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Studies on Seed Fats and Fatty Acids

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Studies on Seed Fats and Fatty Acids STUDIES ON SEED FATS AND FATTY ACIDS RESUME THESIS SUBMITTED FOR THE DEGEEE OF Doctor of Philosophy IN Chemistry TO THE ALIGARH MUSLIM UNIVERSITY, ALIGARH RAFI AHMAD r^^ 3 A^^ DEPARTMENT OF CHEMISTRY^^^ ALIGARH MUSLIM UNIVERSITY ALIGARH (INDIA) 1987 I Resume Two types of investigations have been described in the thesis: First part deals with the compositional studies of minor seed oils. The second part illustrates the results of derivatization of fatty acids. AGO NO. PART ONE In continuation of the chemical screening programme of oil-yielding species to explore the oilseed potential of forest flora, thirteen seed oils have been examined for their gross fatty acid profile. A, Minor Seed Oils Six wild oil-bearing species, namely Embelia ribes (Myrsinaceae), Chenopodium album (Chenopodiaceae), Alstonia verticillosa (Apocynaceae), Dolichos biflorus (Leguminosae), Acer negundo (Sapindaceae), Quercus incana (Fagaceae) have been analyzed by various chromatographic and spectroscopic techniques. : ii : Palmitic, stearic, oleic and linoleic acids were found as common constituents of all the seed oils. Three seed oils namely, Embelia ribes, Chenopodium album and Alstonia verticillosa were found to contain 61,4yif 64,Oyi and 73.7>< oleic + linoleic acids, respectively. A, verticillosa is rich in oil content (25,5><) and was significantly found comparable with that of groundnut oil with respect to their fatty acid composition [especially to the contents of oleic (-^ 54j<) and linoleic ('^20><) acids], B, Cyanolipid in Seed Oil of Koelreuteria apiculata(Sapindaceae) Four types of cyanolipids present individually or in pairs have been identified in the seed lipids of Sapindaceae and Boraginaceae, During our compositional studies on indigenous seed oils, Koelreuteria apiculata seed oil responded to Prussian blue test indicating the presence of cyanolipid. Cyanolipid was separated by preparative TLC (33,4^) and characterized by spectroscopic and chromatographic analyses as a diester of l-cyano-2-hydroxymethylprop-l-ene-3-ol. The seed oil also con­ tains 44,6j< of a C2Q-nionoenoic acid besides other usually occurring fatty acids, C, Palmitoleic Acid in Zanthoxylum budrunga(Rutaceae) Seed Oil Seed oil of Zanthoxylum budrunga (Rutaceae) contains Cj^^ monoenoic acid (10,0^<) which is an unusual acid among the : iii : common unsaturated acids. This monoenoic acid was characterized as cis-9-hexadecenoic acid from the GLC analysis of methylated fragments obtained by oxidative cleavage of the acid using permanganate-periodate reagent. The fatty acid composition was found to be 16:0, 26.2; 16:1, 10.0; 18:0, 5ol; 18': 1, 34.1; 18:2, 14o2 and 18:3, 10.4^<. Do Cyclopropenoid Fatty Acids in Seed Oil of Firmiana colorata (Sterculiaceae) The seed oil of Firmiana colorata of family Sterculi­ aceae responded to Halphen test and showed characteristic spectral data for cyclopropenoid fatty acids (CPFA). GLC analysis of the silver nitrate-methanol treated methyl esters using Sterculia foetida esters as reference standard showed the presence of 14.7>< sterculic (9,10-methyleneoctadec-9-enoic) acid and 4,3j< malvalic (8,9-methyleneheptadec-8-enoic) acid. E. Epoxy Fatty Acids ( i) Seed Oils Containing Vernolic Acid The seed oils of Centratherum ritchiei and