Sodium benzoate

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Sodium benzoate
Sodium Benzoate V.1.svg
Sodium benzoate-substance.jpg
Sodium-benzoate-xtal-rod-micelle-b-3D-bs-17.png
Sodium-benzoate-xtal-rod-micelle-packing-3D-bs-17.png
Ball-and-stick model of packing in the crystal structure
Names
Preferred IUPAC name
Sodium benzoate
Other names
  • E211
  • benzoate of soda
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.760 OOjs UI icon edit-ltr-progressive.svg
E number E211 (preservatives)
PubChem CID
RTECS number
  • DH6650000
UNII
  • InChI=1S/C7H6O2.Na/c8-7(9)6-4-2-1-3-5-6;/h1-5H,(H,8,9);/q;+1/p-1 Yes check.svgY
    Key: WXMKPNITSTVMEF-UHFFFAOYSA-M Yes check.svgY
  • InChI=1/C7H6O2.Na/c8-7(9)6-4-2-1-3-5-6;/h1-5H,(H,8,9);/q;+1/p-1
    Key: WXMKPNITSTVMEF-REWHXWOFAY
  • [Na+].[O-]C(=O)c1ccccc1
Properties
C7H5NaO2
Molar mass 144.105 g·mol−1
Appearancewhite or colourless crystalline powder
Odor odorless
Density 1.497 g/cm3
Melting point 410 °C (770 °F; 683 K)
62.65 g/100 mL (0 °C)
62.84 g/100 mL (15 °C)
62.87 g/100 mL (30 °C)
74.2 g/100 mL (100 °C) [1]
Solubility soluble in liquid ammonia, pyridine [1]
Solubility in methanol 8.22 g/100 g (15 °C)
7.55 g/100 g (66.2 °C) [1]
Solubility in ethanol 2.3 g/100 g (25 °C)
8.3 g/100 g (78 °C) [1]
Solubility in 1,4-Dioxane 0.818 mg/kg (25 °C) [1]
Pharmacology
A16AX11 ( WHO )
Hazards
GHS labelling:
GHS-pictogram-exclam.svg [2]
Warning
H319 [2]
P305+P351+P338 [2]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 100 °C (212 °F; 373 K)
500 °C (932 °F; 773 K)
Lethal dose or concentration (LD, LC):
4100 mg/kg (oral, rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Sodium benzoate also known as benzoate of soda is the sodium salt of benzoic acid, widely used as a food preservative (with an E number of E211) and a pickling agent. It appears as a white crystalline chemical with the formula C6H5COONa.

Production

Sodium benzoate is commonly produced by the neutralization of sodium hydroxide (NaOH) with benzoic acid (C6H5COOH), [3] which is itself produced commercially by partial oxidation of toluene with oxygen.

Reactions

Sodium benzoate can be decarboxylated with strong base and heat, yielding benzene: [4]

Natural occurrence

Many foods are natural sources of benzoic acid, its salts, and its esters. [5] Fruits and vegetables can be rich sources, particularly berries such as cranberry and bilberry. Other sources include seafood, such as prawns, and dairy products.[ citation needed ]

Uses

As a preservative

Sodium benzoate can act as a food preservative. It is most widely used in acidic foods such as salad dressings (for example acetic acid in vinegar), carbonated drinks (carbonic acid), jams and fruit juices (citric acid), pickles (acetic acid), condiments, and frozen yogurt toppings. It is also used as a preservative in medicines and cosmetics. [6] [7] Under these conditions it is converted into benzoic acid (E210), which is bacteriostatic 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. [8] Sodium benzoate is also allowed as an animal food additive at up to 0.1%, per the Association of American Feed Control Officials. [9] Sodium benzoate has been replaced by potassium sorbate in the majority of soft drinks in the United Kingdom. [10]

In the 19th century, sodium benzoate as a food ingredient was investigated by Harvey W. Wiley with his 'Poison Squad' as part of the US Department of Agriculture. This led to the 1906 Pure Food and Drug Act, a key event in the early history of food regulation in the United States.

In pharmaceuticals

Sodium benzoate is used as a treatment for urea cycle disorders due to its ability to bind amino acids. [11] [12] 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. [13] [14] [15] Total Positive and Negative Syndrome Scale scores dropped by 21% compared to placebo.

