Chem 12B—Sp14

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CHEM 12B—Trego Calculating Average Molar Mass of Fatty Acid Triglycerides Animal and vegetable fats are composed of triglycerides. A triglyceride consists of a molecule of glycerol (propane-1,2,3-triol) condensed with three fatty carboxylic acids. A naturally occurring fat will be composed of a number of different fatty acids, varying in the length of the parent chain (~C4-C24). Additionally, some fatty acids contain 1 or more C-C double bonds (unsaturated fatty acids). Because a fat consists of various fatty acids, the triglyceride molecules will have various molecular masses. O O O (CH2)nCH3 (CH )nCH Glycerol O 2 3 Fatty Acids O O (CH2)nCH3 One approach to dealing with the variability in the molar mass is to calculate an average molar mass. The fatty acid composition of most naturally occurring fats has been determined. Using this data, we can calculate a weighed average molar mass as shown below. Average Molar Mass = 3 x Average Molar Masses of Fatty Acids + Molar Mass of C3H2 (glycerol skeleton) Example: Consider a hypothetical fat with the following fatty acid composition. C10 C12 C14 C16 C18 (mono unsaturated) Mol % 5.0 15.0 25.0 25.0 30.0 Fatty acids are often identified by their carbon atom count, since all the structures are straight chain. C10 = CH3(CH2)8CO2H MM = 172.3 g/mol The average molar mass of the fatty acid components of the triglycerides can be calculated in a similar fashion to the manner in which average atomic mass is calculated. Multiply the molar mass of each fatty acid by the decimal equivalent of its percent abundance. The sum of these products will yield the average molar mass. Fatty Acid Mol % / x Molar Mass g/mol = Product 100 CH3(CH2)8CO2H 0.050 172.3 8.62 g/mol CH3(CH2)10CO2H 0.150 200.4 30.06 g/mol CH3(CH2)12CO2H 0.250 228.4 57.10 g/mol CH3(CH2)14CO2H 0.250 256.5 64.13 g/mol CH3(CH2)14CHCHCO2H 0.300 282.5 84.75 g/mol Sum 244.7 g/mol Continued on back… Average molar mass of the triglycerides: (3 x 244.7 g/mol) + 38.03 g/mol = 772.0 g/mol ↑ ↑ molar mass of glycerol CH skeleton ↑ avg. molar mass of free fatty acids Fatty Acid Composition of Coconut Oil Determined by FAME Analysis Mol-%† Pavia Hexanoic Acid (Caproic Acid) 1.1 Octanoic acid (Caprylic Acid) 11.0 10-22 Decanoic Acid (Capric Acid) 9.7 Dodecanoic Acid (Lauric acid) 39.6 45-51 Tetradecanoic Acid (Myristic Acid) 18.9 17-20 Hexadecanoic Acid (Palmitic Acid) 9.2 4-10 9-Octadecenoic Acid (Oleic Acid) 6.2 2-10 Octadecanoic Acid (Steric Acid) 4.3 1-5 †Determined by gas chromatography/mass spectrometry at Laney College, Spring Semester, 2014 .

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The Role of Short Chain Fatty Acids in Appetite Regulation and Energy Homeostasis
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