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Sodium benzoate

Sodium benzoate

Overview
Sodium benzoate has the chemical formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 NaC6H5CO2; it is a widely used food preservative
Food preservation
Food preservation is the process of treating and handling food to stop or slow down spoilage and thus allow for longer storage....

, with E number
E number
E numbers are number codes for food additives that have been assessed for use within the European Union . They are commonly found on food labels throughout the European Union. Safety assessment and approval are the responsibility of the European Food Safety Authority...

 E211. It is the sodium salt of benzoic acid
Benzoic acid
Benzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...

 and exists in this form when dissolved in water
Water
Water is a chemical substance with the chemical formula H2O. A water molecule contains one oxygen and two hydrogen atoms connected by covalent bonds. Water is a liquid at ambient conditions, but it often co-exists on Earth with its solid state, ice, and gaseous state . Water also exists in a...

. It can be produced by reacting sodium hydroxide with benzoic acid
Benzoic acid
Benzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...

.

Sodium benzoate is a preservative
Food preservation
Food preservation is the process of treating and handling food to stop or slow down spoilage and thus allow for longer storage....

. It is bacteriostatic
Bacteriostatic agent
A bacteriostatic agent or bacteriostat, abbreviated Bstatic, is a biological or chemical agent that stops bacteria from reproducing, while not necessarily harming them otherwise. Depending on their application, bacteriostatic antibiotics, disinfectants, antiseptics and preservatives can be...

 and fungistatic under acidic conditions.
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Encyclopedia
Sodium benzoate has the chemical formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 NaC6H5CO2; it is a widely used food preservative
Food preservation
Food preservation is the process of treating and handling food to stop or slow down spoilage and thus allow for longer storage....

, with E number
E number
E numbers are number codes for food additives that have been assessed for use within the European Union . They are commonly found on food labels throughout the European Union. Safety assessment and approval are the responsibility of the European Food Safety Authority...

 E211. It is the sodium salt of benzoic acid
Benzoic acid
Benzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...

 and exists in this form when dissolved in water
Water
Water is a chemical substance with the chemical formula H2O. A water molecule contains one oxygen and two hydrogen atoms connected by covalent bonds. Water is a liquid at ambient conditions, but it often co-exists on Earth with its solid state, ice, and gaseous state . Water also exists in a...

. It can be produced by reacting sodium hydroxide with benzoic acid
Benzoic acid
Benzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...

.

Uses


Sodium benzoate is a preservative
Food preservation
Food preservation is the process of treating and handling food to stop or slow down spoilage and thus allow for longer storage....

. It is bacteriostatic
Bacteriostatic agent
A bacteriostatic agent or bacteriostat, abbreviated Bstatic, is a biological or chemical agent that stops bacteria from reproducing, while not necessarily harming them otherwise. Depending on their application, bacteriostatic antibiotics, disinfectants, antiseptics and preservatives can be...

 and fungistatic under acidic conditions. It is most widely used in acidic foods such as salad dressings (vinegar
Vinegar
Vinegar is a liquid substance consisting mainly of acetic acid and water, the acetic acid being produced through the fermentation of ethanol by acetic acid bacteria. Commercial vinegar is produced either by fast or slow fermentation processes. Slow methods generally are used with traditional...

), carbonated drinks (carbonic acid
Carbonic acid
Carbonic acid is the inorganic compound with the formula H2CO3 . It is also a name sometimes given to solutions of carbon dioxide in water, because such solutions contain small amounts of H2CO3. Carbonic acid forms two kinds of salts, the carbonates and the bicarbonates...

), jams and fruit juices (citric acid
Citric acid
Citric acid is a weak organic acid. It is a natural preservative/conservative and is also used to add an acidic, or sour, taste to foods and soft drinks...

), pickles
Pickling
Pickling, also known as brining or corning is the process of preserving food by anaerobic fermentation in brine to produce lactic acid, or marinating and storing it in an acid solution, usually vinegar . The resulting food is called a pickle. This procedure gives the food a salty or sour taste...

 (vinegar
Vinegar
Vinegar is a liquid substance consisting mainly of acetic acid and water, the acetic acid being produced through the fermentation of ethanol by acetic acid bacteria. Commercial vinegar is produced either by fast or slow fermentation processes. Slow methods generally are used with traditional...

), and condiment
Condiment
A condiment is an edible substance, such as sauce or seasoning, added to food to impart a particular flavor, enhance its flavor, or in some cultures, to complement the dish. Many condiments are available packaged in single-serving sachets , like mustard or ketchup, particularly when supplied with...

s. It is also used as a preservative in medicines and cosmetics. As a food additive, sodium benzoate has the E number
E number
E numbers are number codes for food additives that have been assessed for use within the European Union . They are commonly found on food labels throughout the European Union. Safety assessment and approval are the responsibility of the European Food Safety Authority...

 E211.

It is also used in fireworks
Fireworks
Fireworks are a class of explosive pyrotechnic devices used for aesthetic and entertainment purposes. The most common use of a firework is as part of a fireworks display. A fireworks event is a display of the effects produced by firework devices...

 as a fuel in whistle mix
Whistle mix
Whistle mix is a general term to refer to any pyrotechnic composition that emits a whistling sound when pressed into a tube and ignited. It is used as a rocket propellant, particularly in small bottle rockets...

