E 210 = BENZOIC ACID
CAS number: 65-85-0
EC number: 200-618-2
Molecular formula: C7H6O2
Molecular mass: 122.1
E 210 is called benzoic acid.
E 210 is a white crystalline solid.
E 210 is slightly soluble in water.
E 210 is used to make other chemicals, as a food preservative, and for other uses.
E 210, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid.
E 210 occurs naturally free and bound as benzoic acid esters in many plant and animal species.
Appreciable amounts have been found in most berries (around 0.05%).
Cranberries contain as much as 300-1300 mg free E 210 per kg fruit.
E 210 is a fungistatic compound that is widely used as a food preservative.
E 210 is a byproduct of phenylalanine metabolism in bacteria.
E 210 is also produced when gut bacteria process polyphenols (from ingested fruits or beverages).
E 210 may also be used to investigate the mechanism of complex addition reaction of hydroxyl radicals with various aromatic compounds.
E 210 is one of the preservatives that widely used in the food industry to protect food from any harmful chemical changes and helps to regulate the growth of microbes better.
E 210 is a commonly used antimicrobial preservative in food and beverages, especially in carbonated beverages, as it presents its strongest antibacterial activity at pH 2.5–4.0.
E 210 has inhibitory effects on the proliferation of bacteria and yeasts, a major cause of food spoilage.
E 210, which is usually used in the form of its sodium salt, sodium benzoate, has long been used as an antimicrobial additive in foods.
E 210 is used in carbonated and still beverages, syrups, fruit salads, icings, jams, jellies, preserves, salted margarine, mincemeat, pickles and relishes, pie, pastry fillings, prepared salads, fruit cocktail, soy sauce, and caviar.
The use level of E 210 ranges from 0.05 to 0.1%.
E 210 in the acid form is quite toxic but its sodium salt is much less toxic.
The sodium salt is preferred because of the low aqueous solubility of the free acid.
In vivo, the salt is converted to acid, which is the more toxic form.
E 210 is an organic acid first used in foods almost 100 years ago.
E 210 occurs naturally in prunes, cinnamon, and cloves.
The free acid form is poorly soluble in water and the sodium salt (sodium benzoate) is often used because of its greater solubility.
E 210's antimicrobial activity is primarily against yeasts and molds.
As mentioned for other organic acids, antimicrobial activity is greatest at low pH.
The effect results from greater permeability of the unionized form into microorganisms.
Uses of E 210: Preservative, Cosmetics, Feed, Pharmaceutical, Antimicrobial, Antifungal, Antibacterial, Soft Drink, Alcohol Beverage, Beverage Powder, Ice Cream, Candy, Chewing Gum, Icings, Fruit Juice, Puddings, Sauces, Baking Food, Sauage, Food Colors, Milk, Wine, Flavoring Agent, Dyestuff, Toothpaste, Coating, Rubber.
Applications of E 210:
E 210 is an important precursor for the preparation of many other organic substances viz. benzoyl chloride, benylbenzoate, phenol, sodium benzoate, benzyl alcohol as well as benzoate plasticizers such as glycol-, diethhyleneglycol- and triethyleneglycol esters.
E 210 and its salts are used as food preservatives.
E 210 is involved in rubber polymerization as an activator and a retardant.
E 210 is the main component of benzoin resin and is a constituent of Whitfields ointment, which is used for the treatment of fungal skin diseases such as tinea, ringworm and athletes foot.
E 210 is widely used in cosmetics, dyes, plastics and insect repellents.
Notes about E 210:
E 210 is incompatible with strong oxidizing agents, reducing agents and strong bases.
Benzoic acid (E210) and its salts are also used as food preservatives to prevent the growth of moulds, yeasts and some bacteria
The action of E 210 is highly dependant on the pH of the food to which it is being added and it is predominantly used in acidic foods such as fruit juices, sparkling drinks and pickles.
E 210 is a mono-functional, aromatic acid, which is widely used as a building block for the synthesis of alkyd resins.
When E 210 is used as a component of alkyd resins, it improves gloss, hardness and chemical resistance.
Applications/uses of E 210:
-Agriculture intermediates
-Cosmetic ingredients - lips
-Cosmetic ingredients eyes & face
-Personal care ingredients
E 210 is an aromatic alcohol existing naturally in many plants and is a common additive to food, drinks, cosmetics and other products.
E 210 acts as preservatives through inhibiting both bacteria and fungi.
E 210 is the simplest of the aromatic carboxylic acids, a family of organic compounds containing the carboxyl (-COOH) group.
E 210 occurs in the form of white crystalline needles or thin plates.
Many naturally occurring plants contain E 210, including most types of berries and the natural product called gum benzoin, a plant common to the islands of Java, Sumatra, and Borneo.
Gum benzoin may contain up to 20 percent E 210.
E 210 is also excreted by most animals (except fowl) in the form of a related compound called hippuric acid (C6H5CONHCH2COOH).
E 210 is used as a food preservative.
E 210 inhibits the growth of yeast, mold, and other bacteria.
Acidic food and fruit juices, sparkling drinks, and pickles are preserved with benzoic acid.
E 210 is also used as a preservative in cosmetics.
E 210 is used as an intermediate by manufacturers of alkyd and polyester resins.
E 210 is a compound comprising a benzene ring core carrying a carboxylic acid substituent.
E 210 has a role as an antimicrobial food preservative, an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a plant metabolite, a human xenobiotic metabolite, an algal metabolite and a drug allergen.
