form compounds that have been shown to be toxic to life. Thus, this shows that even a compound that is not dangerous on its own can be harmful due to its byproducts. This implies that there may be other common chemicals that have harmful effects. Lastly, the results show that people must be prudent in choosing what chemicals to use to ensure that it is safe. 11:39 – 11:51 Mary Clare Houlihan The Role of Riboflavin in Cellular Respiration The micronutrient riboflavin is essential for cellular respiration in the human body. Through its role as a component of flavocoenzymes, riboflavin plays a major role in the electron transport chain of cellular respiration. It is used in oxidation-reduction reactions in the cell in order to synthesize electron carriers essential to oxidative phosphorylation. Studies from journal articles have shown that this essential molecule is biosynthesized through enzymatic reactions from the substrates GTP and two molecules of ribulose-5-phosphate. Though riboflavin deficiencies or problems with riboflavin biosynthesis are uncommon, a lack of this molecule would impede the primary energy producing step of cellular respiration causing growth failure or weakened metabolism. Further studies of the importance of riboflavin in cellular respiration could help with the understanding of metabolic diseases. 22 November 2011 11:00 – 11:12 Cam Houk Theophylline: Friend or Foe? Asthma as well as other respiratory diseases, plagues numerous Americans, both young and old. With numerous pathways of synthesis ranging from the expensive to the most efficient, this compound seems to be ideal for the treatment of these detrimental diseases. However, the unstable physical properties of un-isolated theophylline have been inferred to cause a multitude of very harmful side effects. The bicyclic, conjugated interfaces and quickly rotating bonds play a key role. Consulting literature and clinical trials, research has indicated that harmful side effects are significant due to the compounds diastereomeric pair, caffeine; but indication on the label prevents pending lawsuits derived from harmful by-products of theophylline reactivity in the body! So, how can we isolate one form of the epimeric pair to maximize efficiency?