Sonchus oleraceus both of family Compositae responded to picric acid test and showed diagnostic spectral data, has been found to contain : iv : vernolic ( cis--12t 13~epoxvoctadec-cis-9-enoic) acid, 30.1>< and 13,7><^respectivelyo The occurrence of this acid was confirmed by TLC, GLC, IR, NMR and MS and chemical methods. ( ii) Seed Oil Containing Coronaric Acid Acacia albida (Leguminosae) seed oil was found to con­ tain 7,8j< coronaric (cis-9,10~epoxyoctadec-ci5-'12~enoic) acid in addition to the other common fatty acids. Direct acetolysis of the oil followed by saponification yielded corresponding dihydroxy acid which was characterized by various spectroscopic and chemi­ cal transformations. Quantitation of coronaric acid was done by GLC using Chrysanthemum coronarium seed oil as reference standard and by HBr-titration at 3 C. F, HBr-Reactive Fatty Acids of Helicteres isora(Sterculiaceae) Seed Oil Seed oil of Helicteres isora of family Sterculiaceae was found to contain both epoxy and cyclopropenoid fatty acids alongwith common fatty acids. Its oil contained malvalic (0.6;<), sterculic 1.0^^ and epoxy (vernolic) 5,8A Characterization of HBr-reactive acids was carried out by chromatographic, spectro­ scopic and chemical methods. PART TWO The second part illustrates the results of synthetic reactions on 10-undecenoic acid , The structure of each product has been established by combustion and spectral data, A, Olefin-Aldehyde Condensation Reaction of 10-undecenoic acid (I) and formaldehyde in the presence of acetic acid and sulphuric acid at 50-70 C afforded 3-(carboxyoctyl)-2,5-dihydrofuran (II) and 5-(carboxy- octyl)-l,3-dioxane (III) (Scheme-l). Scheme - 1 CH2 = CH - (CH2)g - COOH (I) 1. HCHO 2. AcOH 3. H2SO4 50-70 C C-(GH2)Q-COOH HC "2P ^^"^ ^"2 ^ 8"^^" H2C. CH, 0 CH2 •^0 Hj:—0 (II) (III) VI : Similar treatment of lO-undecenoic acid (I) with benzaldehyde yielded 2,5-diphenYl-3-CcarboxY0ctyl)-2>3-dihYdro- furan (IV) and 2,4-diphenyl-5-(carboxyoctyl)-l,3-dioxane (V) (Scheme-2). Scheme - 2 CH2 = CH - (^2)3 - COOH (I) 1. U 2. AcOH 3. H^SO^ 50-70 C •'V HC C-(CH2)g-.C00H + HoC CH-(CH^)p-COOH rV—v/ "^ \ /^H-^ (IV) (V) lO-Undecenoic acid, was allowed to react with salicyl- aldehyde under the similar conditions described in previous two schemes. The products were characterized as 2,5-di-(2'-acetoxy- phenyl)-3-(carboxyoctyl)-2,5-dihydrofuran (VI) and 2,4-di-. (2'-hydroxyphenyl)-5-(carboxyoctyl)-l,3-dioxane (VII) (Scheme-3)c : vii : Scheme - 3 CH^ = CH - (CH2)g - COOH (I) 1. 2. AcOH 3. H2SO4 50-70 C V HC C-(CH2)g-C00H -CH-(CHO)Q-COOH / \ r^ Ht in 0 ^0^ \ HC- -O HO H3C-C-S 0 9 j^0-C-CH3 -OH ^ "^ (VI) (VII) B, Carbon-Carbon Bond Formation Reactions Oxymercuration of 10-undecenoic acid (I) in the pre­ sence of tetrahydrofuran and water gave mercuric acetate adduct (VIII), The adduct was demercurated in the presence of sodium borohydride and acrylic acid in DMF and afforded 5-hydroxytetra- decanedioic acid (IX) (Scheme-4), : viii Scheme - 4 CH2 = CH - (CH2)g - COOH (I) Hg(0Ac)2 THF, H2O CH, o2 - C,H - (CHo)2 «8 - COOH \jg OH OAc (VIII) NaBH^ CH2=CH-C00H DMF HOCC- (CH2)3 - CH - (CH2)8 - COOH OH (IX) The mercury acetate adduct (VIII), on demercuration in the presence of NaBH. and acryx^onitrile in DMF, yielded u>- cyano-10-hydroxytridecanoic acid (X) (Scheme-5). IX Scheme - 5 CH2 - CH - (CH2)8 COOH Hg OH OAc (VIII) NaBH^ CH2=CH-CN DMF NC - (^2)3 - CH - (CH2)g - COOH OH (X) STUDIES ON SEED FATS AMD FATTY ACIDS