FISHERIES AND MARINE SERVICE. Translation Series Na by F. Tunis, and T. Sciortino

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1 4tr e, i v es FISHERIES AND MARINE SERVICE Translation Series Na Gas-chromatographic determination of cod liver cil ln an clin Linon:, by F. Tunis, and T. Sciortino Original title: Determinazione gas,-cromatografica delllolio di fegato di merluzzo in una pomata From: Bolletino di chimaca farmaceutica (Bulletin of pharmaceutical chemistry),.111 : , 1972 Translated by the Translation Bureau( le) 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 DGPARTMENT OF THE SECRETARY OF STATE TRANSLATION BUREAU I e tie k - SECRÉTARIAT D'ÉTAT BUREAU DES TRADUCTIONS MULTILIMGUAL SERVICES DIVISION ree. CANADA DIVISION DES SERVICES MULTILINGUES TRANSLATED FROM - TRADUCTION DE INTO - EN F.e8 3eibe,/ AUTHOR - AUTEUR Italian English Tunis, F. et al. TITLE IN ENGLISH - TITRE ANGLAIS Gas-chromatographic determination of cod liver oil in an ointment TITLE IN FOREIGN LANGUAGE (TRANSLITERATE FOREIGN CHARACTERS) TITRE EN LANGUE ÉTRANGÉRE (TRANSCRIRE EN CARACTÉRES ROMAINS) Determinazione gas-cromatografièa delltolio di fegato di merluzzo in una pomata 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 CARACTÈRES ROMAINS. Bolletino di chimica farmaceutica REFERENCE IN ENGLISH - RÉFÉPENCE EN ANGLAIS Bulletin of pharmaceutical chemistry PUBLISHER ÉDITEUR PLACE OF PUBLICATION LIEU DE PUBLICATION YEAR ANNÉE DATE OF PUBLICATION DATE DE PUBLICATION VOLUME ISSUE NO. NUMÉRO PAGE NUMBERS IN ORIGINAL NUMÉROS DES PAGES DANS L'ORIGINAL NUMBER OF TYPED PAGES NOMBRE DE PAGES DACTYLOGRAPHIÉES REQUESTING DEPARTMENT MIN -ISTÈRE-CLIENT TRANSLATION BUREAU NO. Environment NOTRE DOSSIER NCI BRANCH OR DIVISION DIRECTION OU DIVISION Fisheries Service TRANSLATOR (INITIALS) t.q. Butler TRADUCTEUR (INITIALES) PERSON REQUESTING DEMANDÉ PAR Dr. R.G. Ackman APR 2 2 i74 YOUR NUMBER VOTRE DOSSIER N 0.. DATE OF REQUEST DATE DE LA DEMANDE March 11, S (It E V. 2/60)

3 ,. DEPARTMENT OF THE SECRETARY OF STATE TRANSLATION BUREAU MULTILINGUAL SERVICES DIVISION SECRÉTARIAT D'ÉTAT BUREAU DES TRADUCTIONS DIVISION DES SERVICES MULTILINGUES CLIENT'S NO. DEPARTMENT DIVISION/BRANCH CITY NO DU CLIENT MINISTÉRE DIVISION/DIRECTION VILLE Environment Fisheries Service Ottawa BUREAU NO. LANGUAGE TRANSLATOR (INITIALS) N DU BUREAU LANGUE TRADUCTEUR (INITIALES) Italian M. Butler April 12, 1974 y.y.ft) GAS-CHROMATOGRAPHIC DETERMINATION OF COD LIVER OIL'" - Fcr IN AN OINTMENT ent SUMMARY. - The fatty acids composition of a sample oj cod liver oil, present in an ointment, has been compared with that Of a F.U. commercial sample. The qualitative and quantitative determinations of the fatty acids have been performed by ti.c.. _ Info rw:aiion SeIQnt There are numerous studies on cod liver oil, given the interest of this product for the industrial and pharmaceutical fields: the proof of this is that it is still entered in the most widely circulated pharmacopeiae. The Official Italian Pharmacopeia, 7th Ed. (1965) in the monograph on cod liver.oil, in addition to controls of a physical nature, requires determinations of the indices of acidity, iodine, saponification and the vitamin A and D levels, which must be no less than 600 and 85 I.U. per gram of oil, respectively. Since the presence of the vitamins determines the value and efficacity of the medicine and its preparations, many researchers have concentrated on the study of these substances as present in the natural product. More recently, several authors (1-12) have concerned themselves mainly with the basic components of the oil, the fatty acids, SOS

