Department of the Environment Fisheries and Marine Service Halifax Laboratory. Halifax, N.S.

Transcription

1 FISHERIES AND MARINE SERVICE Translation Series No On the determination of strongly unsaturated fatty acids in fish oils by Henrik. Bull Original title: 'Ùber die Bestimmung stark ungesittigter Fettsàuren in den Thranen. From: Chemiker-Zeitung (Journal for Chemists), 23(99) : , 1899 Translated by the Translation Bureau(RS) Multilingual Services Division Department of the Secretary of State of Canada Department of the Environment Fisheries and Marine Service Halifax Laboratory. Halifax, N.S pages typescript

2 .11> DEPARTMENT OF THE SECRETARY OF STATE TRANSLATION BUREAU geem :f-eu SECRÉTARIAT D'ÉTAT BUREAU DES TRADUCTIONS MULTILINGUAL SERVICES keite DIVISION DES SERVICES. CANADA DIVISION MULTILINGUES TRANSLATED FROM - TRADUCTION DE AUTHOR - AUTEUR German Henrik Bull INTO - 7inglish 1er-M_5_- 735 TITLE IN ENGLISH - TITRE ANGLAIS On tbe Determination of Strongly Unsaturated Fatty Acids in Fish Oils TITLE IN FOREIGN LANGUAGE (TRANSLITERATE FOREIGN CHARACTERS) TITRE EN LANGUE ÉTRANGÉRE (TRANSCRIRE EN CARACTÈRES ROMAINS) ner die Bestimmung stark ungesâttigter Fettsauren in den Thranen REFERENCE IN FOREIGN LANGUAGE (NAME OF BOOK OR PUBLICATION) IN FULL. TRANSLITERATE FOREIGN CHARACTERS. RÉFÉRENCE EN LANGUE ÉTRANGÉRE (NOM DU LIVRE OU PUBLICATION), AU COMPLET, TRANSCRIRE EN CARACTE'RES ROMAINS. Chemiker-Zeitung REFERENCE IN ENGLISH - RÉFÉRENCE. EN ANGLAIS Journal for Chemists PUBLISHER - ÉDITEUR not given PLACE OF PUBLICATION LIEU DE PUBLICATION not given YEAR ANNÉE DATE OF PUBLICATION DATE DE PUBLICATION VOLUME ISSUE NO. NUMÉRO PAGE NUMBERS IN ORIGINAL NUMÉROS DES PAGES DANS L'ORIGINAL 2 NUMBER OF TYPED PAGES NOMBRE DE PAGES DACTYLOGRAPHIÉES Jk -7 REQUESTING DEPARTMENT TRANSLATION BUREAU NO. Dept. of Environnent MINISTRE-CLIENT NOTRE DOSSIER Ne) BRANCH OR DIVISION DIRECTION OU DIVISION "h_sheries Service TRANSLATOR (INITIALS) TRADUCTEUR (INITIALES) PERSON REQUESTING DEMANDÉ PAR Dr. R. (. Ackman YOUR NUMBER VOTRE DOSSIER N 0 DATE OF REQUEST DATE DE LA DEMANDE Ar)ril 9, 1P"4. JUL 3 O974 1JNWUN5 TRÂNSWION kt* dôrtliation only TRADUCTION NON fk EVSCÀ: (REV. 2/.58)

3 a DEPARTMENT OF THE SECRETARY OF. STATE TRANSLATION BUREAU SECRÉTARIAT D'ÉTAT BUREAU DES TRADUCTIONS MULTILiNGUAL SERVICES DIVISION DIVISION DES SERVICES MULTILINGUES CLIENTS NO. DEPARTMENT DI VISI ON/BRANC H CITY N DU CLIENT MINISTÉRE DIVISION/DIRECTION VILLE Environment Fisheries Service Ottawa BUREAU NO. LANGUAGE TRANSLATOR (INITIALS) N I) DU BUREAU LANGUE TRADUCTEUR (INITIALES) C;-erman R.S. JUL 3 0 OM Reports from Analytical.Uractice On the Determination of Stronndz Unsaturated Fatty Acids in Fish Oils (Report from the Fisheries Iroducts Research Station in Bergen) Henrik Bull Methods for the quantitative separation of fatty acids which occur in fats have not yet been developed because, until now, it has only been Possible to separate the saturated acids. In order to remedy this lack to some extent, the method described below for the separation of strongly unsaturated fatty acids has been worked out. It is based on the solubility in ether of the sodium salts of the-. se acids,as briefly stated in my ast report (2 ). As is well known, large quantities of fish oils from different. sources are used in tanneries and it is now reasonable to assume that their usefulness is directly dependent on the presence of these strongly unsaturated fatty acids and that it would therefore be profitable to have accurate methods for the determination of these components. It would thus be very desirable if the tannery chemists were to investigate (2) Chemiker-Zeitung 1899, 996 UNEDITED TRANSIATi0 11 For informatiqn only TRADUCTION NON ravisu Information seuletncni-

