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Organic Chemistry II

Organic Chemistry II. “Alcohol-Free” Cosmetics (p.186) Alcohol. Alcohol: an organic compound with the functional group –OH (hydroxyl group). Methanol is CH 3 OH Ethanol (Fig 13.11.7) is CH 3 CH 2 OH Hexadecanol (Fig 13.11.1) is CH 3 (CH 2 ) 14 CH 3 OH

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Organic Chemistry II

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  1. Organic Chemistry II

  2. “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.

  3. 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

  4. 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)

  5. 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).

  6. 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 (£££)

  7. 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.

  8. 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.

  9. 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.

  10. Birch Bark  Biological ActivityTriterpene • 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/

  11. Molecular Structures

  12. 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/features/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.htm

  13. http://www.coolhemp.com/healingtrees/beaver/birch.shtml • http://lib.bioinfo.pl/pmid:16503940 • http://www.freepatentsonline.com/7264184.html • http://www.medwire-news.md/52/59358/Consumer_Health/Birch_bark_compound_may_provide_prostate_cancer_treatment_hope.html • http://www.allbusiness.com/company-activities-management/company-locations/5367391-1.html

  14. 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)

  15. 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.

  16. 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

  17. 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/molymod-tripalmitin-model-kit.html • As more ester bonds are broken, olive oil breaks down, the pH decreases and quality decreases.

  18. 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

  19. 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)

  20. Amide: C=O bonded to N

  21. Penicillin G has two amide groups

  22. A 3-Di View of Penicillin G

  23. 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.phy-astr.gsu.edu/hbase/Organic/amine.html

  24. 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.

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