4 2 using the gas chromatographic technique. However, also in relation to the sampling and particular methodology, it seemed to us that the results obtained are still very contradictory. In the present work, we undertook the identification and percentage calculation of the main fatty acids of the cod liver oil present in an ointment used pharmaceutically, and at the same time, on an F.U. commercial sample of cod liver oil. The ointment showed the following composition: Cod liver oil (corresponding to 24,000 I.U. of vit. A and 3,400 I.U. of vit. D.) Purified yellow wax Yellow vaseline 40 gr. 10 gr. 50 gr. EXPERIMENTAL PORTION Preparation of samples Saponification was carried out on a 3.75 gr. sample of ointment and a 1.5 gr. sample of oil, with the addition, in both cases, of 20 ml of an alcoholic solution of 10% potassium hydroxide, placing the samples in a bain-marie for an hour in a distilling flask with a cooling coil. Only the sample containing the ointment was cooled to about o. 20 C with continuous shaking and then filtered through a paper filter. The residue was recoveredmith about 10 ml of the alcoholic potassium hydroxide solution, heated and then cooled as above; the filtrate thus obtained was added to the preceding one.

5 3 Following acidification with sulfuric acid 1:4, the fatty acids of each of the two solutions were extracted with two portions of 20 ml of ethyl ether each, and left in an ethereal solution for a few hours in the presence of anhydrous sodium sulfate. Following evaporation of the solvent in a nitrogen current with a rotating evaporator, methylation was carried out with trifluoride of boromethanol (13) and the methyl esters of the fatty acids wem then extracted with 30 ml of petroleum ether at C. In this case as well, the solvent was removed by distillation in a nitrogen current, with a rotating evaporator, avoiding any oxidation to the air. Gas-chromatographic analysis The methyl esters thus obtained were analyzed with a gas chromatograph FRACTOVAP mod. D of the C. Erba firm, using a flame ionization detector. The stainless steel column 2 meters long with an inside diameter of 2 mm, was filled with Chromosorb W mesh containing 20% of EAS.. The conditions of analysis were: temp. of column 205 C, temp. of detector 255 C, temp. of evaporator 300 C, nitrogen flow 20 ml/min., hydrogen flow 25 ml/min., sample injected 0.25 pl. The theoretical number of plates of the column used was calculated at 1800, as regards the acid C18t1. The peaks revealed were identified by comparing the retention times with those of the reference samples, according to the diagram log t.r. / number of C atoms for the saturated acids and the t.r.l :l

6 4 monoenoic acids (21-23); the polyunsaturated acids according to Ackmann (14-20). Figure 1 shows a chromatogram relative to the oil extracted from the ointment; Table 1, on the other hand lists the % areas of the two samples occupied by each acid present, with the probable position of the double bonds, and the t.r. relative to the C18:1. S(,3 St.i... 1.,.f.) I 7a Fig. 1- Gas-cromato,ramma dei metil-esteri de; ]i acid:- grassi deli'olio di fe;at4 di merluzzo. Fig. 1 - Gas chromatogram of the methy^!esters of the fatty acids in cod liver oil. RESULTS AND DISCUSSION Using a gas chromatograph with a flame ionization detector, we proceeded, following extraction, with the identification and percentage calculation of the main fatty acids in cod liver oil, a component of an ointment. From the comparative examination of the values obtained with those of an F.U. commercial sample, it was possible to confirm the optimal separation of the fatty acids from the wax-vaseline mixture of the ointment in question. In addition, in the two samples, no qualitative differences were noted, while on the other hand, there were some quantitative discrepancies in some fatty acids.

