LIPID

Dian Agung Pangaribowo

Content
• Definition and Classification of Lipid
• Waxes
• Triacylglycerols / Triglycerides
• Phospholipids
What do the following have in common ?

All these actions involve the use,

misuse, or manipulation of lipids
Definition and Classification
• Lipids ( lipos : fat ) : organic compounds, found in living
organisms, that are soluble in nonpolar organic solvents
• Lipids is defined on the basis of a physical property and not by
the presence of a particular functional group
Definition and Classification
Lipids can be categorized as: (Smith, J.G., 2011)
• Hydrolyzable lipids: can be cleaved into smaller molecules by
hydrolysis with water. Most hydrolyzable lipids contain an ester
unit.

• Nonhydrolyzable lipids: cannot be cleaved into smaller units by

aqueous hydrolysis. Nonhydrolyzable lipids tend to be more varied
in structure.
Waxes
• Waxes : esters (RCOOR') formed from a high molecular weight
alcohol (R'OH) and a fatty acid (RCOOH).
• Long hydrocarbon chains  waxes are very hydrophobic
 Triacylglycerols / Triglycerides
• Triacylglycerols : compounds in which the three OH groups of glycerol are esterified with
fatty acids

• Simple triacylglycerol: If the three fatty acid components of a triacylglycerol are the same
• Mixed triacylglycerols: contain two or three different fatty acid components
 Triacylglycerols / Triglycerides
• Triacylglycerols that are liquids at room temperature are generally called
oils; those that are solids are called fats
• Hydrolysis of a fat or oil produces a mixture of fatty acids

• The fatty acids of common triglycerides are long, unbranched carboxylic

acids with about 12 to 20 carbon atoms.
• Most fatty acids contain even numbers of carbon atoms because
they are derived from two-carbon acetic acid units
 Triacylglycerols / Triglycerides
• Saturated fatty acids have no double bonds in their long
hydrocarbon chains
• Unsaturated fatty acids have one or more double bonds in
their hydrocarbon chains.
• in the unsaturated fatty acids, the double bonds are all cis

• Monounsaturated fatty acid : has only one

double bond
• Polyunsaturated fatty acids : have more
than one double bond
Triacylglycerols / Triglycerides
Saturated fatty acids
• tend to be fully extended because this minimizes steric repulsions
between neighboring methylene groups
• pack efficiently into crystals, and because dispersion force attractions
are large  high melting points.
• The melting points increase with increasing molecular weight
Triacylglycerols / Triglycerides
The cis configuration of the double bond of an unsaturated fatty acid puts
a rigid bend in the carbon chain

Interferes with crystal packing, causing reduced dispersion force

attractions between molecules.

Unsaturated fatty acids have lower melting points.

Triacylglycerols / Triglycerides
• A triglyceride derived from saturated fatty acids has a higher
melting point because it packs more easily into a solid lattice
than a triglyceride derived from kinked, unsaturated fatty
acids.
Hydrogenation of Triacylglycerols
• The C=C bonds in vegetable oils can be
reduced by catalytic hydrogenation,
typically carried out at high temperature
using a nickel catalyst to produce
saturated solid or semisolid fats
• Advantage of partial hydrogenation: give
the fat a longer shelf life.
Polyunsaturated oils tend to react by
autoxidation  become rancid
 Hydrogenation of Triacylglycerols
• Problem : the catalyst isomerizes some of the unreacted double
bonds from the natural cis arrangement to the unnatural trans
arrangement  increased risk of cardiovascular disease
 Saponification of Triacylglycerols

• Saponification : the alkaline hydrolysis of triacylglycerols, leading to

glycerol and a mixture of salts of long-chain carboxylic acids
 Saponification of Triacylglycerols
• Soaps exists as micelles
• Soap micelles are usually spherical clusters of carboxylate anions that are
dispersed throughout the aqueous phase
• Carboxylate groups at the surface and with their nonpolar hydrocarbon chains
on the interior.
• The sodium ions are scattered throughout the aqueous phase as individual
solvated ions.
 Saponification of Triacylglycerols
• Soap solutions separate the individual particles because their
hydrocarbon chains can “dissolve” in the oily layer
• Each individual particle develops an outer layer of carboxylate anions and
presents the aqueous phase
• The individual globules repel each other and thus become dispersed
throughout the aqueous phase
Reactions of the Carboxyl Group of Fatty Acids
Reactions of the Alkenyl Chain of Unsaturated Fatty Acids
 Phospholipids
• Phospholipids : lipids that contain groups derived from phosphoric acid
• The most common phospholipids : phosphoglycerides /
phosphoacylglycerols  phosphoric acid group in place of one of the
fatty acids of a triglyceride
 Phosphatides
• The phosphate group of a phosphatidic acid is bound through another
phosphate ester linkage to one of the following nitrogen-containing
compounds:
 Phosphatides
• Phophatides form lipid bilayers in biological systems
 Sphingomyelins
• Sphingomyelins: derivatives of the amino alcohol sphingosine

• The coating that surrounds and insulates nerve cells, the myelin
sheath  rich in sphingomyelins, and is vital for proper nerve
function.
TERIMA KASIH