Lycopene

An Overview

Tahirah Farrer-Bradley
Tuskegee University
 Lycopene is responsible for the
red pigment in…

Grapefruit Flamingoes Apricot

Rose hips Pink Guava

Watermelon
 Lycopene
• Is the carotenoid responsible for the red pigment of
many fruits and vegetables.

• There are more than 600 naturally occurring

carotenoids, of these lycopene is the largest and most
abundant.

• Tomatoes and its food products are the most

important source of lycopene.

• Lycopene is the major carotenoid in the diet of North

Americans and Europeans. It is thus the most
abundant carotenoid in the human body.
Importance of Lycopene
• Research suggests a correlation
between the intake of carotenoids and
reduced risks of degenerative diseases
such as prostate, bladder, cervix,
breast and digestive tract cancer.

• Carotenoids are non-polar, conjugated,

lipophilic antioxidants.
Lycopene is assembled from 8 isoprene units

Isoprene
(common name)
Methane
Ethane

2 4 Propane
1 3 Butane

2-Methyl-buta-1,3-diene Pentane
(IUPAC) Hexane
Double bonds
Heptane
1-ene
Octane
2-diene Nonane
3-triene
Decane
 Definition of Terms
• Antioxidants- substances which slow the oxidation
rate in autoxidizable substances. Present in fruits and
vegetables; protectors against degenerative diseases.

• Extraction- the removal of soluble material from a

solid mixture by means of a solvent.

• Filtration- the process of separating a solid from a

liquid or gas by use of a membrane of medium (e.g.
filter paper, glass sinter).

• Isomer- one of two or more compounds that have the

same chemical formula but different arrangements of
the atoms within the molecules and that may have
different physical/chemical properties.
 Lycopene

Conjugated

Trans-Lycopene

Non polar: Will not dissolve in water

Conjugation: Alternating double bonds

Lipophilic: Will dissolve in lipids. “lipid

like” or “fat loving” (defines: oils,
cholesterols and waxes).
 Cis/Trans
Trans configuration- opposite position of
atoms/substituents between a double bond.

Ex. H
Trans is often denoted E

Cis configuration- atoms on the same side of a double bond

Ex.
H
Cis is often denoted Z
H

Cis (Z) and Trans (E) configurations occur in isomers

Isomers:

Trans-Lycopene
C40H56
M.W. 536.873 g/mole
Melting Pt. 172-173ºC

β-Carotene
C40H56
M.W. 536.873 g/mole
Melting Pt. 180-182ºC
Common Forms of lycopene
5Z-Lycopene

C-27

9Z-Lycopene

C-23
13Z-Lycopene

C-19
 Bioavailability
• Bioavailability- the degree and rate at which a
substance, such as a drug, is absorbed into a living
system or is made available at the site of
physiological activity.
• More than 85% of the lycopene in the
body is found in its cis (Z) form while in
nature (tomatoes) it is found
predominately in its trans (E) form. It is
therefore said that lycopene is more
bioavailable in its cis form.
 Possible reasons for different
isomers in the body.
• Lycopene can be isomerized by:
–Heat
–Light
–pH
–Catalyst (KI)-speeds reaction w/o being
consumed (interfering).
In the body the change of temperature (25°C
(RT) to 37°C (BT)) and the change in pH
~2.0 in the stomach may be the cause of
isomerization in the body.
 Method of Extraction
• 15 g of tomato food source/carotenoid
source
• In 21 mL of acetone
• Stir until no longer gummy
• Vacuum filtration
• Place solid material in 15 mL CH2Cl2
(Methylene Chloride)
• Vacuum filtration
• Evaporate CH2Cl2 via heat (B.P.)/vacuum
 Reading liquid volumes
What is the volume?
• Meniscus
The curved top of a column of liquid in a small tube

18 ml
Vacuum Filtration

Buchner Funnel

Rubber Cork

Flask
 Spectrophotometer
• Spectronic 20 (Spec. 20)
• Spectroscopy deals with H

Absorption, which occurs when

Light( UV and visible) excites
H
the double bonds
Of molecules such as lycopene
To different energy levels.
Excited state

H H

H spectra
H e-
Light source
Cuvette Before
(sample) excitation Ground state
 UV/Vis
Ultraviolet-Visible Spectoscopy

In hexane
λmax
maximum
absorption
 The ultraviolet (UV) region is normally from
200 to 400 nm, and the visible portion is from
400 to 800 nm.

The longest visible wavelength is red and the

shortest is violet.
•Violet: 400 - 420 nm

•Indigo: 420 - 440 nm

•Blue: 440 - 490 nm

•Green: 490 - 570 nm

•Yellow: 570 - 585 nm

•Orange: 585 - 620nm

Lycopene absorbs blue light giving it a •Red: 620 - 780 nm
red color and its Lambda max (λmax)
 The End

Eat more Tomatoes®!