Chemistry

Antioxidants

Oxidation reactions happen when chemicals in the food are exposed to oxygen in the air. In
natural conditions, animal and plant tissues contain their own antioxidants but in foods, these natural
systems break down and oxidation is bound to follow.
Oxidation of food is a destructive process, causing loss of nutritional value and changes in
chemical composition. Oxidation of fats and oils leads to rancidity and, in fruits such as apples, it can
result in the formation of compounds which discolor the fruit.

The effects of
oxidation on
cut apple.

Antioxidants are added to food to slow the rate of oxidation and, if used properly, they can extend the
shelf life of the food in which they have been used.

Oxidation of Fats

Fats and oils, or foods containing them, are the most likely to have problems with oxidation. Fats
react with oxygen and even if a food has a very low fat content it may still need the addition of an
antioxidant. They are commonly used in:

vegetable oil
snacks (extruded)
animal fat
meat, fish, poultry
margarine

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dairy products
mayonnaise / salad dressing
baked products
potato products (instant mashed
potato)

Chemistry

Fats are broken down when they react with oxygen. This makes the food
containing the fats go off.

As the fat decomposes and reacts with oxygen, chemicals called peroxides are produced. These change
into the substances characteristic of the smell and soapy flavor of a rancid fat.
Antioxidants prevent the formation of peroxides and so slow the process of the food 'going off'. Some
antioxidants react with oxygen itself and so prevent the formation of peroxides.
Air-tight packaging, using inert gases like nitrogen, vacuum packing and refrigeration can all be used to
delay the oxidation process. However, these can still be inefficient and adding antioxidants can be an
effective way of extending the shelf life of a product.

Antioxidants in Food
People want to eat more healthily and this includes eating
unsaturated and polyunsaturated fats rather than saturated animal
fats. Unfortunately, unsaturated fats are more susceptible to oxidation.
Antioxidants are added to foods that contain unsaturated fats
to make them last longer and prevent them from turning rancid.
Processing techniques have also been developed to reduce the risk of
oxidation. For example, many snack food manufacturers fry crisps
under a blanket of steam to reduce the amount of oxygen that can get
into the frying oil. This extends the life of both the oil itself and the
crisps.

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Consumers
now
want
foods
containing more unsaturated and
polyunsaturated fats.

Chemistry

The range of antioxidants

The number of antioxidants available to the food technologist is small. Synthetic and natural
antioxidants give similar performance and they are often used in combination. This gives a more
effective action.
There are naturally occurring and man-made antioxidants.

Natural occurring antioxidants

One simple way, for example, of stopping apples going brown is to add a small amount of lemon juice.
The ascorbic acid (vitamin C) contained in many citrus fruits is a natural antioxidant and for this reason
finds frequent use in food production (E 300-E 304). Vitamin C and its various salts are added to protect
soft drinks, jams, condensed milk and sausage.
Other natural antioxidants are the tocopherols (E 306-E309), which are members of the vitamin E family.
Tocopherols are found mainly in nuts, sunflower seeds and soya and maize shoots, and they are mostly
used for preserving vegetable oils, margarine and cocoa products.
Since both compounds are very popular antioxidants and the requirements for them cannot be met
completely from natural sources, ascorbic acid and tocopherols have also been produced artificially for
quite some time. It is nowadays possible to copy the molecular structure of these compounds so closely
that there are no longer any differences in either structure or effects, which means that these natureidentical substances are essentially identical to their originals.
Citric acid, a food acid, is also a known antioxidant naturally occurring from citrus fruits, although
commercial process is by fermentation of molasses. It is used in food as an antioxidant as well as
enhancing the effect of other antioxidants, and also as an acidity regulator. Present in virtually all plants,
it was first isolated in 1784 from lemon juice, by the Swedish chemist Carl Wilhelm Scheele, and has
been used as a food additive for over 100 years. Used in biscuits, canned fish, cheese and processed
cheese products, infant formulas, cake and soup mixes, rye bread, soft drinks, fermented meat
products.

Man-made antioxidants
Man-made antioxidants are used as well as natural ones. The most important artificial antioxidants
belong to the group of gallates (E 310-E 312). Gallates are added mostly to vegetable oils and margarine
to stop them from going rancid and preserve their taste.
Two other substances, which do not belong to the above groups, are BHA (butylhydroxyanisol, E 320)
and BHT (butylhydroxytoluene, E 321).