, a powder that emits a whistling noise when compressed into a tube and ignited. The fuel is also one of the fastest burning rocket fuels and provides a lot of thrust and smoke. It does have its downsides: there is a high danger of explosion when the fuel is sharply compressed because of the fuel's sensitivity to impact.

Sodium benzoate is produced by the neutralization of benzoic acid
Benzoic acid
Benzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...

 with sodium hydroxide. Benzoic acid is detectable at low levels in cranberries
Cranberry
Cranberries are a group of evergreen dwarf shrubs or trailing vines in the subgenus Oxycoccus of the genus Vaccinium. In some methods of classification, Oxycoccus is regarded as a genus in its own right...

, prunes, greengage plums
Greengage
The greengages, also known as the Reine Claudes, are the edible drupaceous fruits of a cultivar group of the common European plum. The first true greengage was bred in Moissac, France, from a green-fruited wild plum originally found in Asia Minor; the original greengage cultivar nowadays survives...

, cinnamon
Cinnamon
Cinnamon is a spice obtained from the inner bark of several trees from the genus Cinnamomum that is used in both sweet and savoury foods...

, ripe clove
Clove
Cloves are the aromatic dried flower buds of a tree in the family Myrtaceae. Cloves are native to the Maluku islands in Indonesia and used as a spice in cuisines all over the world...

s, and apple
Apple
The apple is the pomaceous fruit of the apple tree, species Malus domestica in the rose family . It is one of the most widely cultivated tree fruits, and the most widely known of the many members of genus Malus that are used by humans. Apple grow on small, deciduous trees that blossom in the spring...

s. Though benzoic acid is a more effective preservative, sodium benzoate is more commonly used as a food additive because benzoic acid does not dissolve well in water. Concentration as a preservative is limited by the FDA in the U.S. to 0.1% by weight. The International Programme on Chemical Safety found no adverse effects in humans at doses of 647–825 mg/kg of body weight per day.

Cat
Cat
The cat , also known as the domestic cat or housecat to distinguish it from other felids and felines, is a small, usually furry, domesticated, carnivorous mammal that is valued by humans for its companionship and for its ability to hunt vermin and household pests...

s have a significantly lower tolerance against benzoic acid and its salts than rat
Rat
Rats are various medium-sized, long-tailed rodents of the superfamily Muroidea. "True rats" are members of the genus Rattus, the most important of which to humans are the black rat, Rattus rattus, and the brown rat, Rattus norvegicus...

s and mice
Mouse
A mouse is a small mammal belonging to the order of rodents. The best known mouse species is the common house mouse . It is also a popular pet. In some places, certain kinds of field mice are also common. This rodent is eaten by large birds such as hawks and eagles...

. Sodium benzoate is, however, allowed as an animal food additive at up to 0.1%, according to AFCO's official publication.

Mechanism of food preservation


The mechanism starts with the absorption of benzoic acid into the cell. If the Intracellular pH
Intracellular pH
All cells contain an intracellular fluid whose pH value is known as the intracellular pH . The pHi plays a critical role in the function of the cell, and close regulation is required for cells to survive...

 changes to 5 or lower, the anaerobic fermentation
Fermentation (food)
Fermentation in food processing typically is the conversion of carbohydrates to alcohols and carbon dioxide or organic acids using yeasts, bacteria, or a combination thereof, under anaerobic conditions. Fermentation in simple terms is the chemical conversion of sugars into ethanol...

 of glucose
Glucose
Glucose is a simple sugar and an important carbohydrate in biology. Cells use it as the primary source of energy and a metabolic intermediate...

 through phosphofructokinase
Phosphofructokinase
Phosphofructokinase-1 is the most important regulatory enzyme of glycolysis. It is an allosteric enzyme made of 4 subunits and controlled by many activators and inhibitors...

 is decreased by 95%, thereby inhibiting the growth and survival of micro-organisms causing food spoilage.

Safety and health



In combination with ascorbic acid
Ascorbic acid
Ascorbic acid is a naturally occurring organic compound with antioxidant properties. It is a white solid, but impure samples can appear yellowish. It dissolves well in water to give mildly acidic solutions. Ascorbic acid is one form of vitamin C. The name is derived from a- and scorbutus , the...

 (vitamin C, E300), sodium benzoate and potassium benzoate
Potassium benzoate
Potassium benzoate , the potassium salt of benzoic acid, is a food preservative that inhibits the growth of mold, yeast and some bacteria...

 form benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

, a known carcinogen
Carcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...

. However, in most beverages that contain both, the benzene levels are below those considered dangerous for consumption. Heat, light and shelf life can affect the rate at which benzene is formed.

