Benzoic acid

Organic compound (C6H5COOH)

Benzoic acid  |

|

Names
Preferred IUPAC name

Benzoic acid[1]

Systematic IUPAC name

Benzenecarboxylic acid

Other names

* Carboxybenzene
* E210
* Dracylic acid
* Phenylmethanoic acid
* BzOH

Identifiers

CAS Number

* 65-85-0 Y

3D model (JSmol)

* Interactive image

3DMet  |

* B00053

Beilstein Reference

| 636131
ChEBI |

* CHEBI:30746 Y

ChEMBL |

* ChEMBL541 Y

ChemSpider |

* 238 Y

DrugBank |

* DB03793 Y

ECHA InfoCard | 100.000.562
EC Number |

* 200-618-2

E number | E210 (preservatives)

Gmelin Reference

| 2946
KEGG |

* D00038 Y

MeSH | benzoic+acid

PubChem CID

* 243

RTECS number |

* DG0875000

UNII |

* 8SKN0B0MIM Y

CompTox Dashboard (EPA)

* DTXSID6020143

InChI

* InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9) Y

Key: WPYMKLBDIGXBTP-UHFFFAOYSA-N Y

* InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)

Key: WPYMKLBDIGXBTP-UHFFFAOYAD

SMILES

* O=C(O)c1ccccc1

Properties

Chemical formula

| C7H6O2
Molar mass | 122.123 g/mol
Appearance  | Colorless crystalline solid
Odor | Faint, pleasant odor
Density | 1.2659 g/cm3 (15 °C)
1.0749 g/cm3 (130 °C)[2]
Melting point | 122 °C (252 °F; 395 K)[7]
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)[2][3]
Solubility | Soluble in acetone, benzene, CCl4, CHCl3, alcohol, ethyl ether, hexane, phenyls, liquid ammonia, acetates
Solubility in methanol | 30 g/100 g (−18 °C)
32.1 g/100 g (−13 °C)
71.5 g/100 g (23 °C)[2]
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)[2]
Solubility in acetone | 54.2 g/100 g (20 °C)[2]
Solubility in olive oil | 4.22 g/100 g (25 °C)[2]
Solubility in 1,4-Dioxane | 55.3 g/100 g (25 °C)[2]
log P | 1.87
Vapor pressure | 0.16 Pa (25 °C)
0.19 kPa (100 °C)
22.6 kPa (200 °C)[4]
Acidity (pKa)  |

* 4.202 (H2O)[5]
* 11.02 (DMSO)[6]

Magnetic susceptibility (χ)

| −70.28·10−6 cm3/mol

Refractive index (nD)

| 1.5397 (20 °C)
1.504 (132 °C)[2]
Viscosity | 1.26 mPa (130 °C)
Structure

Crystal structure

| Monoclinic

Molecular shape

| Planar

Dipole moment

| 1.72 D in dioxane
Thermochemistry

Heat capacity (C)

| 146.7 J/mol·K[4]

Std molar
entropy (S⦵298)

| 167.6 J/mol·K[2]

Std enthalpy of
formation (ΔfH⦵298)

| −385.2 kJ/mol[2]

Std enthalpy of
combustion (ΔcH⦵298)

| −3228 kJ/mol[4]
Hazards
Occupational safety and health (OHS/OSH):

Main hazards

| Irritant
GHS labelling:

Pictograms

| [8]

Signal word

| Danger

Hazard statements

| H318, H335[8]

Precautionary statements

| P261, P280, P305+P351+P338[8]
NFPA 704 (fire diamond)  |

Flash point | 121.5 °C (250.7 °F; 394.6 K)[7]

Autoignition
temperature

| 571 °C (1,060 °F; 844 K)[7]
Lethal dose or concentration (LD, LC):

LD50 (median dose)

| 1700 mg/kg (rat, oral)
Safety data sheet (SDS)  | JT Baker
Related compounds

Related carboxylic acids

| Hydroxybenzoic acids
Aminobenzoic acids,
Nitrobenzoic acids,
Phenylacetic acid

Related compounds

| Benzaldehyde,
Benzyl alcohol,
Benzoyl chloride,
Benzylamine,
Benzamide

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)

Infobox references

Chemical compound

Benzoic acid /bɛnˈzoʊ.ɪk/ is a white (or colorless) solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring (C6H6) with a carboxyl (−C(=O)OH) substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.

