38 Chapter 2
are sufficient amounts of ketone bodies in the blood to lower
the blood pH, the condition is called ketoacidosis. Severe
ketoacidosis, which may occur in diabetes mellitus, can lead
to coma and death.
Phospholipids
The group of lipids known as phospholipids includes a num-
ber of different categories of lipids, all of which contain a
phosphate group. The most common type of phospholipid mol-
ecule is one in which the three-carbon alcohol molecule glyc-
erol is attached to two fatty acid molecules; the third carbon
atom of the glycerol is attached to a phosphate group, and the
phosphate group, in turn, is bound to other molecules. If the
phosphate group is attached to a nitrogen-containing choline
Ketone Bodies
Hydrolysis of triglycerides within adipose tissue releases free
fatty acids into the blood. Free fatty acids can be used as an
immediate source of energy by many organs; they can also be
converted by the liver into derivatives called ketone bodies
( fig. 2.21 ). These include four-carbon-long acidic molecules
(acetoacetic acid and b -hydroxybutyric acid) and acetone (the
solvent in nailpolish remover). A rapid breakdown of fat, as
may occur during strict low-carbohydrate diets and in uncon-
trolled diabetes mellitus, results in elevated levels of ketone
bodies in the blood. This is a condition called ketosis. If there
Figure 2.20 The formation of a triglyceride (triacylglycerol) molecule from glycerol and three fatty acids by
dehydration synthesis reactions. A molecule of water is produced as an ester bond forms between each fatty acid and the
glycerol. Sawtooth lines represent hydrocarbon chains, generally 16 to 22 carbons long, which are symbolized by an R.
Glycerol
Carboxylic
acid
Fatty acids
R
Hydrocarbon chain
Triglyceride
Glycerol
Ester
bond
Hydrocarbon
chain
3H 2 O
H
HC
HC
OH
OH
H
H
C
H
HC C
O
O R
C
O
O R
C
O
O R
HC
H
H
OH C
OHHHHHH
HHHHHH
HOCCCCCCC
OHHHHHH
HHHHHH
HOCCCCCCC
OHHHHHH
HHHHHH
HOCCCCCCC
+
Figure 2.21 Ketone bodies. Acetoacetic acid, an acidic
ketone body, can spontaneously decarboxylate (lose carbon
dioxide) to form acetone. Acetone is a volatile ketone body that
escapes in the exhaled breath, thereby lending a “fruity” smell to
the breath of people with ketosis (elevated blood ketone bodies).
O
COH
H CH
CO
H CH
H
Acetoacetic
acid
H
H CH
CO
H CH
H
Acetone
+ CO 2
Clinical Investigation CLUES
When Brian’s urine is tested in the laboratory, they dis-
cover that he has ketonuria (an elevated level of ketone
bodies in his urine).
- What are ketone bodies, and how do they originate?
- What is the relationship between Brian’s ketonuria
and his weight loss?