Chapter 19 Lipids - Websites.rcc.edu
Chapter 19–1Chapter 19 LipidsSolutions to In-Chapter Problems19.1 Recall from Example 19.1 that lipids contain many nonpolar C–C and C–H bonds and few polarbonds.CH3 OHCH3CH3a.HO2CCH2 C CH2CH2OHb.c.OHOHtwo polar OH groupsand a COOHsix carbonsnot a lipidCH(CH3)2HOtwo polar OH groups18 carbonslipidone polar OH group10 carbonslipid19.2 Since lipids contain many nonpolar C–C bonds, they are soluble in nonpolar and weakly polarorganic solvents. Therefore, lipids are likely to be soluble in (a) CH2Cl2 and (c)CH3CH2CH2CH2CH3. The 5% aqueous NaCl solution (b) is not a solution in which lipids aresoluble since it is a polar solvent.19.3 Answer the questions as in Example 19.2. Skeletal structures have a carbon at the intersection of two lines and at the end of every line.The double bond must have the cis arrangement in an unsaturated fatty acid. The nonpolar C–C and C–H bonds comprise the hydrophobic portion of a molecule and thepolar bonds comprise the hydrophilic portion. For the same number of carbons, increasing the number of double bonds decreases the meltingpoint of a fatty acid.a. and b.OCH3(CH2)16COOH AOHhydrophobic portionhydrophilic portionOOHCH3(CH2)4CH CHCH2CH CH(CH2)7COOH Bhydrophobic portionhydrophilic portionc. A will have the higher melting point because the molecules can pack together better. 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Lipids 19–219.4 In omega-n acids, n is the carbon at which the first double bond occurs in the carbon chain,beginning at the end of the chain that contains the CH3 group.1a.COOH3b.first C C at C3an omega-3 acid19.5 In omega-n acids, n is the carbon at which the first double bond occurs in the carbon chain,beginning at the end of the chain that contains the CH3 group.an omega-9 acidfirst C C at C9a.CH3CH2CH2CH2CH2CH2CH2CH2CH CHCH2CH2CH2CH2CH2CH2CH2COOH123456789first C C at C6b.an omega-6 acidCH3CH2CH2CH2CH2CH CHCH2CH CHCH2CH CHCH2CH CHCH2CH2CH2COOH12345619.6 Use the steps in Example 19.3 to draw each wax.Oa.CH3(CH2)16COOH H O(CH2)9CH3CH3(CH2)16Ob.CH3(CH2)16CCO(CH2)9CH3 H2O H2O H2OOOH H O(CH2)11CH3CH3(CH2)16OCc. CH (CH )OH32 16CO(CH2)11CH3O H O(CH2)29CH3CH3(CH2)16CO(CH2)29CH319.7 Draw the structure of the wax formed from eicosenoic acid.OO19.8 Beeswax is hydrophobic since it contains very long hydrocarbon chains. It will therefore beinsoluble in a very polar solvent like water, only slightly soluble in the less polar solvent ethanol,and very soluble in the weakly polar solvent chloroform. 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Chapter 19–319.9 Draw the products of the hydrolysis of cetyl myristate.OCCH3(CH2)12OH2SO4O(CH2)15CH3 H2OCCH3(CH2)12 OHHO(CH2)15CH3fatty acidcetyl myristatealcohol19.10 Draw the structure of each triacylglycerol as in Example 19.4.CH2 OHa. CH OHCH2 OHCH2 OHb. CH OHCH2 OHOOHO CO(CH2)16CH3CH2 O CO(CH2)16CH3HO CO(CH2)16CH3CHO CO(CH2)16CH3HO CO(CH2)16CH3CH2 O C(CH2)16CH3OH HHO CO(CH2)7CH CH(CH2)7CH3CH2 O CO(CH2)7C C(CH2)7CH3H HHO CO(CH2)7CH CH(CH2)7CH3CHO CO(CH2)7C C(CH2)7CH3H HHO C(CH2)7CH CH(CH2)7CH3CH2 O C(CH2)7C C(CH2)7CH319.11 Draw two different triacylglycerols.OOCH2 O CO(CH2)16CH3CH2 O CO(CH2)16CH3CHO CO(CH2)16CH3CHO CO(CH2)14CH3CH2 O C(CH2)14CH3CH2 O C(CH2)16CH319.12 Draw a triacylglycerol to fit each description.OOOa.three 12-C fatty acidsOOOOOOb.Othree cis double bondsOO 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Lipids 19–4OOOc.Otrans double bondsOO19.13 Draw the products of the hydrolysis of each