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Chemistry
The table shows some typical antioxidants:
Antioxidant

Enumber

Typical foods

Ascorbic acid
(vitamin C)

E300

Beers, cut fruits, jams, dried potato. Helps to prevent cut and pulped foods from
going brown by preventing oxidation reactions that cause the discoloration. Can
be added to foods, such as potato, to replace vitamin C lost in processing.

Tocopherols

E306

Oils, meat pies. Obtained from soya beans and maize. Reduces oxidation of
fatty acids and some vitamins.

Butylated
hydroxyanisole
(BHA)

E320

Oils, margarine, cheese, crisps. Helps to prevent the reactions that break down
fats and cause the food to go rancid.

Citric acid

E330

Jam, tinned fruit, biscuits, alcoholic drinks, cheese, dried soup. Naturallyoccuring in citrus fruits like lemons. Helps to increase the anti-oxidant effects of
other substances. Helps to reduce the reactions that can discolor fruits. May also
be used to regulate pH in jams and jellies.

Extended list of antioxidants:

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Chemistry

Antioxidants and health benefits

There may be health benefits from the use of antioxidants. Oxidation reactions in the body
could be linked to the build-up of fatty deposits that cause blockages in arteries that can cause heart
attacks. Antioxidants may be important in preventing this and there could also be a link with the
prevention of certain cancers, arthritis and other conditions. The picture is not yet clear and a great deal
of research needs to be undertaken.

Antioxidants and some negative effects

Taken from the website: www.mbm.net.au/health/296-385.htm, Acids, Antioxidants, Mineral Salts
Number

Name

300
E300

Ascorbic
acid

302
E302

Calcium
ascorbate

310
E310

311
E311

312
E312

314

Comments
Vitamin C has been shown to prevent scurvy, and is essential for
healthy blood vessels, bones, and teeth. Vitamin C also helps form
collagen, a protein that holds tissues together. Ascorbic acid is
industrially synthesised using a number of different biological
techniques. Flour treating agent, 'vitamin C'; may be made synthetically
from glucose, naturally occurs in fruit and vegetables; added to products
as diverse as cured meat, breakfast cereals, frozen fish and wine. Large
doses can cause dental erosion, vomiting, diarrhoea dizziness, and
could possibly cause kidney stones if more than 10g is taken. Should be
taken under medical advice if suffering from kidney stones, gout or
anaemia. Other names: l-ascorbic acid, l,3-ketothreohexuronic acid.
Vitamin C, may increase the formation of calcium axalate stones.

Used to prevent rancidity in oily substances; derived from nutgalls; may

cause gastric or skin irritation, gallates are not permitted in foods for
infants and small children because of their known tendency to cause the
Propyl
blood disorder, methemoglobinemia; used in oils, margarine, lard and
gallate
salad dressings, sometimes used in packaging. It is used as an
antioxidant in food, often with BHT (E321) and BHA (E320), although it
has limited use as it is unstable at high temperatures.
Octyl gallate is synthesised by the esterification of gallic acid. It is used
as an antioxidant in food, often with BHT (E321) and BHA (E320),
Octyl gallate
although it has limited use as it is unstable at high temperatures. Typical
products include oils and fats, cereals, snack foods, dairy produce.
Dodecyl gallate is synthesised by the esterification of gallic acid. It is
Dodecyl
used as an antioxidant in food, often with BHT (E321) and BHA (E320),
gallate
although it has limited use as it is unstable at high temperatures. Typical
products include oils and fats, cereals, snack foods, dairy produce.
Natural resin from the tree Guajacum officinale and some related
tropical trees. Anti-oxidant in cola products. Up to 2.5 mg/kg body
Guaiac Gum
weight. No known side effects in the concentrations used, although
some allergies have been reported. Can normally be consumed by all

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Chemistry

319
E319

320
E320

321
E321

330
E330

334
E334

335
E335

religious groups, vegans and vegetarians.

