:Sodium benzoate

Sodium benzoate is commonly produced by the neutralization of sodium hydroxide (NaOH) with benzoic acid (C₆H₅COOH),{{cite web|title=International Programme on Chemical Safety|url=https://inchem.org/documents/cicads/cicads/cicad26.htm#SectionNumber:4.1|access-date=2022-02-09|publisher=Inchem.org}} which is itself produced commercially by partial oxidation of toluene with oxygen.

Sodium benzoate can be decarboxylated with strong base and heat, yielding benzene:{{cite book|title= Introductory Organic Chemistry with Certain Chapters of Biochemistry|last1=Wertheim|first1=Edgar|year=1942|publisher=The Blakistan Company|url=https://archive.org/details/introductoryorga00wert/mode/1up|page=236}}

:{{chem2 | C6H5COONa + NaOH -> C6H6 + Na2CO3 }}

Sodium benzoate is not a naturally occurring substance. However many foods are natural sources of benzoic acid, its salts, and its esters.{{cite journal |last1=del Olmo |first1=Ana |last2=Calzada |first2=Javier |last3=Nuñez |first3=Manuel |title=Benzoic acid and its derivatives as naturally occurring compounds in foods and as additives: Uses, exposure, and controversy|journal=Critical Reviews in Food Science and Nutrition|date=20 November 2015 |volume=57 |issue=14 |pages=3084–3103 |doi=10.1080/10408398.2015.1087964|pmid=26587821 |s2cid=205692543 }} 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|date=February 2022}}

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.{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/Sodium-benzoate | title = Sodium benzoate | work = PubChem}} National Library of Medicine

{{cite web |url=https://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20(General%20Monographs-%20R)/ROBITUSSIN.html |title=Robitussin (Guaifenesin) |publisher=Rxmed.com |access-date=2013-01-14}} 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.{{cite web |url=https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=184.1733 |archive-url=https://web.archive.org/web/20030510182037/http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?FR=184.1733 |url-status=dead |archive-date=10 May 2003 |title=Code of Federal Regulations Title 21 |website=www.accessdata.fda.gov}} Sodium benzoate is also allowed as an animal food additive at up to 0.1%, per the Association of American Feed Control Officials.{{cite journal | author=AAFCO | title=Official Publication | year=2004 | page=262}}

Sodium benzoate has been replaced by potassium sorbate in the majority of soft drinks in the United Kingdom.{{cite journal |last=Saltmarsh |first=Mike |date=2015-03-15 |title=Recent trends in the use of food additives in the United Kingdom |journal=Journal of the Science of Food and Agriculture |volume=95 |issue=4 |pages=649–652 |doi=10.1002/jsfa.6715 |issn=1097-0010 |pmid=24789520 |bibcode=2015JSFA...95..649S |quote=... the preservative used in the study, sodium benzoate, has been replaced by potassium sorbate in the majority of soft drinks.}}

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.{{cite journal | pmid = 22642880 | year = 2012 | last1 = Häberle | first1 = J | last2 = Boddaert | first2 = N | last3 = Burlina | first3 = A | last4 = Chakrapani | first4 = A | last5 = Dixon | first5 = M | last6 = Huemer | first6 = M | last7 = Karall | first7 = D | last8 = Martinelli | first8 = D | last9 = Crespo | first9 = PS | last10 = Santer | first10 = R | last11 = Servais | first11 = A | last12 = Valayannopoulos | first12 = V | last13 = Lindner | first13 = M | last14 = Rubio | first14 = V | last15 = Dionisi-Vici | first15 = C | title = Suggested guidelines for the diagnosis and management of urea cycle disorders | volume = 7 | page = 32 | doi = 10.1186/1750-1172-7-32 | pmc = 3488504 | journal = Orphanet Journal of Rare Diseases | doi-access = free }}{{cite journal | pmid = 15050980 | year = 2004 | last1 = Wilcken | first1 = B | title = Problems in the management of urea cycle disorders | volume = 81 | pages = S86–91 | doi = 10.1016/j.ymgme.2003.10.016 | journal = Molecular Genetics and Metabolism| issue = Suppl 1 }} 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.[https://archpsyc.jamanetwork.com/article.aspx?articleID=1746121 Add-on Treatment of Benzoate for Schizophrenia A Randomized, Double-blind, Placebo-Controlled Trial of d-Amino Acid Oxidase Inhibitor] December 2013{{cite web|url=https://books.google.com/books?id=BKwHAAAAIAAJ&q=benzoic+acid+schizophrenia|title=Digest of Neurology and Psychiatry|date=16 April 2018|publisher=Institute of Living.|via=Google Books}}[https://books.google.com/books?id=oYgrAAAAMAAJ&dq=benzoic+acid+schizophrenia&pg=PA438 Mental Health Research Institute Staff Publications], University of Michigan. Mental Health Research Institute Total Positive and Negative Syndrome Scale scores dropped by 21% compared to placebo.