E 210 is a conjugate acid of a benzoate.
E 210 is a chemical intermediate for benzoates, alkyd resins and other organic derivatives.
E 210 is an excellent vulcanisation retardant in rubber industry.
E 210 is also utilised in various varnishes and lacquer paints it enhances the lustre, eases application and is an effective fungicide.
APPLICATIONS of E 210: Rubber, Varnishes, Lacquers
INDUSTRIES of E 210: Rubber Industry, Paints and Coatings
E 210 is a white (or colorless) solid with the formula C6H5CO2H.
E 210 is the simplest aromatic carboxylic acid.
The name is derived from gum benzoin, which was for a long time its only source.
E 210 occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary metabolites.
Salts of E 210 are used as food preservatives.
E 210 is an important precursor for the industrial synthesis of many other organic substances.
The salts and esters of benzoic acid are known as benzoates
Benzoic acid and its salts (Na or K salts) is a bacteriostatic antiseptic that is only active in an acidic environment (pH 2.5 to 4.5).
In mammals, E 210 is primarily metabolized to its glycine conjugate, hippuric acid, which is readily excreted via the renal organic anion transport system.
Moreover, E 210 is also found as a metabolite of benzyl alcohol (for more information on benzyl alcohol see the dedicated questions and answers document).
E 210 is mainly used as preservative at levels from 0.01 to 0.2%.
E 210 is a key raw material in the production of alkyd resins to control viscosity and enhance desirable characteristics in the fi nal alkyd coating film, including gloss, adhesion, hardness, and chemical resistance, particularly resistanceto alkaline substances.
E 210 is also used as an additive for e ffective corrosion inhibition.
E 210 is the most basic of aromatic carboxylic acids.
E 210 is a building block used in the manufacture of many end products including alkyd resins.
When used in alkyd resin applications, E 210 improves gloss, hardness and chemical resistance.
E 210 is also used in other applications including pharmaceuticals, personal care and select industrial applications.
E 210 can be used as a preservative given that it increases storage stability and mitigates corrosion when used in emulsion formulations, liquid detergents, paints, polishes and waxes.
General description of E 210:
E 210 is an organic aromatic monocarboxylic acid.
E 210 can be synthesized by the cobalt or manganese catalyzed atmospheric oxidation of toluene.
Recently, E 210 has been prepared from toluene by employing TiO2 nanotubes electrode.
E 210 reacts with hydrogenating reagents to afford hexahydrobenzoic acid.
The thermal decomposition of E 210 in the presence of lime or alkali produces benzene and carbon dioxide.
E 210 is a colourless crystalline solid and the simplest aromatic carboxylic acid.
KEYWORDS:
65-85-0, 200-618-2, BENZOIC ACID, Benzenecarboxylic acid, Benzeneformate, Benzeneformic acid, Benzenemethanoate, Benzenemethanoic acid, Benzoate, Carboxybenzene
Application of E 210:
E 210 has been used in the preparation of vials for the HPLC analysis of various polyamines in biological fluids, tissues and isolated/cultured cells.
E 210 may be employed as an intermediate in the synthesis of the following:
-paints
-pigments
-varnish
-wetting agents
-aroma compounds
-benzoyl chloride
-benzotrichloride
E 210's most common uses are in carbonated beverages, pickles, sauces, and jelly.
Non-food applications for benzoic acid's antibacterial function are found in cosmetics.
E 210 itself has low toxicity, but there has been concern because of a potential reaction that converts it to benzene.
Although benzene is a toxic and carcinogenic compound, the reaction causing this change has a very low chance of occurring in food.
Typically, benzene is rapidly converted to hippuric acid in the body and excreted in the urine.
Parabens are antimicrobial compounds chemically derived from benzoic acid.
Chemically, parabens are esters made by combining benzoic acid and alcohols such as methanol or propanol.
Paraben esters have antimicrobial activity against molds and yeasts and are used in beer, soft drinks, and olives.
Cosmetics and pharmaceuticals represent the largest use of parabens.
E 210 is most commonly found in industrial settings to manufacture a wide variety of products such as perfumes, dyes, topical medications and insect repellents.
E 210’s salt (sodium benzoate) is commonly used as a pH adjustor and preservative in food, preventing the growth of microbes to keep food safe.
E 210 works by changing the internal pH of microorganisms to an acidic state that is incompatible with their growth and survival.
E 210, a white, crystalline organic compound belonging to the family of carboxylic acids, widely used as a food preservative and in the manufacture of various cosmetics, dyes, plastics, and insect repellents.
First described in the 16th century, E 210 exists in many plants; it makes up about 20 percent of gum benzoin, a vegetable resin.
E 210 was first prepared synthetically about 1860 from compounds derived from coal tar.
E 210 is commercially manufactured by the chemical reaction of toluene (a hydrocarbon obtained from petroleum) with oxygen at temperatures around 200° C (about 400° F) in the presence of cobalt and manganese salts as catalysts.
Pure E 210 melts at 122° C (252° F) and is very slightly soluble in water.
Among the derivatives of benzoic acid are sodium benzoate, a salt used as a food preservative; benzyl benzoate, an ester used as a miticide; and benzoyl peroxide, used in bleaching flour and in initiating chemical reactions for preparing certain plastics.
E 210 is an alkyl benzoate preservative that occurs in nature in cherry bark, raspberries, tea, anise, and cassia bark.
