CHEM 109C Zhang

CLAS, F10
Lipids - KEY

1. Indicate which class of lipids each of the following belongs to.

a.

A fat, saturated triacylglycerol, simple (tristearin)

b.
A vitamin or a terpene (Vitamin A, 20 Cs)

c.
A prostaglandin (PGE1)

d.
A steroid or a hormone (cortisone)

e.
A fatty acid or polyunsaturated fatty acid (arachidonic acid)

f.
A wax/ester of fatty acid and long chain alcohol (component of
spermaceti wax)

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CHEM 109C Zhang

CLAS, F10
Lipids - KEY

g.

An oil, saturated triacylglycerol, simple (trilinoleic)

h.

A membrane lipid, phosphatidylcholine

2. What fatty acids are produced by the hydrolysis of 2-oleyl-1,3-distearylglycerol?
O
O

16

stearic acid

16

3 H2 O

16

7
oleic acid
7

OH

HO

OH

glycerol
3. Spermaceti is a
wax
from a sperm whale which contains as a major
component hexadecyl hexadecanoate. Draw hexadecyl hexadecanoate.
O

15

14

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CHEM 109C Zhang

CLAS, F10
Lipids - KEY

4. Cembrene is a

diterpene

C20H32
Be able to mark the isoprene units below shown with dotted lines or colors

5. (Ch 26 # 1 & 3) Which of each of the following pairs of fatty acids or fats would
have the higher melting point and explain why.
a. palmitic acid & stearic acid
O

HO

14 <

63 oC

HO

16

69 oC
18 Cs so more van der Waals IMF, higher MP

b. palmitic acid & palmitoleic acid

O
O

HO
HO

14 >

63 oC
0 oC
saturated fatty acid so more van der Waals IMF, higher MP
c. oleic acid & linoleic acid

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CHEM 109C Zhang

CLAS, F10
Lipids - KEY
O

HO

HO

>
13 C
-5 oC
only one double bond so more van der Waals IMF, higher MP
7

d. glyceryl tripalmitoleate & glyceryl tripalmitate

fats made with
palmitoleic acid & palmitic acid
O
O
HO

7
HO

<

14

0 oC
63 oC
saturated fatty acid, so saturated fat which has more van der Waals
IMF, higher MP.
Identifying Lipids (nonpolar compounds)
- Fatty acids
Long chain carboxylic acids (Table 26.1)
-

Fats
Triacylglycerols (glycerol + 3 fatty acids (0-1 double bond) triester) simple &
mixed solid or semi-solid at RT

Oils
Triacylglycerols (glycerol + 3 fatty acids (1+ double bond) triester) simple &
mixed liquid at RT

Waxes
Ester of fatty acid and long chain alcohol

Phospholipids (membrane lipids)

o Phosphoacylglycerol:
Fat where one fatty acid has been replaced by phosphoric acid
Phosphoacyldiester
Phosphoacylglycerol where phosphate forms ester with another group
phosphatidylethanolamine (a cephalin)
phosphatidylcholine (a lecithin)
phosphatidylserine
o Sphingolipid:
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CHEM 109C Zhang

CLAS, F10
Lipids - KEY

Phospholipid where amino alcohol (sphingosine) is backbone instead of

glycerol
sphingomyelin
-

Prostaglandins
5 member ring with 2 substituents (7-C carboxylic acid group (R1) and an 8-C
hydrocarbon (R2))

Terpenes
Contains Cs in multiples of 5 (Table 26.3)
- Steroids
Have 4 fused rings (A, B & C are cyclohexane rings and D is a cyclopentane)
Mechanisms:
Oxidation of fats and oils by oxygen
Synthesis of prostaglandins from arachidonic acid
Chemistry of vision isomerization of retinal
Biosynthesis of terpenes
Synthesis of isopentyl pyrophosphate from acetyl-CoA and malonyl-CoA
Synthesis of dimethylallyl pyrophosphate from isopentyl pyrophosphate
Synthesis of terpenes from isopentyl pyrophosphate & dimethylallyl
pyrophosphate
Synthesis of cholesterol from squalene

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