Sodium benzoate, along with phenylbutyrate, is used to treat hyperammonemia.{{cite web|url=https://www.rush.edu/news/press-releases/cinnamon-may-help-halt-parkinsons-disease-progression|title=Cinnamon May Help Halt Parkinson's Disease Progression - News Releases - Rush University Medical Center}}{{cite book|url=https://livertox.nih.gov/PhenylbutyrateSodiumBenzoate.htm|title=PHENYLBUTYRATE, SODIUM BENZOATE|publisher=National Institute of Diabetes and Digestive and Kidney Diseases|year=2012|pmid=31643176 }}

Sodium benzoate, along with caffeine, is used to treat postdural puncture headache, respiratory depression associated with overdosage of narcotics,{{cite journal| pmid=9952095 | volume=24 | title=Intravenous administration of caffeine sodium benzoate for postdural puncture headache | year=1999 | journal=Reg Anesth Pain Med | pages=51–4 | last1 = Yücel | first1 = A | last2 = Ozyalçin | first2 = S | last3 = Talu | first3 = GK | last4 = Yücel | first4 = EC | last5 = Erdine | first5 = S | issue=1 | doi = 10.1097/00115550-199924010-00010}}[https://www.mayoclinic.org/drg-20075607?p=1 mayoclinic.org, Caffeine And Sodium Benzoate (Injection Route)] and with ergotamine to treat vascular headache.[https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32140 ebi.ac.uk, CHEBI:32140 - sodium caffeine benzoate]

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.{{Cite journal |last=Öztap |first=Selçuk |title=The pyrotechnic whistle and its applications |url=http://www.freepyroinfo.com/Pyrotechnic/Pyrotechnic_Articles/Whistles_Pyrotechnica_Xi.pdf |journal=Pyrotechnica |volume=11 |pages=46–54}}{{Cite journal |last1=Verbovytskyy |first1=Yuriy |last2=Juknelevicius |first2=Dominykas |date=2023 |title=Pyrotechnic whistles: An overview |url=https://onlinelibrary.wiley.com/doi/10.1002/prep.202300044 |journal=Propellants, Explosives, Pyrotechnics |volume=48 |issue=6 |pages=e202300044 |doi=10.1002/prep.202300044 |issn=0721-3115|url-access=subscription }}

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,{{cite journal |author=Krebs H. A. |author2=Wiggins D. |author3=Stubbs M. |author4=Sols A. |author5=Bedoya F. |title=Studies on the mechanism of the antifungal action of benzoate |journal= Biochemical Journal|volume=218 |issue=3 |pages=657–663 |date=September 1983 |pmid=6226283 |pmc=1152300 |doi=10.1042/bj2140657 }} which inhibits the growth and survival of microorganisms that cause food spoilage.