Benefits of benzoic acid in skincare include anti-aging, soothing, and moisturizing properties.
In addition, a major derivative of benzoic acid, known as phenolic veratric acid, contains high concentrations of antioxidants to help neutralize free-radicals present in the environment.
As a preservative, benzoic acid possesses a wide variety of cosmetic applications, including product stabilizer, fragrance additive, and emollient.
For this reason, E 210 can be found diversely throughout products such as sunscreens, lipsticks, and lotions.
As a product stabilizer, benzoic acid helps to regulate pH and protect the integrity of ingredients.
Topical application of benzoic acid may also play a role in reinforcing skin barrier function, thus promoting the skin’s ability to retain moisture.
With its benefits combined, benzoic acid is equipped to improve the quality of both skin and skincare products.
Together, these characteristics help to alleviate dry skin and improve the skin’s ability to retain moisture.
History of E 210:
E 210 was discovered in the sixteenth century.
The dry distillation of gum benzoin was first described by Nostradamus (1556), and then by Alexius Pedemontanus (1560) and Blaise de Vigenère (1596).
Justus von Liebig and Friedrich Wöhler determined the composition of benzoic acid.
These latter also investigated how hippuric acid is related to benzoic acid.
In 1875 Salkowski discovered the antifungal abilities of benzoic acid, which was used for a long time in the preservation of benzoate-containing cloudberry fruits.
Production of E 210:
E 210 is produced commercially by partial oxidation of toluene with oxygen.
The process is catalyzed by cobalt or manganese naphthenates.
The process uses abundant materials, and proceeds in high yield.
The first industrial process involved the reaction of benzotrichloride (trichloromethyl benzene) with calcium hydroxide in water, using iron or iron salts as catalyst.
The resulting calcium benzoate is converted to benzoic acid with hydrochloric acid.
The product contains significant amounts of chlorinated benzoic acid derivatives.
For this reason, benzoic acid for human consumption was obtained by dry distillation of gum benzoin.
Food-grade benzoic acid is now produced synthetically.
BENZOIC ACID
Benzenecarboxylic acid
Phenyl carboxylic acid
CAS #: 65-85-0
EC Number: 200-618-2
Formula: C7H6O2 / C6H5COOH
Molecular mass: 122.1
Boiling point: 249°C
Melting point: 122°C
See Notes.
Density: 1.3 g/cm³
Solubility in water, g/100ml at 20°C: 0.29
Vapour pressure, Pa at 25°C: 0.1
Relative vapour density (air = 1): 4.2
Relative density of the vapour/air-mixture at 20°C (air = 1): 1
Flash point: 121°C c.c.
Auto-ignition temperature: 570°C
Octanol/water partition coefficient as log Pow: 1.87
Laboratory synthesis of E 210:
E 210 is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value.
E 210 is a common undergraduate preparation.
E 210 can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water.
The avoidance of organic solvents for the recrystallization makes this experiment particularly safe.
This process usually gives a yield of around 65%.
From Grignard reagent:
Bromobenzene can be converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide.
This synthesis offers a convenient exercise for students to carry out a Grignard reaction, an important class of carbon–carbon bond forming reaction in organic chemistry.
Oxidation of benzyl compounds:
Benzyl alcohol and benzyl chloride and virtually all benzyl derivatives are readily oxidized to benzoic acid.
Uses of E 210:
E 210 is mainly consumed in the production of phenol by oxidative decarboxylation at 300−400 °C:
C6H5CO2H + 1/2 O2 → C6H5OH + CO2
The temperature required can be lowered to 200 °C by the addition of catalytic amounts of copper (II) salts.
The phenol can be converted to cyclohexanol, which is a starting material for nylon synthesis.
Precursor to plasticizers:
Benzoate plasticizers, such as the glycol-, diethyleneglycol-, and triethyleneglycol esters, are obtained by transesterification of methyl benzoate with the corresponding diol.
These plasticizers, which are used similarly to those derived from terephthalic acid ester, represent alternatives to phthalates.
Precursor to sodium benzoate and related preservatives
E 210 inhibits the growth of mold, yeast and some bacteria.
E 210 is either added directly or created from reactions with its sodium, potassium, or calcium salt.
The mechanism starts with the absorption of benzoic acid into the cell.
If the intracellular pH changes to 5 or lower, the anaerobic fermentation of glucose through phosphofructokinase is decreased by 95%.
The efficacy of benzoic acid and benzoate is thus dependent on the pH of the food.
Acidic food and beverage like fruit juice (citric acid), sparkling drinks (carbon dioxide), soft drinks (phosphoric acid), pickles (vinegar) or other acidified food are preserved with benzoic acid and benzoates.
Reactions of E 210:
Reactions of E 210 can occur at either the aromatic ring or at the carboxyl group.
Aromatic ring:
Electrophilic aromatic substitution reaction will take place mainly in 3-position due to the electron-withdrawing carboxylic group; i.e. benzoic acid is meta directing.
Carboxyl group:
Reactions typical for carboxylic acids apply also to E 210.
Benzoate esters are the product of the acid catalysed reaction with alcohols.
E 210 amides are usually prepared from benzoyl chloride.
Dehydration to benzoic anhydride is induced with acetic anhydride or phosphorus pentoxide.
Highly reactive acid derivatives such as acid halides are easily obtained by mixing with halogenation agents like phosphorus chlorides or thionyl chloride.