Benzoic acid occurs naturally in many plants[9] and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates /ˈbɛnzoʊ.eɪt/.

## Contents

* 1 History
* 2 Production
* 2.1 Industrial preparations
* 2.2 Laboratory synthesis
* 2.2.1 By hydrolysis
* 2.2.2 From Grignard reagent
* 2.2.3 Oxidation of benzyl compounds
* 3 Uses
* 3.1 Precursor to plasticizers
* 3.2 Precursor to sodium benzoate and related preservatives
* 3.3 Medicinal
* 3.4 Niche and laboratory uses
* 4 Biology and health effects
* 5 Reactions
* 5.1 Aromatic ring
* 5.2 Carboxyl group
* 6 Safety and mammalian metabolism
* 7 References
* 8 External links

## History[edit]

Benzoic acid 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).[10]

Justus von Liebig and Friedrich Wöhler determined the composition of benzoic acid.[11] These latter also investigated how hippuric acid is related to benzoic acid.

In 1875 Salkowski discovered the antifungal properties of benzoic acid, which was used for a long time in the preservation of benzoate-containing cloudberry fruits.[12][disputed - discuss]

## Production[edit]

### Industrial preparations[edit]

Benzoic acid 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.[13]

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.

### Laboratory synthesis[edit]

Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value. It is a common undergraduate preparation.

Benzoic acid 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%.[14]

#### By hydrolysis[edit]

Like other nitriles and amides, benzonitrile and benzamide can be hydrolyzed to benzoic acid or its conjugate base in acid or basic conditions.

#### From Grignard reagent[edit]

Bromobenzene can be converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide.[15] 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.[16][17][18][19][20]

#### Oxidation of benzyl compounds[edit]

Benzyl alcohol[21] and benzyl chloride and virtually all benzyl derivatives are readily oxidized to benzoic acid.

## Uses[edit]

Benzoic acid is mainly consumed in the production of phenol by oxidative decarboxylation at 300−400 °C:[22]

C 6 H 5 CO 2 H + 1 2 O 2 ⟶ C 6 H 5 OH + CO 2 {\displaystyle {\ce {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[edit]

Benzoate plasticizers, such as the glycol-, diethyleneglycol-, and triethyleneglycol esters, are obtained by transesterification of methyl benzoate with the corresponding diol.[22] These plasticizers, which are used similarly to those derived from terephthalic acid ester, represent alternatives to phthalates.[22]

### Precursor to sodium benzoate and related preservatives[edit]

Benzoic acid and its salts are used as food preservatives, represented by the E numbers E210, E211, E212, and E213. Benzoic acid inhibits the growth of mold, yeast[23] and some bacteria. It 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.[24] Benzoic acid, benzoates and their derivatives are used as preservatives for acidic foods and beverages such as citrus fruit juices (citric acid), sparkling drinks (carbon dioxide), soft drinks (phosphoric acid), pickles (vinegar) and other acidified foods.

Typical concentrations of benzoic acid as a preservative in food are between 0.05 and 0.1%. Foods in which benzoic acid may be used and maximum levels for its application are controlled by local food laws.[25][26]

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 carcinogenic benzene.[27]

See also: Benzene in soft drinks

### Medicinal[edit]

Benzoic acid is a constituent of Whitfield's ointment which is used for the treatment of fungal skin diseases such as ringworm and athlete's foot.[28][29] As the principal component of gum benzoin, benzoic acid is also a major ingredient in both tincture of benzoin and Friar's balsam. Such products have a long history of use as topical antiseptics and inhalant decongestants.

