Sodium benzoate 901291 225486076 2008-07-13T23:08:40Z Avnjay 4433881 Reverted edits by [[Special:Contributions/71.162.161.198|71.162.161.198]] to last version by Danhm (using [[WP:HG|Huggle]]) {{Chembox new | Name = '''Sodium benzoate''' | ImageFile = Sodium-benzoate-skeletal.png | ImageSize = 100px | ImageName = Sodium benzoate | IUPACName = Sodium benzoate | OtherNames = E211, benzoate of soda | Section1 = {{Chembox Identifiers | CASNo = 532-32-1 | SMILES = O=C([O-])C1=CC=CC=C1.[Na+] }} | Section2 = {{Chembox Properties | Formula = Na</sub>C<sub>6</sub>H<sub>5</sub>C</sub>O<sub>2 | MolarMass = 144.11 g mol<sup>−1</sup> | Density = 1.44 g cm<sup>−3</sup> | MeltingPt = >300 °C | BoilingPt = N/A }} }} '''Sodium benzoate''' ('''E211'''), also called '''benzoate of soda''', has [[chemical formula]] Na</sub>C<sub>6</sub>H<sub>5</sub>C</sub>O<sub>2</sub>. It is the sodium salt of [[benzoic acid]] and exists in this form when dissolved in [[water]]. It can be produced by reacting [[sodium hydroxide]] with [[benzoic acid]]. ==Uses== Sodium benzoate is a [[food preservation|preservative]]. It is [[Bacteriostatic agent|bacteriostatic]] and [[Fungistat|fungistatic]] under acidic conditions. It is used most prevalently in acidic foods such as salad dressings ([[vinegar]]), carbonated drinks ([[carbonic acid]]), jams and fruit juices ([[citric acid]]), [[pickling| pickles]] ([[vinegar]]), and [[Chinese food]] sauces (soy, mustard, and duck).{{Fact|date=October 2007}} It is also found in alcohol-based [[mouthwash]] and silver polish. Sodium benzoate is declared on a product label as 'sodium benzoate' or E211. The taste of sodium benzoate cannot be detected by around 25 percent of the population, but for those who can taste the chemical, it tends to be perceived as sweet, sour, salty, or sometimes bitter. It is also used in [[fireworks]] as a fuel in [[whistle mix]], a powder which imparts a whistling noise when compressed into a tube and ignited. It is found naturally in [[cranberries]], [[prune (fruit)|prunes]], greengage [[plums]], [[cinnamon]], ripe [[cloves]], and [[apples]]. Concentration as a preservative is limited by the FDA in the U.S. to 0.1% by weight though organically-grown cranberries and prunes can conceivably contain levels exceeding this limit.{{Fact|date=June 2008}} The International Programme on Chemical Safety found no adverse effects in humans at doses of 647-825 mg/kg of body weight per day.<ref>[http://www.inchem.org/documents/cicads/cicads/cicad26.htm Concise International Chemical Assessment Document 26: BENZOIC ACID AND SODIUM BENZOATE]</ref><ref>{{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 | issue= 20 (Suppl. 3) | pages=23–50 }}</ref> [[Cats]] have a significantly lower tolerance against benzoic acid and its [[salts]] than [[rats]] and [[mouse|mice]].<ref>{{cite journal| author= Bedford PG, Clarke EG |title=Experimental benzoic acid poisoning in the cat|journal=Vet Rec |year=1972|pages=53–58|issue=90}} PMID</ref> Sodium benzoate is, however, allowed as an animal food additive at up to 0.1%, according to AFCO's official publication.<ref>{{cite journal | author=AFCO | title=Official Publication | year=2004 | pages=262}}</ref> ==Mechanism of food preservation== The mechanism starts with the absorption of benzoic acid into the cell. If the intracellular [[pH]] changes to 5 or lower, the [[fermentation (food)|anaerobic fermentation]] of [[glucose]] through [[phosphofructokinase]] is decreased by 95%.<ref>{{cite journal | author=Krebs HA | coauthors = Wiggins D, Stubbs M | title= Studies on the mechanism of the antifungal action of benzoate | journal= Biochem J | year=1983 | issue=214 | pages=657–663 | url= http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1152300 | pmid= 6226283 }}</ref> ==Safety and health== {{main|benzene in soft drinks}} In combination with [[ascorbic acid]] (vitamin C, E300), sodium benzoate and [[potassium benzoate]] may form [[benzene]]<ref>FDA, 2006. "Data on Benzene in Soft Drinks and Other Beverages, " United States Food and Drug Administration. Accessed June 2nd at: http://www.cfsan.fda.gov/~dms/benzdata.html</ref>, a known [[carcinogen]]. Heat, light and shelf life can affect the rate at which benzene is formed. Professor Peter Piper of the University of Sheffield claims that sodium benzoate by itself can damage and inactivate vital parts of DNA in a cell's [[mitochondrion|mitochondria]]. "The mitochondria consumes the oxygen to give you energy and if you damage it - as happens in a number of diseased states - then the cell starts to malfunction very seriously. And there is a whole array of diseases that are now being tied to damage to this DNA - Parkinson's and quite a lot of neuro-degenerative diseases, but above all the whole process of aging."