Sodium benzoate is the sodium salt of

benzoic acid Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin ...

, widely used as a food preservative (with an

E number E numbers ("E" stands for "Europe") are codes for substances used as food additives, including those found naturally in many foods such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly ...

of E211) and a pickling agent. It appears as a white crystalline chemical with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

C₆H₅COONa.

Production

Sodium benzoate is commonly produced by the neutralization of

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and al ...

(NaOH) with

(C₆H₅COOH), which is itself produced commercially by partial oxidation of

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) ...

with

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements ...

Natural occurrence

Many foods are natural sources of benzoic acid, its salts, and its

esters In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

Fruits In botany, a fruit is the seed-bearing structure in flowering plants that is formed from the ovary after flowering. Fruits are the means by which flowering plants (also known as angiosperms) disseminate their seeds. Edible fruits in partic ...

and

vegetables Vegetables are parts of plants that are consumed by humans or other animals as food. The original meaning is still commonly used and is applied to plants collectively to refer to all edible plant matter, including the flowers, fruits, stems ...

can be rich sources, particularly berries such as

cranberry Cranberries are a group of evergreen dwarf shrubs or trailing vines in the subgenus ''Oxycoccus'' of the genus '' Vaccinium''. In Britain, cranberry may refer to the native species '' Vaccinium oxycoccos'', while in North America, cranberry ...

and

bilberry Bilberries (), or sometimes European blueberries, are a primarily Eurasian species of low-growing shrubs in the genus '' Vaccinium'' (family Ericaceae), bearing edible, dark blue berries. The species most often referred to is ''Vaccinium myrti ...

. Other sources include

seafood Seafood is any form of sea life regarded as food by humans, prominently including fish and shellfish. Shellfish include various species of molluscs (e.g. bivalve molluscs such as clams, oysters and mussels, and cephalopods such as octopus an ...

, such as

prawns Prawn is a common name for small aquatic crustaceans with an exoskeleton and ten legs (which is a member of the order decapoda), some of which can be eaten. The term "prawn"Mortenson, Philip B (2010''This is not a weasel: a close look at nature ...

, and

dairy products Dairy products or milk products, also known as lacticinia, are food products made from (or containing) milk. The most common dairy animals are cow, water buffalo, nanny goat, and ewe. Dairy products include common grocery store food items in ...

Uses

As a preservative

Sodium benzoate can act as a food preservative. It is most widely used in acidic foods such as

salad dressings A salad dressing is a sauce for salads. Used on virtually all '' leafy salads'', dressings may also be used in making salads of beans (such as three bean salad), noodle or pasta salads and antipasti, and forms of potato salad. Salad dressings ...

(for example

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main componen ...

vinegar Vinegar is an aqueous solution of acetic acid and trace compounds that may include flavorings. Vinegar typically contains 5–8% acetic acid by volume. Usually, the acetic acid is produced by a double fermentation, converting simple sugars to eth ...

), carbonated drinks ( carbonic acid), jams and fruit juices (

citric acid Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in ...

), pickles (

condiment A condiment is a preparation that is added to food, typically after cooking, to impart a specific flavor, to enhance the flavor, or to complement the dish. A table condiment or table sauce is more specifically a condiment that is served separat ...

s, and frozen yogurt toppings. It is also used as a preservative in medicines and cosmetics. Under these conditions it is converted into

(E210), which is

bacteriostatic A bacteriostatic agent or bacteriostat, abbreviated Bstatic, is a biological or chemical agent that stops bacteria from reproducing, while not necessarily killing them otherwise. Depending on their application, bacteriostatic antibiotics, disinfect ...

and fungistatic. Benzoic acid is generally not used directly due to its poor water solubility. Concentration as a food preservative is limited by the FDA in the U.S. to 0.1% by weight. Sodium benzoate is also allowed as an animal food additive at up to 0.1%, per the Association of American Feed Control Officials. Sodium benzoate has been replaced by potassium sorbate in the majority of soft drinks in the

United Kingdom The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom (UK) or Britain, is a country in Europe, off the north-western coast of the continental mainland. It comprises England, Scotland, Wales and ...

. Sodium benzoate was one of the chemicals used in 19th century industrialised food production that was investigated by Dr. Harvey W. Wiley with his famous 'Poison Squad' as part of the US Department of Agriculture. This led up to the 1906

Pure Food and Drug Act The Pure Food and Drug Act of 1906, also known as Dr. Wiley's Law, was the first of a series of significant consumer protection laws which was enacted by Congress in the 20th century and led to the creation of the Food and Drug Administratio ...