Sodium benzoate, along with phenylbutyrate, is used to treat hyperammonemia. [16] [17]

Sodium benzoate, along with caffeine, is used to treat postdural puncture headache, respiratory depression associated with overdosage of narcotics, [18] [19] and with ergotamine to treat vascular headache. [20]

Other uses

Sodium benzoate is also used in fireworks as a fuel in whistle mix, a powder that emits a whistling noise when compressed into a tube and ignited. [21] [22]

Mechanism of food preservation

The mechanism starts with the absorption of benzoic acid into the cell. If the intracellular pH falls to 5 or lower, the anaerobic fermentation of glucose through phosphofructokinase decreases sharply, [23] which inhibits the growth and survival of microorganisms that cause food spoilage.

Health and safety

1909 Heinz advertisement against sodium benzoate Benzoateofsoda.jpg
1909 Heinz advertisement against sodium benzoate

In the United States, sodium benzoate is designated as generally recognized as safe (GRAS) by the Food and Drug Administration. [24] The International Programme on Chemical Safety found no adverse effects in humans at doses of 647–825 mg/kg of body weight per day. [25] [26]

Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice. [27]

The human body rapidly clears sodium benzoate by combining it with glycine to form hippuric acid which is then excreted. [26] The metabolic pathway for this begins with the conversion of benzoate by butyrate-CoA ligase into an intermediate product, benzoyl-CoA, [28] which is then metabolized by glycine N-acyltransferase into hippuric acid. [29]

Association with benzene in soft drinks & pepper sauces

In combination with ascorbic acid (vitamin C, E300), sodium benzoate and potassium benzoate may form benzene. 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 for drinking water. [30] Most of the beverages that tested above the limit have been reformulated and subsequently tested below the safety limit. [30] 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" [31] ) so the observation about beverages applies to pepper sauces containing sodium benzoate, like Texas Pete.

ADHD and hyperactivity

Research published, including in 2007 for the UK's Food Standards Agency (FSA) suggests that certain artificial colors, when paired with sodium benzoate, may be linked to hyperactive behavior and other ADHD symptoms. The results were inconsistent regarding sodium benzoate, so the FSA recommended further study. [32] [33] [34] 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. [34] The report's author, Jim Stevenson from Southampton University, 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." [34]

Compendial status

See also

Related Research Articles

<span class="mw-page-title-main">Benzoic acid</span> Organic compound (C6H5COOH)

Benzoic acid is a white solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring with a carboxyl substituent. The benzoyl group is often abbreviated "Bz", thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.

<span class="mw-page-title-main">Glycine</span> Amino acid

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). In the gas phase, it is a molecule with the chemical formula NH2CH2‐COOH. In solution or in the solid, glycine exists as the zwitterion. Glycine is one of the proteinogenic amino acids. It is encoded by all the codons starting with GG (GGU, GGC, GGA, GGG). Glycine is integral to the formation of alpha-helices in secondary protein structure due to the "flexibility" caused by such a small R group. Glycine is also an inhibitory neurotransmitter – interference with its release within the spinal cord (such as during a Clostridium tetani infection) can cause spastic paralysis due to uninhibited muscle contraction.

A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by undesirable chemical changes. In general, preservation is implemented in two modes, chemical and physical. Chemical preservation entails adding chemical compounds to the product. Physical preservation entails processes such as refrigeration or drying. Preservative food additives reduce the risk of foodborne infections, decrease microbial spoilage, and preserve fresh attributes and nutritional quality. Some physical techniques for food preservation include dehydration, UV-C radiation, freeze-drying, and refrigeration. Chemical preservation and physical preservation techniques are sometimes combined.

<span class="mw-page-title-main">Quinoline Yellow WS</span> "Mixture of water-soluble organic compounds from Quinoline Yellow dye"

Quinoline Yellow WS is a mixture of organic compounds derived from the dye Quinoline Yellow SS. Owing to the presence of sulfonate groups, the WS dyes are water-soluble (WS). It is a mixture of disulfonates (principally), monosulfonates and trisulfonates of 2-(2-quinolyl)indan-1,3-dione with a maximum absorption wavelength of 416 nm.p. 119

<span class="mw-page-title-main">Sunset yellow FCF</span> Chemical compound used as colorant

Sunset yellow FCF is a petroleum-derived orange azo dye with a pH dependent maximum absorption at about 480 nm at pH 1 and 443 nm at pH 13 with a shoulder at 500 nm. When added to foods sold in the United States it is known as FD&C Yellow 6; when sold in Europe, it is denoted by E Number E110.