Orthoesters can be obtained by the reaction of alcohols under acidic water free conditions with benzonitrile.
Reduction to benzaldehyde and benzyl alcohol is possible using DIBAL-H, LiAlH4 or sodium borohydride.
Decarboxylation to benzene may be effected by heating in quinoline in the presence of copper salts. Hunsdiecker decarboxylation can be achieved by heating the silver salt.
E 210 and its sodium salt are used as preservatives, which are mainly used in pickled products and beverages.
The maximum amount used in foods ranges from 0.2 to 2.0 g/kg.
If E 210 is excessively added to the food, it will destroy the VB1 in the food and make the calcium insoluble, which can destroy the absorption of calcium by the human body.
Furthermore, a long-term intake of E 210 will increase the risk of cancer.
Therefore, E 210 is necessary to ensure low levels of these preservatives in food to meet regulatory standards.
E 210 or its sodium salt, benzoate, was the first chemical preservative permitted in foods in the USA.
E 210 is still widely used today for a large number of foods.
The pK of benzoic acid is rather low (pK 4.20), so its main antimicrobial effect, due to the undissociated acid, will be for high acid foods such as ciders, soft drinks and dressings.
E 210 is most suitable for foods with a pH lower than 4.5, but has also found use in margarine, fruit salads, sauerkraut, jams and jellies.
Benzoate acts essentially as a mould and yeast inhibitor in high acid foods and the poor activity at pH values above 4.0 limits its use against bacteria.
E 210 naturally occurs in cranberries, prunes, strawberries, apples and yogurts.
In certain foods, benzoate may impart a disagreeable taste described as ‘peppery’ or burning.
The antimicrobial effect of benzoic acid has been assumed only to be expressed by the undissociated acid interfering with the permeability of the cell membrane and the proton-motive force.
However, as for sorbic and propionic acid, benzoic acid has a certain antimicrobial activity in the dissociated form.
Benzoate also specifically inhibits amino acid uptake and certain enzymes within the cell: alpha-ketoglutarate, succinate dehydrogenase, 6-phosphofructo-2-kinase and lipase.
In a comparative study, Islam (2002) investigated the effect of dipping turkey frankfurters in 25 per cent solutions of propionate, benzoate, diacetate or sorbate on the growth of Listeria monocytogenes.
The organic acids were equally effective in reducing L. monocytogenes when the frankfurters were stored at 4°C for 14 days (reduction around 3–4 log cfu/g) but when stored at 13°C, benzoate and diacetate were more effective than propionate and sorbate.
A quite new application method for benzoic acid is active packaging.
Weng et al. (1997) treated ionomer films with alkali.
The resulting release of benzoic acid inhibited Penicillium and Aspergillus in microbial media.
E 210, added as either its sodium or its potassium salt, is a preservative permitted in the United Kingdom by the Miscellaneous Additives in Food Regulations 1995.
E 210 is necessary to use preservatives in some soft drinks to ensure the safety of the product by protecting it from spoilage micro-organisms.
E 210 has been widely tested (see 2.6.6) and accepted as safe by the European Union and United Kingdom authorities.
E 210 is an intermediary metabolite in this pathway with further metabolism to hippuric acid which is ultimately excreted in the urine where it can be used as a biomarker of acetophenone exposure.
E 210 or benzene-carbonic-acid is a monobasic aromatic acid, moderately strong, white crystalline powder, very soluble in alcohol, ether, and benzene, but poorly soluble in water (0.3 g of benzoic acid in 100 g of water at 20 °C).
E 210 has the advantage that it does not affect the odor or taste of the soft drink, if used in small quantities.
The preserving quality of benzoic acid is based on its activity to delay the multiplication of several groups of microorganisms, which, however, are not killed by this product.
The low solubility of benzoic acid in water complicates its application in products containing large amounts of water.
Therefore, the water-soluble salt sodium benzoate is used.
This product, which is the salt of benzoic acid, has no preserving activity by itself.
Therefore, after addition of sodium benzoate, the acidity of the soft drink is increased (pH < 3.5), with the result that free undissociated benzoic acid is formed, which has a preserving property. In an alkaline environment, benzoic acid is split into ions and thus loses its preserving activity.
Sodium benzoate is the sodium salt of benzoic acid used as a white crystalline or amorphous (without crystal structure) powder, very soluble in water (66 g of sodium benzoate in 100 g of water at 20 °C) but poorly soluble in alcohol.
E 210 is generally recognized as safe (GRAS) for use as a food preservative in high-acid foods and occurs naturally in some organisms.
Among foods commonly preserved with the acid are soft drinks, fruit juices, fermented vegetables, and high-sugared foods.
The mechanism of antimicrobial action occurs through acidification of cytoplasm and inhibition of critical metabolic enzymes and processes, including macroautophagy.
E 210 tolerance by certain yeast species and other factors militating against its effectiveness necessitate combination treatments with other synergistic methods.
E 210 is rapidly metabolized and excreted as hippuric acid.
E 210 is a white (or colorless) solid with the formula C6H5CO2H.
E 210 is the simplest aromatic carboxylic acid.
The name is derived from gum benzoin, which was for a long time its only source.
E 210 occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary metabolites.
Salts of E 210 are used as food preservatives.
E 210 is an important precursor for the industrial synthesis of many other organic substances.
The salts and esters of E 210 are known as benzoates .
Application(s) of E 210:
A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria.
