Biochemistry I

(SGS 236)
Lipid Chemistry I

Biochemistry I
Lecture 4
Dr. Ahmed Maher
Learning Outcomes
By the end of this lecture the students will be
able to:
1. State the importance of lipids.
2. Classify lipids.
3. Classify fatty acids.
4. Name fatty acids.
5. Chemical properties of fats.
Nature of Lipids
• They consist of heterogeneous groups of compounds related
to fatty acids.
• They are water-insoluble organic molecules (hydrophobic)
due to their hydrocarbon chain.
• They can be extracted by non-polar solvents as chloroform
and benzene.
• Body lipids are generally found in compartments (because
they are insoluble in aqueous solution) for example
membrane associated lipids, triacylglycerol in adipocytes.
• Plasma lipids are transported as lipoproteins in association
with proteins.
Occurrence of Lipids
Fat depots (large amount of fats):
• Subcutaneous tissues
• Mesenteric tissues
• Fatty tissues around the
kidney
• Yellow bone marrow
Food sources:
Milk, Egg, Meat, Liver
Fish oils, nuts, seeds and oils

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Importance of Lipids
1. Major source of energy for the body when stored in adipose tissue (caloric value:
9 Kcals/gm).
2. Serves as a thermal insulator in the subcutaneous tissue and around certain
organs.
3. Important component of nervous system (act as electrical insulators in the
myelinated nerves).
4. Fat-soluble vitamins which act as co-enzymes and have regulatory functions in
metabolism.
5. Precursors of prostaglandins and steroid hormones which has an important role
in body homeostasis.
6. Combinations of lipids and proteins (lipoproteins) are important cellular
constituents occurring both in cell membrane and mitochondria and as the
means of transporting lipids in the blood.
N.B.: Deficiencies or imbalance in lipid metabolism leads to some problems as
obesity and atherosclerosis.
 Lipoprotein &
Acts as fuel in Insulating effect
Phospholipids (cell
wall & mitochondrion the body
constituents)

Padding &
protection of
internal organs
Vitamin
A,D,E,K fat
soluble Building
vitamins Materials
(hormones)

Supply essential
Nervous
fatty acids
system: Rich in
lipids
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Lipids Classification
1- Simple Lipids:
• Esters of fatty acids with alcohols.
• Classified according to the alcohol type to:
A- Triacylglycerols (triglycerides, neutral fats).
• Alcohol is glycerol which is esterified with 3 fatty acids.
• Fatty acids lose their negative charges on esterification.
B- Waxes:
• A higher molecular weight monohydric alcohol esterifies
with one fatty acid.
Lipids Classification
2- Conjugated Lipids:
• Esters of fatty acids with alcohols but contain additionally
another group such as:
➢ Phospholipids
➢ Glycolipids
➢ Amino Lipids
➢ Sulfolipids
3- Derived Lipids:
• They include substances obtained by hydrolysis of simple
and conjugated lipids.
 Lipid Classification

Lipids

Complex Derived
Simple (Comps derived from
(alcohol + F.A + other gp)
(alcohol + Fatty acids) simple and Complex
-Phospholipids: alc+F.A+P
-Fats: glycerol+F.A. lipids on hydrolysis)
-Glycolipids: alc+F.A+CHO
-Waxes: other alcohol+F.A Fatty acids, glycerol,
-Sulpholipids: alc+F.A+S
-Aminolipids: alc+F.A+Amino gp steroids, alcohols,
ketone bodies, fatty
aldehydes,
prostaglandins,
leukotrienes etc.
Simple Lipids: Triacylglycerols
• Esters of 3 fatty acids with glycerol.

N.B.: Glycerol and fatty acids are derived lipids.

Components of triacylglycerols: Glycerol

1- Glycerol:
• Colorless and odorless liquid
miscible with water.
• Trihydric alcohol that
contains 2 primary and 1
secondary hydroxyl group.
• It can esterify with one, two
or three fatty acids to
produce monoacylglycerol,
diacylglycerol and
triacylglycerol respectively.
Components of triacylglycerols: Fatty acids

2- Fatty acids
• Monocarboxylic organic acids.
• Amphipathic because a fatty acid consists of:
➢ Hydrophobic part due to its hydrocarbon chain.
➢ Hydrophillic part because at physiological pH, the COOH ionizes to
become COO-
• Fatty acids exist in two forms:
1. Free Fatty acids (unesterified): low levels of free fatty acids occur
in all tissues, but may increase in plasma to substantial amounts
during fasting.
2. Esterified Fatty acids: more than 90% of fatty acids found in
plasma are in the form of fatty acid ester (triacylglycerol,
cholesterol esters and phospholipids) contained in lipoprotein
particles.
Fatty acid

