THE PHILIPPINE WOMEN’S UNIVERSITY

School of Pharmacy

COURSE: Biochemistry
UNIT NO.: 4 TOPIC: LIPIDS
WEEK: 7 FACULTY: SIGNATURE
:

CONTENT:
● Definitions of Lipid

● Biological Functions of Lipid

● Classification

● Structure and Nomenclature

● Properties

Definitions:
⮚ Lipids are heterogeneous organic compound composed of C,H, O, and may contain P, N, and S.

⮚ Made up of fatty acids and their naturally existing compounds and derivatives.

⮚ May also be defined as:

1. esters or potential esters,
2. soluble in Fat solvents like ether, acetone, chloroform and carbon tetrachloride,
3. biologically active compounds.
⮚ They are not classified as biopolymer.

Functions:
1. Structural components of membrane (plays an important role in permeability of cellular
membrane).
2. Source of caloric energy (fats and oils constitute 20-25% of daily diet. Fat can provides 9.3 Kcal
of energy per gram whereas carbohydrates and proteins can only give 4.1 Kcal/g).
3. Insulating material for internal organs (fat depot of animals derived from ingested foods are
abundant in subcutaneous and intramuscular connective tissues).
4. Vehicle for the transport of fat soluble vitamins.
5. Enzyme cofactor
6. Regulatory substance (steroid hormones).
7. Vitamins (A, D, E, and K)

Classification:
I. Derived lipids – products of the hydrolysis of simple and compound lipids.
1. Fatty acids
A. Saturated
B. Unsaturated
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2. Alcohols
A. Glycerol
B. High molecular weight monohydric alcohol
C. Sphingosinol
D. Sterol

II. Simple lipids – esters of fatty acid.

1. Fats and oils (Neutral Fats or Acylglycerol) 🡪 Fatty acid + Glycerol
2. Waxes 🡪 Fatty acid + High molecular weight monohydric alcohol

III. Compound lipids – lipids in combination with other compounds.

1. Phospholipids
A. Phosphoglycerides
a. Lecithin
b. Cephalin
B. Sphingomyelin
2. Glycolipids
3. Sulfolipids
4. Lipoproteins

FATTY ACIDS – are high molecular weight carboxylic acid. R-(CH 2)n-COOH
Common Characteristics:
1. monocarboxylic
2. even number carbon atoms
3. acyclic and unbranched
4. achiral

Classifications:
I. According to the length of Carbon chain
1. Short Chain Fatty Acid (SCFA) – arefatty acids with aliphatic tails of fewer than 6 C.
2. Medium Chain Fatty Acids (MCFA) – arefatty acids with aliphatic tails of 6–12 C.
3. Long Chain Fatty Acids (LCFA) – are fatty acids with aliphatic tail longer than 12 C.
4. Very Long Chain Fatty Acids (VLCFA) – are fatty acids with aliphatic tails longer than 22 C.

II. According to the type of bond

1. Saturated Fatty Acids – are fatty acids that contain only single bonds.
2. Unsaturated Fatty Acids – are fatty acids that contain double bonds

SATURATED FATTY ACIDS – belong to the acetic acid series.

Empirical formula: CnH2n+1COOH or CnH2nO2
Examples:
Common name Chemical Formula IUPAC name Sources
Butyric acid CH3(CH2)2COOH Butanoic acid Butter
Caproic acid CH3(CH2)4COOH Hexanoic acid Butter, coconut, palm
Caprylic acid CH3(CH2)6COOH Octanoic acid Butter, coconut, palm
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Capric acid CH3(CH2)8COOH Decanoic acid Butter, coconut, palm

Lauric acid CH3(CH2)10COOH Dodecanoic acid Laurel and coconut oil
Myristic acid CH3(CH2)12COOH Tetradecanoic acid Coconut, nutmeg, animal fat
Palmitic acid CH3(CH2)14COOH Hexadecanoic acid Plant and animal fat
Stearic acid CH3(CH2)16COOH Octadecanoic acid Plant and animal fat
Arachidic acid CH3(CH2)18COOH Eicosanoic acid Peanut oil and Lard
Lignoceric acid CH3(CH2)22COOH Tetracosanoic acid Glycolipid and Phospholipid
Cerotic acid CH3(CH2)24COOH Hexacosanoic acid

Properties:
1. solid at ordinary temperature
2. high melting point
3. volatile
4. those with 4 or less carbon are soluble in water in all proportions but as the chain increases,
solubility decreases

