Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Sodium benzoate: Difference between pages

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Use dmy dates|date=October 2020}}

| Verifiedfields = changed

| verifiedrevid = 477001450

| Name = Sodium benzoate

| ImageFile = Sodium Benzoate V.1.svg

| ImageSize = 100px

| ImageName = Sodium benzoate

| ImageCaption = [[Skeletal formula]]

| ImageFile1 = Sodium_benzoate-substance.jpg

| ImageName1 = Powder of sodium benzoate

| ImageFile2 = Sodium-benzoate-xtal-rod-micelle-b-3D-bs-17.png

| ImageCaption2 = [[Ball-and-stick model]] of part of the [[crystal structure]]

| ImageFile3 = Sodium-benzoate-xtal-rod-micelle-packing-3D-bs-17.png

| ImageCaption3 = Ball-and-stick model of packing in the crystal structure

| PIN = Sodium benzoate

| OtherNames = {{Unbulleted list|E211|benzoate of soda}}

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 113455

| SMILES = [Na+].[O-]C(=O)c1ccccc1

| PubChem = 517055

| RTECS = DH6650000

|Section2={{Chembox Properties

| Na=1 | C=7 | H=5 | O=2

| Appearance = white or colourless crystalline powder

| Odor = odorless

| Density = 1.497 g/cm³

| MeltingPtC = 410

| BoilingPt =

| Solubility = 62.65 g/100 mL (0&nbsp;°C)<br /> 62.84 g/100 mL (15&nbsp;°C)<br /> 62.87 g/100 mL (30&nbsp;°C)<br /> 74.2 g/100 mL (100&nbsp;°C)<ref name=chemister />

| SolubleOther = soluble in liquid [[ammonia]], [[pyridine]]<ref name=chemister>{{cite web|url=https://chemister.ru/Database/properties-en.php?dbid=1&id=1004|title=sodium benzoate|website=chemister.ru}}</ref>

| Solubility1 = 8.22 g/100 g (15&nbsp;°C)<br /> 7.55 g/100 g (66.2&nbsp;°C)<ref name=chemister />

| Solvent1 = methanol

| Solubility2 = 2.3 g/100 g (25&nbsp;°C)<br /> 8.3 g/100 g (78&nbsp;°C)<ref name=chemister />

| Solvent2 = ethanol

| Solubility3 = 0.818 mg/kg (25&nbsp;°C)<ref name=chemister />

| Solvent3 = 1,4-Dioxane

| Section6 = {{Chembox Pharmacology

| ATCCode_prefix = A16

| ATCCode_suffix = AX11

}}

|Section7={{Chembox Hazards

| ExternalSDS =

| GHSPictograms = {{GHS07}}<ref name="sigma">{{Sigma-Aldrich|id=w302503|name=Sodium benzoate|accessdate=2014-05-23}}</ref>

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|319}}<ref name="sigma" />

| PPhrases = {{P-phrases|305+351+338}}<ref name="sigma" />

| NFPA-H = 2

| NFPA-F = 1

| NFPA-R = 0

| NFPA-S =

| FlashPtC = 100

| AutoignitionPtC = 500

| LD50 = 4100 mg/kg (oral, rat)

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

==Production==

Sodium benzoate is commonly produced by the neutralization of [[sodium hydroxide]] (NaOH) with [[benzoic acid]] (C₆H₅COOH),<ref name="sodium benzoate">{{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}}</ref> which is itself produced commercially by [[partial oxidation]] of [[toluene]] with [[oxygen]].

== Reactions ==

Sodium benzoate can be [[Decarboxylation|decarboxylated]] with strong [[Base (chemistry)|base]] and heat, yielding [[benzene]]:<ref>{{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}}</ref>

<chem>C6H5COONa + NaOH -> C6H6 + Na2CO3</chem>

==Natural occurrence==

Many foods are natural sources of benzoic acid, its salts, and its [[ester]]s.<ref>{{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 }}</ref> [[Fruit]]s and [[vegetable]]s can be rich sources, particularly berries such as [[cranberry]] and [[bilberry]]. Other sources include [[seafood]], such as [[prawn]]s, and [[dairy product]]s.{{Citation needed|date=February 2022}}

==Uses==

===As a preservative===

Sodium benzoate can act as a food preservative. It is most widely used in acidic foods such as [[salad dressing]]s (for example [[acetic acid]] in [[vinegar]]), [[Soft drink|carbonated drinks]] ([[carbonic acid]]), [[Fruit preserves|jams]] and [[Juice|fruit juices]] ([[citric acid]]), [[pickling|pickles]] ([[acetic acid]]), [[condiment]]s, and [[frozen yogurt]] toppings. It is also used as a preservative in medicines and cosmetics.<ref>{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/Sodium-benzoate | title = Sodium benzoate | work = PubChem}} National Library of Medicine

</ref><ref>{{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}}</ref> Under these conditions it is converted into [[benzoic acid]] (E210), which is [[bacteriostatic agent|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.<ref>{{cite web |url=https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=184.1733 |title=Code of Federal Regulations Title 21 |website=www.accessdata.fda.gov}}</ref> Sodium benzoate is also allowed as an animal food additive at up to 0.1%, per the Association of American Feed Control Officials.<ref>{{cite journal | author=AAFCO | title=Official Publication | year=2004 | page=262}}</ref>

