LIPEDS

See discussions, stats, and author profiles for this publication at: https://www.researchgate.
net/publication/340610325
Chemistry of fats and oils (Lipids)
Presentation · April 2020

DOI: 10.13140/RG.2.2.27778.22722
CITATIONS READS
2 23,060
1 author:
Adnan Wahhab Al-Mudhafr

Faculty of Agriculture / University of Kufa
44 PUBLICATIONS 12 CITATIONS
SEE PROFILE
Some of the authors of this publication are also working on these related projects:
Biotechnology View project
Cereal Chemistry View project
All content following this page was uploaded by Adnan Wahhab Al-Mudhafr on 11 May 2021.
The user has requested enhancement of the downloaded file.

Chemistry of fats and oils (Lipids)
Prof. Dr. ADNAN AL-MUDHAFR
Lipids are naturally occurring molecules from plants or animals
that are soluble in nonpolar organic solvents.
Lipid molecules contain large hydrocarbon portion and not many
polar functional group, , which accounts for their solubility
behavior..
• Lipids are essential components of all living organisms
• Lipids are water insoluble organic compounds
• They are hydrophobic (nonpolar) or amphipathic
(containing both nonpolar and polar regions)
1. Free fatty acids
2. Triglyceride (Triacylglycerol)
3. Phospholipids
4. Glycolipids
5. Steroids
Professor Dr. Adnan Al-Mudhafr ………………………………………………………………………….. Iraq- Kufa University - Faculty of Agriculture ‫الصفحة‬1
Classification of Lipids
(a)Lipids that are ester or amides of fatty acids
Waxes – are carboxylic acid esters where both R groups
are long straight hydrocarbon chain.. Performs external
protective functions..
Triglyceride – are carboxylic acid triesters of glycerols.
They are a major source of biochemical energy.
Glycerophopholipids - tri-esters of glycerol that contain
charged phosphate di-esters. They help to control the flow
of molecules into and out of cells
Sphingomyelins – amides derived from an amino
alcohol, also contain charged phosphate di-ester groups. They are
essential to the structure of cell membranes.
Glycolipids – amides derived from sphingosine, contain polar
carbohydrate groups. On the cell surface, they connect with by
intracellular messengers.
(b)Lipids that are not esters or amides:
Steroids – They performs various functions such as hormones
and contributes to the structure of cell membranes.
Eicosanoids – They are carboxylic acids that are a special type
of intracellular chemical messengers.
Properties of Fats and Oils
Oils: (Solid Triglyceride) A mixture of Triglyceride that is
liquid because it contains a high proportions of unsaturated fatty
acids.
Fats:( Solid Triglyceride) A mixture of Triglyceride that is solid
because it contains a high proportions of saturated fatty acids.
Properties of Triglyceride in natural fats and oils:
Nonpolar and hydrophobic No ionic charges
Saturated Fatty acid
Common name Chemical structure C:D
Acitic Acid CH3COOH 2:0
Butyric acid CH3(CH2)2COOH 4:0
Caproic acid CH3(CH2)4COOH 6:0
Caprylic acid CH3(CH2)6COOH 8:0
Capric acid CH3(CH2)8COOH 10:0
Lauric acid CH3(CH2)10COOH 12:0
Stearic acid CH3(CH2)16COOH 18:0
Arachidic acid CH3(CH2)18COOH 20:0
Behenic acid CH3(CH2)20COOH 22:0
Lignoceric acid CH3(CH2)22COOH 24:0
Cerotic acid CH3(CH2)24COOH 26:0
Unsaturated Fatty acid
Common name Chemical structure C:D IUPAC
Myristoleic acid CH3(CH2)3CH=CH(CH2)7COOH 14:1 14:1(9)
Palmitoleic acid CH3(CH2)5CH=CH(CH2)7COOH 16:1 16:1(9)
Sapienic acid CH3(CH2)8CH=CH(CH2)4COOH 16:1 16:1(6)
Oleic acid* CH3(CH2)7CH=CH(CH2)7COOH 18:1 18:1(9)
Elaidic acid CH3(CH2)7CH=CH(CH2)7COOH 18:1
Vaccenic acid CH3(CH2)5CH=CH(CH2)9COOH 18:1
Linoleic acid* CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH 18:2 18:2(9,12)
Linoelaidic acid* CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH 18:2
18:3(9,12,1
α-Linolenic acid CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH 18:3
5)
CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2CH=C 20:4(5,8,11
Arachidonic acid* 20:4
H(CH2)3COOH ,14)
Eicosapentaenoic CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHC 20:5(5,8,11
20:5
acid H2CH=CH(CH2)3COOH ,14,17)
Erucic acid CH3(CH2)7CH=CH(CH2)11COOH 22:1 22:1(13)
Docosahexaenoic CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHC 22:6(4,7,10
22:6
acid H2CH=CHCH2CH=CH(CH2)2COOH ,13,16,19
Fatty Acids
OH
Common = lauric acid
O 1
2 IUPAC = dodecanoic acid
Fatty acid
3
4 Abbrev. = C12:0
5 Fatty acyl
6 group
Other fatty acids (examples)
7 Hydrocarbon •Myristic, tetradecanoic, C14:0
8 tail. •Palmitic, hexadecanoic, C16:0
9
•Stearic, octadecanoic, C18:0
10
11
12 CH3
Unsaturated Fatty Acids
O OH
1
2 Common = palmitoleic acid