triacylglycerol as in Example 19.5.Oa.CH2 O CO(CH2)12CH3O CO(CH2)12CH3CH2 O C(CH2)12CH3CHCH2 OH3 H OHH2SO4OCHOH 3 HO C(CH2)12CH3CH2 OHOOCH2 O COb. CH O CCH2 OH(CH2)12CH3(CH2)7CH CH(CH2)5CH3OCH2 O CHO C3 H OHH2SO4OCHOH HO C(CH2)7CH CH(CH2)5CH3OCH2 OH(CH2)7CH CH(CH2)7CH3(CH2)12CH3HO C(CH2)7CH CH(CH2)7CH319.14 Balance the equation for the combustion of tristearin.O2CH2 O CO(CH2)16CH3CHO CO(CH2)16CH3CH2 O C(CH2)16CH3tristearinC57H110O6 163 O2114 CO2enzymes 110 H2Ototal of 338 O atoms on each side220 H atoms114 C atoms19.15 Draw the soap prepared by saponification of each triacylglycerol.Oa.CH2 O CO(CH2)12CH3CHO CO(CH2)12CH3CH2 O C(CH2)12CH3NaOHH2OO3 Na –O C(CH2)12CH3 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Chapter 19–5OOCH2 O CONa –O C(CH2)12CH3NaOHb. CH O C(CH2)7CH CH(CH2)5CH3CH2 O CNa –O CH2OO(CH2)12CH3O(CH2)7CH CH(CH2)5CH3ONa –O C(CH2)7CH CH(CH2)7CH3(CH2)7CH CH(CH2)7CH319.16 Draw the structure of the two cephalins as in Example 19.6.Ofrom palmitic acidCH2 O CO(CH2)14CH3H HCH(CH2)7C C(CH2)7CH3O COfrom oleic acid CH2 O P O CH2CH2NH3O–OH HCH2 O CO(CH2)7C C(CH2)7CH3CH(CH2)14CH3O COfrom oleic acidfrom palmitic acid CH2 O P O CH2CH2NH3O–19.17 A triacylglycerol has glycerol as the backbone, and three nonpolar side chains formed from esterswith fatty acids.A phosphoacylglycerol has glycerol as the backbone, a phosphodiester on a terminal carbon, andtwo nonpolar side chains formed from esters with fatty acids.A sphingomyelin has sphingosine as the backbone, one amide, and a phosphodiester on a terminalcarbon.c.a. phosphoacylglycerol, cephalinHO CHCH2 O CO(CH2)12CH3CH(CH2)12CH3O COestersformed fromfatty acids CH2 O P O olOCH CH(CH2)12CH3OCH NH COCH2 OphosphateO–(CH2)12CH3amide formedwith myristic acid P O CH2CH2N(CH3)3O–derived from cholinederived from ethanolaminetriacylglycerolglycerolOCH2 O CO(CH2)12CH3CH(CH2)7CH CH(CH2)5CH3O COCH2 O Cestersformed fromfatty acids(CH2)12CH3 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Lipids 19–619.18 Phospholipids are present in cell membranes because they have an ionic polar head and twononpolar tails, and can form a lipid bilayer needed for cell membrane function. Triacylglycerols arebasically nonpolar compounds, so they have no polar head to attract water on the outside of amembrane.19.19 Membrane A is formed from the phospholipids linoleic and oleic acids, and will be more fluid orpliable because it contains unsaturated fatty acids. Membrane B is formed from the saturated fattyacids stearic and palmitic acids, which have no double bonds and therefore pack very tightly,making it more rigid.19.20 Ions don’t diffuse readily through the interior of the cell membrane because it is hydrophobic andions are insoluble in a nonpolar medium.19.21 Cholesterol is a lipid since it contains many C–C and C–H bonds and it is insoluble in water.19.22 Answer each question about cholesterol.181219a.b. and c.DC109HOOH at C31614 1583HO171312BA115476double bond betweenC5 and C6d. Cholesterol contains one polar C–O bond and one polar O–H bond from the polar OH group. Thelarge hydrocarbon skeleton with nonpolar C–C and C–H bonds makes it water insoluble.19.23 Triacylglycerols would be found in the interior of a lipoprotein particle, since this is thehydrophobic region of lipoproteins.19.24 Label the functional groups.hydroxylcarboxylic acidHOhalidea.b.Ohydroxylalkenearomatic ringamineHOHO(CH3)2CHHN COamideFaromatic ringNalkeneHOO esterOOesterOaromatic ringalkene 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Chapter 