CH-103 Chap 17
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are non polar compounds that are not in water, but soluble in organic solvents. Includes waxes, fats and oils, glycerophospholipids and steroids.
Lipids that conatain no fatty acids:
A Fatty acid:
contains a long unbranched carbon chain attached to a carboxylic acid group at one end.
A Saturated Fatty acid:
contains only one carbon-carbon bonds. (properties similar to an alkane.)
In a Monounsaturated fatty acid:
the long carbon chain has one double bond. (properties similar to an alkene.)
A Polyunsaturated fatty acid:
has at least two carbon-carbon double bonds.
Saturated Fatty Acid, 12 Carbon atoms. CH3--(CH2)10--COOH
Saturated Fatty Acid, 14 Carbon Atoms: CH3--(CH2)12--COOH
Saturated Fatty Acid, 16 Carbons: CH3--(CH2)14--COOH
Saturated Fatty Acid, 18 Carbons: CH3--(CH2)16--COOH
Monounsaturated Fatty acid: 16 Carbons CH3--(CH2)5--CH==CH--(CH2)7--COOH
Monounsaturated Fatty Acids; 18 Carbons CH3
- Polyunsaturated Fatty Acid; 18 Carbons
Polyunsaturated Fatty Acids; 18 Carbons; CH3
Polyunsaturated Fatty Acids; 20 Carbons; CH3--(CH2)3--(CH2--CH==CH)4--(CH2)3--COOH
- 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.
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.
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.
Saturated fatty acids:
- Lauric Acid
- Myristic Acid
- Palmitic Acid
- Stearic Acid
- Palmitoleic Acid
- Oleic Acid
Polyunsaturated Fatty Acids:
- Linoleic Acid
- Linolenic Acid
- Arachidonic Acid
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).
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).
Sources of Omega-3 fatty acids:
fish oils (linolenic acid).
Sources of Omega-6 fatty acids:
- vegetable oils.
- meat (land animals)
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.
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.
A Wax is:
an ester of a long-chain saturated fatty acid and a long-chain alcohol; containing 14-30 carbon atoms.
Fatty acid(--C==O), ester bond (--O--), Long chain alcohol
Triglycerides, are triesters of glycerol (trihydroxy alcohol) and fatty acids.
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).
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).
A Fat is:
- A triacylglycerol that is solid at room temperature.
- Obtained from an animal source (meat, whole milk, butter & cheese).
An Oil is:
- A triacylglycerol that is usually a liquid at room temperature.
- Obtained from a plant source.
In Hydrogenation of an unsaturated fat:
hydrogen is added to carbon-carbon double bonds to form carbon-carbon single bonds.
Glycerol + 3 Fatty Acid molecules --> triacylglycerol + 3H2O
Hydrogenation of Triacylglycerols:
Tracylglycerol (unsaturated) + H2 -(Ni)->Triacylglycerol (saturated).
Oxidation of Unsaturated Fatty Acids:
Fatty Acids (unsaturated) --> (short-chain aldehydes) --> (short-chain carboxylic acids)
Hydrolysis of Triacylglycerols:
Triacylglycerol + 3H2O -HCl-> glycerol + 3 fatty acid molecules
Saponification of Triacylglycerols:
Triacylglycerol + 3NaOH --> glycerol + 3 sodium salts of fatty acids
A nonpetroleum fule that can be used in place of diesel fuel; produced from renewable biological resources.
A glycerophospholipid found in brain and nerve tissues that incorporates the amino alcohol serine or ethanolamine.
A lipid in which sphingosine is attached to a fatty acid by an amide link.
The most prevalent of the steroid compounds; needed for cellular membranes and the synthesis of vitamin D, hormones, and bile salts.
A long-chain carboxylic acid found in many lipids.
Glycerophospholipids containing choline as the amino alcohol.
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