THESIS SUBMITTED FOR THE DEGREE OF Doctor of Philosophy IN Chemistry TO THE ALICARH MUSLIM UNIVERSITY, ALICARH RAFI AHMAD DEPARTMENT OF CHEMISTRY ALICARH MUSLIM UNIVERSITY ALICARH (INDIA) 1987 v^, JUL 1988 ^•^• m T3426 ^. Section of Oils 8 Fats Department of Chemistry Aligarh Muslim University Pr fossor of Chemistry ALIGARH-202001 (India) Ref No DATE This is to certify that the work embodied in this thesis entitled, 'Studies on Seed Fats and Fatty Acids', is the original work of Mr. Rafi Ahmad carried out under my supervision. The thesis is suitable for submission for the award of the degree of Doctor of Philosophy in Chemistry. ^ (S.M. Osman) Dedicated To My Parents, Sister & Brother Acknowledgments I wish to express my deep sense of gratitude to Professor S.M. Osman for his valuable guidance and consistent encouragement throughout this research work. I am thankful to Professor W. Rahman and Professor M.S. Ahmad, Chairman, Depart­ ment of Chemistry for providing necessary facilities and useful discussions. It is with pleasure, that I thanks Drs. Fasih Ahmad, Ishtiaque Ahmad and Mushfiquddin Khan, whose generous help at every stage greatly eased the task of the completion of this work. In addition I thanks my other research colleagues who have rendered assistance in different ways. The valuable instru­ mentation services of Aligarh Muslim University, Aligarh; RSIC, Lucknow and RFIL, Hyderabad are appreciated much. Finally I acknowledge university grants commission, New Delhi for financial assistance. ( Rafi Ahmad ) Contents Page Summary i-ix Introduction 1 PART ONE : COMPOSITIONAL STUDIES OF MINOR SEED OILS Chapter-1 : a. Fatty Acid Composition of Vegetable Seed Fats b. Analysis of Minor Seed Oils 9 Experimental 16 Chapter-2 a, Cyanolipids 20 b, A Cyanolipid from Koelreuteria apiculata Seed Oil 30 Experimental 36 Chapter-3 a, Palmitoleic Acid (cis-9-hexadecenoic acid) 39 b. Palmitoleic Acid in Zanthoxylum budrunga (Rutaceae) Seed Oil 40 Experimental 46 Chapter-4 a. Cyclopropenoid Fatty Acids 48 b, Cyclopropenoid Fatty Acids in Seed Oil of Firmiana colorata (Sterculiaceae) 56 Experimental 60 Chapter-5 : a, Epoxy Fatty Acids ., .. 63 b. Seed Oils Containing Epoxy Fatty Acids .. .. 69 Experimental ,. .. 86 Chapter-6 : a. HBr-Reactive Fatty Acids ., ,. 91 b. HBr-Reactive Fatty Acids of Helicteres isora CSterculiaceae) Seed Oil ,, ,. 92 Experimental „, ,, 97 Bibliography ,<> ., 98 PART TWO : DERIVATIZATION OF FATTY ACIDS Chapter-7 : Olefin-Aldehyde Condensation Reaction ,, ,, 116 Chapter-8 : Carbon-Carbon Bond Formation Reaction ., ., 129 Experimental ., ,. 135 Bibliography ., ,. 143 Publications and Presentations ,. ,. 146 Summary Two types of investigations have been described in the thesis: First part deals with the compositional studies of minor seed oils. The second part illustrates the results of derivatization of fatty acids. PART ONE In continuation of the chemical screening programme of oil-yielding species to explore the oilseed potential of forest flora, thirteen seed oils have been examined for their gross fatty acid profile, A, Minor Seed Oils Six wild oil-bearing species, namely Embelia ribes (Myrsinaceae), Chenopodium album (Chenopodiaceae), Alstonia verticillosa (Apocynaceae), Dolichos biflorus (Leguminosae), Acer negundo (Sapindaceae), Quercus incana (Fagaceae) have been analyzed by various chromatographic and spectroscopic techniques.
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