4 2 the relationship mentioned above more closely. The method is as follows: 7 g of fish oil are accurately ^.'eighed into an -i^r1enmeyer flask of approximately 200 ml A capacity and boiled for dhour with 25 ml of sodium alcohblate (obtained by dissolvinf; 235 g of pure sodium metal in absolute alcohol and making up to 1 liter) under reflux on. a water bath, shakin,; vigorously.f.ro.m time to time. 7ven "^rhile boiling, an appreciable Guantity of soap usually separates out. After standing for approxi:nately 2 hours in the stoppered flask, the soap mass is broken down to a fine paste with a spatula and ml of anhydrous and alcohol-free ether is added. (thé ether must have been standing over a large quanti -:-y of dry calcium chloride for at least 24 hou.-s). The flask is immediately closed with a rubber stopper and vigorously shaken several times at approximately 2 hour inter^'a vals. Should. the solution gelatinire, this can be counteracted by shakin;. The mass is now filtered through a dry filter paper of approximately 150 mm diameter while the funnel, which should have aground. rim, is covered with a glass plate 7uhich has been moistened :aith a drop of g1yc,erine. The flask which receives the filtrate is connected to the funnel stem t.hrou.!:^:â P. perforated cork; for nurposes of air circulation, a short len;th of string is placed bet: reen the filter pa-cr and the funnel, as far 'doa;n as the funnel nec'^. An alicuot nortion i s,i )etted out fro:n the filtrate, for exa?nnle

5 100 ml, corresponding to 4 g of fish oil; the entire volume of liquid is assumed to be 175 ml. The fatty acid salt is separated from the unsaponified portion in the filtrate by shaking three times in a separatory funnel, each time with 20 ml of water; since the water partially dissociates the soap into acid salt and free alkali, some phenolphtalein and, before each shaking, some alkali must be added until a clear alkaline reaction results. If ah emulsion is formed, and this happens frequently, it must be broken down by the addition of as little alcohol as possible or of a few drops of alcoholic potassium hydroxide. Unsaponifiables are'obtained by distil-. ling the ether from the thoroughly shaken ethereal liquid. Free fatty acids are. obtained from the aqueous extract in the known manner. A very rapid and suitable method for drying the fatty acids or the unsaponifiables consists of evacuating, gently warming ( and vigorously shaking the substances, after. accurate weighing, in a round-bottom flask of amproximately 150 ml capacity; this takes only a few minutes, and oxidation of the fatty acids is completely avoided. It should also be noted that the above procedure can be combined with the determination of the acid number of the fatty acid. As the analyses given in the table prove, the method yields comparable and reliable results. The high iodine number of the acids is striking..*fr cod liver oil, the senarated fatty acids belong, on the avcrage,to the C nh2n _p,02 series.

6 4 The method also offers a very convenient means for the preparation of these strongly unsaturated acids from fish oil. rurther, it can be seen that the various fish oils contain very different quantities of these acids. Cod liver oil, with the exception of the Japanese variety, shows a high per- centage, especially the light-coloured samples. Remarkably low values are. shown for the whale oil of the northern seas. The cloudy' sardine oil appears to be r suspicious with only also the dark Japanese shark oil, whose content of unsaponifiables comes up to only In the case of porpoise p.1044 jaw oil, the figures obtained indicate that a nearly satura- ted acid of low molecular weight has been dissolved. As could be expected from the.start, almost nothing is dissolved when last-mentioned the three e vegetable oile reported last are examined. It is obvious that, with suitable modifications, the above procedure could be used with potassium salts; however, it has not been possible, until now, to obtain uniform results;. the solubility of potassium salts is apprecia- bly greater than that of sodium salts and it is influenced in great measure by the quantity of alcohol, glycerine and moisture.