In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299).
Any drug which causes the onset of an allergic reaction.
E 210 is rarely used as such in medicines whereas its salts (benzoates) are more commonly used.
Sodium benzoate is found as excipients in some medicinal products administered orally, topically(e.g. antifungals) or injected.
E 210 has a long history of use as an antifungal agent in topical therapeutic preparations such as Whitfield's ointment (benzoic acid 6% and salicylic acid 3%).
Sodium benzoate is also administered intravenously and orally as an active substance to infants and children for the treatment of hyperammonaemia related to urea cycle disorders
E210: benzoic acid
E211: sodium benzoate
E212: potassium benzoate
E 210, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid.
E 210 occurs naturally free and bound as benzoic acid esters in many plant and animal species.
Appreciable amounts have been found in most berries (around 0.05%).
Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit.
E 210 is a fungistatic compound that is widely used as a food preservative.
E 210 often is conjugated to glycine in the liver and excreted as hippuric acid.
E 210 is a byproduct of phenylalanine metabolism in bacteria.
E 210 is also produced when gut bacteria process polyphenols (from ingested fruits or beverages).
E 210 can be found in Serratia (PMID: 23061754 ).
As a kind of antibacterial and antifungal preservative, benzoic acid is widely used in foods and feeds.
Recently, many studies showed that it could improve the growth and health, which should, at least partially, be derived from the promotion of gut functions, including digestion, absorption, and barrier.
Based on the similarity of gut physiology between human and pigs, many relative studies in which piglets and porcine intestinal epithelial cells were used as the models have been done.
And the results showed that using appropriate benzoic acid levels might improve gut functions via regulating enzyme activity, redox status, immunity, and microbiota, but excess administration would lead to the damage of gut health through redox status.
However, the further mechanisms that some intestinal physiological functions might be regulated are not well understood.
The present review will, in detail, summarize the effect of benzoic acid on gut functions.
Uses of E 210: Preservative in food and pharmaceutical applications to inhibit microbial growth at the optimum pH of 2.5-4.0.
Main uses are preparations such as mouthwashes, lotions and toothpastes.
Use: E 210 is a mono-functional, aromatic acid, which is widely used as a building block for the synthesis of alkyd resins.
E 210 is also used as a preservative in select industrial applications.
When used as a component of alkyd resins, it improves gloss, hardness and chemical resistance.
When used as a preservative, E 210 increases storage stability and reduces corrosion for emulsions, polishes, waxes, paints and liquid detergents.
-E 210 is the chemical benzenecarboxylic acid (C7H6O2), occurring in nature in free and combined forms.
Among the foods in which benzoic acid occurs naturally are cranberries, prunes, plums, cinnamon, ripe cloves, and most berries. benzoic acid is manufactured by treating molten phthalic anhydride with steam in the presence of a zinc oxide catalyst, by the hydrolysis of benzotrichloride, or by the oxidation of toluene with nitric acid or sodium bichromate or with air in the presence of a transition metal salt catalyst.
E 210 is a solid that is crystalline in appearance, similar to white needles.
A natural source of E 210 is gum benzoin, which comes from certain tree barks; however, benzoic acid can also be made by synthetic means.
The chemical formula of E 210 is C7H6O2: E 210 has seven carbon (C) atoms, six hydrogen (H) atoms and two oxygen (O) atoms.
This chemical formula can also be written as C6H5COOH.
On the left, we see that all the carbon and hydrogen atoms on the benzene ring are drawn out, and on the right, we see the shorthand way to draw a benzene ring (in blue).
E 210 is an organic compound because it contains carbon, and it is also an aromatic carboxylic acid.
E 210 is aromatic because it has a benzene ring in its chemical structure.
Benzene is aromatic because it has alternating double bonds between each carbon.
E 210's classified as a carboxylic acid because it has a carboxyl group in its structure, which is the COOH group boxed in red.
Preferred IUPAC name: Benzoic acid
Systematic IUPAC name: Benzenecarboxylic acid
Other names:
Carboxybenzene
E210
Dracylic acid
Phenylmethanoic acid
BzOH
Identifiers:
CAS Number: 65-85-0
EC Number: 200-618-2
E number: E210 (preservatives)
Properties of E 210:
Chemical formula: C7H6O2
Molar mass: 122.123 g·mol−1
Appearance: Colorless crystalline solid
Odor: Faint, pleasant odor
Density:
1.2659 g/cm3 (15 °C)
1.0749 g/cm3 (130 °C)
Melting point: 122 °C (252 °F; 395 K)
Boiling point: 250 °C (482 °F; 523 K)[7]
Solubility in water :
1.7 g/L (0 °C)
2.7 g/L (18 °C)
3.44 g/L (25 °C)
5.51 g/L (40 °C)
21.45 g/L (75 °C)
56.31 g/L (100 °C)
Solubility in methanol:
30 g/100 g (-18 °C)
32.1 g/100 g (-13 °C)
71.5 g/100 g (23 °C)
Solubility in ethanol
25.4 g/100 g (-18 °C)
47.1 g/100 g (15 °C)
52.4 g/100 g (19.2 °C)
55.9 g/100 g (23 °C)
Solubility in acetone: 54.2 g/100 g (20 °C)
Solubility in olive oil: 4.22 g/100 g (25 °C)
Solubility in 1,4-Dioxane: 55.3 g/100 g (25 °C)
log P: 1.87
Vapor pressure:
0.16 Pa (25 °C)
0.19 kPa (100 °C)
22.6 kPa (200 °C)
Acidity (pKa)
4.202 (H2O)
11.02 (DMSO)
Magnetic susceptibility (χ): -70.28·10−6 cm3/mol
Refractive index (nD)
1.5397 (20 °C)
1.504 (132 °C)
Viscosity: 1.26 mPa (130 °C)
Structure of E 210:
Crystal structure: Monoclinic
Molecular shape planar
Dipole moment: 1.72 D in dioxane
Thermochemistry of E 210:
Heat capacity (C): 146.7 J/mol·K
Std molar entropy (So298): 167.6 J/mol·K
Std enthalpy of formation (ΔfH⦵298): -385.2 kJ/mol
Std enthalpy of combustion (ΔcH⦵298): -3228 kJ/mol
Related compounds:
Related carboxylic acids
Hydroxybenzoic acids
Aminobenzoic acids,
Nitrobenzoic acids,
Phenylacetic acid
Benzaldehyde,
Benzyl alcohol,
Benzoyl chloride,
Benzylamine,
Benzamide
Common Uses - Preservative:
E 210 is very useful in the food industry, personal care industry and in medicine as well
E 210 is a plant polyphenol and a natural aromatic acid used in a wide variety of cosmetics as a pH adjuster and preservative.
