Coined from 2 Greek words

› Isos which means SAME

› Meros which means PARTS

 When the same molecular formula
represents two or more compounds
which differ in their physical or chemical
properties, then such compounds are
called ISOMERS or ISOMORPHS

 The phenomenon is called

ISOMERIZATION
 Isomerism

Stereo Isomerism

Structural Isomerism

Optical Functional
Isomerism Isomerism Position Metamerism
Isomerism

Tautomerism
Geom
etrical
Isomeri
sm Chain
Isomerism Ring Chain
Isomerism
 This isomerization converts glucose which is
not very sweet to fructose, the most sweet
of the natural sugars

 Syrups from this process compete with

sucrose (cane sugar) in many food
applications

 Almost all manufacturers of soft drinks use

high fructose syrups because they are less
expensive than sucrose
 Glucose isomerase (D-glucose keto
isomerase) causes the isomerization of
glucose to fructose.

 Glucose has 70-75% the sweetening

strength of beet sugar (sucrose), but
fructose is twice as sweet as sucrose.

 Thus, processes for the manufacture of

fructose are of considerable value.
 The isomerization of glucose to fructose is part of the glycolysis
cycle that converts glucose to pyruvate.

 The way this is done is to isomerize the aldehyde (hemiacetal)

glucose to the ketone (as a hemiacetal) fructose, and make
another phosphate ester.

 The isomerization takes advantage of the ease of breakage of a

C-H bond which involves a carbon next to a carbonyl carbon.

 This is important in the next step which cleaves the bond

between carbons three and four of fructose.

 It is noted that this bond involves the carbon next to the

carbonyl carbon of fructose.
 This cleavage would not have been possible
without the isomerization of glucose to fructose,
because the carbonyl group of glucose is too
far from carbons three and four to make that
bond breakable.

 Novo Industries has developed glucose isomerase

from B. coagulans for commercial use. In this
immobilized enzyme process, the microorganism
carries out a direct isomerization of the glucose.
This glucose isomerase is primarily a xylose
isomerase, so xylose, or a xylose-containing
compound must be added for the induction of the
enzyme.
 Pigment principally responsible for the characteristic
deep-red color of ripe tomato fruits and tomato products

 It is a natural antioxidant

 Increasing clinical evidence supports the role of lycopene

as a micronutri-ent with important health benefits,
because it appears to provide protection against a broad
range of epithelial cancers

 helps reduce cholesterol levels in the blood

 Undesirable degradation of lycopene not only affects the

sensory quality of the final products, but also the health
benefit of tomato-based foods for the human body
 Lycopene in fresh tomato fruits occurs
essentially in the all-trans configuration.

 The main causes of tomato lycopene

degradation during processing are
isomerization and oxidation

 Isomerization converts all-trans isomers

to cis-isomers due to additional energy
input and results in an unstable, energy-
rich station
 Thermal processing (bleaching, retorting, and freezing
processes) generally cause some loss of lycopene in
tomato-based foods. Heat induces isomerization of the all-
trans to cis forms. The cis-isomers increase with
temperature and processing time

 Dehydrated and powdered tomatoes have poor

lycopene stability unless carefully processed and promptly
placed in a hermetically sealed and inert atmosphere for
storage

 Significant increase in the cis-isomers with a simultaneous

decrease in the all-trans isomers can be observed in the
dehydrated tomato samples using the different
dehydration methods

 Frozen foods and heat-sterilized foods exhibit excellent

lycopene stability throughout their normal temperature
storage shelf life
 Lycopene bioavailability (absorption) can be influenced by many
factors.

 The bioavailability of cis-isomers in food is higher than that of all-

trans isomers.

 Lycopene bioavailability in processed tomato products is higher than in

unprocessed fresh tomatoes.

 The composition and structure of the food also have an impact on the
bioavailability of lycopene and may affect the release of lycopene from
the tomato tissue matrix.

 Food processing may improve lycopene bioavailability by breaking

down cell walls, which weakens the bonding forces between lycopene
and tissue matrix, thus making lycopene more accessible and
enhancing the cis-isomerization.

 More information on lycopene bioavailability, however, is needed

 Consumer demand for healthy food products
provides an opportunity to develop lycopene-
rich food as new functional foods, as well as
food-grade and pharmaceutical-grade
lycopene as new nutraceutical products.

 An industrial scale, environmentally friendly

lycopene extraction and purification
procedure with minimal loss of bioactivities is
highly desirable for the foods, feed, cosmetic,
and pharmaceutical industries.

 High-quality lycopene products that meet food

safety regulations will offer potential benefits to
the food industry.
 Conjugated linoleic acid (CLA) is naturally
found in dairy and beef products at 0.2% to 2%
of total fat content.

 However, in order for us to obtain optimum

CLA levels, more animal fat would have to be
ingested, which would increase one's level of
dietary saturated fat.

 A more concentrated source of dietary CLA,

which is low in saturated fat, would be highly
desirable.
 Scientists at the University of Arkansas have come up with
a much simpler way of producing CLA in the laboratory
without using a lot of energy or expensive enzymes and
microorganisms.

 Their approach involves the photo-isomerization of soy oil

linoleic acid to CLA. This produces soy oil with about 20%
CLA content.

 Specifically, their process uses simple photo-isomerization

with an iodine sensitizer at 20 C, which yields few oxidation
products.

 But its only a pilot scale study. They are looking into the
economical aspect now.
 Retinoids comprise a family of polyisoprenoid
lipids which include vitamin A (retinol) and its
natural and synthetic analogs.

 Vitamin A deficiency is ranked along with

protein calorie malnutrition and iron deficiency
anaemia as one of the three top priority
nutritional diseases.

 Vitamin A blindness is both the easiest and the

cheapest major nutritional illness to cure .
 Technical Barrier to the fortification with vitamin A is its
susceptibility to oxidation and isomerization which
results in loss of nutritional efficacy

 The basic structure of the retinoid molecule consist of

a cyclic end group, a polyene side chain and a
polar end group.

 The conjugated system formed by alternating C=C

double bonds in the polyene side chain are
responsible for the color of retinoids (typically yellow,
orange, or red)

 Hence, many retinoids are chromophores.

Alternation of side chains and end groups creates
the various classes of retinoids
 The double bonds in the polyene chain of
retinoids can undergo cis-trans
isomerization especially at positions 9, 11
and 13

 All trans - isomers are predominant in food

 Minor amounts of other isomers also present

 All trans – retinoids have maximal vit A

activity but isomerization during processing
and storage of food results in partial loss of
activity
 Several reactions schemes for
geometric isomerization but mechanistic
understanding of the isomerization
reactions are limited

 Heat induced isomerization of retinoids

produces mainly 13-cis isomers in milk