Benzoic acid was used as an expectorant, analgesic, and antiseptic in the early 20th century.[30]

### Niche and laboratory uses[edit]

In teaching laboratories, benzoic acid is a common standard for calibrating a bomb calorimeter.[31]

## Biology and health effects[edit]

Benzoic acid occurs naturally as do its esters in many plant and animal species. Appreciable amounts are found in most berries (around 0.05%). Ripe fruits of several Vaccinium species (e.g., cranberry, V. vitis macrocarpon; bilberry, V. myrtillus) contain as much as 0.03–0.13% free benzoic acid. Benzoic acid is also formed in apples after infection with the fungus Nectria galligena. Among animals, benzoic acid has been identified primarily in omnivorous or phytophageous species, e.g., in viscera and muscles of the rock ptarmigan (Lagopus muta) as well as in gland secretions of male muskoxen (Ovibos moschatus) or Asian bull elephants (Elephas maximus).[32] Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters.[33]

In terms of its biosynthesis, benzoate is produced in plants from cinnamic acid.[34] A pathway has been identified from phenol via 4-hydroxybenzoate.[35]

## Reactions[edit]

Reactions of benzoic acid can occur at either the aromatic ring or at the carboxyl group.

### Aromatic ring[edit]

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.[36]

### Carboxyl group[edit]

Reactions typical for carboxylic acids apply also to benzoic acid.[22]

* Benzoate esters are the product of the acid catalysed reaction with alcohols.
* Benzoic acid 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.

## Safety and mammalian metabolism[edit]

It is excreted as hippuric acid.[37] Benzoic acid is metabolized by butyrate-CoA ligase into an intermediate product, benzoyl-CoA,[38] which is then metabolized by glycine N-acyltransferase into hippuric acid.[39] Humans metabolize toluene which is also excreted as hippuric acid.[40]

For humans, the World Health Organization's International Programme on Chemical Safety (IPCS) suggests a provisional tolerable intake would be 5 mg/kg body weight per day.[32] Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice. Lethal dose for cats can be as low as 300 mg/kg body weight.[41] The oral LD50 for rats is 3040 mg/kg, for mice it is 1940–2263 mg/kg.[32]

In Taipei, Taiwan, a city health survey in 2010 found that 30% of dried and pickled food products had benzoic acid.[42]