3 IUPAC = cis- 9-hexadecenoic acid
4
5 Abbrev. = C16:19
6
7 Other unsaturated fatty acids (examples)

H 8 •Oleic, cis- 9-octadecenoic, C18:19
9 •Linoleic, cis,cis- 9,12-octadecadienoic, C18:29,12
10
H
11 12
13
Another nomenclature system:
14
C18:29,12 is also known as an -6 fatty acid (i.e. the
15 last double bond is 6 carbons from the end of the
CH
16 3 fatty acid chain.)
Oleate Linolenate
9,12,15
C18:19 C18:3
Stearate
C18:0
Melting points: 70oC 13oC -17oC

Polyunsaturated
Eicosanoids
• Eicosanoids are oxygenated derivatives of C20 polyunsaturated fatty

acids (e.g. arachidonic acid)
• Prostaglandins - eicosanoids having a cyclopentane ring
• Aspirin alleviates pain, fever, and inflammation by inhibiting the
synthesis of prostaglandins
Triglycerides
• Fatty acids are important metabolic fuels (2-3 times the energy of
proteins or carbohydrates)
• Fatty acids are stored as neutral lipids called Triglycerides (TGs)
• TGs are composed of 3 fatty acyl residues esterified to a glycerol (3-

carbon sugar alcohol)
• TGs are very hydrophobic, and are stored in cells in an anhydrous

form (e.g. in fat droplets)
TGs are catabolized by lipases. Digestion requires bile salts (solubilize

TGs). Transport of TGs is accomplished through lipoproteins
Chemical Reactions of Triglyceride
Hydrogenation:
The carbon-carbon double bonds in unsaturated fatty acids can be
hydrogenated by reacting with hydrogen to produce saturated
fatty acids. For example, margarine is produced when two thirds
of the double bonds present in vegetable oil is hydrogenated.
Hydrolysis of Triglyceride:
Triglyceride like any other esters react with water to form their
carboxylic acid and alcohol – a process known as hydrolysis..
*In body, this hydrolysis is catalyzed by the enzyme hydrolase
and is the first step in the digestion of dietary fats and oils.
*In the laboratory and commercial production of soap, hydrolysis
of fats and oils is usually carried out by strong aqueous bases
such as NaOH and KOH and is called saponification
Phospholipids
• The most abundant lipids in membranes

