Fundamentals of Medicinal Chemistry

(Brent) #1

1.5 Lipids


1.5.1 Introduction


The term lipid is the collective name given to a wide variety of classes of naturally

occurring compounds isolated from plant and animal material by extraction

with nonpolar solvents. This section discusses a selection of the classes of

compound that are classified as lipids. However, not all classes of compound

obtained by extraction with nonpolar solvents are classified as lipids.

1.5.2 Fatty acids


This is the most abundant group of compounds that are classified as lipids. They

occur as isolated molecules and are more commonly found as residues in other

lipid structures. The fatty acids and residues that are commonly found are

normally referred to by trivial names (Table 1.4). They usually have ‘straight

chain structures’ with even numbers of between 14 and 22 carbon atoms inclu-

sive. Both saturated and unsaturated residues are found. In the latter case both

cisandtransisomers are known but thecisisomers are more common. A few

residues have structures that have side chains and/or other functional groups.

Table 1.4 Fatty acids that are commonly found in lipids. Ricinoleic acid is optically active


because its number 12 carbon atom is chiral


Trivial name Systematic name Structure


Palmitic acid Hexadecanoic acid CH 3 (CH 2 ) 14 COOH


Palmitoleic acid cis-Hexadecenoic acid CH 3 (CH 2 ) 5 CH¼CH(CH 2 ) 7 COOH


Stearic acid Octadecanoic acid CH 3 (CH 2 ) 16 COOH


Oleic acid cis-9-Octadecanoic acid CH 3 (CH 2 ) 7 CH¼CH(CH 2 ) 7 COOH


Linoleic acid cis-9-cis-12-


Octadecadienoic acid

CH 3 (CH 2 ) 3 (CH 2 CH¼CH) 2 (CH 2 ) 7 COOH

Linolenic acid cis-9-cis-12-cis-15-


Octadecatrienoic acid

CH 3 (CH 2 CH¼CH) 3 (CH 2 ) 7 COOH

Ricinoleic acid 12-hydroxy-cis-9-


Octadecanoicacid

CH 3 (CH 2 ) 5 CHOHCH 2 CH¼CH(CH 2 ) 7 COOH

Arachidonic acid cis-5-cis-8-cis-11-cis-14-


Eicosatetraenoic acid

CH 3 (CH 2 ) 3 (CH 2 CH¼CH) 4 (CH 2 ) 3 COOH

20 BIOLOGICAL MOLECULES

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