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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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alcohol free cosmetics p 186 alcohol
“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
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
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
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
  • 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
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
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
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  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.
technology transfer from research lab to startup company
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.
  • This company was spun off from research done at UMD – Chem Dept and NRRI

olive oil p 199 triglycerides
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
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
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.
  • 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.
  • As more ester bonds are broken, olive oil breaks down, the pH decreases and quality decreases.
fatty acids
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 (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)
penicillin acid
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
penicillin derivatives
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.