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Triglycerides: Esters of glycerol with fatty acids

Fats are solids at room temperature


Oils are liquids at room temperature
These biomolecules are comprised solely of Carbon, Hydrogen
and Oxygen. They make up 40% of the calories in the average
diet.
Fats (solid triglycerides) and
an oil (a liquid triglyceride)
C
O
OH
Carboxyl end
Polar head
Long hydrocarbon chain
Nonpolar tail
General Fatty Acid Structure
Saturated Fats
Contain no C=C double bonds
Generally are solids or semisolids at room temp
Animal fat is a major source
Should not make up more than 30% of your total
fat intake per day
Unsaturated Fats
Contain one or more C=C double bonds
Generally are liquids at room temp
Vegetable oils are major source
Fatty Acid
Micelle Formation
COOH
COOH
COOH
COOH
COOH
COOH
Palmitic acid
Stearic Acid
Saturated Fatty Acids
Unsaturated Fatty Acids
Oleic Acid
Linoleic Acid
Linolenic Acid
Arachidonic Acid
NOTE: Linoleic, linolenic, and aracidonic acids are examples of polyunsaturated fatty acids.
Linoleic and linolenic acids are also the two essential fatty acids your body needs.
HOOC CH
3
12 C's
HOOC CH
3
14 C's
HOOC CH
3
16 C's
HOOC CH
3
16C's 1 C=C
HOOC CH
3
16C's 2 C=C
HOOC CH
3
16C's 3 C=C
Myristic Acid
14 C's
Palmitic Acid
16 C's
Stearic Acid
18 C's
Oleic Acid
18 C's 1 C=C
Linoleic Acid
18 C's 2 C=C
Linolenic Acid
18 C's 3 C=C
Molecular factors affecting
Melting Points
Molecular Weight
Myristic Acid 58
o
C
Palmitic Acid 63
o
C
Stearic Acid 71
o
C

COOH
COOH
COOH
COOH
COOH
COOH
COOH
COOH
COOH
semisolid at
room temp
liquid at
room temp
solid at
room temp
Degree of unsaturation
Monounsaturated one C=C

Polyunsaturated 2 or more C=C
Oleic Acid 16
o
C
Linoleic Acid -5
o
C
Linolenic Acid -11
o
C

Fatty Acids
COOH
COOH
COOH
COOH
COOH
COOH
Palmitic acid
Stearic Acid
Saturated Fatty Acids
Unsaturated Fatty Acids
Oleic Acid
Linoleic Acid
Linolenic Acid
Arachidonic Acid
NOTE: Linoleic, linolenic, and aracidonic acids are examples of polyunsaturated fatty acids.
Linoleic and linolenic acids are also the two essential fatty acids your body needs.
Essential Fatty Acids
Linoleic Acid and Linolenic Acid
Sources:
Green leafy vegetables
and fish oils
glycerol
Fatty Acid
Fatty Acid
Fatty Acid
CH
2
CH
OH
CH
2
OH
OH
Glycerol
+ 3 Fatty Acids
Yields a Triglyceride
CH
2
CH
O
CH
2
O
O
C
C
C
O
O
O
CH
2
(CH
2
)
13
CH
3
CH
2
(CH
2
)
13
CH
3
CH
2
(CH
2
)
13
CH
3
Glycerol
backbone
Ester bonds
Fatty acids
( palmitic acid)
Building a triglyceride structure
Lets draw a triglyceride made from palmitic,
stearic and oleic acids.
Building a triglyceride structure
Draw backbone
C
C
C
O
O
O
CH
3
CH
3
CH
3
g
l
y
c
e
r
o
l
O
O
O
Building a triglyceride structure
Put in the correct number of carbons
14 C's
16 C's
16 C's 1 C=C
C
C
C
O
O
O
CH
3
CH
3
CH
3
g
l
y
c
e
r
o
l
O
O
O
This triglyceride is a fat WHY?
It is comprised of one or less double bonds and
is primarily made from saturated fatty acids.
Make another using oleic, linolenic and
myristic acids.
Is this triglyceride is a solid or a liquid at
room temp?
Is this triglyceride a fat or an oil?
16 Cs 1 C=C
16 Cs 3 C=C
12 Cs
C
C
C
O
O
O
CH
3
CH
3
CH
3
g
l
y
c
e
r
o
l
O
O
O
This Triglyceride is ______________
an oil
It contains 4 double bonds therefore it is
an oil at room temp. Oils are liquids at this
temp.
This is a chemical reaction that decreases the amount of
unsaturation in a fat or oil by the addition of H
2
in the presence
of a metal catalyst.
C C
H
3
C
H
CH
3
H
+ H
2
Pt
C C
CH
3
H
CH
3
H
H H
Unsaturated fat
Saturated Fat
O C
O C
O C
CH
3
=
CH
3
= =
CH
3
= = =
g
l
y
c
e
r
o
l
O
O
O
+ 6 H
2
Pt
O C
O C
O C
CH
3
CH
3
CH
3
g
l
y
c
e
r
o
l
O
O
O
Partial hydrogenation of vegetable oils produces a
mixture of triglycerides that soften and melt near body
temperature
Steroids
Basic steroid Structure
HO
cholesterol
Cholesterol
Essential component of cell membranes
Used as raw material for sex hormones
and adrenocorticoid hormones
Used to make bile salts
High blood levels also associated with
heart disease, atherosclerosis, arterial
plaques

Cholesterol transported as Lipoprotein
complex (LDL)
Lipoproteins classified by
Density
HDL: High-density Lipoprotein
LDL: Low-density Lipoprotein
VLDV: Very low-density Lipoprotein
Triglycerides and cholesterol
Chylomicron
Mostly triglycerides
COO
-
HO
O
OH
Prostaglandins
Prostaglandin E
2
Lipoproteins classified by
Density
HDL: High-density Lipoprotein
LDL: Low-density Lipoprotein
VLDV: Very low-density Lipoprotein
Triglycerides and cholesterol
Chylomicron
Mostly triglycerides