Survey
* Your assessment is very important for improving the workof artificial intelligence, which forms the content of this project
Download organic chemistry ii - University of Minnesota Duluth
Transcript
Organic Chemistry II Topic Organic Functional Group Page Cosmetics Alcohol 186 Balsamic Vinegar Carboxylic Acid Carbohydrates Ester, Ether Triterpene Triglycerides Fatty Acids Amide, Amine 175 Willow Birch Olive Oil Penicillin 172 199 178 “Alcohol-Free” Cosmetics (p.186) Alcohol • Alcohol: an organic compound with the functional group –OH (hydroxyl group). – Methanol is CH3OH – Ethanol (Fig 13.11.7) is CH3CH2OH – Hexadecanol (Fig 13.11.1) is CH3(CH2)14CH3OH – Octadecanol (Fig 13.11.4) is CH3(CH2)16CH3OH • Alcohols are hydrophillic and can absorb water from skin; drying effect. Desirable Properties • • • • • Moisturizer Antioxidant Preservative Fragrance Helps dissolve components Emulsifier pH control Note the long repeating CH2 portions of the molecule – these are hydrophobic • “alcohol-free” means ethanol-free Balsamic Vinegar (p. 175) Carboxylic Acid, Carbohydrates • Most vinegars are produced when grain alcohol is converted to acetic acid (an organic acid, carboxylic acid) by a bacteria. • How are alcohols formed? Sucrose + water + yeast glucose and fructose (Eqn p. 176) • Then these simpler sugars + enzyme ethanol or grain alcohol (Eqn p 176) • Note sugars have C-H-O (carbohydrates, saccharides) Alcohol to Vinegar • Then grain alcohol is oxidized to vinegar aerobically (in the presence of oxygen) • CH3CH2OH + O2 CH3COOH + H2O • Functional group = COOH • Different vinegars start out as different alcoholic solutions (red wine, cider, grain alcohol, white wine, etc). Balsamic Vinegar • Balsamic vinegar starts as Trebbiano white grape juice (sweet) that ferments naturally to alcohol. • Then a bacteria is added which causes a second fermentation to acetic acid (sour). • Subsequent aging takes 10-30 years (£££) Nature’s Aspirin (p. 172) Ester, Ether • The first medications were from plants. Trial and error helped define their use and lead to improvements . • As organic chemistry developed as a subdiscipline, chemists were able to extract the active ingredient, separate, purify and characterize it (i.e. chemical formula and structure, physical and chemical properties). • Then the med was synthesized and marketed. Willow Bark Aspirin • Historical record – 1763: tree bark was defined as an astringent and med for malaria (ague) and various disorders. – 1876: Salicylic acid (Fig 13.4.2) was used to control fever, gout and arthritis. – 1899: first mentioned in medical literature to treat rheumatic fever. Chemistry of Aspirin • The active ingredient in aspirin is salicylic acid or SA. • Aspirin = acetylsalicylic acid is an ester which hydrolyzes to SA (organic or carboxylic acid) + alcohol. • Willow bark contains salicin (Fig 13.4.5) which is an ether. Salicin hydrolyzes to two alcohols. One of them produces SA. Birch Bark Biological Activity Triterpene • Birch bark contains betulin (C30H50O2), (turpentine source, steroids) • Betulin Betulinic acid (BA; convert OH to COOH) • BA has considerable biological activity: antiviral, antibacterial, antifungal, antimalarial, anti-HIV, anticancer. • http://www.betulin.ca/ Molecular Structures Technology Transfer from Research Lab to Startup Company • Several companies are working to develop approved pharmaceuticals from birch bark. • One of these is NaturNorth located in Duluth. • http://news.minnesota.publicradio.org/featur es/2005/03/10_hemphills_birchbark/ • This company was spun off from research done at UMD – Chem Dept and NRRI • http://www.nrri.umn.edu/cartd/lce/default.ht m • http://www.coolhemp.com/healingtrees/beaver/birch. shtml • http://lib.bioinfo.pl/pmid:16503940 • http://www.freepatentsonline.com/7264184.html • http://www.medwirenews.md/52/59358/Consumer_Health/Birch_bark_co mpound_may_provide_prostate_cancer_treatment_ho pe.html • http://www.allbusiness.com/company-activitiesmanagement/company-locations/5367391-1.html Olive Oil (p. 199) Triglycerides • World-wide production in 2005: About 3E6 metric tons from Spain (36%), Italy (25%), Greece (18%), Tunesia (8%), Turkey (5%) • Oil must be extracted from olive meat. – Wash, grind and make a paste from olives. – Let stand to allow oil to coalesce. – Separate oil/water from pulp using a centrifuge or press. – Separate oil (hydrophobic) and water (hydrophilic) Virgin Olive Oil • Classification of Olive Oil = f( physical vs chemical preparation, acidity level, additives, temperature). • Virgin oil: prepared using physical means (grinding olives and collecting oil) only, no chemicals added, no heat applied. Chemistry: Formation of Triglycerides • All oils contain triglycerides = ester • Triglycerides form when glycerol (alcohol) + 3 fatty acids (carboxylic acids with a long carbon backbone of 12-24 carbons) release water. • Most fat in food and in our bodies are triglycerides (necessary to health but too much is bad for heart). • Let’s look at glycerol, fatty acids, then fats and oils. • http://www.scientificpsychic.com/fitness/fattyacids1 .html Saponification • Let’s look at the reverse reaction. When the ester R-O-R’ bond in a triglyceride is hydrolyzed, the two products are an alcohol and a carboxylic acid. Saponification. • http://www.indigo.com/models/gphmodel/m olymod-tripalmitin-model-kit.html • As more ester bonds are broken, olive oil breaks down, the pH decreases and quality decreases. Fatty Acids • Fatty acids can contain single C-C bonds (saturated) only or C=C double bonds (unsaturated). • Molecule structure can be linear (straight chain) or branched. • Olive oil has oleic (C-18, unsat, 85%), palmitic (C-16, sat, 7%), others. See Tables 13.2, 13.3 Penicillin (p.178) Amide, Amine • Penicillin is an antibiotic used to treat bacterial infections. • 1928 – discovered by Alexander Fleming in London. He was growing staphylococcus culture and noticed no growth around a contaminant mold. • 1939 – in vivo bactericidal activity demonstrated by Howard Florey at Oxford. (Museum of Science, Oxford) Amide: C=O bonded to N Penicillin G has two amide groups A 3-Di View of Penicillin G Penicillin + Acid • Penicillin attacks the cell wall of the bacterium and causes the cell to die. • In the presence of acid, penicillin loses its biological activity because • Amide group + water + H+ RCOOH + amine • Amine: based on NH3 with R groups substituting for hydrogens • http://hyperphysics.phyastr.gsu.edu/hbase/Organic/amine.html Penicillin Derivatives • Penicillin G – Core structure, cannot be taken orally as acid breaks it down. • Other forms of drug can be made by modifying Pen G. For example, Penicillin V is less active but can be taken orally. • Other antibiotics are available.