Benzyl Alcohol is metabolized to Benzoic Acid in the body.
E 210 was originally found as a by-product of the distillation of gum benzoin during the 1600th century.
Now E 210 is mostly commercially manufactured from toluene.
E 210 often appears in a cosmetic formulation as Sodium benzoate, the inactive salt of a benzoic acid which is soluble in water.
At low pH levels in water, sodium benzoate converts to benzoic acid, the active form.
The activity of benzoic acid is very pH dependent, showing low activity above pH 6 and most active at pH 3.
As a preservative in cosmetic formulations, it is primarily an anti-fungal agent that prevents fungi from developing in products and formulas and changing their composition.
E 210 is less effective against bacteria.
E 210 has a long history of use as an antifungal agent in topical therapeutic preparations such as Whitfield’s ointment (benzoic acid 6% and salicylic acid 3%).
E 210 has been used with salicylic acid as a topical antifungal agent and in the treatment of athletes foot and ringworm.
When Sodium benzoate is used as a preservative, the pH of the final formulation may have to be lowered to facilitate the release of the free benzoic acid for useful activity.
Potassium sorbate is often combined with Sodium benzoate in low pH products to provide a synergistic preservative effect against yeast and mold.
E 210 has been concluded that benzoic acid can be used safely at concentrations up to 5%, but that consideration should be given the nonimmunologic phenomena when using this ingredient in cosmetic formulations designed for infants and children.
E 210 is an aromatic acid used in a wide variety of cosmetics as a pH adjuster and preservative.
E 210 has a long history of use as an antifungal agent in topical therapeutic preparations.
E 210 has been concluded that benzoic acid can be used safely at concentrations up to 5%, but that consideration should be given the nonimmunologic phenomena when using this ingredient in cosmetic formulations designed for infants and children.
Uses of E 210:
E 210 and its salts are used as a food preservative, represented by the E-numbers E210, E211, E212, and E213.
E 210 inhibits the growth of mold, yeast and some bacteria.
E 210 is either added directly or created from reactions with its sodium, potassium, or calcium salt.
The mechanism starts with the absorption of E 210 in to the cell.
If the intracellular pH changes to 5 or lower, the anaerobic fermentation of glucose through phosphofructokinase is decreased by 95%.
The efficacy of benzoic acid and benzoate is thus dependent on the pH of the food.
Acidic food and beverage like fruit juice (citric acid), sparkling drinks (carbon dioxide), soft drinks (phosphoric acid), pickles (vinegar) or other acidified food are preserved with benzoic acid and benzoates.
Typical levels of use for benzoic acid as a preservative in food are between 0.05 – 0.1%.
Foods in which benzoic acid may be used and maximum levels for its application are laid down in international food law.
Concern has been expressed that benzoic acid and its salts may react with ascorbic acid (vitamin C) in some soft drinks, forming small quantities of benzene.
Synthesis of E 210:
E 210 is used to make a large number of chemicals, important examples of which are:
Benzoyl chloride, C6H5C(O)Cl, is obtained by treatment of benzoic with thionyl chloride, phosgene or one of the chlorides of phosphorus.
C6H5C(O)Cl is an important starting material for several benzoic acid derivates like benzyl benzoate, which is used as artificial flavours and insect repellents.
Benzoyl peroxide, [C6H5C(O)O]2, is obtained by treatment with peroxide.
The peroxide is a radical starter in polymerization reactions and also a component in cosmetic products.
Benzoate plasticizers, such as the glycol-, diethylengylcol-, and triethyleneglycol esters are obtained by transesterification of methyl benzoate with the corresponding diol.
Alternatively these species arise by treatment of benzoylchloride with the diol.
These plasticizers are used similarly to those derived from terephthalic acid ester.
Phenol, C6H5OH, is obtained by oxidative decarboxylation at 300-400°C.
The temperature required can be lowered to 200°C by the addition of catalytic amounts of copper(II) salts.
The phenol can be converted to cyclohexanol, which is a starting material for nylon synthesis.