7 ! F) Translation of Table A - Type of I+'ish Oil B - Ac i d T!. umb e r C -- Saponification '.'Tu,.iber D - Iodine T^,umber?^ - Suecific sravlty at 15 C F -- of the oil G - Yith Sodium: ' ttnsaponifiables H - Pa.tty Acids I - Acid TÏumber J - Iodine Number 1 - Cod liver oil, steamed, medicinal, Lofoten 2 - ri If it If 11 Ja7Jan it It 3 + crude n " 4- If It n r+ u ^r 5 - " n It " It Finnmark 6 - u u n u u Lofoten 7 - clear.'r It g- 11 if it 9 - it commercial 10 - If clear brown It " 11 - it ^r rr If If If America 12 - n rr u +r n ++ Hamburgr 13 - n " " " it medicinal Lofoten 14 - " it " It if pressed It 15 - brovin Hamburg 16 - " it it 11 Lofoten 17 - Pollack liver oil pale Aalesund 18 - It it it ^ it if 19 - Ling liver oil " 20 - Sardine oil " Japan 22 - it It clear n " if 23 y n u it n 24 - " " clear brown " 25 - if rr cloudy 26 - Herrin-, oil 27 - n n clear n n ^g - u it pale u it It it It " n cloudy " Sl - If " filtered cold it If br. o:vn 7nn-land Antarctic P.iE'-'?Zt whale oil Amer ica -4 -%`P-ia1.e oil No. 1 unrefined I{'innmark -r - It I1 ++ If ref ined Glas^7or7 ü6 - Arctic -iha7.e oil If k!ierica,,7 - Crude White whale oil " ^-3 -'o`ha.1.e oil No. 2 unrefined Finnmr r?<

8 e Yellow whale oil 40 - Whale oil No Brown whale oil Whale oil No Dark whale oil ',Ihitefish oil Fatural.51ackfish body oil.forpoise body 911 Porpoise jaw oil Bleached white sperm oil Natural Arctic sperm oil Arctic sperm Sunfish on Crampfis% oil Sturgeon oil Hooded seal oil (large seal) Polar bear oil Greenland shark oil (small shark) u Shark oil II II Dark Japanese shark oil Extra refined menhaden oil Natural pressed " II Newfoundland àeal oil Seal oil 66 - Three Crown oil 67 - Refined linseed oil 68 - Olive oil Rapeseed oil refined unrefined refined unrefined refined Glasgow Finnmark Glasgow Finnmark Glasgow Pinnmark America u Sandefjord u America Nor'.vegian Sea It tt Finnmark It Japan Hamburg America Hamburg Sandefjord Hamburg