Sodium benzoate has been replaced by [[potassium sorbate]] in the majority of soft drinks in the [[United Kingdom]].<ref name=":0">{{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.}}</ref>

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

===In pharmaceuticals===

Sodium benzoate is used as a treatment for [[urea cycle disorder]]s due to its ability to bind amino acids.<ref>{{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 }}</ref><ref>{{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 }}</ref> 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]].<ref name="Add-on Treatment of Benzoate for Schizophrenia A Randomized, Double-blind, Placebo-Controlled Trial of d-Amino Acid Oxidase Inhibitor">[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</ref><ref>{{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}}</ref><ref>[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</ref> Total [[Positive and Negative Syndrome Scale]] scores dropped by 21% compared to placebo.

Sodium benzoate, along with [[Sodium phenylbutyrate|phenylbutyrate]], is used to treat [[hyperammonemia]].<ref name="rush">{{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}}</ref><ref>{{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 }}</ref>

Sodium benzoate, along with [[caffeine]], is used to treat [[postdural puncture headache]], respiratory depression associated with overdosage of [[narcotics]],<ref>{{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}}</ref><ref>[https://www.mayoclinic.org/drg-20075607?p=1 mayoclinic.org, Caffeine And Sodium Benzoate (Injection Route)]</ref> and with [[ergotamine]] to treat [[vascular headache]].<ref>[https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32140 ebi.ac.uk, CHEBI:32140 - sodium caffeine benzoate]</ref>

===Other uses===

Sodium benzoate is also used in [[fireworks]] as a fuel in [[Pyrotechnic composition|whistle mix]], a powder that emits a whistling noise when compressed into a tube and ignited.<ref>{{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}}</ref><ref>{{Cite journal |last=Verbovytskyy |first=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}}</ref>

==Mechanism of food preservation==

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

==Health and safety==

[[File:Benzoateofsoda.jpg|thumb|1909 Heinz advertisement against sodium benzoate]]

In the [[United States]], sodium benzoate is designated as [[generally recognized as safe]] (GRAS) by the [[Food and Drug Administration]].<ref>{{cite web|url=https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?CFRPart=184|title=CFR - Code of Federal Regulations Title 21|website=www.accessdata.fda.gov}}</ref> The International Programme on Chemical Safety found no adverse effects in humans at doses of 647–825&nbsp;mg/kg of body weight per day.<ref>{{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}}</ref><ref name=Tox-1>{{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}}</ref>

Cats have a significantly lower tolerance against benzoic acid and its [[salts]] than rats and mice.<ref>{{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=31 January 2024 |s2cid=2553612 }}</ref>

The human body rapidly clears sodium benzoate by combining it with [[glycine]] to form [[hippuric acid]] which is then excreted.<ref name=Tox-1 /> The metabolic pathway for this begins with the conversion of benzoate by [[butyrate-CoA ligase]] into an intermediate product, [[benzoyl-CoA]],<ref>{{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</ref> which is then metabolized by [[glycine N-acyltransferase|glycine ''N''-acyltransferase]] into hippuric acid.<ref>{{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</ref>

===Association with benzene in soft drinks & pepper sauces===

{{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 [[Parts-per notation|ppb]] [[Maximum Contaminant Level]] set by the [[Environmental Protection Agency]] for drinking water.<ref name=FDA>{{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}}</ref> Most of the beverages that tested above the limit have been reformulated and subsequently tested below the safety limit.<ref name=FDA/> 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"<ref>{{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 }}</ref>) so the observation about beverages applies to pepper sauces containing sodium benzoate, like [[Texas Pete]].

===ADHD and hyperactivity===

Research published, including in 2007 for the UK's [[Food Standards Agency]] (FSA) suggests that certain [[artificial color]]s, 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.<ref name="Food Standards Agency issues revised advice on certain artificial colours">[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</ref><ref name="myomancy-7-9-7">[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</ref><ref name="(Food Standards) Agency revises advice on certain artificial colours">[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</ref> 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.<ref name="(Food Standards) Agency revises advice on certain artificial colours"/> 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."<ref name="(Food Standards) Agency revises advice on certain artificial colours"/>

==Compendial status==

* [[British Pharmacopoeia]]<ref name=sb /><ref name=cs>{{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}}</ref><ref name=ibp>{{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}}</ref>

* [[European Pharmacopoeia]]<ref name=sb />

* [[Food Chemicals Codex]]<ref name=sb>{{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 }}</ref>

* [[Japanese Pharmacopoeia]]<ref name=jp15e>{{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/

}}</ref>

* [[United States Pharmacopeia]]<ref name=rusp>{{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

}}</ref>

==See also==

* [[Acceptable daily intake]]

* [[List of investigational antipsychotics]]

* [[Potassium benzoate]]

==References==

{{Reflist|30em}}

==External links==

{{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]]

.