Ball-and-stick model of part of the crystal structure | |
Ball-and-stick model of packing in the crystal structure | |
Names | |
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Preferred IUPAC name Sodium benzoate | |
Other names
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Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.007.760 |
E number | E211 (preservatives) |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C7H5NaO2 | |
Molar mass | 144.105 g·mol−1 |
Appearance | white 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: | |
[2] | |
Warning | |
H319 [2] | |
P305+P351+P338 [2] | |
NFPA 704 (fire diamond) | |
Flash point | 100 °C (212 °F; 373 K) |
500 °C (932 °F; 773 K) | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 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). |
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.
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.
Sodium benzoate can be decarboxylated with strong base and heat, yielding benzene: [4]
Sodium benzoate is not a naturally occurring substance. However 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 ]
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.
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]
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]
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.
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]
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.
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]
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.
Glycine is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid. Glycine is one of the proteinogenic amino acids. It is encoded by all the codons starting with GG. 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 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.
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
Tartrazine is a synthetic lemon yellow azo dye primarily used as a food coloring. It is also known as E number E102, C.I. 19140, FD&C Yellow 5, Yellow 5 Lake, Acid Yellow 23, Food Yellow 4, and trisodium 1-(4-sulfonatophenyl)-4-(4-sulfonatophenylazo)-5-pyrazolone-3-carboxylate.
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.
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.
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 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.
Diet Pepsi, currently stylised in all caps as PEPSI DIET, 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.
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.
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.
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.
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.
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.
Propylparaben is the n-propyl ester of p-hydroxybenzoic acid. It occurs as a natural substance found in many plants and some insects. Additionally, it can be manufactured synthetically for use in cosmetics, pharmaceuticals, and foods. It is a member of the class of parabens and can be used as a preservative in many water-based cosmetics, such as creams, lotions, shampoos, and bath products. As a food additive, it has an E number, which is E216.
Allura Red AC, also known as FD&C Red 40 or E129, is a red azo dye commonly used in food. It was developed in 1971 by the Allied Chemical Corporation, who gave the substance its name.
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
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: CS1 maint: DOI inactive as of November 2024 (link)Although the maximum rate of biotransformation of benzoic acid to hippuric acid varied between 17.2 and 28.8 mg.kg-1.h-1 among the six individuals, the mean value (23.0 mg.kg-1.h-1) was fairly close to that provided by daily maximum dose (0.5 g.kg-1.day-1) recommended in the treatment of hyperammonaemia in patients with inborn errors of ureagenesis
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