Professor Peter W. Piper of the University of Sheffield
University of Sheffield
The University of Sheffield is a research university based in the city of Sheffield in South Yorkshire, England. It is one of the original 'red brick' universities and is a member of the Russell Group of leading research intensive universities...

 claims that sodium benzoate by itself can damage and inactivate vital parts of DNA in a cell's mitochondria
Mitochondrion
In cell biology, a mitochondrion is a membrane-enclosed organelle found in most eukaryotic cells. These organelles range from 0.5 to 1.0 micrometers in diameter...

. Mitochondria consume oxygen to generate ATP
Adenosine triphosphate
Adenosine-5'-triphosphate is a multifunctional nucleoside triphosphate used in cells as a coenzyme. It is often called the "molecular unit of currency" of intracellular energy transfer. ATP transports chemical energy within cells for metabolism...

, the body's energy currency. If they are damaged due to disease, the cell malfunctions and may enter apoptosis
Apoptosis
Apoptosis is the process of programmed cell death that may occur in multicellular organisms. Biochemical events lead to characteristic cell changes and death. These changes include blebbing, cell shrinkage, nuclear fragmentation, chromatin condensation, and chromosomal DNA fragmentation...

.

Hyperactivity


Research published in 2007 for the UK's Food Standards Agency
Food Standards Agency
The Food Standards Agency is a non-ministerial government department of the Government of the United Kingdom. It is responsible for protecting public health in relation to food throughout the United Kingdom and is led by a board appointed to act in the public interest...

 (FSA) suggests that certain artificial colours, when paired with sodium benzoate (E211) may be linked to hyperactive behaviour. The results were inconsistent regarding sodium benzoate, so the FSA recommended further study.

Professor Jim Stevenson from Southampton University, and author of the report, said: "This has been a major study investigating an important area of research. The results suggest that consumption of certain mixtures of artificial food colours and sodium benzoate preservative are associated with increases in hyperactive behaviour in children. However, parents should not think that simply taking these additives out of food will prevent hyperactive disorders. We know that many other influences are at work but this at least is one a child can avoid."

Two mixtures of additives were tested in the research:

Mix A:
  • Sunset yellow (E110
    Sunset Yellow FCF
    Sunset Yellow FCF is a synthetic yellow azo dye, manufactured from aromatic hydrocarbons from petroleum. When added to foods, it is denoted by E Number E110...

    )
  • Tartrazine (E102)
  • Carmoisine (E122)
  • Ponceau 4R (E124)
  • Sodium benzoate (E211)

Mix B:
  • Sunset yellow (E110
    Sunset Yellow FCF
    Sunset Yellow FCF is a synthetic yellow azo dye, manufactured from aromatic hydrocarbons from petroleum. When added to foods, it is denoted by E Number E110...

    )
  • Quinoline yellow (E104)
  • Carmoisine (E122)
  • Allura red (E129)
  • Sodium benzoate (E211)


Sodium benzoate was included in both mixes, but the effects observed were not consistent. The Food Standards Agency therefore considers that, if real, the observed increases in hyperactive behaviour were more likely to be linked to one or more of the specific colours tested.

On 10 April 2008, the Foods Standard Agency called for a voluntary removal of the colours (but not sodium benzoate) by 2009. In addition, it recommended that there should be action to phase them out in food and drink in the European Union (EU) over a specified period.

In response to consumer insistence on a more natural product and E211's links to DNA damage and ADHD, the Coca Cola Company is in the process of phasing Sodium Benzoate out of Diet Coke. The company has stated that it plans to remove E211 from its other products — including Sprite
Sprite (soft drink)
Sprite is a transparent, lemon-lime flavored , caffeine free soft drink, produced by the Coca-Cola Company. It was introduced in the United States in 1961. This was Coke's response to the popularity of 7 Up, which had begun as "Bib-Label Lithiated Lemon-Lime Soda" in 1929...

, Fanta
Fanta
Fanta is a global brand of fruit-flavored carbonated soft drinks from the Coca-Cola Company. There are over 90 flavors worldwide. The drink debuted in Germany in 1941 and originally sold only in Europe.-History:...

, and Oasis
Oasis (drink)
Oasis is a non-carbonated bottled soft drink, which is a product of Orangina Schweppes . It originated in France by Volvic in 1966. The drink is described as a "fruit juice drink - with sugar and sweeteners".Advertising campaigns for Oasis target adults and promote the drink as an alternative to...

 — as soon as a satisfactory alternative is discovered.

Compendial status

  • British Pharmacopoeia
    British Pharmacopoeia
    The British Pharmacopoeia is an annual published collection of quality standards for UK medicinal substances. It is used by individuals and organizations involved in pharmaceutical research, development, manufacture and testing....

  • Food Chemical Codex
  • European Pharmacopoeia
    European Pharmacopoeia
    The European Pharmacopoeia of the Council of Europe is a pharmacopoeia, listing a wide range of active substances and excipients used to prepare pharmaceutical products in Europe...

  • Japanese Pharmacopoeia
  • United States Pharmacopeia
    United States Pharmacopeia
    The United States Pharmacopeia is the official pharmacopeia of the United States, published dually with the National Formulary as the USP-NF. The United States Pharmacopeial Convention is the nonprofit organization that owns the trademark and copyright to the USP-NF and publishes it every year...

    29

External links