: . . .

(..)

3.1. ..
3.1.1.
3.2. ..

11

4.1. ..
4.2. 1
4.2. ..
4.2.2.
4.3.
4.4. (>130 C)

-,

-,

22

5.1.
5.2.
5.3.
5.3.1.
5.4.
5.4.1.
5.5. - -

34

36

7.1.
7.2.
7.3. -
7.4.


: . . .

44

8.1.
8.2.

8.2.1.
8.3.

8.3.1.
8.3.2
8.3.3.
8.4.

56

,
( )

,
.


: . . .

1.
?
(
) (lipids)
.

.
W.W. Christie
American Oil Chemists Society

(lipidlibrary.aocs.com).

.

CoA, -CoA,
.
, .

19 .
(lipidomics),

.


(.. , , ).
2.
(simple) (complex)
American Oil Chemists Society


: . . .
.
,
.

mole (..
). .
, , .

mole (.. ,
).
1
.
1.

(.)

., .,
., .

, ,

, (

,D,,

(glycerophospholipids)

(glycolipids).


: . . .
. (
/ ).

.
,
, , .
9 kcal/g,
(4 kcal/g).
130 moles ATP (1) mole
38 moles ATP mole . :
.
(, D, , ) .

(fats) (oils) ( . 8).

,

,
( ).
3. (..)


, , .
..


.


: . . .

16 - 24 .
12 14 .
. (C4 - C10).
,
, . .. C2 6 ( 4) ,
C8 ( 6) 10 C12 24
.
, .. ,
(..) , .
..
cis (Z) .
, .
trans
. .
trans ..
.
-3 (-3 3 n-3) -6 (-6 6 n-6)


. -3 -6

, .
.
-6/-3
.
2
1 -3 -6
.. .


: . . .
2. ..

4:0

6:0

8:0

10:0

12:0

14:0

16:0

18:0

20:0

22:0

(saturated)

() (monounsaturated, monoenoic, MUFA)

cis-9-

16:1 (-7 n-7)*

cis-6-

18:1 (-12)

cis-9-

18:1 (-9)

cis-11-

cis-

, 18:1 (-7)

cis-13-

22:1 (-9)

() (polyunsaturated, polyenoic, PUFA)** all-cis

9,12-

18:2 (-6)

6,9,12-

18:3 (-6)

9,12,15-

18:3 (-3)

5,8,11,14-

18:4 (-6)

5,8,11,14,17-

EPA

20:5 (-3)

4,7,10,13,16,19-

DHA

22:6 (-3)

* n: .. ; n:


: . . .
3 6..
(..)

(18:3n3)

(18:2n6)

(18:4n3)

(18:3n6)

(20:4n3)

(20:3n6)

(20:5n3)

(20:4n6)

(22:5n3)

(22:6n3)

(22:4n6)
(22:5n6)

1. -3 -6 ..
3.1. ..

.
3.1.1. .
(..)
.
,
, ,
, , ..
. .. ..
. ( 3).
(differential scanning
calorimetry, DSC) .. ..

..
() .. (-1).


: . . .

.
3. ..

2:0
4:0
6:0
8:0
10:0
12:0
14:0
16:0
16:1

.. (C)
1
2
16,6
-5,7
-3,0
16,3
15,41
31,9
30,80
43,2
43,29
53,9
53,47
63,1
62,20
0,5
1,22

.. (C)
1
2
68,8
69,29
13,4
12,82
45,0
43,35
-12,0
-7,15
-11,0
-11,58
76,5
74,76
81
79,54

..
18:0
18:1
-t18:1
18:2
18:3
20:0
22:0

1: CRC Handbook of Chemistry and Physics, 81st Edition, 2000-2001, CRC Press
2: Knothe, G., Dum, R. O., A comprehensive evaluation of the melting points of fatty acids and
esters determined by differential scanning calorimetry. J. Am. Oil Soc, 2009, 86, 843-856.

cis ..
.. trans
..
.. , 18:0 (~69 C)
18:1 (~13 oC) (t18:1)
.. 18:0 (~45 oC).
(~40) -cis
. -trans .
.. (..
) ( 4 2).
4. .O. 2, 20oC

2
4
6

(g/L)

9,7

10
12
14

(g/L)
0,15
0,055
0,02

0,7

16

0,007

18

0,003


: . . .
.

18:0
HO

18:1
(cis)

HO

18:1
(trans)

HO

2. 18:0, -c18:1, -t18:1

3.2. ..
..
( ,
, ).

.
.. ,
() (..
). .., ,

10


: . . .
,

( ) ( 5). ..
,


.. ( ).
.
5.
.

, /,

1. ( ;)
2. ;
( www.cyberlipid.com)
3. 2
4.
4.1.
18:1, 18:2, 18:3 ..