19–719.25a. Estrone has a phenol (a benzene ring with a hydroxyl group) and progesterone has a ketone andC C in ring A. Progesterone also has a methyl group bonded to C10.b. Estrone has a ketone at C17 and progesterone has a C–C bond, which is attached to a ketone.OOketone17methyl group10phenolHOketoneC–C bondprogesteroneOestroneketonealkene19.26 Label the functional groups in aldosterone.2o alcoholHOaldehydeOCHOketoneCH2OH1o alcoholketoneOalkene19.27 Testosterone has a methyl group at C10 that nandrolone lacks.OHOHmethyl groupOOtestosteronenandrolone19.28 Water-soluble vitamins are excreted in the urine whereas fat-soluble vitamins are stored in thebody. When a person ingests a large quantity of a water-soluble vitamin, much of it is excreted inthe urine. When a person ingests a large quantity of a fat-soluble vitamin, it can be retained in thefat in the body, potentially building up to toxic levels.19.29 Label the functional groups and draw the skeletal structure for PGE2.carboxylic acidketoneOOCH2CH CH(CH2)3COOHalkenea.cisCH CHCH(CH2)4CH3HOOHCOOHb.HOtrans OHalcohol 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Lipids 19–819.30 Label the functional groups and the double bonds as cis or trans in LTC4.trans alkenea. and b.cis 3COOHSCH2 amidecarboxylic acidCHCONHCH2COOHNHCOCH2CH2CHCOOHcis alkeneNH2amideamineSolutions to End-of-Chapter Problems19.31Hydrolyzable lipids include waxes, triacylglycerols, and phospholipids.Nonhydrolyzable lipids include steroids, fat-soluble vitamins, and eicosanoids.a. prostaglandin—nonhydrolyzableb. triacylglycerol—hydrolyzablec. leukotriene—nonhydrolyzabled. vitamin A—nonhydrolyzable19.32e. phosphoacylglycerol—hydrolyzablef. lecithin—hydrolyzableg. cholesterol—nonhydrolyzableHydrolyzable lipids include waxes, triacylglycerols, and phospholipids.Nonhydrolyzable lipids include steroids, fat-soluble vitamins, and eicosanoids.a. eicosanoids—nonhydrolyzableb. oleic acid—hydrolyzablec. phospholipid—hydrolyzabled. cephalin—hydrolyzablee. wax—hydrolyzablef. estrogen—nonhydrolyzableg. PGE1—nonhydrolyzable19.33A wax is hydrophobic. As a result, it is soluble in (b) CH2Cl2 and (c) CH3CH2OCH2CH3, bothorganic solvents, but insoluble in (a) water, which is polar.19.34A steroid would be soluble in (b) CCl4 but insoluble in (a) blood plasma and (c) 5% NaClsolution.19.35For the same number of carbons, increasing the number of double bonds decreases the meltingpoint of a fatty acid.a. CH3(CH2)3CH CH(CH2)7COOH, CH3(CH2)12COOH, CH3(CH2)14COOHb. CH3(CH2)5CH CH(CH2)7COOH, CH3(CH2)7CH CH(CH2)7COOH, CH3(CH2)16COOH19.36a. The hydrocarbon chain of a saturated fatty acid is comprised of carbon–carbon single bonds.The hydrocarbon chain of a monounsaturated fatty acid contains one carbon–carbon double bond.The hydrocarbon chain of a polyunsaturated fatty acid contains multiple carbon–carbon doublebonds. 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Chapter 19–9b. Stearic acid is a saturated fatty acid, oleic acid is a monounsaturated fatty acid and linoleic acidis a polyunsaturated fatty acid.c. Of the fatty acids in part b, linoleic acid has the lowest melting point and stearic acid has thehighest melting point.19.37a. Increasing the number of carbon atoms increases the melting point of fatty acids.b. Increasing the number of double bonds decreases the melting point of fatty acids.19.38Cis double bonds induce kinks in the long hydrocarbon chain, making it difficult for themolecules to pack closely