, a landmark event in the early history of food regulation in the United States.

In pharmaceuticals

Sodium benzoate is used as a treatment for

urea cycle disorder Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an importan ...

s due to its ability to bind amino acids. This leads to excretion of these amino acids and a decrease in ammonia levels. Recent research shows that sodium benzoate may be beneficial as an add-on therapy (1 gram/day) in

schizophrenia Schizophrenia is a mental disorder characterized by continuous or relapsing episodes of psychosis. Major symptoms include hallucinations (typically hearing voices), delusions, and disorganized thinking. Other symptoms include social w ...

.Add-on Treatment of Benzoate for Schizophrenia A Randomized, Double-blind, Placebo-Controlled Trial of d-Amino Acid Oxidase Inhibitor
December 2013 Total

Positive and Negative Syndrome Scale The Positive and Negative Syndrome Scale (PANSS) is a medical scale used for measuring symptom severity of patients with schizophrenia. It was published in 1987 by Stanley Kay, Lewis Opler, and Abraham Fiszbein. It is widely used in the study of a ...

scores dropped by 21% compared to placebo. Sodium benzoate, along with

phenylbutyrate Sodium phenylbutyrate, sold under the brand name Buphenyl among others, is a salt of an aromatic fatty acid, 4-phenylbutyrate (4-PBA) or 4-phenylbutyric acid. The compound is used to treat urea cycle disorders, because its metabolites offer an ...

, is used to treat

hyperammonemia Hyperammonemia is a metabolic disturbance characterised by an excess of ammonia in the blood. It is a dangerous condition that may lead to brain injury and death. It may be primary or secondary. Ammonia is a substance that contains nitrogen. I ...

. Sodium benzoate, along with

caffeine Caffeine is a central nervous system (CNS) stimulant of the methylxanthine chemical classification, class. It is mainly recreational drug use, used recreationally as a Nootropic, cognitive enhancer, increasing alertness and attentional perfor ...

, is used to treat postdural puncture headache, respiratory depression associated with overdosage of

narcotics The term narcotic (, from ancient Greek ναρκῶ ''narkō'', "to make numb") originally referred medically to any psychoactive compound with numbing or paralyzing properties. In the United States, it has since become associated with opiate ...

, and with

ergotamine Ergotamine, sold under the brand names Cafergot (with caffeine) and Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It possesses structural sim ...

to treat

vascular headache A vascular headache is an outdated term to describe certain types of headache which were thought to be related to blood vessel swelling and hyperemia as cause of pain. There is no doubt that ''some'' headaches are caused by vascular effects. ...

Other uses

Sodium benzoate is also used in

fireworks Fireworks are a class of low explosive pyrotechnic devices used for aesthetic and entertainment purposes. They are most commonly used in fireworks displays (also called a fireworks show or pyrotechnics), combining a large number of devices ...

as a fuel in

whistle mix A pyrotechnic composition is a substance or mixture of substances designed to produce an effect by heat, light, sound, gas/smoke or a combination of these, as a result of non-detonative self-sustaining exothermic chemical reactions. Pyrotechnic s ...

, a powder that emits a whistling noise when compressed into a tube and ignited.

Mechanism of food preservation

The mechanism starts with the absorption of benzoic acid into the cell. If the

intracellular pH Intracellular pH (pHi) is the measure of the acidity or basicity (i.e., pH) of intracellular fluid. The pHi plays a critical role in membrane transport and other intracellular processes. In an environment with the improper pHi, biological cells m ...

falls to 5 or lower, the

anaerobic fermentation Fermentation is a metabolic process that produces chemical changes in organic substrates through the action of enzymes. In biochemistry, it is narrowly defined as the extraction of energy from carbohydrates in the absence of oxygen. In food p ...

glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, u ...

through phosphofructokinase decreases sharply, which inhibits the growth and survival of microorganisms that cause food spoilage.

Health and safety

In the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., ...

, sodium benzoate is designated as generally recognized as safe (GRAS) by the

Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...

