(ARCIIIVES?
FISHERIES RESEARCH BOARD OF CANADA
Translation Series No. 1018
-
Determination of composition of fatty acids in oils of
fish and marine mammals. (Paper No. 5 in collection
of papers on "Technology .of fats,oils and
food products")
By F. M. Rzhavskaya
Original title: K voprosu opredeleniya sostava kislot zhirov
ryb i morskikh mlekopitayushchikh.
Trudy
From: "Tekhnologiya Zhirov i kormovykh produktov'.
Vsesoyuznogo Nauchno-Issledovatel'skogo Instituta
Morskogo Rybnogo Khozyaistva i Okeanografii. (VNIRO)
Vol. 63, pp. 69-72.
Translated by the Translation Bureau(GNK)
Foreign Languages Division •
Department of the SecretarY of State of,Cànada
• Fisheries Research Board of Canada
Arctic Biological Station •
Ste. Anne de Bellevue, Que.
1968
10 pages typescript
DEPARTMEHT OF THE SECRETARY OF STAI:
TRANSI.AT 011 BUB EAU
SECRÉTARIAT 1:,
Ur'"1 1
TAT
BUREAU DES TRADUCTIOMS
Dr.IVÎSiOn DES LÀ1CUES1:7U1A;
FORHG':ILAHCUAGESDP/MON
C:ANADA
DI VIION/ DRANCII
I--)C.RARTMENT
YOUR NO.
IDIVI.C10/1
miNiuTi:RE
V 0 y L:
769-18-14
Fis7pories
VILLE
.Arctic TH.ological
u,ccLoi..!
OUR NC,
LANGUAGE
TRANSLATOR UNI TIALC)
NOTRE N °
LANGUE
rRADuc TEUR (INITIALES)
1560
CITY
TION
Ste Ann,, dr, Bele, vue P
DATE
CNN
Russian
May 1
1968.)
-
Concerning the ,roblem of Determining the Composition ol
the 1, atty Acids in Oils of, J21sn and Marine Mammals,
0
13y F.M. Rzhavskaya.
(From 'Trudy VNIROn / Transactions 'of the All-Union Research
Institute for Marine Fisheries and ) Oceanography (VNIRO)/ D
Volume LXlII
196 7.
Dri.AFT
1•JI
'N
;'•
Oils of fish and of marine mammals are characterized
by the presence of considerable quantities of glycerids of
highIn
7 unsaturated acids. These acids have varying degree;of
unsaturation determined by the number • of double bonds„ Glyeeà_
rd of acids with five or six double bonds are characteristic
•
of the oils of fish and marine mammals. Such glycerieoccur
•.
exclusively in the denizens of rivers and seas.
•
A second charactetic feature -of these oils is the
variety of the fatty acids in respect to the number ,of the car-
bon
atoms, i„e. according . to the molecular weight. This
20
applies in particular - to the unsaturated portion of the oil.
only on
In the plant and animal oils, 5n acid radicals wâth
double bond, only the radical of the oleic acid is present,
this. acid, as we know,
is an acid with 18 atoms of carbo n .
in the oils of fish and marine mammals were observed acids of
this series with 10, 12, 14, 16 9 20, 22, 24 and 26 atoms of
carbon
i1 18 0
C 12 H 22 O 2
C10'e
C lb -F _
96'0_9
etc.) (4 9 7, 11, 15-17).
Among the radicals of acids with two or three double
bonds (dieu and trien aci.ds) we find ac3ds not merely with 18
carbon atoms e what is characteristic of the plant oils e but
also with 16 and 20 atoms of carbon ). (8, 10).
Contrary to the plant and animal oil%* in the oils of
fish and marine mammals 9 in addition to the radical of the
arachidonic acid
(090-H 3.2 0 2 ) with four double bonds (tetraieh
acids), one has observed radicals of acids with 16, 18 9 22 and
(0 1 022.29 e 0 1028 02 etc.)
24 at>oms of carbon
(3, 8, 9,
12 - 1 ) , 18, 21) 9
With five double bonds . (pentaien) acid's have been se-
parated wjth 20, 22 9 24 and 26 carbon atoms
(C 9u-,
H n0 2
-
0 72 H 34 0 2
etc.)
(5, 8, 10).