## References[edit]

1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 745\. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
2. ^ a b c d e f g h i j "benzoic acid". chemister.ru. Retrieved 24 October 2018.
3. ^ Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand.
4. ^ a b c Benzoic acid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-23)
5. ^ Harris, Daniel (2010). Quantitative Chemical Analysis (8 ed.). New York: W. H. Freeman and Company. pp. AP12. ISBN 9781429254366.
6. ^ Olmstead, William N.; Bordwell, Frederick G. (1980). "Ion-pair association constants in dimethyl sulfoxide". The Journal of Organic Chemistry. 45 (16): 3299–3305. doi:10.1021/jo01304a033.
7. ^ a b c d Record  in the GESTIS Substance Database of the Institute for Occupational Safety and Health
8. ^ a b c Sigma-Aldrich Co., Benzoic acid. Retrieved on 2014-05-23.
9. ^ "Scientists uncover last steps for benzoic acid creation in plants". Purdue Agriculture News.
10. ^ Neumüller O-A (1988). Römpps Chemie-Lexikon (6 ed.). Stuttgart: Frankh'sche Verlagshandlung. ISBN 978-3-440-04516-9. OCLC 50969944.
11. ^ Liebig J; Wöhler F (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Chemie. 3 (3): 249–282. doi:10.1002/jlac.18320030302. hdl:2027/hvd.hxdg3f.
12. ^ Salkowski E (1875). Berl Klin Wochenschr. 12: 297–298. `{{cite journal}}`: Missing or empty `|title=` (help)
13. ^ Wade, Leroy G. (2014). Organic Chemistry (Pearson new international ed.). Harlow: Pearson Education Limited. p. 985\. ISBN 978-1-292-02165-2.
14. ^ D. D. Perrin; W. L. F. Armarego (1988). Purification of Laboratory Chemicals (3rd ed.). Pergamon Press. pp. 94. ISBN 978-0-08-034715-8.
15. ^ Donald L. Pavia (2004). Introduction to Organic Laboratory Techniques: A Small Scale Approach. Thomson Brooks/Cole. pp. 312–314. ISBN 978-0-534-40833-6.
16. ^ Shirley, D. A. (1954). "The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium". Org. React. 8: 28–58.
17. ^ Huryn, D. M. (1991). "Carbanions of Alkali and Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition Reactions". In Trost, B. M.; Fleming, I. (eds.). Comprehensive Organic Synthesis, Volume 1: Additions to C--X π-Bonds, Part 1. Elsevier Science. pp. 49–75. doi:10.1016/B978-0-08-052349-1.00002-0. ISBN 978-0-08-052349-1.
18. ^ "The Grignard Reaction. Preparation of Benzoic Acid" (PDF). Portland Community College. Archived from the original (PDF) on 26 February 2015. Retrieved 12 March 2015.>
19. ^ "Experiment 9: Synthesis of Benzoic Acid via Carbonylation of a Grignard Reagent" (PDF). University of Wisconsin-Madison. Archived from the original (PDF) on 23 September 2015. Retrieved 12 March 2015.
20. ^ "Experiment 3: Preparation of Benzoic Acid" (PDF). Towson University. Archived from the original (PDF) on 13 April 2015. Retrieved 12 March 2015.>
21. ^ Santonastaso, Marco; Freakley, Simon J.; Miedziak, Peter J.; Brett, Gemma L.; Edwards, Jennifer K.; Hutchings, Graham J. (21 November 2014). "Oxidation of Benzyl Alcohol using in Situ Generated Hydrogen Peroxide". Organic Process Research & Development. 18 (11): 1455–1460. doi:10.1021/op500195e. ISSN 1083-6160.
22. ^ a b c d Maki, Takao; Takeda, Kazuo (2000). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555..
23. ^ A D Warth (1 December 1991). "Mechanism of action of benzoic acid on Zygosaccharomyces bailii: effects on glycolytic metabolite levels, energy production, and intracellular pH". Appl Environ Microbiol. 57 (12): 3410–4. Bibcode:1991ApEnM..57.3410W. doi:10.1128/AEM.57.12.3410-3414.1991. PMC 183988. PMID 1785916.
24. ^ Pastrorova I, de Koster CG, Boom JJ (1997). "Analytic Study of Free and Ester Bound Benzoic and Cinnamic Acids of Gum Benzoin Resins by GC-MS HPLC-frit FAB-MS". Phytochem Anal. 8 (2): 63–73. doi:10.1002/(SICI)1099-1565(199703)8:2<63::AID-PCA337>3.0.CO;2-Y.
25. ^ GSFA Online Food Additive Group Details: Benzoates (2006) Archived 26 September 2007 at the Wayback Machine
26. ^ EUROPEAN PARLIAMENT AND COUNCIL DIRECTIVE No 95/2/EC of 20 February 1995 on food additives other than colours and sweeteners (Consleg-versions do not contain the latest changes in a law) Archived 19 April 2003 at the Wayback Machine
27. ^ "Indications of the possible formation of benzene from benzoic acid in foods, BfR Expert Opinion No. 013/2006" (PDF). German Federal Institute for Risk Assessment. 1 December 2005. Archived (PDF) from the original on 26 April 2006. Retrieved 30 March 2022.
28. ^ "Whitfield Ointment". Archived from the original on 9 October 2007. Retrieved 15 October 2007.
29. ^ Charles Owens Wilson; Ole Gisvold; John H. Block (2004). Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical. Lippincott Williams & Wilkins. pp. 234. ISBN 978-0-7817-3481-3.
30. ^ Lillard, Benjamin (1919). "Troches of Benzoic Acid". Practical Druggist and Pharmaceutical Review of Reviews.
31. ^ Experiment 2: Using Bomb Calorimetry to Determine the Resonance Energy of Benzene Archived 9 March 2012 at the Wayback Machine
32. ^ a b c "Concise International Chemical Assessment Document 26: BENZOIC ACID AND SODIUM BENZOATE".
33. ^ Tomokuni K, Ogata M (1972). "Direct Colorimetric Determination of Hippuric Acid in Urine". Clin Chem. 18 (4): 349–351. doi:10.1093/clinchem/18.4.349. PMID 5012256.
34. ^ Vogt, T. (2010). "Phenylpropanoid Biosynthesis". Molecular Plant. 3: 2–20. doi:10.1093/mp/ssp106. PMID 20035037.
35. ^ Juteau, Pierre; Valérie Côté; Marie-France Duckett; Réjean Beaudet; François Lépine; Richard Villemur; Jean-Guy Bisaillon (January 2005). "Cryptanaerobacter phenolicus gen. nov., sp. nov., an anaerobe that transforms phenol into benzoate via 4-hydroxybenzoate". International Journal of Systematic and Evolutionary Microbiology. 55 (1): 245–250. doi:10.1099/ijs.0.02914-0. PMID 15653882.
36. ^ Brewster, R. Q.; Williams, B.; Phillips, R. (1955). "3,5-Dinitrobenzoic Acid". Organic Syntheses.; Collective Volume, vol. 3, p. 337
37. ^ Cosmetic Ingredient Review Expert Panel Bindu Nair (2001). "Final Report on the Safety Assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate". Int J Tox. 20 (Suppl. 3): 23–50. doi:10.1080/10915810152630729. PMID 11766131. S2CID 13639993.
38. ^ "butyrate-CoA ligase". BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014. Substrate/Product
39. ^ "glycine N-acyltransferase". BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014. Substrate/Product
40. ^ Krebs HA, Wiggins D, Stubbs M (1983). "Studies on the mechanism of the antifungal action of benzoate". Biochem J. 214 (3): 657–663. doi:10.1042/bj2140657. PMC 1152300. PMID 6226283.
41. ^ Bedford PG, Clarke EG (1972). "Experimental benzoic acid poisoning in the cat". Vet Rec. 90 (3): 53–58. doi:10.1136/vr.90.3.53. PMID 4672555. S2CID 2553612.
42. ^ Chen, Jian; Y.L. Kao (18 January 2010). "Nearly 30% dried, pickled foods fail safety inspections". The China Post.