. The International Programme on Chemical Safety found no adverse effects in humans at doses of 647–825 mg/kg of body weight per day. Cats have a significantly lower tolerance against benzoic acid and its

salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively c ...

than rats and mice. The human body rapidly clears sodium benzoate by combining it with

glycine Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid ( carbamic acid is unstable), with the chemical formula NH2‐ CH2‐ COOH. Glycine is one of the proteinog ...

to form

hippuric acid Hippuric acid ( Gr. ''hippos'', horse, ''ouron'', urine) is a carboxylic acid and organic compound. It is found in urine and is formed from the combination of benzoic acid and glycine. Levels of hippuric acid rise with the consumption of phenolic ...

which is then excreted. The metabolic pathway for this begins with the conversion of benzoate by

butyrate-CoA ligase Butyryl-coenzyme A (or butyryl-CoA) is the coenzyme A-containing derivative of butyric acid. It is acted upon by butyryl-CoA dehydrogenase and an intermediary compound of ABE fermentation. Butyryl-CoA is a precursor to and converted from crotony ...

into an intermediate product, benzoyl-CoA, which is then metabolized by glycine ''N''-acyltransferase into hippuric acid.

Association with benzene in soft drinks & pepper sauces

In combination with

ascorbic acid Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits and vegetables, also sold as a dietary supplement and as a topical 'serum' ingredient to treat melasma (dark pigment spots) ...

(vitamin C, E300), sodium benzoate and

potassium benzoate Potassium benzoate (E212), the potassium salt of benzoic acid, is a food preservative that inhibits the growth of mold, yeast and some bacteria. It works best in low- pH products, below 4.5, where it exists as benzoic acid. Acidic foods and bev ...

may form

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...

. In 2006, the Food and Drug Administration tested 100 beverages available in the United States that contained both ascorbic acid and benzoate. Four had benzene levels that were above the 5 ppb Maximum Contaminant Level set by the

Environmental Protection Agency A biophysical environment is a biotic and abiotic surrounding of an organism or population, and consequently includes the factors that have an influence in their survival, development, and evolution. A biophysical environment can vary in scale ...

for drinking water. Most of the beverages that tested above the limit have been reformulated and subsequently tested below the safety limit. Heat, light and shelf life can increase the rate at which benzene is formed. Hot peppers naturally contain vitamin C ("nearly as much as in one orange"https://www.ahchealthenews.com/2016/11/04/hot-sauce-good-health/) so the observation about beverages applies to pepper sauces containing sodium benzoate, like Texas Pete.

Hyperactivity

Research published in 2007 for the UK's

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 in England, Wales and Northern Ireland. It is led by a board ap ...

(FSA) suggests that certain artificial colors, when paired with sodium benzoate, may be linked to hyperactive behavior. The results were inconsistent regarding sodium benzoate, so the FSA recommended further study.Food Standards Agency issues revised advice on certain artificial colours
6 September 2007Food Colorings and Hyperactivity
"Myomancy" 7 September 2007Agency revises advice on certain artificial colours
Food Standards Agency, 11 September 2007 The Food Standards Agency concluded that the observed increases in hyperactive behavior, if real, were more likely to be linked to the artificial colors than to sodium benzoate. The report's author, Jim Stevenson from

Southampton University , mottoeng = The Heights Yield to Endeavour , type = Public research university , established = 1862 – Hartley Institution1902 – Hartley University College1913 – Southampton University Coll ...

, said: "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. . . . Many other influences are at work but this at least is one a child can avoid."

Compendial status

British Pharmacopoeia The ''British Pharmacopoeia'' (''BP'') is the national pharmacopoeia of the United Kingdom. It is an annually published collection of quality standards for medicinal substances in the UK, which is used by individuals and organisations involv ...

European Pharmacopoeia The ''European Pharmacopoeia'' (''Pharmacopoeia Europaea'', ''Ph. Eur.'') is a major regional pharmacopoeia which provides common quality standards throughout the pharmaceutical industry in Europe to control the quality of medicines, and the ...

Food Chemicals Codex The Food Chemicals Codex (FCC) is a collection of internationally recognized standards for the purity and identity of food ingredients. Scope The FCC features more than 1,250 monographs, including food-grade chemicals, processing aids, foods (suc ...

* Japanese Pharmacopoeia *

United States Pharmacopeia The ''United States Pharmacopeia'' (''USP'') is a pharmacopeia (compendium of drug information) for the United States published annually by the United States Pharmacopeial Convention (usually also called the USP), a nonprofit organization that ...

References

External links

International Programme on Chemical Safety - Benzoic Acid and Sodium Benzoate report
*

The Ketchup Conundrum
{{DEFAULTSORT:Sodium Benzoate Antiseptics Benzoates Preservatives Organic sodium salts E-number additives