'
With six double bonds (hexaier) • cids were found with
22, 24 and . 26 carbon atoms
(0 22 1J32 02
C 9 036 02
and
C,,U
2o -40 2 ) • '(8 10)0
V
When studying the composition of oils e 'it is imoortant
to determine the quantity of acids of various degrees of
3.
(.1. U_Z 111
unsaturatedi;
unsaturation
)
acids of the oleic series (with
one double bond) and highly unsaturated:. Today the content
of the highly uns aturated acids with various numbers of double
bonds (di-,
tri-, tetra-, penta- and he:Ka:Len acids) are most
.c(muonly determined.spectroPhotometrically with utilization
of the spectrophotometer SF- 4 (in the ussn).
animal and plant oi1s 9 if data
highly unsaturated acide and ,
on
on
For anaiysis of
the content of the
, the value of the oil's
led5ne number are available, it is recommended the quaIityb 0 7p
of the oleinic acid be determined by the following formula
•
•
1, 1 ):
)..2:qmber . _ o
W
03
73 .1+7, .335.71
89.9
where
the iodlne number is the iodine number of the
ana-
lyzed specimen;
89.9;
181; 273.7; 333.7
are/Iodine numbers of
oleic acid (C18H- 34 2'
My-Iola:Lc acid (C 18 11 2 02 ), linolenic (0 103002 ) and arachidonic acid: (C„H
fu ),
, 0 00 ) respectively;
X, Y, Z -
content of linoleic9 llnolonic and arachi-
donic acids determined by the spoctrophotometric monod, in %.
In this case the sum of the unsaturated acids H is calculated as the difference between the total quantity of acids
/4
..
in a fat molecule, and the'isum of the mono- and highly unsaturated acids according to such an equation
(2)
H = 95.6 - (x ± Y + z + w),
where 95.6 is the percentaFe of the fatty acids in a fat mole c u l e .
The iodine number of the acids does not
depend exclu
sively upon the number of double bonds e but also upon the
molecular weight, i.e.
acicrs
ofl the number of carbon atoms in the mo-
lecule. Therefore, when the
melecular weight of
saturated acids ( with varying
the highly un-
numbprp of double ,bonds) and
of the unsaturated acids (ofY61eic series) » characteristic of
fish and marine mammal oils e are
of considerable diversity »
the equations for the determination of the acids of thethen
oleic series and of undaturated acids in
these oils are un -
applicable.
When analyzing the composition of various whale oils,
we determined analytically not only the amount of highly unsaturated acids, but also the content of
However, some of the researchers of
ràte the amount of
suggested for
satUrated acids.
fish oils (2) calcu-
saturated acids utilizing the method
plant and animal oilsc; - Tilerefore, we have
compared. the data obtained for
whale oils by
analytical .
determination of the saturated:acids .throughSertram's classical method, with the results calculated by the above-discussed
method.' The following equation was established, which takes
co2rn i zance
the presence of acids with five or si: doube
of
bonds:;
iodine numb -100 - (X.181.0 4 - Y.273.7 4- Zon3.7
89.9 .
-
PoL023
0- )bb,3
L)9.9
•
wheref;
P and Q - are pentaien and hexaien acids;
402 .3
iodine number of the peptaien acids with 20
1D
and 22 carbon atoms (C 20 and C 22 ) at their ratio of 1
which is accepted in the calculation'for determination of the
contents of these acids by the spectrophotometric method;
464.3 . -
the iodine nu mber.of . the hexaien acid with
22 atoms .of carbon.
This comparison indicates that the calculated Quantity
of saturated ae5ds exceeds considerably the quantity determined
analytically.
This excess is found for 14 specimens of ,hale
oils wlth various iodine numbers to be within the range of
4 - 19% at a relative difference of 22
iO4% ,(table 1).
Content; of acids of the oleic series
calcu- /p. 71
lated according to the iodine numbers of the individual
highly unsaturated acids turned out-to be much lowerwhen
comp:Irc'd to the content oLtained as d'Lffernn
>twr:en
total amount of fatty acids in a fat molecule and the sum
G.
of the highly unsaturated and saturated acids - determined
analytically (tab.le 2).
;
2
Table
1
....
iodine
! number 0
the oil
.