.

11


: . . .

(32) .
32
spin ()
. 32 e 2
.
. spin

- .. ..

.
(, , )
( ).
.
RH +

+ R

RH= .., =

R1

-
- (ROO) (R2).
, .
(R3).

R +

O2 ROO

ROO + RH

R2
ROOH + R

R3

H R3 .
( )
.
.

.
C-H .

C-H.
12


: . . .
18:0, 18:1, 18:2, 18:3 25 oC
1, 100, 1200, 2500.
.. .
3
(18:1)
.

3.
(Frankel, 1985)

C8, C9, C10, C11

, (-trans C9 C10, cis C8
C11).
trans
.

C9, C13 ( ) C9 (~33%), C12
(~10%), C13 (~12%), C16 (33%), .
trans .

.
, Fe Cu,

13


: . . .

(R 4).

- (RO ) - (ROO ) (R4 5).

2ROOH

RO + ROO- + 2

R4

ROOH RO +OH

R5

(R7, R8).
-
.

ROO

+ ROO

ROO

+ R ROOR

ROOR + O2

R.7
R.8

.
- RO OH.

-. RO - C-C
- .
, OH
,
, .
.. (off
flavors) 4
.

14


: . . .
-



.

4.

4.2. 1

(AH)
(R9,10)

(R11,12).
ROO

+ AH ROOH

+ A

R.9

15


: . . .
R + AH R + A

R.10

A + ROO

R 11

A+A

R.12

( )

. :
. ,
.

(, ) , .
( ,
, 32, ..).
H
-.
(), -
.
O

- -
.
- -
. - - -
-
.
O

H
O

16


: . . .

,
- (ROO) .

OH

ROO ROOH
OH

OH

OH

OH

OH

ROO ROOH

R.13

.
( ) (
) .
; ,
( ,
, ,
, )
, ,





.
(induction period, h) , ,

17


: . . .
(., , )
( 5).
, .
.

1. (, ., 2004, )
, .
2. .
;

18


: . . .
4.2. ..

,
.
(Sensitizers, Sens)

. ,
.

.

(intersystem crossing)
( 6).

6.

.
, 3Sens*
.. . H R
32 ROO
3

Sens* + RH R + SensH

R 13

+ 3O2
ROO


().
.
19


: . . .
3Sens* 32
(12)
.
3

Sens* + 3O2 1O2 + Sens

RH + 1O2 ROOH

R 14
R 15

Sens= , RH= .

, ,
.
12
.
1500 ' 32. 12
( 7)
- ( cis trans).

. 18:1 trans C9-
trans C10- .

7.

(Frankel, 1985)

20


: . . .
4.2.2.


. 12
.
- .


. ,
1,0:1,7:2,3).

.
.
12
..
, , ..
(ROS, reactive oxygen species)

.
(2 -),
(), ROO, RO, ()
22 3.
4.3.

.. 1-cis-4cis ,
18:2 18:3 18:4 .
: .
.
0-20 oC
.
21


: . . .
() -cis/trans. ( )
.
4.4. (>130 C)

R3
. ()
() .
.. .


.. .
..
.

. .
(.. , )
.. :

() .

1.
, .
2. 4 C8
18:1.

22


: . . .
5. -, -, -
5.1.
,
( C3H8O3) .
(, , TG)
(>95% ).
(,

(,

(<2% )

.

( )
5.2.

.. . 1, 2 3
.

.
( , ,
(1,3-random,2-random distribution)
,
TG, .

1,3--2-

( 5).
sn-1 3
( 6).

23


: . . .
5.

TG

50

3,8

3,4

3,7

3,4

51

52

26,6

23,6

28,0

26,0

53

0,5

0,7

54

52,6

56,2

65,9

67,7

56

8,1

6,7

1,9

1,9

58

6,9

8,2

60

2,0

1,9

.. 1,2,3

16:0

16:1

18:0

18:1

18:2

18:3

13,8

5,9

22,9

49,5

9,1

0,9

0,3

21,5

69,7

7,1

13,1

5,6

28,0

45,2

8,4

13,1

0,9

2,6

71,8

9,8

0,6

1,4

0,7

82,9

14,0

0,8

16,0

0,8

4,2

73,9

5,1

1,3

18,5

0,4

3,5

28,1

48,5

1,3

1,8

0,1

0,2

25,8

71,2

1,0

12,6

0,5

2,2

31,0

52,6

0,8

7.

24


: . . .
7. n .
TG
=n3+n2/2 ( )

N=n3+n2+2n/6 ( )

n=3, =18

n=3, =10
FA=
,, C:

O
:
C (
) C sn-1, o C sn3 C 2 sn-2.
2.
10
( = 550)

(.. ).
TG
, .
.
TGs.

