Lipids

Lipids
(generally soluble in organic solvents

Plant sources Animal sources

(olive, palm) (butter, lard, tallow)
No cholesterol

Oils and Fats

Triacylglycerol

Sterols
Waxes
(monoesters)
 Lipids
Definition of Lipids
 Naturally occurring biological substances made from C, H
and O of pronounced hydrophobicity that are soluble in
organic solvents but not water
 Petroleum distillates (e.g. hexane)
 Chloroform
 Ethers
 Alcohols
 Also classified as “biological molecules containing fatty
acids or the corresponding alcohols or sphingosine bases”
 Lipids have more C and H than carbohydrates, which is why
they generate more energy when utilized  2.25 times
more = 9 kcal/g vs. 4 kcal/g.
 Lipids
Biological role
A. Structural
- found in membranes
- protective barriers
B. Regulatory
- steroids/prostaglandins
- phospholipids
C. Storage
- triglyceride is
storage for energy
D. Vitamins
- solvent
- precursor
 Lipids
Role in foods
A. Calories (kcal)
– energy <30% of all calories
v.s.
(ideal)
- satiety
B. Essential fatty acids
- linoleic acid, linolenic acid
arachadonic acid
C. Flavor
- most lipid soluble (usually off-
flavors)
D. Texture
v.s.
– mouth feel & appearance
E. Color
- carotenoids
F. Heat transfer medium
 Lipids
Classification of lipids (structure)
1) Simple lipids Glycerol
 Mono, Di and Triacylglycerols backbone Fatty acids
 Waxes
2) Compound lipids
 Phospholipids
 Glycolipids
 Sphingolipids (amide to alcohol)
3) Derived lipids
 Free fatty acids
 Sterol esters
 Tocopherol (Vit-E)
 β-carotene
Triacylglycerol
 Lipids
Classifications of lipids (polarity)
1) Non-polar lipids 2) Polar lipids
(neutral lipids)  Glycerophospholipid
 Fatty acids  Glyceroglycolipid
 Mono-, di-, & triacylglycerols  Sphingophospholipid
 Waxes  Sphingoglycolipid
 Sterols
 Carotenoids
 Tocopherols
 Lipids

Structure & properties of fatty acids

 Fatty acid are composed of a hydrocarbon chain with
methyl group (CH3) on one end and a carboxyl group
(COOH) on the other.
 Basic properties common to most fatty acids
1. Most are even carbon #
2. Most are monocarboxylic acids
3. Most are part of triacylglycerides (triglycerides)
 Lipids
NOMENCLATURE
1. Number of carbons
 C4-C24 most common
 E.g. C8 = octa
C12 = dodeca
2. Saturation
 Saturated
(no double bonds)
 Unsaturated
(double bonds)
 Mono (1 = bond)
 Poly (>1 = bond)
 Lipids
2. Saturation (cont.)
 No double bond = Anoic
 E.g. C18:0
 One double bond = Enoic
 E.g. C18:1
 Two double bonds = Dienoic
 E.g. C18:2
 Three double bonds = Trienoic
 E.g. C18:3
3. Geometric configuration
of double bonds
 Cis vs. Trans
 Has an influence on
the fatty acid backbone
structure
 Lipids

4. Position of double bonds

 Delta (Δ) system - count # of carbons to the = bond from the
COOH end
 E.g. Δ 9-octadecenoic acid
 Means: a) C18 = octadecenoic
b) 1 double bond = octadecenoic
c) double bond is 9 carbons from the COOH end
 Omega (ω) system - count # of carbons to the = bond from the
CH3 end – used for abbreviations of fatty acids
 E.g. Δ 9-octadecenoic acid would be C18:1ω9
 ω-3 therefore would mean that the = bond is 3 C from the CH3 end
 ω-3, ω-6 and ω-9 the most common
 Lipids

What is the name of this fatty acid using the delta & omega
systems?

H3C-(CH2)4-CH=CH-CH2-CH=CH-(CH2)7-COOH

Delta: ___________________________

Omega: __________________________

Common name is Linoleic acid (C18:2)

 Lipids
Major fatty acids in foods
 Saturated
 Palmitic (16:0)
 Stearic (18:0)
 Monoenoic
 Oleic (18:1ω9)
 Dienoic
 Linoleic (18:2ω6) – Δ9, 12 - common in plants; some in animal
 Trienoic
 Linolenic (18:3ω3) Δ9, 12, 15
 Tetraenoic
 Arachadonic (20:4ω6) - Δ 5, 8, 11, 14 - part of membrane phospholipids
 Lipids
Factors affecting the properties of fatty acids
1.Length of fatty acids
 Longer chain length leads to increase in melting point and gives
more stable fat crystals
 Classes:
 C4 – C8 - liquid @ room temperature (20-25°)
 These are water soluble  good emulsifiers

