Molecule of the week

Lycopene
Introduction Lycopene is a red carotenoid pigment
that colours tomatoes (Figure 1) as well as many other
red, orange and yellow fruits and vegetables. The name
lycopene comes from that of the genus Lycopersicum
which includes tomatoes. Lycopene has recently been
the focus of extensive research reflecting growing
awareness of its various roles and particularly its
potential health benefits.
Chemical properties Because the molecular
structure of lycopene consists entirely of carbon and
hydrogen (Table 1) it is a non-polar hydrocarbon [1]
with a high melting point. Not only is it completely
insoluble in water, it has relatively low solubility even
in non-polar solvents. These characteristics can be
understood if we consider the arrangement of the atoms
and the bonding within a lycopene molecule (Figure 2).

in the conjugated system. The intermolecular forces

between lycopene molecules are essentially only van
der Waals interactions, which are very weak bonds. In
addition its relatively high molecular weight limits its
solubility even in non-polar solvents [1,2].
The ability of the molecule to absorb particular
wavelengths of visible light so that it appears a bright
colour. The eleven conjugated double bonds, covering
much of the overall structure of the molecule allows the

Table 1 The molecular properties of lycopene [1,2]

Molecular formula

C40H56

Carbon content by weight

89.49%

Hydrogen content by weight

10.51%

Polarity
Molecular weight (MW)
Water solubility
Melting point (mp)

Non-polar
536.87
insoluble
172-173C

Molecular structure Lycopene is polyunsaturated

and in its natural form, all of the double bonds are in the

Figure 1 Ripe tomatoes are rich in lycopene

The significance of conjugation The extensive

conjugation and extended molecular orbital help us to
understand the characteristics, as well as the special and
varied roles, of lycopene in our foods.
The elongated linear shape of the molecule is quite
inflexible compared to that of many other structures
because there is no free rotation about the double bonds

Version 2, July 2012

continued.........

trans- rather than the cis- form. As a result, the

shape of the molecule is extended and straight,
constrained by its system of eleven conjugated
double bonds.
In this context the term conjugation refers to the
pattern of alternating double and single bonds
that can be seen in the structure. In lycopene
there are 22 carbon atoms in the conjugated
system. This means that the bonding electrons
for each of these carbons become delocalised.
They are shared between all 22 of the carbon
atoms which participate in this system and
become a part of a molecular orbital.
There are two ways in which this is quite unlike
the arrangement seen in polyunsaturated fatty
acids (including those that are - 3 and -6).
Firstly, in the latter double bonds occur
naturally in the cis- rather than transFigure 2 Molecular structure of lycopene (with C atoms shown in grey
configuration. Secondly in fatty acids there is
and H in blue) [1]
no pattern of conjugation and the double bonds
are described as isolated.

Food molecule:

Lycopene

absorption of all but the longest wavelengths of light

which is why it appears red [1,3,4].
Generally double bonds are quite reactive so that they
contribute to the instability of many molecules
including unsaturated fats. However in lycopene, the
formation of the extended molecular orbital bestows a
much higher degree of stability on the molecule than
we might have predicted [3,4].
Sterically there are as many as 72 possible geometric
isomers of the molecule. When it is exposed to heat or
light, lycopene can undergo isomerisation to any
number of these cis-isomers, which have a bent rather
than linear shape [4].

Significance of lycopene Within plants, the

molecule is an important intermediate in the
biosynthesis of many other carotenoids including carotene. It is often referred to as a phytochemical
(simply meaning plant molecule) involved both in
photosynthesis as well as photoprotection through its
ability to minimise oxidative damage to the structure of
the chlorophyll molecule [4,5].
Although not an essential nutrient for humans,
lycopene is a powerful antioxidant and consumption is
associated with reduced cancer risks and enhanced
well-being. It is also amongst the phytochemicals
thought to reduce the risks of cancers of the
oesophagus, lungs, prostate and stomach [3-7]. To
obtain the benefits of antioxidants in plants, we should
eat plenty of fruit and vegetables each day [3,5].

Lycopene in food A variety of fruits and vegetables

have high lycopene contents (Table 2) [8,9]. More data
are available in the US food composition database [8]
particularly for processed foods for which tomatoes are
an ingredient. Low levels are found in animal foods
including chicken liver (Table 2). And even green
vegetables can be significant sources. Asparagus,
parsley and basil are examples where the red colour of
lycopene is masked by the chlorophyll present. Other
fruits that appear red, including strawberries and
cherries contain anthocyanins rather than lycopene.

page 2 of 2
Table 2

Dietary sources of lycopene [8,9]

Source

Content (per 100g)

Gac (baby jackfruit)

200-300 mg

Sundried tomato

45.9 mg

Tomato sauce

16.7 mg

Watermelon

4.5 mg

Fresh tomato

2.6 mg

Papaya

1.8 mg

Pink grapefruit

1.4 mg

Baked beans

51 g

Asparagus (cooked)

30 g

Chicken liver

20 g

Carrots (raw)

1 g

mechanism, which is a well-recognised mechanism of

antioxidant action. They react with singlet oxygen, 1O2,
returning it to the relatively unreactive triplet state [3]:
O2 + carotenoid 3O2 + carotenoid*(excited)

carotenoid* carotenoid + heat

Lycopene may be the most powerful carotenoid
quencher of singlet oxygen [6]. Test tube studies
indicate that it is 100 times more efficient at quenching
singlet oxygen than vitamin E. Singlet oxygen produced
during exposure to ultraviolet light is a primary cause of
skin aging [7].
References and further reading
[1] Budavari S. 2006. The Merck index. 14 th ed.
Whitehouse Station, NJ: Merck.
[2] Smith J, Hong-Shum L. 2011. Food additives data
book. 2nd ed. Oxford, UK: Wiley-Blackwell.
[3] Coultate TP. 2009. Food: the chemistry of its
components. 5th ed. Cambridge: Royal Society for
Chemistry.

While gac has the highest concentration of lycopene

[9], it is rarely found outside of Southeast Asia, and
therefore, tomatoes account for about 85% of the
dietary intake for most people. Lycopene is found
tightly bound to vegetable fibre. It is soluble in oil but
not in water, which is why processing tomatoes and
serving them in oil-rich dishes increases the
bioavailability of lycopene [4].

[4] Damodaran S, Parkin KL, Fennema OR, (Eds.).

2008. Fennemas food chemistry, 4th ed. CRC
Press/Taylor & Francis: Boca Raton.

Lycopene is sometimes used to colour food and it is an

approved food additive in some but not all countries
[2,10]. In Australia and Europe it has the designation of
160d (E160d).

[7] Berneburg M, et al. 1999. Journal of Biological

Chemistry 274(22):153459.

Health benefits of antioxidants Antioxidants

are responsible for keeping high-energy reactions from
damaging essential DNA and proteins [3,5]. Lycopene
and other carotenoids operate by a singlet quenching

[5] McGee H. 2004. On food and cooking. 1st Scribner

revised ed. New York, US: Simon & Schuster.
[6] Di Mascio P, Kaiser S, Sies H. 1989. Archives of
Biochemistry and Biophysics 274(2): 5328.

[8] USDA. 2012. USDA Nutrient Database for Standard

Reference. [Online. Internet.] Available from:
http://ndb.nal.usda.gov/.
[9] Ishida BK et al. 2004. Journal of Agricultural and
Food Chemistry 52:274-9.
[10] ANZFSC standards 1.2.4 and 1.3.1.