.
4-6 .
1 3 TG
.
TG
(1--2--3- ).
25


: . . .
.. 2
.. .
:

sn-2 , sn-1 3
.

sn-1 ( 18:1), ( 18:2) sn-2 .
..
C<8 sn-3, C14 - 18
sn-1 2.

2- 16:0 sn-1.

sn- 2 (
sn-3 ) sn-1 3.

(mouth feel)
. ..
, 36 C,
18:0 16:0 sn-1 3 and 18:1 sn-2 .
..

. ,
( )

, structured lipids .
5.3.

26


: . . .
5.3.1.
TG
( )

. .
TG
(
) - .

.
,
( 8). (..),
( )
.

( )

( )

( )
8. TG

27


: . . .


. Gibbs
.
m (
G
).
TG.
( 9)
G

.. .

, ..
.
( )
,

. ..
.

.
() ()
.

28


: . . .

(, , , ) ( 10)
29


: . . .

10.

TG

G .. .

( ) TG
. ..
.
TG .. .
TG ()
() ( 11).

30


: . . .
(1,3)
.
TG

. TG . ..
.

11. () ()
5.4.
5.4.1.

.
, - - .

.
( ) (..

31


: . . .
).
. ( ).

25C .
, , ,
(.. , max.
0.8 % ).

, .

,
,


.
. ( 12)

25 40 oC
.

32


: . . .

12
25 (, ,U ) 40 C (, , S).

. (Fregapane et al., 2006)

( ).
,
()
..

.
.
,

.
.
33


: . . .
(e.g.,
Romano, Provolone) , (PGE)

. H PGE
. (,
)
. .
.. sn-1 3.
sn-1 3,
.
.
(.. , ).
,
.
,
.

,
,
.


.

(.. )

.

Candida

cylindricae,

Corynebacterium

acnes,

Staphylococcus aureus ( ), Aspergillus niger, Mucor javanicus, M.

miehei, Rhizopus arrhizus, R. Delamar, R. niveus ( 1,3-).
5.5. - -
,

34


: . . .
. (sn -1,2 sn-2,3)
sn-1,3
7:3 1,3 .
.

()
- -
(.. 471)
()

. >80% , <20%
TAG <3% . 2011 EFSA
(European Food Safety Authority)
.
6.

( )

.
.
sn-3
, , .
1 2 16:0, 18;0, 18:1, 18:2, 18:3
(sn-1) (sn-2).

35


: . . .
,

13.
(.. , ).

13 (reference: University of Florida Agricultural and

Biological Engineering, Web site of David P. Chynoweth MSPH, Ph.D

[ , , , ].

.


(fishiness)
. (>
20%) (2 - 3%).

.
()
[ (O/W)

36


: . . .
(W/O)] .
.
(HLB: hydrophilic-lipophilic
balance) .
[ HLB<10 W/O, LB>10 O/W].
.
- -
w/o: 20:80.

.
( , ,
,
).

.
:
16:0=15-18 27-29/,18:0=3-6 14-17/ 18:1=9-11 35-38/18:2=56-60 1518/ 18:3=6-9 0-1/18:4=0 3-5
8.

2022

6872

2123

1216

1820

02

~30-40

12-14

, , , ,

(.. ).
, ,
- .

37


: . . .
7.
7.1.
Heinrich Wieland & Adolf Windaus, 1928

( ), ( )
() .
, C17 (
14). C5.
( .. ).


. ,
, 7-

D3.
>250 .

38


: . . .

14. , -
C24
.

.

,
. 2000

, .

.
-

.

39


: . . .
C5

, , .



.
(.. 10-30%).
(mg/100 g)
(919), (909),
(665) (411), (320).
: (360), (300), (276),
(344) (200 mg/g). ,
30-70%.
7.2.

(C30H50,

15)

2,6,10,15,19,23--2,6,10,14,18,22

all-trans

Mitsumaru
Tsujimoto (Squalus spp),
(Tsujimoto, 1916).

15.



(, , ) (, ,
). ,
.
,

40


: . . .
(
. ).

(
).

.

.

,
.

(5-10 g/kg ).


9 17
(.. )
7.3. -
40 (
) ()
).
o - ( 16) .

16. all trans

41


: . . .
,

600
50 .

. 6 g -
1 g .

.

-.
700-800 mg/kg.

.
.

.

12. .
12 ,
.

:
1

O2

Sens* + 1-

O2 +

Sens + 3-

R.16
R.17
R.18

-
. -
1000 12.
.
.
-

42


: . . .
12. (RH)
-

( 17)
.