9 ' 1 10.J.- 1 p ( J `1' '-i V '' tt ' - ' 4, Y.r. -.., 111.1br «drr Thr nh..,.,. 1 11orechirbettlunii, Dampf-, medicinal-, Lofoten t: 11 1, 1 1 I t 11 1, 11 Lofoten 14,9 181,0. 155,0 blank, ,0 18.1, ,5 181,2 induatrieller,... 23,1 181, braimblank, 11 17, , n 11 Amerika 19,2. 12,, 1, l Hamburg... 22, n n medicinal-, Lofoten 24, n gepreggt,,.. 25,1. 15 n brawl, Ilaniburg 31,9. '16 II Lofoten 87,4 17 Sejleberthrail, hell, Aalegund. 7,2. 18 n 21,6. 19 lengleberthrtin, hell, '. 10,9. 2i} Sardinenthran, Japan 2,2. 21 blank, 1 2, » I, n. 12,0. 23 n 1, 14, brannblank, Japan ; ,7. /1. trnbc, Jr.t.pan. 34, Ileringel, blank, Japan 1, , ' 8,2. 28,, hell,,, 10, , 11 15,7 «;11 11 trilbe,, 12, kalt ftltriri,, J apan ' s, knurl w 'England. 40,2. 3:1 Antarctic Ri ght hale oil, Amerika.. 0; Walthran No. 1, unraffinirt, Finmarken. ' ,86 35 n raflinirt, Waggon....,.... ' Arctic 'Whale oil, Amerika... 1,11 37 Crude 1Vhite Whale oil,...." althrmi No. 2, nuraffinirt, Finmarken ; :,.... ;. 3,6 39 Yellow hale oil, raffinirt, Manor.' ,0. 40 Walthran No. 3, limn ffinirt; Fitunarken... 26, ,-rti Whale oil, rnflinirt, Olaagovr. 37, Walthran No. 4, unraflinirt, Finmarken 3 Park Whale oil, raffinirt, Glasgow : 98,5 41 Weig.figclithran, Finmarken 45 D1n1urn1 Blnektigh body nil, Amerika... 0,75.., : Porrmige -body oil, Amerika 0,0 47 l`orrige ja n- oil,,, 5, rIelied white Sperm oil, Amerika 0,0 49 lçal-lral -, il ij Auttic Sperm oil, Sandefiard. 11,4 51 Arctic Sperm, Sandefjord : 0,9 52 Sonfigh oil, Amerika.. ' 2, Crampfigh oil,. -. : 0,79-51 Sturgeon. 0, Klapmydathran (gr. Seehund), Niirdl. Eiameer OS 56 Eigbiirenthi:nn;Niirdl. Eiameer 0,46-57 llaakjiirringthran ell. Ilaifisch), Finmarken Ill lia lit or, Shark oil, Japan 0,88 n 1, n 1,50. 'Milkier Japan-Hrtifigehtliran, Ilamburg 39,0 Extra relined Menhaden oil, _Amerika 0,0. 'Natural incased n 10,81. Newfo undland Seal oil, Hamburg - 0,77. ltublienthran, Sandefjord 12,2. Drei Kronen Thran, Hamburg 20,7. Raflinirtea I.eimil 10,1. Olii emil 1,7 ltapqal 5,7. CI 1 li;n1 II< ,1PATIJ NO. V,,,, 7:1111 7nI 1 0,81 183,2..' n Japan.... 1, , roh, ' 5, ,7 11 u li 11 1;. 187, n II it I. 1. Finmarken 12, ,0 6, r 'Ilram 1) (j Jtulzaht. 144,6 156,0 161,7 I,.., e.". 0, , , Ntlitrn11 I. tut.,i4,17/ _...infq0. 9..?.5; Ogg 152,5 0,9247. if.,e;81 19: ,,11'.1100,4 1115, ,83 13,02 190,7_ ,8 0,9272 2,07 11, ,7 0,9259.2,33. 11,89 180,8 ;io ,2 0,9250 2,1 16, ,5 323,7 1 WV 2,2. 18,03 0, ,83. 20, ,7 313,0 2,11. 20,85 J Id 2,16 17,22 «2,15. 17,70 ' 2 2'2 314,0 2, , ', 2,02. 17,5 " a"." 2,4 18, ,43 17,5 199,8 179,0 141,0. 0,0224 4se M: ,0,1 181, , ,83 18, , ,2 106,8. 0,9256 3,45 15,57 193,7 312,9 180, , : 1.? 180,1 339,21;. 185,0 154,3.. 0, i3,3'. 8.1 ; 183;1:7 :339,8i 175,2. 147,9 -. 0, , ,7 319,5 168, ,5.. 0,9110..,M 71. r 22,! (3) 1 ;);.,03 307,9. 183,7. 102,2.. 0, , ,5 315, 1! 180, , ,83. 16,13 197,9 351,9 181,1 132,6 0,9200 2, , ,6 305,5 189,0. 131, :3. 1,90. 12,12.. 1M,2 285,8 103,7 102,4 0, , ,6. 100,6 398,0. 191,9. 156,2. 0,9279 1,9. : 17,4 193,7 32.1,0. 191,4 138,3 0, , , ,2 305,2. 190,6. 171,3.. 0,9: , , ,5. 858,3 178, , ;27. 6, ,2 292,8. 170,9 131,0. 0, , , ,0 290,2., , ,75. 12,55 187,5 315, ,0. 0, ,58. 12, ,5 310,2, 193,7. 131,8.. 0,9:110. 2,15 13, ,4 289,3 181,6, 134,2. 0, ,33. 9, , , ,5. 0, , , ,2 919,8. 184, ,7. 0, ,61 ;..11, , , ). 0, ,40 19, ,0 315,0. 188,6. 101,0.. 0, , 6. 5,0. 203,0. 184,7. 113,2.. 0,9214. ' , ,5 291,F,. 185, , ,11.. 7, u, 183, ,4. 0, ,37.. 8, E. 188, I8. 3,3., 4, ,3 252,F, 185, ,0. 0, ,89 5, ,8 251,C ,0. 0, ,42. 5, ,f.. 100,0. 125, ,22. 7, ,1 251,11 182,1. 89,0.. 0, ,4. 4, , ,1 0,9170 3,03. 4, ,8. 201, ,4. 0,9208. PHIrct 195,4 287.,1 203,4 120,9 0, ,01. 14,3. 313, ,0. 119,4 0,9258. ; 3,7 19; ,4 392;i: 209,3. 21,5.. 0, ,4 21,13 307,8 129,2 85,7. 0, , , ,4 130,1 136,9 90,1. 0, , , ,9 159,t. 121,5.. 79,7.. 0, ,09. 5, ,0.125, 122,3.. 67, ,61 3,65 105,8 121,1'. 147,fi 102,7 0,901 24,12 10, , ,3. 0, ,97 7,33 1R5,4. 186,3 125,3. 0, ,78. 9, ,7 281,t,.. 186,8. 147,1 0,9250 Vi)64 350,0 187, ,0,. 0, ,18.. 9, ,5 244,4. 148,5. 114,9 0, ;:t.3J 183, , ,9. 0, ,2 230,ç 163,5 136,0. 0, ,54 8,57 >3,0 312., 163,4. 128,3. 0, ,39.. 7, ,9 183,2. 116,3. 0, ,43. 6,7. 197, , ,6.. 0, ,43. 23, ,2 11I.. 193,0 130,2.. 0, , ,24 201,8 302: 100, ,4.. 0, ,83 11, ,8 130:q 187, ,2. 0,9249 1,8. 7, ,8 100,. 174,8. 156, , , , , ,0. 2, ,0.. 83, ,87 1,32 20:4, :4,! , , t ;