7 5 % unsaturated fatty acids Lastly, the ratio which, for the % saturated fatty acids oil extracted from the ointment is 3.84, is 4.36 for the F.U. Probable position Peak Fatty double No., acids bonds Table 1 Oil ex- I F. U. cod tracted liver! from t.r. for oil i ointment 18:1 Area % Area % 1 14: 0 0, : 1 9 0,33 0,36 15 : 0 0, : 2 0,." : 0 0,50 16 : ,59 11,72 12,03 17 : 0,63 0, - o 16 : 17 : 1 5, 9 0 9, ,75 0, : ,28 2,30 12 ( 12 : 1 16 : 3 18 : 2 20: 0 9* 6, 9, 12 9,12 1,00 1,22 1,46 22,80 1,69 0,10 27,31 1,4 8 0, : 1, 9,12,15 11 " 1,69 13,23 12, : 4 20 : 2 6, 9, 12, 15 11, 14 1,89 2,08 1,69 0,27 1,75 0, : 3 8; 11, 14 2,51 0,69 0, :4. 22 : 1 5, 8,11, 14 13? 2,75 6,63 c:, : 4. 8, 11, 11., 17 3,93 0, : 5 5, 8, 11, 14, 17 3, ' : «5 4, 8, 12, 15, 18 3,99 trz.c. trae ^ : : 1 22: 5 22 : 6 7, 10, 13, " 8, 12, 16, 19 o 3, 12, 15, 19 7, - 10, 13, 16, 19 4, 7, 10, 13, 16, 19 4,71 4,90. 5,32 6,11 6,98 0,10 0,8 1 0, ,13 0,68 0, ,e.4 * Other isomers.

8 6 BIBLIOGRAPHY 1) KAUPMANN KHOE T.H. - Fette, Sei/en, Anstrichmittel, 66 (8), 590-7, ) IVERSON J.L. - J. Assoc. 011ie. Anal. Chem., 53 (5), , ) DE: Wrr -r K.W. - J. Sci. Food A gr., 14, 92-8, ) KLENK E., EIERHAGEN D. - Z. Physiol. Chem., 328, 180-8, ) E. - Pkarmazie, " 0, 19(2. 6) CULiCER Ell., NELSON ;JR. R.W., ST N:dn. - J. Am. Oil Chemist's Soc., 41 (10), ) ACK MANN R.G., BURGHER 11.D. - J. Fisheries Res. Board Can., 21 (2), , ) DomEs.ovA S.R. - 1w. Uysshikh. lichebn. Zacedenii, Pishrhevaya Teehnol., (3), 65-8, ) i_.amullurse.n G., DRAEKKAN Fiskeridirektorat. Skrif ter, Sec. Teknol. lindersoek, ( 1),14, ) I Eus.oN J.L. I. Assoc. 011ic. Agr. Chern.,111 (3), 902-4, ) f'.c..mann R.G., Sil'OS JANGAARD. Li pia's, 2 (3) , ) SING, Due. J. GEnsitnEIN, LEON L. - Trans. 111.S tato Accid. Sci., 62 (1), 54-60, ) MuTcAEFE L.D., SCHMiTZ A.A. - Anal. Chin., vol. 33, n. 3, 363, ).2.(:KmAivN :1.G. - J. of Cas-Chrom., junc 11, ) ACKMANN 11.G. - J. Am. Oil Cheat. Soc., XL, 553, ) CNNANN R.G. - J. Am. Oil Chain. Soc., XL, 564, ) ACKàIANN 11.G. - Care..J. Biochem. Physiol., 41, 1267, ) AcKmANN JANG.1ARD P.M. - J. Am. Oil Chem. Soc., XL, 744, ) ACKMANN R.G., BuncuElt R.D. J. Am. Oil Chem. Soc., XLE, 33, ) ACKMANN R.G. - J. Chrom., 49 (3), 534-6, ) CI:umA E., ST,LNCIIElt B., 13ARà0EL P. - Rassegna Chimica, n. 2, 39-43, ) CALZOLARI C., CERMA E., STANCHER flic. Ital. Sostanze Grasse, anno XLVIII, n. 12, , ) STANCHER B., BARADEL P., CE:nmA E.. Univ. degli Studi di Trieste, Fac. di Ec. e Comm. Ist. di Merceologia, Pubblic. n. 43, 1963.

FISHERIES AND MARINE SERVICE. Translation Series No Investigation of the lipid composition of several species of fish

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