together in a solid. The larger the number of cis double bonds, thelower the melting point. The first fatty acid has one trans double bond, whereas the second fattyacid as one cis double bond. The first fatty acid will have a higher melting point than the secondfatty acid.19.39Answer each question about 7,10,13,16,19-docosapentaenoic acid.a. and b.hydrophilichydrophobicOHOc. The melting point of the cis isomer would be lower than the melting point of the trans isomer.d. This fatty acid will be a liquid at room temperature.e. 7,10,13,16,19-Docosapentaenoic acid is an omega-3 fatty acid because there is a double bondat the third C from the left (numbered from the CH3 group).19.40Answer each question about 3,6,9,12,15-octadecapentaenoic acid.a. and b.hydrophilichydrophobicOHOc. The melting point of this fatty acid will be lower than the melting point of oleic acid becausethis fatty acid has multiple double bonds.d. This fatty acid will be a liquid at room temperature.e. 3,6,9,12,15-Octadecapentaenoic acid is an omega-3 fatty acid because there is a double bond atthe third C from the left (numbered from the CH3 group).19.41transcisa.CO2HCO2Hc.Ob. omega-3 acidd.O 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Lipids 19–1019.42transcisCO2Ha.CO2Hc.Ob. omega-5 acid19.43d.ODraw the structure of each wax.Oa.CH3(CH2)14COOH H 14OH H O(CH2)11CH3CH3(CH2)14 H2OCO(CH2)11CH3 H2O H2O H2O H2O H2OOOH H O(CH2)9CH3CH3(CH2)14CO(CH2)9CH3Draw the structure of each wax.Oa.CH3(CH2)10COOH H (CH2)29CH3OOH H 9CH3OOH H O(CH2)29CH3CH3(CH2)22CO(CH2)29CH3Draw the products of the hydrolysis of each wax.Oa. CH (CH )32 16CO(CH2)17CH3 H2OOb. CH (CH )32 12CCCH3(CH2)16O(CH2)25CH3 H2OCH3(CH2)12 H2OOH HO(CH2)17CH3COH HO(CH2)25CH3 HO(CH2)27CH3OH2SO4O(CH2)27CH3COH2SO4Oc. CH (CH )32 14OH2SO4CH3(CH2)14COH 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Chapter 19–11Od. CH (CH )32 2219.46CO(CH2)13CH3 H2Oa. CH (CH )32 18OH HO(CH2)13CH3C HO(CH2)29CH3b. CH (CH )32 24C HO(CH2)23CH3O(CH2)29CH3 H2OCO(CH2)23CH3 CCCH3(CH2)24 H2OCCH3(CH2)14 OH HO(CH2)17CH3 OH2OOd. CH (CH )32 12CCH3(CH2)18H2SO4Oc. CH (CH )32 14OH2SO4OH2OCCH3(CH2)12OHDraw a triacylglycerol that fits each description.OOCH2 O CO(CH2)10CH3lauric acida. CH O C(CH2)12CH3myristic acidc.OCH2 O C(CH2)7CH CHCH2CH CH(CH2)4CH3triacylglycerolCH2 O CO(CH2)12CH3CHO CO(CH2)12CH3CH2 O C(CH2)12CH3saturated triacylglycerollinoleic acidOOCH2 O COCH2 O CO(CH2)12CH3CH(CH2)12CH3d.b. CH O Ctwo cis double bondsOCH2 O CO COCH2 O C(CH2)7C CCH2C C(CH2)4CH3H Hone double bond(CH2)7C C(CH2)7CH3H HH Hmonounsaturated triacylglycerolunsaturated triacylglycerol19.48CCH3(CH2)22Draw the products of the hydrolysis of each wax.O19.47OH2SO4Draw a triacylglycerol that fits each description.OOCH2 O CO(CH2)10CH3lauric acidCH2 O CO(CH2)7CH CHCH2CH CH(CH2)4CH3a. CH O C(CH2)10CH3lauric acidb. CH O C(CH2)7CH CHCH2CH CH(CH2)4CH3OCH2 O CO(CH2)14CH3triacylglycerolpalmitic acidCH2 O C(CH2)7CH CHCH2CH CH(CH2)4CH3polyunsaturated triacylglycerol 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Lipids 19–12OOCH2 O COCH2 O CO(CH2)16CH3CH(CH2)16CH3d.c. CH O COHCH2 O CH(CH2)7C CCH2C C(CH2)4CH3CH2 O CHH(CH2)7CH CHCH2CH CHCH2CH CHCH2CH3unsaturated triacylglyceroltwo trans double bondstrans triacylglycerol19.49O CODraw the triacylglycerol that fits the description.OCH2 O COCH19.50(CH2)3CH CH(CH2)3CH3OhydrolysisO CO(CH2)3CH CH(CH2)3CH3CH2 O C(CH2)3CH CH(CH2)3CH33Na – OCin base(CH2)3CH CH(CH2)3CH3Draw the triacylglycerol that fits the description.OCH2 O