## External links[edit]

Wikimedia Commons has media related to Benzoic acid.

* International Chemical Safety Card 0103
* SIDS Initial Assessment Report for Benzoic Acid from the Organisation for Economic Co-operation and Development (OECD)
* ChemicalLand

* v
* t
* e

Local anesthetics (primarily sodium channel blockers) (N01B)

Esters by acid|

| Aminobenzoic|

* Benzocaine
* Butacaine
* Butamben
* Chloroprocaine
* Dimethocaine
* Lucaine
* Meprylcaine
* Metabutethamine
* Metabutoxycaine
* Nitracaine
* Orthocaine
* Propoxycaine
* Procaine (Novocaine)
* Proxymetacaine
* Risocaine
* Tetracaine

|

Benzoic|

* Amylocaine
* Cocaine
* Cyclomethycaine
* α-Eucaine
* β-Eucaine
* Hexylcaine
* Isobucaine
* Piperocaine

ArCO2- (not para-amino or Ph)|

* Amoproxan (3,4,5-Trimethoxybenzoyl)
* 3-(p-Fluorobenzoyloxy)tropane

Amides|

* Articaine
* Bupivacaine#/Levobupivacaine/Ropivacaine
* Butanilicaine
* Carticaine
* Cinchocaine (Dibucaine)
* Etidocaine
* Lidocaine#
* Mepivacaine
* Prilocaine
* Trimecaine

Combinations|

* Anesthetic/vasoconstrictor
* Bupivacaine/meloxicam
* Lidocaine/prilocaine
* TAC
* Iontocaine

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

* v
* t
* e

Ectoparasiticides / arthropod (P03A)

Insecticide/pediculicide|

| Chlorine-containing products|

* Lindane

|

Chloride channel|

* Ivermectin

Organophosphate|

* Malathion

Acaricide/miticide/scabicide|

| Pyrethrines|

* Permethrin#
* Pyrethrum
* Phenothrin
* Bioallethrin

|

Chloride channel|

* Ivermectin

Sulfur-containing products|

* Disulfiram
* Dixanthogen
* Mesulfen
* Thiram

Chlorine-containing products|

* Lindane

Benzoate|

* Benzyl benzoate#

Organophosphate|

* Malathion

Other/ungrouped|

* Dimethicone
* Quassia
* toluidine (Crotamiton)

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

* v
* t
* e

Consumer food safety

Adulterants, food contaminants|

* 3-MCPD
* Aldicarb
* Antibiotic use in livestock
* Cyanide
* Formaldehyde
* HGH controversies
* Lead poisoning
* Melamine
* Mercury in fish
* Sudan I

Food additives|

* Flavorings
* Monosodium glutamate (MSG)
* Salt
* Sugar
* High-fructose corn syrup