Petroleum based; the HACSG* recommends to avoid it. May cause
Butylhydroxi
nausea, vomiting, delirium. Acceptable Daily Intake: Up to 0.02 mg/kg
non
body weight. A dose of 5g is considered fatal. Typical products are dairy
tertblend edible fats and oils, margarine, dripping, salad dressing, lipsticks.
Butylhydroqu
Can normally be consumed by all religious groups, vegans and
inone
vegetarians.
Typical products include biscuits, cakes, fats and oils, cereals, pastry
and pastry products, sweets, edible oils, chewing gum, fats, margarine,
nuts, instant potato products, polyethylene food wraps; not permitted in
infant foods, can provoke an allergic reaction in some people, may
Butylated
trigger hyperactivity and other intolerances; serious concerns over
hydroxycarcinogenicity and estrogenic effects, in large doses caused tumours in
anisole
lab animals, banned in Japan in 1958, official committees of experts
(BHA)
recommended that it be banned in the UK, however due to industry
pressure it was not banned, McDonald's eliminated BHT from their US
products by 1986. Other names: tert-butyl-4-hydroxyanisole, tert-butyl-4methoxyphenol, BOA, (1,1-dimethylethyl)-4-methoxyphenol
Petroleum derivative; BHT is a synthetic analogue of vitamin E and
operates by reducing oxygen radicals and interrupting the propagation of
oxidation processes. It is widely used as an antioxidant and
Butylated
preservative, and is prepared from p-cresol and isobutylene. It is one of
hydroxythe most commonly used antioxidants for food oils and fats and is much
toluene
cheaper than BHA although it has more limited applications due to
(BHT)
instability at high temperatures. There is evidence that BHT causes cell
division. Typical products include biscuits, cakes, fats and oils, cereals,
pastry and pastry products, sweets.see 320. Other names: 2,6-di-tertbutyl-4-methylphenol, 2,6-bis(1,1-dimethylethyl)-4-methylphenol
Used in biscuits, canned fish, cheese and processed cheese products,
infant formulas, cake and soup mixes, rye bread, soft drinks, fermented
meat products. Damages tooth enamel. Most citric acid is produced
Citric acid
from corn, manufacturers do not always take out the protein which can
be hydrolysed and create MSG (621) causing reactions in MSGsensitive people.
Tartaric acid exists as a pair of enantiomers and an achiral meso
compound. (+)-tartaric acid commonly occurs in nature and can be
found in fruit, and sometimes in wine. Tartaric acid is industrially
synthesised as a by-product during wine making, and it is used in food
Tartaric acid
as an antioxidant and synergist to increase the antioxidant effect of other
(L(+)-)
substances. It is also used as an acidity regulator and sequestrant.
Excessive ingestion of tartaric acid results in laxative effects. Typical
products include baking powder, chewing gum, jams, sweets, jelly,
tinned fruit and vegetables, cocoa powder, frozen dairy produce.
(i) Monosodium tartrate is a sodium salt of tartaric acid, E334, used
Sodium
mainly as an antioxidant and synergist in food, as well as an acidity
tartrates
regulator. See E334. Typical products include sweets, jelly, jams,
carbonated beverages.

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Chemistry

338
E338

Phosphoric
acid

(ii) Disodium tartrate is a sodium salt of tartaric acid, E334, used mainly
as an antioxidant and synergist in food, as well as an acidity regulator.
Typical products include sweets, jelly, jams, carbonated
beverages. People with cardiac failure, high blood pressure, damaged
liver or kidneys, and fluid retention. Found in most types of foods.
Phosphoric acid is added to food to enhance the antioxidant effects of
other compounds present, and also as an acidity regulator. Typical
products include carbonated beverages, processed meat, chocolate,
fats and oils, beer, jam, sweets. Too much in diet leads to loss of
calcium in bones and onset of osteoporosis. In fizzy drinks it allows
more carbon dioxide concentration without bottle burst. Soft drinks,
beer, cheese products, snacks, and most processed foods. Other
names: orthophosphoric acid.
Phosphoric acid is banned in organic food and drinks. Phosphoric acid is
a highly acidic ingredient in cola drinks, used to offset the extreme
sweetness. The way the kidneys excrete it is by bonding it with calcium
taken from the bones, which can then leave the bones porous and
brittle, and increase the risk of osteoporosis. Phosphoric acid and
phosphates can normally be consumed by all religious groups, vegans
and vegetarians. Although animal bones are mainly made up of
phosphates, commercial phosphate is not made from bones.

Sources:
http://www.understandingfoodadditives.org/pages/ch2p8-1.htm
http://www.understandingfoodadditives.org/pages/Ch2p8-2.htm
http://www.mbm.net.au/health/296-385.htm
http://www.foodadditivesworld.com/antioxidants.html
http://www.eufic.org/article/en/food-safety-quality/food-additives/artid/food-look-good-antioxidants/

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