<span class="mw-page-title-main">Potassium benzoate</span> Chemical compound

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.

<span class="mw-page-title-main">Benzyl alcohol</span> Aromatic alcohol

Benzyl alcohol (also known as α-cresol) is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a useful as a solvent for its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

<span class="mw-page-title-main">Diet Pepsi</span> Sugar-free, artificially sweetened soda

Diet Pepsi is a diet carbonated cola soft drink produced by PepsiCo, introduced in 1964 as a variant of Pepsi with no sugar. First test marketed in 1963 under the name Patio Diet Cola, it was re-branded as Diet Pepsi the following year, becoming the first diet cola to be distributed on a national scale in the United States. In the 1960s and 1970s, its competition consisted of the Coca-Cola Company's subsequently discontinued Tab. The United States represents the largest single market for Diet Pepsi.

<span class="mw-page-title-main">Sorbic acid</span> Organic compound (CH3(CH)4COOH)

Sorbic acid, or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative. It has the chemical formula CH3(CH)4CO2H and the structure H3C−CH=CH−CH=CH−C(=O)OH. It is a colourless solid that is slightly soluble in water and sublimes readily. It was first isolated from the unripe berries of the Sorbus aucuparia, hence its name.

<span class="mw-page-title-main">Shasta (drink)</span> American soft drink brand

Shasta Beverages is an American soft drink manufacturer that markets a value-priced soft drink line with a wide variety of soda flavors, as well as a few drink mixers, under the brand name Shasta. The company name is derived from Mount Shasta in northern California and the associated Shasta Springs.

<span class="mw-page-title-main">Hippuric acid</span> Chemical compound

Hippuric acid 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 compounds. The phenols are first converted to benzoic acid, and then to hippuric acid and excreted in urine.

<span class="mw-page-title-main">Ponceau 4R</span> Chemical compound

Ponceau 4R is a synthetic colourant that may be used as a food colouring. It is denoted by E Number E124. Its chemical name is 1-(4-sulfo-1-napthylazo)-2-napthol-6,8-disulfonic acid, trisodium salt. Ponceau is the generic name for a family of azo dyes.

<span class="mw-page-title-main">Potassium sorbate</span> Chemical compound

Potassium sorbate is the potassium salt of sorbic acid, chemical formula CH3CH=CH−CH=CH−CO2K. It is a white salt that is very soluble in water (58.2% at 20 °C). It is primarily used as a food preservative (E number 202). Potassium sorbate is effective in a variety of applications including food, wine, and personal-care products. While sorbic acid occurs naturally in rowan and hippophae berries, virtually all of the world's supply of sorbic acid, from which potassium sorbate is derived, is manufactured synthetically.

<span class="mw-page-title-main">Allura Red AC</span> Chemical compound

Allura Red AC is a red azo dye that goes by several names, including FD&C Red 40. It is used as a food dye and has the E number E129.

<span class="mw-page-title-main">Calcium benzoate</span> Chemical compound

Calcium benzoate refers to the calcium salt of benzoic acid. When used in the food industry as a preservative, its E number is E213 ; it is approved for use as a food additive in the EU, USA and Australia and New Zealand.

Benzene in soft drinks is of potential concern due to the carcinogenic nature of the molecule. This contamination is a public health concern and has caused significant outcry among environmental and health advocates. Benzene levels are regulated in drinking water nationally and internationally, and in bottled water in the United States, but only informally in soft drinks. The benzene forms from decarboxylation of the preservative benzoic acid in the presence of ascorbic acid and metal ions that act as catalysts, especially under heat and light. Hot peppers naturally contain vitamin C so the observation about soft drinks applies to pepper sauces containing sodium benzoate, like Texas Pete.

In enzymology, a glycine N-acyltransferase (GLYAT), also known as acyl-CoA:glycine N-acyltransferase (ACGNAT), is an enzyme that catalyzes the chemical reaction

Fungistatics are anti-fungal agents that inhibit the growth of fungus. The term fungistatic may be used as both a noun and an adjective. Fungistatics have applications in agriculture, the food industry, the paint industry, and medicine.

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