Acyl
Components of triacylglycerols: Fatty acids

• The most common fatty acids in nature are:

➢ Long chain
➢ Straight chain
➢ Having even number of carbons.
• Fatty acids can be classified according to:
➢ Chain length
➢ Saturation
➢ Nutritional classification
Classification of Fatty acids
Classification of fatty acids according to chain length:
1) Short chain: <6 carbon atoms
CH3COOH acetic acid
CH3CH2CH2COOH butyric acid
2) Medium chain: 6-10 carbon atoms
CH3(CH2)4COOH caproic acid
3) Long chain: 12-18 carbon atoms.
CH3(CH2)14COOH palmitic acid
CH3(CH2)16.COOH stearic acid
4) Very long chain: ≥20 carbon atoms
CH3.(CH2)18.COOH arachidic acid
Classification of Fatty acids
Classification of fatty acids according to saturation
1- Saturated fatty acids:
Fatty acids with no double bonds.
2- Unsaturated fatty acids:
Fatty acids with one or more double bonds.
• Cis double bonds: nearly all naturally occurring fatty acids have
double bonds in the cis configuration. The cis double bond causes
fatty acid to bend or “kink” at that position.
• Trans double bonds: Fatty acids having trans double bonds behave
more like saturated fatty acids, they elevate serum LDL and
increase the risk of coronary heart disease. They are not present in
plants.
Classification of Fatty acids
• Monoethenoid:
These contain one double bond in their structure, examples:
palmitoleic acid CH3(CH2)5CH═CH(CH2)7COOH ω7 16:1 Δ9
oleic acid CH3(CH2)7CH═CH(CH2)7COOH ω9 18:1 Δ9
• Polyethenoids (PUFA):
Diethenoids:
linoleic acid CH3(CH2)3(CH2CH═CH)2(CH2)7COOH ω6 18:2 Δ9,12

Triethenoids:
α-linolenic acid CH3(CH2CH═CH)3(CH2)7COOH ω3 18:3 Δ9,12,15

Tetraethenoids:
arachidonic acid CH3(CH2)3(CH2CH═CH)4(CH2)3COOH ω6 20:4 Δ5,8,11,14
Classification of Fatty acids
Nutritional classification of fatty acids:
1. Essential Fatty acids:
• They cannot be synthesized in human or animal body. So they should
be taken in diet.
• Humans cannot synthesize fatty acids which have double bond beyond
C9.
• They include linoleic acid and linolenic acid.
• Note that arachidonic acid can be synthesized in humans from linoleic
acid.
2. Non-essential fatty acids:
• They can be synthesized de novo in the animals from carbohydrates or
proteins.
Nomenclature of Fatty acids
Fatty Acids Nomenclature:
1. Common Name: It is the name by which the fatty acid is
known.
2. Systemic Name: It is derived from the no of carbons in
the hydrocarbon chain. Then changing the suffix -e with
-oic
Examples:
• C18 saturated fatty acid is called Ocatadecanoic.
• C18 with one dB is called Octadecenoic.
• C18 with 2 dB is called Octadecadienoic
Nomenclature of Fatty acids
3. Δ-system: In this case the number before the Δ denote the number of carbons in
the chain and number of dB. The number after the Δ indicate the position of
double bonds.
Examples
• 18 Δ 0 denotes a C18 fatty acid with no dBs.
• 18:1 Δ 9denotes a C18 fatty acid with 1 double bond.
• Cis18 Δ9 means that there is a cis dB between C 9 & 10.
• Trans 18:2 Δ9,12 means that there is 2 trans dBs at C9 & C12
4. ω-system: The carbon of the terminal methyl group is called the ω-carbon
regardless of the chain length
Examples:
• ω-3 fatty acid means that there is a dB at C3 from the methyl terminus.
• ω-6 fatty acid means that db at C6 from the methyl terminus.
• Fatty acids carbon atoms are numbered starting at the COO- terminus.
• Carbon 2 & 3 are always referred as α & β respectively.
• The methyl carbon atom at the distal end of the chain is called the ω carbon.
Practice Question
• For each of the following four naturally occurring fatty acids,
give the systematic name, the common name, and the
abbreviations.
Answer
Common Systemic Δ abbreviation ω abbreviation
Name Name
(a) palmitic hexadecanoic acid C16:0
acid
(b) oleic acid cis-octadecenoic C18:1 cis-Δ9 ω-9
acid
(c) linoleic acid cis,cis C18:2 cis, cis Δ9,12 ω -6
octadecadienoic acid

(d) linolenic cis,cis,cis C18:3cis,cis,cis-Δ9, ω -3

12, 15
acid octadecatrienoic
acid
Memorize
Thank You