Content of sa4
t, 0 C.1 acids
D5fference
absolutd rela
in %
1
(1)
o
ur3
(1)
(Ï51
ttj
r-1
;13
CH
ri
•r1
o
17,1
18,6
21,6
24,0
17,0
18,4
21,2
18,7
17,8
18,5
17,8
23,0
21,8
20,4
5
.
r-1
(:1
120,7
121,6
124,6
. 108,1
130,3
127,3
114,7
126,4
135,5
138,5
130,5
108,8
115,6
120,2
7.11
r
. •
32,4
25,9
26,3
32,3
23,9
24,2
40,8
24,4
36,3
28,8
22,0
30,5
31,6
34,8
- 15,3
7,3
4,7
8,3
6,9
5,8
19,6
5,7
18,5
10,3
4,2
16,5
9,8
14,4
89,5
39,2
21,8
34,6
40,6
31,5
92,4
30,5
103,9
55,7
23,6
71,7
11,9
70,6
As shoUld , have been e.mected; tfie difference here
.
Î.n the content .of acids of the oleic serieS caluaated by these
two methods corresponds to the différence in .the quantity of
saturated acids determined analytically and by calculation (see
tables 1 and 2). Insofar as the analyzed oils contain mor acids
7
Table 2
Content of
acids of oleic
ser ies in oi j
Difference
.
,
/0
-e-1
0
i
•1
fl
OD
1
i
!
Ti
:-)
(D 0.)
.. ) .!..)
0
Ti ;'-;
cc
I
ni
F1
!t
F-3
i
(1)
1
li
..0
,-,
9
;7.5
:1
;
(7)
I
1
;
i
'1
I
i
i
F.;
'CI
0
0-) )
120,7
121, (t
124,6
108,1 130,3
127,3
114,7
126,4
135,5
138,5
130,5
108,8
115,6
120,2
0)
f:', hp ,-•
-H ..--1 (1)
i
, Ti
,f1; '0
0
.ri
1
OM
-;-)
-;-) (*:-1 --:1
t.--1
03 fr■
c'
r.; 0 ( )
115 • r1 Ti
I!
.
i
!
j
4) • r! i
..,.-.) c‘j 0
;
<C, r:1 03
;
54,9
51,9
50,5
51,7
55,5
54,9
50,4
52,3
49,6
49,2
54,5
50,9
51,9
51,5
CD i
.f,1 03
r--; 4)
(73 M
el-I
Ti
(I )
hi) 0 -t -)
-7.i
•
CC
Is..
M
Ti i .,
;:--1.
-
f J 0) .J.)
0 .0 C,.1
0 N U)
CID
! i!!!!;
•D
0)
<1 f:".;
39,6
47,6
45,8
43,4
48,6
49,1
30,8
46,6
31,1
38,9
50,3
31,4
42,1
37,1
;•/
15,3
1,3
4,7
8,3
6,9.
5,8
19,6
5,7
18,5
10,3
4,2
16,5
9,8
14,4
27,9
13,3
9,3
16,0
12,4
10,6
38,9
10,9
37,3
20,9
7,7
32,4
18,9
27,9
of the oleic series than saturated ones the relative differ.
once in the amount of aci.ds of the oleic series is lower than
the relative difference
the content of the. saturated acids.
Uowever, a relative difference betvieeil the amount of acids o r
oleic series calculated according to the iodine - numbers of the
the
8.
hiely unsaturated acids, and the analytical determination
of the saturated acids - attains 59%.
Our data on the content in the whale oils of
•
0
57
.acids/the oleic series oi
saturated acids, when the
coincide with
latter are analytically determined,
the data in the literature (6, 19, 20).
CONCLUS.IONS.
:Lo
Owing to the peculiarities of the composition of
fish and marine mammal oils, .the- quantity of
satura-
ted acids in these oils should be determined analytically.
The method of calculating . the content of acids
of the oleic series suggested for plant and animal oils is
not suitable for fish and marine mammal oils°
13 "13 LIOGRAPHY.
Kryloya,N.N and_Lyaskovskaya_) Yu..
›
cheskiye metody issledoVaniya pl'oduktov zhivotnogo
proïskhe7,hdeniya. n /Physical-cherdcal methods of
. analysis for products of animal origin/, Pishchopromizdat, 1961.
9
.._.‘„
c,
A.hy.:u.,,ofeizen ,_2G.,
n ,locierv,haniye
c'
polinenasyshchennykh
9
zhiinykh
.
kislot v zhiran osnovnykh promyslovykh ryb
A-.0vo-Chernomorskogo basseyna.'' / The content of
polyunsaturated fatty acids in the oil of the basic
commercial aishes of the Azov and Black Sea }3asin/.