COCH19.51(CH2)8CH3hydrolysisO CO(CH2)8CH3CH2 O C(CH2)8CH3in baseO3 Na – O C(CH2)8CH3Answer each question.Compounda. Generalstructure[1] Fatty acidRCOOH–[2] SoapRCOO Na[3] WaxRCOOR'[4] Triacylglycerolb. ExampleCOOH COO– Na COOOCH2 O CO(CH2)12CH3CHCHO CO(CH2)12CH3CH2 O C(CH2)12CH3CH2 O C R''d. Hexanesoluble(Y/N)YYNNYNYOCH2 O C ROO C R'Oc. Watersoluble(Y/N)N 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Chapter 19–1319.52Answer each question about fats and oils.a. Fats and oils are both derived from fatty acids and are triacylglycerols (i.e., they contain threeester groups).b. Fats contain few carbon–carbon double bonds, whereas oils contain a larger number of carbon–carbon double bonds.c. Fats have higher melting points and are solids at room temperature. Oils have lower meltingpoints and are liquids at room temperature. The melting point decreases as the number of carbon–carbon double bonds increases.d. Natural sources of fats include lard, butter, and whale blubber. Natural sources of oils includecanola oil, peanut oil, coconut oil, and fish oils.19.53Answer each question about the triacylglycerol.a.e.OCH2 OHHOOC(CH2)18CH3arachidic acidCH2 O CO(CH2)18CH3CHO CO(CH2)16CH3stearic acidCH2 O C(CH2)10CH3lauric acidCHOHCH2 OH HOOC(CH2)16CH3HOOC(CH2)10CH3b. It would be a solid at room temperature since it is formed from saturated fatty acids.c. The long hydrocarbon chains are hydrophobic.d. The ester linkages are hydrophilic.19.54Answer each question about the triacylglycerol.Oa.CH2 O CO(CH2)14CH3CH(CH2)7(CH CHCH2)2(CH2)3CH3O COCH2 O Cpalmitic acid(CH2)7CH CH(CH2)5CH3linoleic acidpalmitoleic acidb. It would be a liquid at room temperature because it is formed from two unsaturated fatty acidsand one saturated fatty acid.c. The long hydrocarbon chains are hydrophobic.d. The ester linkages are hydrophilic.OCH2 OHe.CHOHCH2 OH HO CO(CH2)14CH3HO CO(CH2)7(CH CHCH2)2(CH2)3CH3HO C(CH2)7CH CH(CH2)5CH3 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Lipids 19–1419.55Draw the products of triacylglycerol hydrolysis.Oa.CH2 O CO(CH2)14CH3O CO(CH2)14CH3CH2 O C(CH2)16CH3CHCH2 OHH2OH2SO4CHOHO 2 HOC(CH2)14CH3OHOCCH2 OH(CH2)16CH3OCH2 O COH2OO CO(CH2)14CH3CH2 O C(CH2)16CH3CHNaOH2CHOHONa –OCCH2 OH(CH2)14CH3H2OO CO(CH2)7CH CH(CH2)7CH3CH2 O C(CH2)7CH CH(CH2)5CH3CHH2SO4OHHOC(CH2)16CH3(CH2)14CH3O HOC(CH2)7CH CH(CH2)7CH3OCH2 OHHOC(CH2)7CH CH(CH2)5CH3OO19.56(CH2)14CH3OCH2 O COCHNa –OC CH2 OHOb.OCH2 OH(CH2)14CH3Na –OCCH2 OHCH2 O CO(CH2)14CH3CHO CO(CH2)7CH CH(CH2)7CH3CH2 O C(CH2)7CH CH(CH2)5CH3(CH2)14CH3OH2OCHNaOHOH Na –OC(CH2)7CH CH(CH2)7CH3OCH2 OHNa –OC(CH2)7CH CH(CH2)5CH3Draw the products of triacylglycerol hydrolysis.OOa.CH2 O CO(CH2)10CH3CHO CO(CH2)14CH3CH2 O C(CH2)16CH3HOCCH2 OHH2OH2SO4OCHOH (CH2)14CH3HOC(CH2)16CH3OH2O(CH2)14CH3CH2 O C(CH2)16CH3Na –OCCH2 OH(CH2)10CH3O COCHHOCOCH2 OHOCH2 O CO(CH2)10CH3NaOHCHOHCH2 OH (CH2)10CH3ONa –OC(CH2)14CH3ONa –OC(CH2)16CH3 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Chapter 19–15OOb.CH2 O CO(CH2)7CH CH(CH2)7CH3CH(CH2)16CH3O COCH2 O CHOCCH2 OHOH2OCHH2SO4OH HOC(CH2)16CH3(CH2)7CH CH(CH2)5CH3OOCH2 O CO(CH2)7CH CH(CH2)7CH3CH(CH2)16CH3CH2 O CHOCOCH2 OH(CH2)7CH CH(CH2)5CH3O CO(CH2)7CH CH(CH2)7CH3Na –OCCH2 OH(CH2)7CH CH(CH2)7CH3OH2OCHNaOH(CH2)7CH CH(CH2)5CH3OH Na –OC(CH2)16CH3OCH2 OHNa –OC(CH2)7CH CH(CH2)5CH319.57Phospholipids are lipids that contain a phosphorus atom. Sphingomyelins (c) contain phosphorus.Triacylglycerols (a), leukotrienes (b), and fatty acids (d) do not.19.58Cephalins (b) and lecithins (c) are