MONOUNSATURATED AND

POLYUNSATURATED
FATTY ACIDS
Monounsaturated fatty acids
contain one double bond
usually liquid at room temperature
found primarily in plant foods like avocados,
olives and nuts and in various vegetable oils
like olive oil and canola oil
Common monounsaturated fatty acids are:
palmitoleic acid
oleic acid
Polyunsaturated fatty acids
contain two or more double bonds
like monounsaturated fat, is usually liquid
at room temperature
polyunsaturated fat is mostly found in plant
foods like most nuts and in vegetable oils
like corn, soybean and safflower
Common polyunsaturated fatty acids are:
linoleic acid
linolenic acid
arachidonic acid
TO DESCRIBE THE UNSATURATED FATTY ACIDS,
TWO WAYS ARE OFFERED:
The chemist's terminology:
The carbon atoms are counted from the carboxyl
group which put the emphasis on the double bond
closest to this group (D-notations)
As an example: 18:2
A
9,12 or cis-9, cis-12-
octadecadienoic acid, the trivial name: linoleic
acid
The biochemist's and physiologist's terminology:
Holman RT proposed in 1964 a new numbering
system for the unsaturation of fatty acids, the "omega
nomenclature".
The double bonds are counted from the methyl group
determining the metabolic family, noted by wx (w for
the terminal carbon) or better n-x (n for the total
number of carbon, x being the position of the distal
double bond)
Thus, linoleic acid or cis-9, cis-12-octadecadienoic acid
is also named in the shorthand nomenclature 18:2 (n-
6). This compound has 18 carbon atoms, 2 double
bonds and 6 carbon atoms from the last double bond
to the terminal methyl group. In the old literature it
was designated 18:2w6.
18-6=12, 12-3=9, hence
A
9,12.
NOMENCLATURE
Fatty acids can be named in many ways:
symbolic name: given as x:y
(A a,b,c)
where x is
the number of C·s in the chain, y is the
number of double bonds, and a, b, and c are
the positions of the start of the double bonds
from C1 - the carboxyl C
Example:
y OLEIC ACID 18:1
A7
or [7, l?l
Oleic acid contains 18 carbon atoms and a double
bond between positions 9 and 10, indicated by
18:1
A7
The number 18 indicates the number of carbon
atoms, 1 indicates the number of double bonds
and the
A
and superscript indicate the position of
double bond
Fatty acids may also be classified by the distance
of the first double bond from the [-carbon
systematic name using IUPAC
nomenclature. The systematic name
gives the number of C·s (e.g.
hexadecanoic acids for 16:0)
If the fatty acid is unsaturated, the
base name reflects the number of
double bonds (e.g. octadecenoic acid for
18:1
A9
and octadecatrienoic acid for
18:3
A 9,12,15
)
Monounsaturated fatty acids contain 1
C=C while polyunsaturated fatty acids
contain more than 1 C=C. Double bonds
are usual cis.
There is an alternative to the symbolic
representation of fatty acids, in which the
C's are numbered from the distal end (the
n or w end) of the acyl chain (the other
end from the carboxyl group)
Hence 18:3
A 9,12,15
could be written as 18:3
(w -3) or 18:3 (n -3) where the terminal C
is numbered one and the first double bond
starts at C3
Arachidonic acid is an (w -6) fatty acid
while docosahexaenoic acid is an (w -3)
fatty acid
Symbol common
name
systematic
name
structure Mp
(C)
16:1
A7
Palmitoleic
acid
Hexadecenoic
acid
CH
3
(CH
2
)
5
CH=CH-
(CH
2
)
7
COOH
-0.5
18:1
A7
Oleic acid 9-Octadecenoic
acid
CH
3
(CH
2
)
7
CH=CH-
(CH
2
)
7
COOH
13.4
18:2
A7,l2
Linoleic
acid
9,12 ²Octadeca-
dienoic acid
CH
3
(CH
2
)
4
(CH=CHCH
2
)
2
(
CH
2
)
6
COOH
-9
18:3
A7,l2,lª
eLinolenic
acid
9,12,15 -
Octadecatrienoic
acid
CH
3
CH
2
(CH=CHCH
2
)
3
(CH
2
)
6
COOH
-17
20:4
A5,8,11,14
arachidonic
acid
5,8,11,14-
Eicosatetraenoic
acid
CH
3
(CH
2
)
4
(CH=CHCH
2
)
4
(
CH
2
)
2
COOH
-49
20:5
A5,8,11,14,17
EPA 5,8,11,14,17-
Eicosapentaenoic
- acid
CH
3
CH
2
(CH=CHCH
2
)
5
(CH
2
)
2
COOH
-54
22:6
A4,7,10,13,16,19
DHA Docosohexaenoic
acid
22:6w3