File:Benzoateofsoda.jpg

In the United States, sodium benzoate is designated as generally recognized as safe (GRAS) by the Food and Drug Administration.{{cite web|url=https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?CFRPart=184|archive-url=https://web.archive.org/web/20030507070953/http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?CFRPart=184|url-status=dead|archive-date=7 May 2003|title=CFR - Code of Federal Regulations Title 21|website=www.accessdata.fda.gov}} The International Programme on Chemical Safety found no adverse effects in rats at doses of 647–825 mg/kg of body weight per day.{{cite web|url=https://www.inchem.org/documents/cicads/cicads/cicad26.htm |title=Concise International Chemical Assessment Document 26: Benzoic acid and sodium benzoate |publisher=Inchem.org |access-date=2013-01-14}}{{cite journal | author= Cosmetic Ingredient Review Expert Panel Bindu Nair | title= Final Report on the Safety Assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate| journal=Int J Tox | year=2001 |volume=20 |issue=Suppl 3 | pages=23–50 | doi= 10.1080/10915810152630729 | pmid=11766131| s2cid= 13639993}}

Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice.{{cite journal |vauthors=Bedford PG, Clarke EG |title=Experimental benzoic acid poisoning in the cat |journal=Vet. Rec. |volume=90 |issue=3 |pages=53–8 |date=January 1972 |pmid=4672555 |doi=10.1136/vr.90.3.53|doi-broken-date=1 November 2024 |s2cid=2553612 }}

The human body rapidly clears sodium benzoate by combining it with glycine to form hippuric acid which is then excreted. The metabolic pathway for this begins with the conversion of benzoate by butyrate-CoA ligase into an intermediate product, benzoyl-CoA,{{cite web|title=butyrate-CoA ligase|url=https://www.brenda-enzymes.org/php/result_flat.php4?ecno=6.2.1.2&Suchword=&organism%5B%5D=Homo+sapiens&show_tm=0|work=BRENDA|publisher=Technische Universität Braunschweig.|access-date=7 May 2014}} Substrate/Product which is then metabolized by glycine N-acyltransferase into hippuric acid.{{cite web|title=glycine N-acyltransferase|url=https://www.brenda-enzymes.org/php/result_flat.php4?ecno=2.3.1.13&Suchword=&organism%5B%5D=Homo+sapiens&show_tm=0|work=BRENDA|publisher=Technische Universität Braunschweig.|access-date=7 May 2014}} Substrate/Product

{{Main|Benzene in soft drinks}}

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.{{cite web|url=https://www.fda.gov/food/foodborneillnesscontaminants/chemicalcontaminants/ucm055815.htm |title=Data on Benzene in Soft Drinks and Other Beverages | publisher = United States Food and Drug Administration |date=16 May 2007 |access-date=7 November 2013 | archive-url = https://wayback.archive-it.org/7993/20170112012123/https://www.fda.gov/Food/FoodborneIllnessContaminants/ChemicalContaminants/ucm055815.htm | archive-date = 12 January 2017}} Most of the beverages that tested above the limit have been reformulated and subsequently tested below the safety limit. Heat, light and shelf life can increase the rate at which benzene is formed. Hot peppers naturally contain vitamin C ("nearly as much as in one orange"{{cite web | url=https://www.ahchealthenews.com/2016/11/04/hot-sauce-good-health/ | title=Is hot sauce good for your health? | date=4 November 2016 }}) 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.[https://www.food.gov.uk/news/pressreleases/2007/sep/colours Food Standards Agency issues revised advice on certain artificial colours] {{Webarchive|url=https://web.archive.org/web/20111206130638/http://www.food.gov.uk/news/pressreleases/2007/sep/colours |date=6 December 2011 }} 6 September 2007[https://www.myomancy.com/2007/09/food-colorings-and-hyperactivity Food Colorings and Hyperactivity] {{Webarchive|url=https://web.archive.org/web/20230520211829/http://www.myomancy.com/2007/09/food-colorings-and-hyperactivity |date=20 May 2023 }} "Myomancy" 7 September 2007[https://www.food.gov.uk/news/newsarchive/2007/sep/foodcolours Agency revises advice on certain artificial colours] {{Webarchive|url=https://web.archive.org/web/20120412115355/http://www.food.gov.uk/news/newsarchive/2007/sep/foodcolours |date=12 April 2012 }}, Food Standards Agency, 11 September 2007 The Food Standards Agency concluded that the observed increases in hyperactive behavior, if real, were more likely to be linked to the artificial colors than to sodium benzoate. The report's author, Jim Stevenson from Southampton University, 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."

