LIPIDS

LIPIDS
CH3(CH2)14-
Non-polar
- terminal carboxylic acid moiety
and long saturated or unsaturated
carbon atoms

- from fatty acids & glycerol-3-

phosphate, and triglycerides
 - from fatty acids and sphingosine

- four fused rings (the steroid

nucleus)

- isoprene units (2-methyl-1,3-

butadiene)
Vitamins A, E, K, β-carotene, essential oils from
Saturated Fatty Acids
- Fatty acid with a carbon chain in which all
C-C bonds are single bonds
- Numbering starts at the end of -COOH grp
- Structural notation: it indicates number of
C atoms
- e.g. Lauric acid has 12 C atoms and
no double bonds so it is (12:0) O

H 3C (CH) 10 C OH
O
or
C
11 9 7 5 3 1 OH
12 10 8 6 4 2
Unsaturated Fatty Acids
- A monounsaturated fatty acid is a fatty acid
with a carbon chain in which one carbon–
carbon double bond is present.
- Different ways of depicting the structure
Polyunsaturated Fatty Acids
(PUFAs)
- a fatty acid with a carbon chain in which
two or more carbon–carbon double bonds
are present.
- Up to six double bonds are found in
biochemically important PUFAs.
2 types of unsaturated fatty acids:

- An unsaturated fatty acid with its

endmost double bond three carbon
atoms away from its methyl end.

- An unsaturated fatty acid with its

endmost double bond six carbon atoms
away from its methyl end.
H 2 C OH O
H2 C O C (CH2 )16 CH3
HC OH O
HC OH O
H 2 C O C (CH2 )16 CH3 H2 C O C (CH2 )16 CH3

Monoglyceride ( - monostearin) Diglyceride ( ' - distearin)

O
H2 C O C (CH 2 )16 CH3 ( C18 )
O
HC O C (CH 2 )14 CH3 (C16 )
O
H2 C O C (CH 2 )16 CH3 (C18 )

Triglyceride ( - palmityl distearin)

Triglycerides
- the most common lipid
materials

Mono- and diglycerides

- only one or two –OH
groups of the glycerol
are esterified by fatty
acids.
 O O
H2C O C
H2C O C
O
O
HC O C + 2H2
HC O C
O O
H2C O C H2C O C

Oil Solid
 O
H 2C OH
H2C O C R
O
+ 3NaOH HC OH + 3RCOONa
R C O CH
O
Soap
H2C O C R H 2C OH
The Melting Point
Melting Point
Depends Upon:
o Length of
carbon chain
o Degree of
unsaturation
(number of
double bonds
in a molecule)
Space-Filling Molecules
The number of bends in a fatty acid chain increase
as the number of double bonds increase
o Less packing occurs
o Melting point is lower
o Tend to be liquids at room temp.
Selected Unsaturated Fatty
Acids of Biological Importance
o Numbering starts from the other end of -COOH
o Structural notation: It indicates number of C
atoms
e.g. 18:2 – 18 carbons, 2 double bonds
Saturated Fatty Acids
O
8 7 6 5 4 3 2 1
CH3 CH2 CH2 CH2 CH2 CH2 CH2 C OH

Octanoic Acid

Unsaturated Fatty Acids

O
8 7 6 5 4 3 2 1
CH3 CH2 CH2 CH2 CH2 CH2 CH2 C OH

3 - Octenoic Acid 8:1 (D3)

O
8 7 6 5 4 3 2 1
CH3 CH2 CH2 CH2 CH2 CH2 CH2 C OH
3, 6 - Octadienoic Acid 8:2 (D3,6)
 Cis and Trans Bonds
• In unsaturated fatty acids,
there are two ways the pieces
of the hydrocarbon tail can be
arranged around a C=C
double bond.
• In cis bonds, the two
hydrogens on either side of
the double bond are either
both “up” or both “down,”
(both are on the same side of
the molecule).
•In trans bonds, the two
hydrogens are on opposite
sides of the double bond, One
is “up” and one is “down”.
 Cis and Trans Bonds
o Fatty acids with trans bonds are carcinogenic, or cancer-
causing. The levels of trans fatty acids in highly-processed,
lipid-containing products such as margarine are quite high.
o Cis fats exist naturally and, because the hydrogen atoms
are crowded on one side of the molecule, they bend,
allowing other chemicals and enzymes to bind to them.
o Trans fats do not exist naturally, with a very few
exceptions. Because the structure is uncrowded, they do not
bend and so other molecules and enzymes find it more
difficult to bind to them.
Cis And Trans Fatty Acids
H H O
CH3 (CH2 )7 C C (CH2 )7 C OH
10 9

H O
CH3 (CH2 )7 C C (CH2 )7 C OH
H
Trans 9 - Octadecenoic Acid (elaidic
acid)
 CN IUPAC MP RCOOH CS Formula
Formula

Capric Decanoic 32 C9H19COOH CH3(CH2)8COOH

Lauric Dodecanoic 44 C11H23COOH H3(CH2)10COOH

Myristic Tetradecanoic 54 C13H27COOH H3(CH2)12COOH

Palmitic Hexadecanoic 63 C15H31COOH H3(CH2)14COOH

Stearic Octadecanoic 70 C17H35COOH H3(CH2)16COOH

Arachidic Eicosanoic 77 C19H39COOH H3(CH2)18COOH

 CN IUPAC MP RCOOH No. Position
Formula DB of DB
Palmitoleic cis-9- 0 C15H29COOH 1 C9
Hexedecenoic
acid
Oleic cis-9- 16 C17H33COOH 1 C9
Octadecenoic
acid
Linoleic cis,cis-9,12- 5 C17H31COOH 2 C9,12
cis,cis-9,12-
Linolenic All cis-9,12,15- 11 C17H29COOH 3 C9,12,15
Octadecatrienoic
acid
Arachidonic All cis-5,8,11,14- 50 C19H31COOH 4 C5,8,11,
Eicosatetraenoic 14
Palmitoleic acid = CH3(CH2)5CH=CH(CH2)7COOH
Oleic acid = CH3(CH2)7CH=CH(CH2)7COOH
Linoleic acid = CH3(CH2)4CH=CH2-
CH=CH(CH2)7COOH
Linolenic acid
= CH3CH2CH=CH-CH2-CH=CH-CH2-
CH=CH(CH2)7COOH
Arachidonic acid
= CH3(CH2)4CH=CH-CH2-CH=CH-CH2-CH=CH-CH2-CH=CH-
(CH2)3COOH
 Property SFA UsFA
Chemical C,H,O C,H,O
composition
Chemical Structure HC chain w/ a HC chain w/ a
terminal terminal
carboxyl group carboxyl group
C-C bonds w/in the Only C-C single At least one C-C
hydrocarbon chain bonds double
HC chains are Alkanes Alkenes
charac. of what
group of HC
 Property SFA UsFA
“Shape” of HC chains Linear, fully bend in C chain at
extended site of
C-C double bond
Physical state at Solid Liquid
room temp.
MP for 2 fatty acids higher Lower
of
the same HC length
Rel. bet. MP and longer chain longer chain
chain length length higher length higher MP
MP