ROO +
R
O
O

17. -

-
.
7.4. -
-
( 18)
R1
HO
CH3

CH3

CH3

R2

CH3
CH3

R3

R1

R2

R3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

CH3

18.
43


: . . .
, -, -, , -,
- .
- , - - - , - .
(C3', C7', C11')
. R,R,R-- 1,49
all-rac-- 1,0
IU/mg.
. - .

.
.
- (
) - ( ).
- ,
90% 300
mg/kg.

.
,
-. 20-40%

. 20%
. -
15 mg .
-
( 1 mg 8 g
) .
.
- -

. -
- .

44


: . . .
( )
- 2 .

, -, .
.
O

O
HO

ROO

RO

O
CHOH
CH 2 OH

OH

ROOH
O

ROH

O
CHOH

CH 2 OH

R. 19

-
()
:
Car+ + TOH Car + TO + H+

R.20

.

.
TO + Car TOH + Car+

R 21

12
.

2 .

.
1,4-
.

45


: . . .

8.
8.1.
.. ( 9) .

( 10).
(12:0 14:0)
.
( 11).
-
.
.
9.

evening black current

Tallow

primorose
jojoba

babassu

borrage

macadamia

Hard butter illipe

butter

(Borneo

tallow) sal fat and

shea butter

()

/ Canola

46


: . . .

10 ,
.

16:0

24-28

32

27

18:0

8-16

20

27

18:1

40-49

42

35

18:2

6-15

1-12

11.

,
( ) (25 oC)
(, , ,
, , , ),
(, + , )
(, , ,

47


: . . .
) .
~ 80:20.

( + , , (canola)
( 19).
.

(, ) .


. 2002-2012 6.5 million tones
.

19. 2009 (1000 T)

(
: 19-23% , 36-44% )

.

, .. 10% .
, .. ,

48


: . . .
(
).
185 million tonnes e
(FAO, Food and Agriculture Organization)
.
, ,

(, ).

(, )
( ).

.
,
(CO2, SO2, )
.

( 20 ).

20.

20

(, )

49


: . . .
8.2.

( , , ),
, . ,
, ,
(
, , , )

.
. ,
tallow oil

prions. ,

. ( , )
,
(virgin oils)
.


.

ethnic
.

.

.

.
. .
8.2.1.
50


: . . .

). .
- -
.

.
(.. ) .., ,
.
, , .
, .. ,

.
:

(, )

. 2-3% (80 oC)
.


.

0,1% , w/w
, .
.
: ..

( 15%) ~70 oC
. ,
.
.

51


: . . .

.
: ,
,
.

.
.
100 oC 30 min .

. .

.
: (3-5
mm Hg) .
200260 C .
(20 min -6h, 1h) .
,
.., - .
220C
-trans ..
8.3.

(.. , ..,
) (.. ..)
. , ,
.
,
H.Mge Mouris (1870)

52


: . . .

8.3.1.

..,
.

..

(winterization)
,

.

( 5.3.1.)
.
.
21.

53


: . . .

21.
V= iodine value,
,
8.3.2. ( )

.. TGs
.
.. trans
(-), , (9 cis)
+ (9 trans) + (8 cis trans ). ..
.


.. (tailored oils and fats).

trans ..

()

()

54


: . . .
( ) ( )
.

8.3.3.

( )
trans
..

) (80 oC).


.

.
(), ..

() () .
55


: . . .

8.4.




,

(,

DHA,

EPA,

..).

,
( )
.

).
9.
, , ,

Belitz, H.D., Grosch, W. & Scieberle, P. (2009) Food Chemistry (4th, revised &
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paperbacks, Cambridge, U.K
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and beverages and antioxidant applications. Woodhead Publ. Ltd. Philadelphia,
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56


: . . .
Gunstone, F.D. (Ed). (2003) Lipids for functional foods and nutraceuticals. The
Oily Press, Bridgwater, UK
Gunstone, F.D. (Ed.) (2006). Modifying lipids for use in food. Woodhead Publ.
Ltd, cabridge UK & CRC Press LLC, Boca Raton, FL., USA
Gurr, M.I & James, A.T. (1980) Lipid Biochemistry (3rd ed.) Science paperbacks
Chapman & Hall. London & NY
Heimann, W. (1982) Fundamentals of Food Chemistry Ellis Horwood Ltd
Chichester, WS, UK
Henry, J. (2009). Processing, manufacturing, uses and labelling of fats in food
supply, Ann. Nutr. Metab., 55, 273-300
Linden, G & Lorient, D. (2000). New ingredients in food processing. Woodhead
Publ. Ltd. Cambridge, UK & CRC Press LLC, Boca Raton, FL., USA
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Sheffield, UK and CRC press LLC Boca Raton, FL., USA
Ratnayake, N.W.M. & Galli, C. (2009). Fat and fatty acid terminology, methods
of nalysis and fat digestion and metabolism: a background review paper, Ann.
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