phospholipids. Prostaglandins (a) and steroids (d) are not.19.59Draw a phosphoacylglycerol that fits each description.Oa.CH2 O CO(CH2)7CH CH(CH2)5CH3frompalmitoleic acidCH(CH2)7CH CH(CH2)5CH3frompalmitoleic acidO CO CH2 O P O CH2CH2NH3O–cephalinOb.CH2 O CO(CH2)10CH3fromlauric acidCH(CH2)10CH3fromlauric acidCH2O COc.CH CH(CH2)12CH3OCH NH COCH2 O O P O CH2CH2N(CH3)3O–19.60HO CH(CH2)16CH3fromstearic acid P O idylcholineDraw a phosphoacylglycerol that fits each description.Oa.CH2 O CO(CH2)7CH CH(CH2)7CH3fromoleic acidCH(CH2)7CH CH(CH2)7CH3fromoleic acidO CO CH2 O P O CH2CH2N(CH3)3O–lecithin 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Lipids 19–16Ob.CH2 O CO(CH2)12CH3frommyristic acidCH(CH2)12CH3frommyristic acidO CO CH2 O P O CH2CH2NH3O–HO CHc.CHCH2fromethanolamineCH CH(CH2)12CH3OfromHN C (CH2)14CH3palmitic acidO O P O dylethanolamine19.61Triacylglycerols do not have a strongly hydrophilic region contained in a polar head, so theycannot form a lipid bilayer.19.62A cell membrane having phospholipids that contain a high percentage of oleic acid would bemore fluid than a cell membrane having phospholipids that contain a high percentage of stearicacid.19.63Diffusion is the movement of small molecules through a membrane along a concentrationgradient. Facilitated transport is the transport of molecules through channels in the cellmembrane. O2 and CO2 move by diffusion, whereas glucose and Cl– move by facilitatedtransport.19.64Facilitated transport is the transport of molecules through channels in the cell membrane. Glucoseand Cl– move by facilitated transport. Active transport is the transport of ions across the cellmembrane against the concentration gradient. K ions move by active transport.19.65Draw the anabolic steroid 4-androstene-3,17-dione.methyl group at C13Ocarbonyl at C17methyl group at C10Odouble bondbetween C4 and C5carbonyl at C319.66Draw the anabolic steroid methenolone.methyl group at C13methyl group at C10methyl group at C1OHhydroxyl at C17double bondbetween C1 and C2Ocarbonyl at C3 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Chapter 19–1719.67Cholesterol is insoluble in the aqueous medium of the bloodstream. By being bound to alipoprotein particle, however, it can be transported in the aqueous solution of the blood.19.68LDLs are soluble in the blood because the polar heads of the phospholipids and the polar portionsof protein molecules are arranged on the surface. The nonpolar portions of the molecules areburied in the interior of the particle. This allows the LDL to be soluble in blood.19.69Low-density lipoproteins (LDLs) transport cholesterol from the liver to the tissues where it isincorporated in cell membranes. High-density lipoproteins (HDLs) transport cholesterol from thetissues back to the liver. When LDLs supply more cholesterol than is needed, LDLs depositcholesterol on the walls of arteries, forming plaque. Atherosclerosis is a disease that results fromthe buildup of these fatty deposits, restricting the flow of blood, increasing blood pressure, andincreasing the likelihood of a heart attack or stroke. As a result, LDL cholesterol is often called“bad” cholesterol. Since HDL cholesterol transports cholesterol back to the liver and removes itfrom the bloodstream, high levels of HDLs reduce the risk of heart disease and stroke, and it iscalled “good” cholesterol.19.70Anabolic steroids are synthetic analogues of androgens or male sex hormones. An example of ananabolic steroid is stanozolol. Long term use of anabolic