UNSATURATED FATTY ACIDS – degree of Unsaturation depends on the number of double bond present.
Empirical formula: CnH2n+1–2mCOOH where m stands for the number of double bonds.
Examples:
Common name Chemical structure Δx
9
Myristoleic acid CH3(CH2)3CH=CH(CH2)7COOH 14:1 (cis-Δ )
Palmitoleic acid CH3(CH2)5CH=CH(CH2)7COOH 16:1 (cis-Δ9)
Sapienic acid CH3(CH2)8CH=CH(CH2)4COOH 16:1 (cis-Δ6)
Oleic acid CH3(CH2)7CH=CH(CH2)7COOH 18:1 (cis-Δ9)
Elaidic acid CH3(CH2)7CH=CH(CH2)7COOH 18:1 (trans-Δ9)
Vaccenic acid CH3(CH2)5CH=CH(CH2)9COOH 18:1 (cis-Δ11)
Linoleic acid CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH 18:2 (cis,cis-Δ9,Δ12)
Linoelaidic acid CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH 18:2 (trans,trans-Δ9,Δ12)
α-Linolenic acid CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH 18:3 (cis,cis,cis-Δ9,Δ12,Δ15)
CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3- 20:4 (cis,cis,cis,cis-
Arachidonic acid
COOH Δ5Δ8,Δ11,Δ14)
CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=C
Eicosapentaenoi 20:5 (cis,cis,cis,cis,cis-
H
c acid Δ5,Δ8,Δ11,Δ14,Δ17)
(CH2)3COOH
Erucic acid CH3(CH2)7CH=CH(CH2)11COOH 22:1 (cis-Δ13)
Docosahexaenoi CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=C 22:6 (cis,cis,cis,cis,cis,cis-
c acid HCH2CH=CH(CH2)2COOH Δ4,Δ7,Δ10,Δ13,Δ16,Δ19)

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Conformational Structure of Unsaturated Fatty Acids: Three dimensional representations:

Properties:
1. unstable (reactive due to double bond)
2. reactivity is directly proportional to the number of double bonds
3. insoluble in ordinary solvents
4. liquid at ordinary temperature (non-volatile)
5. melting point is inversely proportional to the degree of unsaturation

ALCOHOLS
Glycerol Properties:
CH2 – OH
⮚ Oily, colorless, heavy liquid
│
CH – OH ⮚ Undergo oxidation and esterification
│
CH2 – OH ⮚ Undergo dehydration when heated at high
temperature forming Acrolein.
⮚ Sp. gr. 1.26 at 20oC
High Molecular Weight Monohydric Alcohol
CH3 (CH2)17-OH
Sphingosinol Properties:
⮚ n=12 is the most common
HO – CH – CH=CH – (CH2)n – CH3
│ ⮚ forms N-acyl linkage with fatty acids
CH – NH2
│ ⮚ undergo esterification reaction
CH2 – OH
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Sterol (Solid alcohol) –

Cyclopentanoperhydrophenanthrene (CPPP)

SIMPLE LIPIDS
Fats and oils (Neutral Fats) – esters of Fatty acids Properties:
and Glycerol
⮚ Fats are solid whereas oils are liquid at
CH2–O–CO–R1
│ ordinary temperature.
CH–O–CO–R 2 ⮚ Can be mono, di or triacylglycerol form
│
CH2–O–CO–R3 ⮚ Can be simple or mixed triacylglycerol

⮚ Undergo hydrolysis

⮚ Can be saponified

Simple triacylglycerol – R1, R2& R3 are made up of Mixed triacylglycerol – contain different types of
only one type of fatty acid (e.g. Palmitic acid) fatty acids.
Ex. Tripalmitin Ex. α-palmitoyl-α’-stearoyl-β-olein

CH2–O–CO–(CH2)14–CH3 CH2–O–CO–(CH2)14–CH3
│ │
CH–O–CO–(CH 2)14–CH3 CH–O–CO–(CH2)7 –CH=CH– (CH2)7–CH3
│ │
CH2–O–CO–(CH2)14–CH3 CH2–O–CO–(CH2)16 –CH3

Waxes – esters of Fatty acid and High molecular Properties:

weight monohydric alcohol.
⮚ Insoluble in water/soluble in fat solvents
CH3–(CH2)n–O–CO–(CH2)n –CH3 ⮚ Not easily hydrolyzed

⮚ Not digested by fat-splitting enzymes (no

food value)

Examples of Wax Chief constituent Occurence

1. Spermaceti wax Cetylpalmitate Skull of whale / dolphins
2. Beeswax Myricylpalmitate Honey comb
3. Chinese wax / Carnauba wax Cuticle of leaves

Importance of Wax:
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❖ Manufacture of shoe polishes, varnish, candles, lubricants, and cosmetics.

❖ Protective coating on the surface of leaves and animal skin to protect them from excessive loss
of moisture and from invasion of harmful microorganism.
❖ In the body, waxes are found in the form of cholesterol esters.

COMPOUND LIPIDS
1. Phospholipids
C. Phosphoglycerides
c. Lecithin
d. Cephalin
D. Sphingomyelin
2. Glycolipids
3. Sulfolipids
4. Lipoproteins
Structures and Nomenclature of Compound Lipids

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