Intestinal parasites and parasitic disease|

* Amoebiasis
* Anisakiasis
* Cryptosporidiosis
* Cyclosporiasis
* Diphyllobothriasis
* Enterobiasis
* Fasciolopsiasis
* Fasciolosis
* Giardiasis
* Gnathostomiasis
* Paragonimiasis
* Toxocariasis
* Toxoplasmosis
* Trichinosis
* Trichuriasis

Microorganisms|

* Botulism
* Campylobacter jejuni
* Clostridium perfringens
* Cronobacter
* Enterovirus
* Escherichia coli O104:H4
* Escherichia coli O157:H7
* Hepatitis A
* Hepatitis E
* Listeria
* Norovirus
* Rotavirus
* Salmonella
* Vibrio cholerae

Pesticides|

* Chlorpyrifos
* DDT
* Lindane
* Malathion
* Methamidophos

Preservatives|

* Benzoic acid
* Ethylenediaminetetraacetic acid (EDTA)
* Sodium benzoate

Sugar substitutes|

* Acesulfame potassium
* Aspartame
* controversy
* Saccharin
* Sodium cyclamate
* Sorbitol
* Sucralose

Toxins, poisons, environment pollution|

* Aflatoxin
* Arsenic contamination of groundwater
* Benzene in soft drinks
* Bisphenol A
* Dieldrin
* Diethylstilbestrol
* Dioxin
* Mycotoxins
* Nonylphenol
* Shellfish poisoning

Food processing|

* 4-Hydroxynonenal
* Acid-hydrolyzed vegetable protein
* Acrylamide
* Creutzfeldt–Jakob disease
* Food additives
* Food irradiation
* Heterocyclic amines
* Modified starch
* Nitrosamines
* Polycyclic aromatic hydrocarbon
* Shortening
* Trans fat
* Water fluoridation controversy

Food contamination incidents|

* Devon colic
* Swill milk scandal
* Esing Bakery incident
* 1858 Bradford sweets poisoning
* 1900 English beer poisoning
* Morinaga Milk arsenic poisoning incident
* Minamata disease
* 1971 Iraq poison grain disaster
* Toxic oil syndrome
* 1985 Austrian diethylene glycol wine scandal
* United Kingdom BSE outbreak
* 1993 Jack in the Box E. coli outbreak
* 1996 Odwalla E. coli outbreak
* 2006 North American E. coli outbreaks
* ICA meat repackaging controversy
* 2008 Canada listeriosis outbreak
* 2008 Chinese milk scandal
* 2008 Irish pork crisis
* 2008 United States salmonellosis outbreak
* 2011 Germany E. coli outbreak
* 2011 United States listeriosis outbreak
* 2013 Bihar school meal poisoning incident
* 2013 horse meat scandal
* 2015 Mozambique funeral beer poisoning
* 2017 Brazil Operation Weak Meat
* 2017–2018 South African listeriosis outbreak
* 2018 Australian rockmelon listeriosis outbreak
* 2018 Australian strawberry contamination
* Food safety incidents in China
* Food safety incidents in Taiwan
* Foodborne illness
* outbreaks
* death toll
* United States

Regulation, standards, watchdogs|

* Acceptable daily intake
* E number
* Food labeling regulations
* Food libel laws
* Food safety in Australia
* International Food Safety Network
* ISO 22000
* Nutrition facts label
* Organic certification
* Quality Assurance International
* United Kingdom food information regulations

Institutions|

* Centre for Food Safety (Hong Kong)
* European Food Safety Authority
* Food and Drug Administration
* Food Information and Control Agency (Spain)
* Food Standards Agency (United Kingdom)
* Institute for Food Safety and Health
* International Food Safety Network
* Ministry of Food and Drug Safety (South Korea)
* Spanish Agency for Food Safety and Nutrition

Related topics|

* Curing (food preservation)
* Food and drink prohibitions
* Food marketing
* Food politics
* Food preservation
* Food quality
* Genetically modified food
* Conspiracy theories

* Food portal Drink portal
* Category
* Commons
* Cookbook
* WikiProject

Authority control: National libraries |

* Germany
* Israel
* United States

|

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H318]: H318: Causes serious eye damage
*[H335]: H335: May cause respiratory irritation
*[P261]: P261: Avoid breathing dust/fume/gas/mist/vapours/spray.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P305+P351+P338]: P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template