steroids can cause health problems suchas high blood pressure, liver damage, and cardiovascular disease.19.71Answer each question about estrone and testosterone.a.OHO1313OHOestronetestosteroneb. The estrogen (left) and androgen (right) both contain the four rings of the steroid skeleton.Both contain a methyl group bonded to C13.c. The estrogen has an aromatic A ring and a hydroxyl group on this ring. The androgen has acarbonyl on the A ring but does not contain an aromatic ring. The androgen also contains aC C in the A ring and an additional CH3 group at C10. The D rings are also different. Theestrogen contains a carbonyl at C17, whereas the androgen has an OH group.methyl groupOketonemethyl groupOH17hydroxylgroupmethyl group10aromatic ringHOphenolOdouble bondketone 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Lipids 19–18d. Estrogens, synthesized in the ovaries, control the menstrual cycle and secondary sexualcharacteristics of females. Androgens, synthesized in the testes, control the development ofmale secondary sexual characteristics.19.72Answer each question about testosterone and rogesteroneOb. The androgen (left) and progestin (right) both contain the four rings of the steroid skeleton.Both contain methyl groups at C10 and C13, a carbonyl group at C3 and a double bondbetween C4 and C5.c. The androgen has a hydroxyl group at C17, whereas the progestin has a ketone group at C17.d. Androgens, synthesized in the testes, control the development of male secondary sexualcharacteristics. Progestins, synthesized in the ovaries, are responsible for the preparation of theuterus for implantation of a fertilized egg.19.73Prostaglandins and leukotrienes are two types of eicosanoids, a group of biologically activecompounds containing 20 carbon atoms derived from the fatty acid arachidonic acid.Prostaglandins are a group of carboxylic acids that contain a five-membered ring. Leukotrienesdo not contain a ring. They both mediate biological activity at the site where they are formed.Prostaglandins mediate inflammation and uterine contractions. Leukotrienes stimulate smoothmuscle contraction in the lungs, leading to the narrowing of airways in individuals with asthma.HO(CH2)6COOHCH CHCH(CH2)4CH3HOHCCCHa prostaglandinPGE1five-membered CH2COOHHNHCOCH2CH2CHCOOHCa leukotrieneLTC4no ringNH219.74Prostaglandins are not classified as hormones because they mediate biological activity at the sitewhere they are formed, whereas hormones are synthesized in one part of an organism and thenelicit a response at a different site.19.75All prostaglandins contain a five-membered ring and a carboxyl group (COOH). 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Chapter 19–1919.76Three biological functions of prostaglandins in the body are inhibition of blood plateletaggregation, relaxation of the smooth muscles in the uterus, and stimulation of uterinecontractions.19.77Aspirin and celecoxib are both anti-inflammatory medicines. Aspirin inhibits the activity of boththe COX-1 and COX-2 enzymes, whereas celecoxib inhibits the activity of COX-2 only.19.78Zileuton treats the cause of asthma by blocking the synthesis of leukotriene C4 from arachidonicacid by inhibiting the lipoxygenase enzyme needed in the first step.19.79Vitamins are organic compounds required in small quantities for normal metabolism and must beobtained in the diet since our cells cannot synthesize these compounds.19.80Vitamin D is technically not a vitamin because it can be synthesized