Monounsaturated fatty acids  contain  usually one double bond liquid at room temperature  found primarily in plant foods like avocados. olives and nuts and in various vegetable oils like olive oil and canola oil  Common monounsaturated fatty acids are:  palmitoleic acid  oleic acid .

soybean and safflower  Common polyunsaturated fatty acids are: linoleic acid  linolenic acid  arachidonic acid  . Polyunsaturated fatty acids  contain two or more double bonds  like monounsaturated fat. is usually liquid at room temperature  polyunsaturated fat is mostly found in plant foods like most nuts and in vegetable oils like corn.

TO DESCRIBE THE UNSATURATED FATTY ACIDS. cis-12octadecadienoic acid. TWO WAYS ARE OFFERED: The chemist's terminology: The carbon atoms are counted from the carboxyl group which put the emphasis on the double bond closest to this group (D-notations) As an example: 18:2 (9. the trivial name: linoleic acid .12 or cis-9.

2 double bonds and 6 carbon atoms from the last double bond to the terminal methyl group. cis-12-octadecadienoic acid is also named in the shorthand nomenclature 18:2 (n6). hence (9. the "omega nomenclature". . In the old literature it was designated 18:2w6. 18-6=12. 12-3=9. noted by wx (w for the terminal carbon) or better n-x (n for the total number of carbon. linoleic acid or cis-9. This compound has 18 carbon atoms.12. The double bonds are counted from the methyl group determining the metabolic family.The biochemist's and physiologist's terminology: Holman RT proposed in 1964 a new numbering system for the unsaturation of fatty acids. x being the position of the distal double bond) Thus.

NOMENCLATURE Fatty acids can be named in many ways:  symbolic name: given as x:y (( a.c) where x is the number of C·s in the chain. and c are the positions of the start of the double bonds from C1 . y is the number of double bonds.the carboxyl C . b.b. and a.

indicated by 18:1(  The number 18 indicates the number of carbon atoms. 1 indicates the number of double bonds and the ( and superscript indicate the position of double bond  Fatty acids may also be classified by the distance of the first double bond from the [-carbon . Example: y OLEIC ACID  18:1( or [ Oleic acid contains 18 carbon atoms and a double bond between positions 9 and 10.

.

the base name reflects the number of double bonds (e. hexadecanoic acids for 16:0)  If the fatty acid is unsaturated.g.12.15) . octadecenoic acid for 18:1 (9 and octadecatrienoic acid for 18:3( 9.g. systematic name using IUPAC nomenclature. The systematic name gives the number of C·s (e.

 Monounsaturated fatty acids contain 1 C=C while polyunsaturated fatty acids contain more than 1 C=C. Double bonds are usual cis. in which the C's are numbered from the distal end (the n or w end) of the acyl chain (the other end from the carboxyl group)  There . is an alternative to the symbolic representation of fatty acids.

 Hence 18:3 ( 9.15 could be written as 18:3 (w -3) or 18:3 (n -3) where the terminal C is numbered one and the first double bond starts at C3 Arachidonic acid is an (w -6) fatty acid while docosahexaenoic acid is an (w -3) fatty acid  .12.

14.19 DHA 22:6w3 .5 13.11.11.8.Symbol common name Palmitoleic acid Oleic acid Linoleic acid ELinolenic acid systematic name Hexadecenoic acid 9-Octadecenoic acid 9.14 arachidonic 5.acid Docosohexaenoic acid 22:6 (4.4 -9 16:1( 18:1( 18:2( 18:3( CH3(CH2)5CH=CH(CH2)7COOH CH3(CH2)7CH=CH(CH2)7COOH CH3(CH2)4(CH=CHCH2)2( CH2)6COOH CH3CH2(CH=CHCH2)3(CH -17 2)6COOH CH3(CH2)4(CH=CHCH2)4( CH2)2COOH -49 20:4(5.14.8.13.15 Octadecatrienoic acid structure Mp (C) -0.11.8.17CH3CH2(CH=CHCH2)5(CH -54 Eicosapentaenoic 2)2COOH .12.12 ²Octadecadienoic acid 9.17 EPA 5.16.11.14acid Eicosatetraenoic acid 20:5(5.7.10.8.