• Possess a glycerol backbone
• A phosphate is esterified to both glycerol and another compound bearing
an -OH group
• Phosphatidates are glycerophospholipids with two fatty acid groups
esterified to C-1 and C-2 of glycerol 3-phosphate
Steroids
• Classified as isoprenoids - related to 5-carbon isoprene (found
in membranes of eukaryotes)
• Steroids contain four fused ring systems: 3-six carbon rings
(A,B,C) and a 5-carbon D ring
• Ring system is nearly planar
Substituents point either down (a) or up (b)
OH = “ol”
-C=O = “one”
-COOH = “ate
Ergosterol
Functions and Properties of Cholesterol
• Cholesterol modulates the fluidity of mammalian cell
membranes
• It is also a precursor of the steroid hormones and bile salts
• It is a sterol (has hydroxyl group at C-3)
• The fused ring system makes cholesterol less flexible than most
other lipids
• Cholesterol is converted to cholesteryl esters for cell storage or transport

in blood
• Fatty acid is esterified to C-3 OH of cholesterol
• Cholesterol esters are very water insoluble and must be
complexed with phospholipids or amphipathic proteins for
transport
Cell Membrane Lipids Phospholipids and
Glycolipids
• Cell membranes establish a hydrophobic barrier between the

watery environment in the cell and outside the cell. Lipids are
ideal for this function.
• The three major kinds of cell membrane lipids in animals are
phospholipids, glycolipids,, and cholesterol.
Phosphoilipids contain an ester link between aa phosphoric

acid and an alcohol. The alcohol is either a glycerol to give a
glycerophopholipid or a sphingosine to give sphingomyelins.
• Glycolipids: Glycolipids are derived from
sphingosine. They differ from sphingomyelins by having a
carbohydrate group at C1 instead of a phosphate bonded to a
choline.
Cell Membrane Lipids Cholesterol
Animal cell membranes contain significant amount of

cholesterol
• Cholesterol is a steroid, a member of the class of lipids
that all contain the same four ring system.
Cholesterol serves two important purposes: as a component
of cell membranes and as a starting materials for the
synthesis of all other steroids
Structure of Cell Membranes
The basic structural unit of cell membrane is lipid bilayer which is
composed of two parallel sheets of membrane lipid molecules
arranged tail to tail.. Bilayers are highly ordered and stable, but
still flexible.
The amount of cholesterol in animal sources
Source mg / 100 g Source mg / 100 g
Beef 90 the heart 150
Lamb 70 the brain ˂0222
Chicken 60 milk 11
The liver 300 butter 250
Kidney 375 yolk 150 For each yolk
β-Oxidation of free fatty acids
β-Oxidation of fatty acids occurs within the mitochondrial matrix.
Sarcoplasmic short and medium-chain fatty acids (chain lengths up
to 12 carbons) can freely enter the mitochondrial matrix. In
contrast, long-chain fatty acids must be transported into the
mitochondria, which is a rate-limiting step. β-Oxidation involves
the sequential removal of 2-carbon segments in the form of acetyl-
CoA and production of shortened acyl-CoA, with concurrent
reduction of one FAD and one NAD+. The electrons carried by
NADH + H+ and FADH2 immediately enter the electron transfer
system (ETS) of the oxidative phosphorylation (OXPHOS) system,
whereas acetyl-CoA enters the TCA cycle
Beta oxidation of free fatty acid
Prof. Dr. Adnan Al-Mudhafr
Iraq - Kufa University - Faculty of Agriculture
View publication stats

LIPEDS

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

LIPEDS

Uploaded by

Copyright:

Available Formats

See discussions, stats, and author profiles for this publication at: https://www.researchgate.

Chemistry of fats and oils (Lipids)

Presentation · April 2020

Adnan Wahhab Al-Mudhafr

Biotechnology View project

Cereal Chemistry View project

The user has requested enhancement of the downloaded file.

2 Common = palmitoleic acid

7 Other unsaturated fatty acids (examples)

Melting points: 70oC 13oC -17oC

• Eicosanoids are oxygenated derivatives of C20 polyunsaturated fatty

• Fatty acids are stored as neutral lipids called Triglycerides (TGs)

• TGs are composed of 3 fatty acyl residues esterified to a glycerol (3-

• TGs are very hydrophobic, and are stored in cells in an anhydrous

TGs are catabolized by lipases. Digestion requires bile salts (solubilize

• The most abundant lipids in membranes

• Cholesterol is converted to cholesteryl esters for cell storage or transport

• Cell membranes establish a hydrophobic barrier between the

Phosphoilipids contain an ester link between aa phosphoric

Cell Membrane Lipids Cholesterol

Animal cell membranes contain significant amount of

You might also like