in the body from cholesterol.19.81Answer each question about vitamins A and D.a.b.e.f.g.Vitamin A10 Tetrahedral carbons10 Trigonal planar carbonsRequired for normal visionDeficiency causes night blindness.Found in liver, kidney, oily fish,and dairyVitamin D21 Tetrahedral carbonsSix trigonal planar carbonsRegulates calcium and phosphorus metabolismDeficiency causes rickets and skeletal deformities.Found in milk and breakfast cerealsc. and d.alkenealkeneHCH3Cvitamin ACCH3HCCHCH3CH3CHalkenealcoholCH3CHCCCH2O HHpolar C–O,O–HCH3alkeneCH(CH3)(CH2)3CH(CH3)2HC Cvitamin DalcoholH Opolar C–O,O–HHCH2alkene 2013 by McGraw-Hill Education. This is proprietary material solely for authorized instructor use. Not authorized for sale or distribution in anymanner. This document may not be copied, scanned, duplicated, forwarded, distributed, or posted on a website, in whole or part.
Lipids 19–2019.82Answer each question about vitamins E and K.Vitamin E23 tetrahedral carbons6 trigonal planar carbonsAnti
Chapter 19–3 19.9 Draw the products of the hydrolysis of cetyl myristate. CH3(CH2)12 C O(CH2)15CH3 O cetyl myristate H2O fatty acid H2SO4 alcohol CH3(CH2)12 C OH O HO(CH2)15CH3 19.10 Draw the structure of each triacylglycerol as in Example 19.4. CH CH2 O O CH2 O C O C O C O (CH2)16CH3 (CH2)16CH3 (CH2)16CH 3 a. CH CH2 2 OH OH OH HO C (CH2)16CH3 O HO C (CH2)16CH3 O
Lipids are one of the macronutrients. Lipids provide a concentrated source of energy. The term ‘lipid’ refers to both fats (solid at room temperature) and oils (liquid at room temperature). Elemental composition of lipids Lipids are made up of three elements: carbon (C), hydrogen (H) and oxygen (O). Chemical structure of lipids
Part One: Heir of Ash Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18 Chapter 19 Chapter 20 Chapter 21 Chapter 22 Chapter 23 Chapter 24 Chapter 25 Chapter 26 Chapter 27 Chapter 28 Chapter 29 Chapter 30 .
Chapter 8 Lipids Classification of Lipids Lipids are divided into: –Saponifiable lipids — contain esters, which can undergo saponification (hydrolysi
animals few lipids can be used to synthesize carbohydrates or amino acids. Lipids include the vitamins A, D, E, and K, and include some non-vitamin enzyme cofactors. Lipids include a number of hormones, of which the most important are steroids and prostaglandins. Lipids act as insulation, and play a role in physical appearance of animals.
TO KILL A MOCKINGBIRD. Contents Dedication Epigraph Part One Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 Part Two Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18. Chapter 19 Chapter 20 Chapter 21 Chapter 22 Chapter 23 Chapter 24 Chapter 25 Chapter 26
cement concrete. In this paper we design RCC dome roof structure by using manual methods which gives detail design of RCC domes. The procedure of designing RCC domes was clearly explained and from the Analysis and design we get the Meridional Reinforcement, hoop Reinforcement of a dome and ring beam Reinforcement
Chapter 11 - Lipids Problems: 2-8,10-12,15-17. Lipids are essential components of all living organisms Lipids are water insoluble organic compounds They are hydrophobic (nonpolar) or amphipathic (containing both nonpolar and polar regions) 1. Free fatty acids 2. Triacylglycerols 3. Phospholipids 4. Glycolipids 5. Steroids
DEDICATION PART ONE Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 PART TWO Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18 Chapter 19 Chapter 20 Chapter 21 Chapter 22 Chapter 23 .
