Lipids

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 Introduction to Fatty Acid
Structure, Nomenclature, and Physical Properties

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 Types of Lipids

• Lipids with fatty acids

- Waxes
- Fats and oils (trigycerides)
- Phospholipids
- Sphingolipids

• Lipids without fatty acids

- Steroids

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Fatty Acids

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 Fatty Acids
• consist of a long HC chain with a terminal COOH functional group

• have four major physiologic roles:

- 1. are building blocks of membrane phospholipids,

- 2. can be covalently attached to proteins & serve as targeting signals,

- 3. are the major fuel molecules in most animals, and

- 4. their derivatives serve as hormones and intracellular messengers.

• Fatty acids are insoluble in water, vary in chain length (typically 12

– 18 C) and degree of unsaturation (C=C double bonds).

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 Saturated Vs. Unsaturated Fatty Acids
• Saturated fatty acids have no double bonds

• Unsaturated fatty acids have one or more double bonds

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 Cis and Trans Fatty Acids

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 Properties of Saturated vs. Unsaturated FA
• no carbon–carbon double bonds, can stack
in a regular array.
• have a close packing enables strong London
Dispersion forces to form b/n the chains
• have higher melting temperatures.
• they are typically solids at room
temperature.
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 one or more cis carbon–carbon double bonds,
 have kinked structures that cannot pack closely
together.
 fewer intermolecular force attractions b/n
strandslower melting temperatures.
 most unsaturated fats are liquids at room
temperature.
Naming Fatty Acids - IUPAC
• Carbon 1 is always the carbonyl carbon of the
carboxylic acid functional group

• Double bond positions are determined by the carbon closest to

the carbonyl carbon position – this fatty acid has a double bond at
C-9, NOT at C-10!
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Naming Fatty Acids - IUPAC
• Suffix for carboxylic acids = ‘oic acid’ and the
conjugate base = ‘oate’

• The base name is determined by the number

of carbons in the chain

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 IUPAC Prefixes

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Naming Fatty Acids - IUPAC
• Octadecanoic Acid is the base. How are double bonds
incorporated into the name?

• Double bonds need to be given the number position where they

occur as well as their conformation and the designation ‘-ene’
instead of ‘-ane’ must be incorporated.
• 9-cis-Octadecenoic Acid / Common name = oleic acid
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Naming Fatty Acids - IUPAC
• What about Fatty Acids with more than one double bond?

• Add in ‘di, tri, tetra, penta, etc before the ‘-ene-’ for fatty acids
with multiple double bonds.
• 9-cis, 11-trans-Octadecadienoic Acid

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 Delta Nomenclature

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 Omega Nomenclature

b
a

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 Food Sources of Fatty Acids

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 Triacylglycerides

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TAGS are Fats and Oils
• composed of 3 fatty acids and a glycerol backbone
• are also known as triacylglycerol or triglycerides.
• the 3 FA are usually different from one another on any single
• TAG and pools of fats/oils are typically mixtures of many
different TAGs

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TAGS are built by Dehydration Synthesis

Alcohol + Carboxylic Acid = Ester

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General properties of TAGs

• Hydrophobic/Nonpolar
• Most are mixtures
• Melting points and Boiling points
are not sharp
• When shaken with water they
emulsify
• Colorless
• Odorless

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 Emulsification

An emulsion is a mixture of
two or more liquids that are
normally immiscible

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Fats vs. Oils

• Determined by degree of saturation/unsaturation

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 Examples of Oils

• Olive oil – from Oleo europa (olive tree)

• Corn oil – from Zea mays
• Peanut oil – from Arachis hypogaea
• Cottonseed oil – from Gossypium
• Sesame oil – from Sesamum indicum
• Linseed oil – from Linum usitatissimum
• Sunflower seed oil – from Helianthus annuus
• Rapeseed oil – from Brassica rapa
• Coconut oil – from Cocos nucifera