• British Pharmacopoeia{{cite web| last =Therapeutic Goods Administration| author-link =Therapeutic Goods Administration| title =Chemical Substances| url =https://www.tga.gov.au/docs/pdf/aan/aanchem.pdf| access-date =17 July 2009| archive-url =https://web.archive.org/web/20090615083950/https://www.tga.gov.au//docs/pdf/aan/aanchem.pdf| archive-date =15 June 2009}}{{cite web| last =British Pharmacopoeia Commission Secretariat| title =Index (BP)| url =https://www.pharmacopoeia.co.uk/pdf/2009_index.pdf| access-date =2 March 2010| archive-url =https://web.archive.org/web/20090411071437/https://www.pharmacopoeia.co.uk/pdf/2009_index.pdf| archive-date =11 April 2009}}
• European Pharmacopoeia
• Food Chemicals Codex{{cite web

| last = Sigma Aldrich

| author-link = Sigma Aldrich

| title = Sodium benzoate

| url = https://www.sigmaaldrich.com/catalog/Lookup.do?N5=CAS%20No.&N3=mode+matchpartialmax&N4=532-32-1&D7=0&D10=532-32-1&N25=0&N1=S_ID&ST=RS&F=PR

| access-date= 17 July 2009 }}

• Japanese Pharmacopoeia{{cite web

| title = Japanese Pharmacopoeia 15th Edition

| url = https://jpdb.nihs.go.jp/jp15e/

| access-date = 2 March 2010

| archive-date = 28 March 2010

| archive-url = https://web.archive.org/web/20100328112853/http://jpdb.nihs.go.jp/jp15e/

}}

• United States Pharmacopeia{{cite web

| last = The United States Pharmacopeial Convention

| author-link = The United States Pharmacopeial Convention

| title = Revisions to USP 29–NF 24

| url = https://www.usp.org/USPNF/revisions/usp29nf24firstSupplement04.html

| access-date = 17 July 2009

| archive-date = 4 April 2009

| archive-url = https://web.archive.org/web/20090404064345/http://www.usp.org/USPNF/revisions/usp29nf24firstSupplement04.html

}}

• Acceptable daily intake
• List of investigational antipsychotics
• Potassium benzoate

{{Reflist|30em}}

{{Commons category|Sodium benzoate}}

• [https://www.inchem.org/documents/cicads/cicads/cicad26.htm#SubSectionNumber:11.1.1 International Programme on Chemical Safety - Benzoic Acid and Sodium Benzoate report]
• {{cite journal |vauthors=Kubota K, Ishizaki T |title=Dose-dependent pharmacokinetics of benzoic acid following oral administration of sodium benzoate to humans |journal=Eur. J. Clin. Pharmacol. |volume=41 |issue=4 |pages=363–8 |year=1991 |pmid=1804654 |quote=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 |doi=10.1007/BF00314969|s2cid=8196430 }}
• [https://msds.chem.ox.ac.uk/SO/sodium_benzoate.html Safety data for sodium benzoate] {{Webarchive|url=https://web.archive.org/web/20111211073854/https://msds.chem.ox.ac.uk/SO/sodium_benzoate.html |date=11 December 2011 }}

{{Sodium compounds}}

{{Other alimentary tract and metabolism products}}

{{Diagnostic agents}}

{{Consumer Food Safety}}

{{DEFAULTSORT:Sodium Benzoate}}

Category:Antiseptics

Category:Benzoates

Category:Preservatives

Category:Organic sodium salts

Category:E-number additives

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