Medicinal:
E 210 is a constituent of Whitfield Ointment which is used for the treatment of fungal skin diseases such as tinea, ringworm, and athlete's foot.
Purification of E 210:
E 210 is purified by recrystallisation of the crude product.
This involves dissolving the material and allowing it to recrystallize (or re-solidify), leaving any impurities in solution and allowing the pure material to be isolated from the solution.
Biology and health effects of E 210:
E 210 occurs naturally free and bound as benzoic acid esters in many plant and animal species.
Appreciable amounts have been found in most berries (around 0.05%).
Ripe fruits of several Vaccinium species (e.g., cranberry, V. vitis idaea; bilberry, V. macrocarpon) contain as much as 300-1300 mg free benzoic acid per kg fruit.
E 210 is also formed in apples after infection with the fungus Nectria galligena.
Among animals, E 210 has been identified primarily in omnivorous or phytophageous species, e.g., in viscera and muscles of the ptarmigan (Lagopus mutus) as well as in gland secretions of male muskoxen (Ovibos moschatus) or Asian bull elephants (Elephas maximus).
Chemistry of E 210:
Reactions of E 210 can occur at either the aromatic ring or the carboxylic group:
Aromatic ring:
Electrophilic aromatic substitution reaction will take place mainly in 3-position to the electron-withdrawing carboxylic group.
The second substitution reaction (on the right) is slower because the first nitro group is deactivating.
Conversely, if an activating group (electron-donating) was introduced (e.g., alkyl), a second substitution reaction would occur more readily than the first and the disubstituted product might not accumulate to a significant extent.
Carboxylic group:
All the reactions mentioned for carboxylic acids are also possible for E 210.
E 210 esters are the product of the acid catalysed reaction with alcohols.
E 210 amides are more easily available by using activated acid derivatives (such as benzoyl chloride) or by coupling reagents used in peptide synthesis like DCC and DMAP.
The more active benzoic anhydride is formed by dehydration using acetic anhydride or phosphorus pentoxide.
Highly reactive acid derivatives such as acid halides are easily obtained by mixing with halogenation agents like phosphorus chlorides or thionyl chloride.
Orthoesters can be obtained by the reaction of alcohols under acidic water free conditions with benzonitrile.
Reduction to benzaldehyde and benzyl alcohol is possible using DIBAL-H, LiAlH4 or sodium borohydride.
The copper catalysed decarboxylation of benzoate to benzene may be effected by heating in quinoline.
Also, Hunsdiecker decoarboxylation can be achieved by forming the silver salt and heating.
Laboratory preparations of E 210:
E 210 is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedogical value.
E 210 is a common undergraduate preparation and a convenient property of the compound is that its melting point equals its molecular weight (122).
For all syntheses, E 210 can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water.
The avoidance of organic solvents for the recrystallization makes this experiment particularly safe.
By hydrolysis:
Like any other nitrile or amide, benzonitrile and benzamide can be hydrolyzed to benzoic acid or its conjugate base in acid or basic conditions.
From benzaldehyde:
The base-induced disproportionation of benzaldehyde, the Cannizzaro reaction, affords equal amounts of benzoate and benzyl alcohol; the latter can be removed by distillation.
From bromobenzene:
Bromobenzene in diethyl ether is stirred with magnesium turnings to produce phenylmagnesium bromide (C6H5MgBr).
This Grignard reagent is slowly added to dry-ice (solid carbon dioxide) to give benzoate.
Dilute acid is added to form benzoic acid.
From benzyl alcohol:
Benzyl alcohol is refluxed with potassium permanganate or other oxidizing reagents in water.
The mixture hot filtered to remove manganese oxide and then allowed to cool to afford E 210.
Synonyms
Benzenecarboxylic acid
Benzeneformate
Benzeneformic acid
Benzenemethanoate
Benzenemethanoic acid
Benzenemethonic acid
Benzoate
benzoic acid
Benzoic acid sodium salt
Carboxybenzene
Diacylate
Diacylic acid
Dracylate
Dracylic acid
Oracylic acid
Phenylcarboxylate
Phenylcarboxylic acid
Phenylformate
Phenylformic acid
Sodium benzoate
Sodium benzoic acid
Benzenecarboxylate
Acide benzoique
Aromatic carboxylic acid
Benzenecarboxylic acid
Benzeneformic acid
Benzenemethanoic acid
Benzoesaeure
Dracylic acid
e210
Phenylcarboxylic acid
Phenylformic acid
Aromatic carboxylate
Benzeneformate
Benzenemethanoate
Dracylate
Phenylcarboxylate
Phenylformate
Benzoate
Benzenemethonic acid
Benzoic acid sodium salt
Carboxybenzene
Diacylate
Diacylic acid
Oracylic acid
Sodium benzoate
Sodium benzoic acid
Acid, benzoic
Kendall brand OF benzoic acid sodium salt
Benzoate, potassium
Potassium benzoate
Ucephan
benzene carboxylic acid
benzene formic acid
benzene methanoic acid
benzenecarboxylic acid
benzeneformic acid
benzenemethanoic acid
nat.benzoic acid
benzoic acid crystal FCC
benzoic acid natural
benzoic acid U.S.P.
