CH-103 Chap 17

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Allistermark
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118554
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CH-103 Chap 17
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2011-11-25 17:54:59
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Organic Chemistry Lipids Waxes Oils
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CH 103 Chapter 17
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  1. Lipids
    are non polar compounds that are not in water, but soluble in organic solvents. Includes waxes, fats and oils, glycerophospholipids and steroids.
  2. Lipids that conatain no fatty acids:
    Steroids.
  3. A Fatty acid:
    contains a long unbranched carbon chain attached to a carboxylic acid group at one end.
  4. A Saturated Fatty acid:
    contains only one carbon-carbon bonds. (properties similar to an alkane.)
  5. In a Monounsaturated fatty acid:
    the long carbon chain has one double bond. (properties similar to an alkene.)
  6. A Polyunsaturated fatty acid:
    has at least two carbon-carbon double bonds.
  7. Lauric Acid:
    Saturated Fatty Acid, 12 Carbon atoms. CH3--(CH2)10--COOH
  8. Myristic Acid:
    Saturated Fatty Acid, 14 Carbon Atoms: CH3--(CH2)12--COOH
  9. Palmitic Acid:
    Saturated Fatty Acid, 16 Carbons: CH3--(CH2)14--COOH
  10. Stearic Acid:
    Saturated Fatty Acid, 18 Carbons: CH3--(CH2)16--COOH
  11. Palmitoleic acid:
    Monounsaturated Fatty acid: 16 Carbons CH3--(CH2)5--CH==CH--(CH2)7--COOH
  12. Oleic Acid:
    Monounsaturated Fatty Acids; 18 Carbons CH3--(CH2)7--CH==CH--(CH2)7--COOH
  13. Linoleic Acid:
    • Polyunsaturated Fatty Acid; 18 Carbons
    • CH3-(CH2)4-CH=CH-CH2-CH=CH-(CH2)7-COOH
  14. Linolenic Acid:
    Polyunsaturated Fatty Acids; 18 Carbons; CH3--(CH2--CH==CH)3--(CH2)7--COOH
  15. Arachidonic Acid:
    Polyunsaturated Fatty Acids; 20 Carbons; CH3--(CH2)3--(CH2--CH==CH)4--(CH2)3--COOH
  16. Prostaglandins:
    • hormone-like substances formed from Arachidonic acid.
    • raise or lower blood pressure.
    • stimulate contraction & relaxation of smooth muscle.
    • PGE & PGF produce inflammation and pain.
    • NSAIDs block the production of prostaglandins; decrease pain.
  17. Similarities in the structures of a saturated fatty acid and an unsaturated fatty acid.
    All fatty acids contain a long chain of carbon atoms with a carboxylic acid group.
  18. Differences in the structures of a saturated fatty acid and an unsaturated fatty acid.
    Saturated fatty acids contain only carbon-carbon single bonds; unsaturated fatty acids contain one or more double bonds.
  19. Saturated fatty acids:
    • Lauric Acid
    • Myristic Acid
    • Palmitic Acid
    • Stearic Acid
  20. Monounsaturated acids:
    • Palmitoleic Acid
    • Oleic Acid
  21. Polyunsaturated Fatty Acids:
    • Linoleic Acid
    • Linolenic Acid
    • Arachidonic Acid
  22. How does the structure of a fatty acid with a cis double bond differ from the structure of a fatty acid with a trans double bond?
    • In a cis fatty acid the H atoms are on the same side of the double bond (produces a bend in the carbon chain).
    • In a trans fatty acid the H atoms are on opposite sides of the double bond (no bond in carbon chain).
  23. What is the difference in the location of the first double bond in an Omega-3 and an Omega-6 fatty acid?
    • Omega-3: double bond on carbon 3 (counting from methyl group).
    • Omega-6: double bond on carbon 6 (counting from methyl group).
  24. Sources of Omega-3 fatty acids:
    fish oils (linolenic acid).
  25. Sources of Omega-6 fatty acids:
    • vegetable oils.
    • meat (land animals)
  26. Compare Arachidonic acid and Prostagland E (PGE):
    • arachiodonic acid has four double bonds and no side group.
    • PGE1 has cyclopentane, and hydroxyl and ketone functional groups.
  27. Compare structures of and functional groups of PGE and PGF
    • PGE has a ketone group on carbon 9.
    • PGF has a Hydroxyl group on carbon 9.
  28. A Wax is:
    an ester of a long-chain saturated fatty acid and a long-chain alcohol; containing 14-30 carbon atoms.
  29. Waxes:
  30. Wax structure:
    Fatty acid(--C==O), ester bond (--O--), Long chain alcohol


  31. Triacylglycerols:
    Triglycerides, are triesters of glycerol (trihydroxy alcohol) and fatty acids.
  32. The triglycerol that is formed by the esterification of glycerol with CH3--(CH2)12--COOH:
    • The saturated fatty acid is: Myristic acid.
    • It forms glyceryl trimystate or trimyristin (common).
  33. The triglycerol that is formed by the esterification of glycerol with CH3--(CH2)5--CH==CH--(CH2)7--COOH:
    • The monounsaturated fatty acid with 16 carbons is Palmitoleic acid.
    • It forms glyceryl tripalmitoleate or tripalmitolein (common).
  34. A Fat is:
    • A triacylglycerol that is solid at room temperature.
    • Obtained from an animal source (meat, whole milk, butter & cheese).
  35. An Oil is:
    • A triacylglycerol that is usually a liquid at room temperature.
    • Obtained from a plant source.
  36. In Hydrogenation of an unsaturated fat:
    hydrogen is added to carbon-carbon double bonds to form carbon-carbon single bonds.
  37. Esterification Reaction:
    Glycerol + 3 Fatty Acid molecules --> triacylglycerol + 3H2O
  38. Hydrogenation of Triacylglycerols:
    Tracylglycerol (unsaturated) + H2 -(Ni)->Triacylglycerol (saturated).
  39. Oxidation of Unsaturated Fatty Acids:
    Fatty Acids (unsaturated) --> (short-chain aldehydes) --> (short-chain carboxylic acids)
  40. Hydrolysis of Triacylglycerols:
    Triacylglycerol + 3H2O -HCl-> glycerol + 3 fatty acid molecules
  41. Saponification of Triacylglycerols:
    Triacylglycerol + 3NaOH --> glycerol + 3 sodium salts of fatty acids
  42. Biodiesel:
    A nonpetroleum fule that can be used in place of diesel fuel; produced from renewable biological resources.
  43. Cephalin:
    A glycerophospholipid found in brain and nerve tissues that incorporates the amino alcohol serine or ethanolamine.
  44. Ceramide:
    A lipid in which sphingosine is attached to a fatty acid by an amide link.
  45. Cholesterol:
    The most prevalent of the steroid compounds; needed for cellular membranes and the synthesis of vitamin D, hormones, and bile salts.
  46. Fatty Acid:
    A long-chain carboxylic acid found in many lipids.
  47. Lecithins:
    Glycerophospholipids containing choline as the amino alcohol.

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