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Reactions
Hydrogen-ation Unsaturated

Reduces the C=C double

bonds with H2

Saturated

Structure by: Ju

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Saponification and Soap
Saponification
• Is the reaction of a fat with a strong base
• Splits triacylglycerols into glycerol and the salts of
fatty acids
• Is the process of forming “soaps” (salts of fatty
acids)
• With KOH gives softer soaps
O

H 2C O C (CH2)14CH3 H 2C OH
O O
NaOH
HC O C (CH2)14CH3 HC OH + 3 Na O C (CH2)14CH3
O
(Soap)
H 2C O C (CH2)14CH3 H 2C OH

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 TAGS as Energy

 are the body’s main energy source and it is

stored in fat tissue  adipose tissue

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 Waxes and Related Compounds

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 Waxes

Waxes are formed when a fatty acid combines with a

long chain alcohol forming an ester bond

Stearic Acid

Oleic Alcohol

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Waterproofing Bird Waxes

Waxes can be found throughout the biological

world, in all kingdoms of life. Example, water birds
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 Beeswax

Triacontanyl Palmitate

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Waxes on the Plant Cuticle

Picture by: Rei

Figure by: Diah, S.Z.M., et al (2014) Article ID: 878409

Figure by: Graca, J. (2015) Frontiers in Chemistry 3:62
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 Human Skin

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 Phospholipids and Sphingolipids

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 Phospholipid Structure

Figure from: OpenStax Anatomy and Physiology Figure from: School of Biomedical Sciences Wiki

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 Phospholipid Structure
• most common constituent of any lipid bilayer making up a cell
membrane is the phospholipid.
• base structure of a phospholipid is similar to that of a triacylglyceride,
however, one of the glycerol positions is modified as a phosphoester,
instead of an ester with a fatty acid component are only two fatty
acids incorporated into the phospholipid structure.
• the phosphate functional group is then further modified by the addition
of other functional groups that are shown in more detail on the next
slide. All phospholipids are amphipathic.
• have a polar head and two nonpolar hydrocarbon tails. Of the fatty
acids incorporated into the phospholipid structure, one is usually
saturated and the other unsaturated.
• Unsaturated fatty acids result in kinks in the hydrophobic tails

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 Typical Phospholipids in the PM

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 Sphingolipids

Sphingolipids
• Are similar to phospholipids.
• Contain sphingosine (a long-chain amino alcohol), a
fatty acid, phosphate, and a small amino alcohol
• Have polar and non-polar regions

fatty acid

sphingosine

amino
PO4
alcohol
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 Sphingolipids
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ASTU-2021 Sphingolipids
 Phospholipid Bilayer

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 Steroids

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Steroid nucleus

A steroid nucleus consists of

• 3 cyclohexane rings
• 1 cyclopentane ring
• No fatty acids

steroid nucleus

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 Steroids

• A steroid is a terpenoid lipid

• Steroids vary by the functional

groups Lanosterol

• Hundreds of types

• lanosterol (animals and fungi)

• cycloartenol (plants).
Cycloartenol

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Steroid Numbering System

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Terpenes and Terpenoids

Isoprene Unit

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 +
GPP

FPP

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 FPP FPP

NADPH
Squalene
Synthase
NADP+ + H+ + 2PPi

Squalene

Figure modified from: Jag123

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 Cholesterol

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 Cholesterol in the Body

A normal, open artery.

Cholesterol in the body
• Is obtained from meats, milk,
and eggs
• Is synthesized in the liver
• Is needed for cell membranes,
brain and nerve tissue, steroid
hormones, and Vitamin D.
• Clogs arteries when high
levels form plaque

An artery clogged by
cholesterol plaque

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 Cholesterol in Foods

Cholesterol is
• Synthesized in the liver.
• Obtained from foods.
• Considered elevated if
plasma cholesterol
exceeds 200 mg/dL.

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 Lipid Biosynthesis

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