'Woprosy p5taniyan /Problems of Alimentation/ D 1964 D
Mo. 5, 17 — 19.
•
3. Brown J. B. a. 13 (' a I G. 1). The Highly Unsaturate.d Fatty Acids of Fish Oils, J. Am.12/39, 192;3.
( hem. Soc., 45,
4. 131111 11. Mitielltingan ans der analylischen Praxis ziir Analyse von Thulium, Chenilker
22, 9:3, 996, 18(.19.
5. ( regor R. R. a. li e a I G. I). The Highly Insaturated Fatty Acids of Fish ()ils. 'file
Limit of thisaturation in Menhaden' ()il, .1. Ain. (hem, Soc., •8, 12, 3150, 1926.
6. 11e 1 c 11 e r •1. 1). A/Urine OjI. Prodution, General Chemistry and Uli1isaton„1. Ani. Oil
Chemists Soc., 31, 11, 503 - •506, 1954.
7. 1111 ditch T. P. ;Hie Chemical Constitution of Natural Fats, London, 19;36.
8. I( a ii d a T. .Inpaiii,che studion iiher den 1\liihrwert von 1isli5len, Fqtte-Seiien-Anstrich'MUM, 61, 6, 469---174, 1959:
0. Kimura W. On the chemistry of Highly unsaturated Fatty Acids of Marine-Animal
Congreses, 5, 3663----3671, 1931
Oils, Proceedings of the Fifth Pacific
. A. The Lipids of Fisli;Hui cilanges occurring in them during Processing
10. Love f 11
and Storage, Fish in Nutrition, 86---109, London, 19 62.
11. S in i t h F. II. and Brown .J. B. The Fatty Acids from Menhaden Oil, Oil a. Soap,
22, 11, 277---283, 1945.
i U. n.
asuda Y. On the Separation of Glycerides Cod Liver Oil, Proceed12. S 7.
ings-of the Imperial Academy, Japan, 4, 4 ; 1(35--168, 1928.
13. 5 0 7. ilk i B. ()11 the Separation of Glycerides, ibid., 5, 7, 265-268, 1929.
14. Suzuki B. On Hie Separation of Glycerides Sand e.el ((Ammodytes personatus) Oil,
ibid., 5, 7, 269, 1920.
a. Tsuchi ya T. Gadoleic Acid in Cod Liver Oil, J. Soc , Chem. Ind.
15. Toyama
Japan, 37, 1, 156-17 6, 1934.
16. Toyama .1. Ickuilificalion of Gadoleic Acid in Japanese Sardine Oil, Herring Oil a.
Liver Oil, ibid., 37, 1, 176-206, 1934.
17. Toyama .1. a. T sti chiya T. Separation of Physeteric Acid from Sardine and
Pilot-Whale Oils, ibid., 38, 11, 6806-61316, 1935.
18. Toyama J. a. Tsuchiya 1'. The Highly thisatiirated Acids in Sardine Oil. The
Separation of Highly Unsaturated C2I— Acids,.Bull. Chem. Soc. Japan, 113, 7, 543-517,
1935.
19. Toya ni a J. a. II o ?. a 8 i K. 13106ber Oil of Sei-Whale, Fin \Vhale and Humpback
Whale, J. Soc. Chem, Ind. Japan, 40, 11, 3986,-1937.
20. 1' o y a ni a J. a. Uozaki K. Antarctic Whale ()ils, J. Soc. Clie.in. Ind. Japan, 40, 12,
-1626, 1(J37.
21 , Ueno S. und 1 w a i Al. Die Bestandleile des Menuke-Oels. Bestimmung .dcr Fettsilures, J. Soc. Chem. Ina. Japan, 37, 2, 52 6-53 b;
r),
Translation of items 4, 8 and
21
See next page.
10.
o
-
Reports f'rom the analytical practice
•
of oil anajysis. 'Chemiker Zeitung" /Chemist's
a
journa1/ 9 22, 93, 1289 9 1923.
o
Kaneda
T.
•
japanese studies of the food value
in fish oil, ratoap and Daint Droducts n , 61, 6,
469 - 474, 1959.
21
Ueno, S
and Iwai
M.
gomponents of the menuke oil,.
Determination of the fat acids. 'Journal of the Society of the Chemical Industry in Japan.'
53b,
•
t
1934.
37 9 2, 52b