benzoic acid USP FCC granular
benzoic acid USP/EP/JP
carboxybenzene
diacylic acid
dracyclic acid
dracylic acid
oracylic acid
phenyl carboxylic acid
phenyl formic acid
phenylcarbinolum
phenylcarboxylic acid
phenylformic acid
retardex
tenn-plas
unisept BZA
Acide benzoique
Aromatic carboxylic acid
Benzenecarboxylic acid
Benzeneformic acid
Benzenemethanoic acid
Benzoesaeure
Dracylic acid
e210
Phenylcarboxylic acid
Phenylformic acid
Aromatic carboxylate
Benzenecarboxylate
Benzeneformate
Benzenemethanoate
Dracylate
Phenylcarboxylate
Phenylformate
Benzoate
Benzenemethonic acid
Benzoic acid sodium salt
Carboxybenzene
Diacylate
Diacylic acid
Oracylic acid
Sodium benzoate
Sodium benzoic acid
Acid, benzoic
Kendall brand OF benzoic acid sodium salt
Benzoate, potassium
Potassium benzoate
Ucephan
Acid benzoic (ro)
Acide benzoïque (fr)
acide benzoïque (fr)
Acido benzoico (it)
Aċidu benżojku (mt)
Bensoehape (et)
Bensoesyra (sv)
Bentsoehappo (fi)
Benzenkarboksirūgštis (lt)
Benzoe-säure (de)
Benzoesav (hu)
Benzoesyre (da)
Benzoic acid (no)
Benzojeva kiselina (hr)
Benzojska kislina (sl)
Benzoová kyselina (cs)
Benzoskābe (lv)
benzosyre (no)
Benzoëzuur (nl)
Kwas benzoesowy (pl)
Kyselina benzoová (sk)
Ácido benzoico (es)
Ácido benzoico (pt)
Βενζοϊκό οξύ (el)
Бензоена киселина (bg)
Benzoic acid
benzene carboxylic acid
Benzenecarboxylic acid
Benzoesäure
BENZOIC ACID
Benzoic Acid
Benzoic Acid Zone Refined (number of passes:20)
Benzonic acid
Phenylformic acid, Benzene carboxylic acid
acide benzoïque Français
Aromatic carboxylic acid
Benzenecarboxylic acid
Benzeneformic acid
Benzenemethanoic acid
Benzoesäure Deutsch
Benzoic acid
BENZOIC ACID
Dracylic acid
E210
Phenylcarboxylic acid
Phenylformic acid
benzoic acid
65-85-0
Dracylic acid
benzenecarboxylic acid
Carboxybenzene
Benzeneformic acid
phenylformic acid
Benzenemethanoic acid
Phenylcarboxylic acid
Retardex
Benzoesaeure GK
Benzoesaeure GV
Retarder BA
Tenn-Plas
Acide benzoique
Salvo liquid
Solvo powder
Benzoesaeure
Flowers of benzoin
Flowers of benjamin
Benzoic acid, tech.
Unisept BZA
HA 1 (acid)
Kyselina benzoova
Benzoic acid (natural)
Benzoate (VAN)
HA 1
Benzoesaeure [German]
Caswell No. 081
Diacylic acid
Oracylic acid
Acide benzoique [French]
Acido benzoico [Italian]
Benzenemethonic acid
Kyselina benzoova [Czech]
NSC 149
E 210
FEMA No. 2131
CCRIS 1893
Diacylate
HSDB 704
UNII-8SKN0B0MIM
AI3-0310
Salvo, liquid
Solvo, powder
AI3-03710
phenyl formic acid
EPA Pesticide Chemical Code 009101
Benzoic acid Natural
E210
:30746
Aromatic carboxylic acid
MFCD00002398
8SKN0B0MIM
Benzeneformate
Phenylformate
Benzenemethanoate
Phenylcarboxylate
Benzenecarboxylate
DSSTox_CID_143
DSSTox_RID_75396
DSSTox_GSID_20143
Benzoic acid, 99%, extra pure
benzoic-acid
Acido benzoico
Benzoic acid, 99.5%, for analysis
Benzoic acid, 99.6%, ACS reagent
Carboxypolystyrene
Benzoic acid [USAN:JAN]
CAS-65-85-0
NSC7918
Benzoic acid (TN)
EINECS 200-618-2
Benzoic acid [USP:JAN]
phenylcarboxy
Dracylate
benzoic aicd
bezoic acid
Aromatic acid
benzenecarboxylic
Salvo powder
benzoic- acid
Retarder BAX
1gyx
1kqb
benzoic acid group
Benzoic Acid USP
Sodium benzoic acid
Benzoic Acid,(S)
Natural Benzoic Acid
Benzoic acid solution
BENZOICACID-D5
Benzoic acid-[13C7]
WLN: QVR
benzene-2-carboxylic acid
Benzoic Acid-[18O2]
Benzoic acid, ACS reagent
bmse000300
CHEMBL541
BENZENE CARBOXYLIC ACID
BENZENE FORMIC ACID
BENZENECARBOXYLIC ACID
BENZENEFORMIC ACID
BENZENEMETHANOIC ACID
BENZENEMETHONIC ACID
BENZOATE
BENZOIC ACID
CARBOXYBENZENE
CARBOXYLBENZENE
DIACYCLIC ACID
DRACYCLIC ACID
DRACYLIC ACID
E 210
HA 1
HA 1 (ACID)
PHENYL CARBOXYLIC ACID
PHENYLCARBOXYLIC ACID
PHENYLFORMIC ACID
RETARDED BA
RETARDER BA
RETARDEX
SALVO LIQUID
SALVO POWDER
SOLVO POWDER
TENN-PLAS
TENNPLAS