 C10 - C14 - viscous @ room temperature

 C16 - C26 - solid @ room temperature
 For example:
 C6:0  MP = -2°C
 C10:0  MP = 31.5°C
 C16:0 MP = 63°C
 Lipids
Factors affecting the properties of fatty acids
2. Double bonds
 An increase in double bonds decreases melting point
Example:
18:0 = 70°C
18:1 = 15°C
18:2 = -5°C
18:3 = -11°C
 Lipids

Factors affecting the properties of fatty acids

3. Cis vs. Trans
 Cis has lower melting point than Trans
 Cis produces a kink in the fatty acid chain which creates a more
open fatty crystal structure

Melting Point

Kink 18:1c 15°C

18:1t 44 °C

18:2c -5 °C
18:2t 29 °C

18:3c -11 °C
18:3t 71 °C
 Lipids

Arrangement of fatty acids on triacylglycerides

1. Not random (usually)
2. Specificity controlled
3. General pattern

Position Plant Mammal Milk Bird Fish

1 S S S S S-LC
2 U U S U U
3 U LC U or SC S or U LC
 The arrangement can significantly affect physical properties of fat
LC : Long chain; SC: Short chain
 Lipids
Importance of sn position; Cocoa butter vs. Tallow

Cocoa Butter Tallow

High mp % 16:1 62.00 64.00

Consistency hard sharp mp greasy broad mp

SSS 0.03 0.28

SSU 0.01 0.16

SUS 0.81 0.32

SUU 0.15 0.18

Low mp USU 0.01 0.02

UUS 0.01 0.03

 Lipids
Important Compound Lipids
1. Phospholipids
 Make up cellular membranes
 Lipid molecules that contain a phosphate
group attached to a functional group
 Have both hydrophobic
(fatty acids) and hydrophilic
(phosphate and functional
group) portions
 Good emulsifiers
 May have a protective effect
against ulcers (milk PL)
 Lipids
2. Glycolipids
 Contain at a minimum one sugar
 Some may also have a phosphate group (glycosphingolipids)
 Found in all tissues of animals
 Have same solubility characteristics as regular lipids
3. Sterols
 Made of four fused hydrophobic rings with a hydrophilic OH group
 Not so important as a food ingredient but important for dietary reasons
 Cholesterol in animal foods
 Can contribute to coronary heart
disease (arteriosclerosis)
 300 mg/day the recommended intake limit
 Lipids
4. Fat substitutes
 Sucrose fatty acid polyesters
 Olestra ® (Procter and Gamble Co.)
 6-8 fatty acids (>C12) esterified to sucrose
 Caloric free due to its bulky structure and because lipases cannot
hydrolyze it
 May lead to loss of fat soluble vitamins and can give diarrhea
 Approved for use in frying oils (snacks)
 Sucrose and polyol fatty acid esters
 1-3 fatty acids esterified to sucrose or a polyol (e.g. sorbitol)
 Have caloric value (polyol fatty acid esters only about 1.5 kcal/g)
 Used as emulsifiers and stabilizers
 Triacylglycerol

Sterols

Wax
(bees wax)
Simple lipids

Monoglyceride

Diglyceride

Triglyceride
 Compound Lipids

Phosphate Sugar unit

group

Phospholipid
Glycolipid
 Derived Lipids

Sterols Carotene

 Peptide based liquid
 Tube or oral feeding
 Efficient energy utilization
 MCT OIL (Novartis nutrition)
 unable to digest or absorb
conventional fats
 Less enzymes and bile acids
for digestion
 Fish Lipids
 Fish are classified as lean, semi-fatty or fatty.
 Fish that store lipids only in the liver as lean and fish
storing lipids in fat cells distributed in other body tissues as
fatty.
 Typical lean species are bottom-dwelling ground fish like
cod, and hake.
 Fatty species include pelagic such as herring, mackerel
and sprat.
 Some species store lipids in limited parts of their body
tissues only, or in lower quantities than typical fatty
species, and are consequently termed semi- fatty species
(e.g. barracuda, mullet and shark).
 Type of lipids in fish
 The lipids present in teleost fish species may be
divided into two major groups:
 Phospholipids
 The phospholipids make up the integral structure of the unit
membranes in the cells; thus, they are often called structural
lipids.
 Triglycerides
 The triglycerides are lipids used for energy storage in fat
depots, usually within special fat cells surrounded by a
phospholipid membrane and a rather weak collagen network.
 The triglycerides are often termed depot fat. A few fish
have wax esters as part of their depot fats.
 Fish & Mammals lipids

 Fish and mammalian lipids differ mainly in that

fish lipids include up to 40 percent of long-chain
fatty acids (14-22 carbon atoms) which are highly
unsaturated.
 Mammalian fat rarely contains more than two
double bonds per fatty acid molecule while the
depot fats of fish contain several fatty acids with
five or six double bonds.
 Lipids: marine & freshwater fish

 The percentage of polyunsaturated fatty acids

with four, five or six double bonds is slightly lower
in the polyunsaturated fatty acids of lipids from
freshwater fish (approximately 70 percent)
 Lipids from marine fish (approximately 88
percent).
 However, the composition of the lipids is not completely
fixed but can vary with the feed intake and season
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