<ref>Martin Hickman [http://news.independent.co.uk/health/article2586652.ece Caution: Some soft drinks may seriously harm your health] ''The Independent on Sunday'' 27 May 2007</ref><ref>Martin Hickman [http://news.independent.co.uk/health/article2586653.ece E211 Revealed: Evidence highlights new fear over drinks additive] ''The Independent on Sunday'' 27 May 2007</ref><ref> [http://comment.independent.co.uk/leading_articles/article2586569.ece Leading article: Children deserve our doubts] ''The Independent on Sunday'' 27 May 2007</ref><ref>Chris Mercer [http://www.beveragedaily.com/news/ng.asp?id=76895 Fresh health fears hit benzoate in soft drinks] BeverageDaily 29 May 2007</ref><ref>Piper PW [http://www.ncbi.nlm.nih.gov/sites/entrez?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=10641714 Yeast superoxide dismutase mutants reveal a pro-oxidant action of weak organic acid food preservatives] ''Free Radic Biol Med'' 1999 Dec;27(11-12):1219-27</ref> ===ADHD=== Research published in 2007 for the UK's [[Food Standards Agency]] suggests that sodium benzoate (E211) is linked to [[hyperactive]] behaviour and decreased intelligence in children. According to the report, a high consumption of sodium benzoate is associated with a reduction in [[IQ]] of close to 5.5 points. <ref>[http://www.telegraph.co.uk/news/main.jhtml?xml=/news/2008/04/07/nfood107.xml Graham Tibbetts. "Artificial colourings as harmful as leaded petrol for children", ''Telegraph'', 7 April 2008]</ref> On [[6 September]] 2007, the British [[Food Standards Agency]] issued revised advice on certain artificial food additives, including sodium benzoate (E211)<ref name="Food Standards Agency issues revised advice on certain artificial colours">[http://www.food.gov.uk/news/pressreleases/2007/sep/colours Food Standards Agency issues revised advice on certain artificial colours] [[6 September]] 2007</ref><ref name="myomancy-7-9-7">[http://www.myomancy.com/2007/09/food-colorings-and-hyperactivity Food Colorings and Hyperactivity] "Myomancy" [[7 September]] 2007</ref><ref name="(Food Standards) Agency revises advice on certain artificial colours">[http://www.food.gov.uk/news/newsarchive/2007/sep/foodcolours Agency revises advice on certain artificial colours] Food Standards Agency [[11 September]] 2007</ref>. Professor Jim Stevenson from Southampton University, and author of the report, said: "This has been a major study investigating an important area of research. 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. "However, parents should not think that simply taking these additives out of food will prevent hyperactive disorders. We know that many other influences are at work but this at least is one a child can avoid." Two mixtures of additives were tested in the research: Mix A: * Sunset yellow ([[E110]]) * Tartrazine ([[E102]]) * Carmoisine ([[E122]]) * Ponceau 4R ([[E124]]) * Sodium benzoate (E211) Mix B: * Sunset yellow ([[E110]]) * Quinoline yellow ([[E104]]) * Carmoisine ([[E122]]) * Allura red ([[E129]]) * Sodium benzoate (E211) Sodium benzoate was included in both mixes, but the effects observed were not consistent. The Food Standards Agency therefore considers that, if real, the observed increases in hyperactive behaviour were more likely to be linked to one or more of the specific colours tested. On [[10 April]] 2008, the Foods Standard Agency called for a voluntary removal of the colours (but not sodium benzoate) by 2009.<ref>BBC [http://news.bbc.co.uk/1/hi/health/7340426.stm Europe-wide food colour ban call] [[10 April]] 2008</ref> In addition, it recommended that there should be action to phase them out in food and drink in the European Union (EU) over a specified period.<ref>FSA [http://www.food.gov.uk/news/newsarchive/2008/apr/coloursadvice Board discusses colours advice] [[10 April]] 2008</ref> In response to consumer insistence on a more natural product and E211's links to DNA damage and ADHD, the Coca Cola Company is in the process of phasing Sodium Benzoate out of Diet Coke. The company has stated that it plans to remove E211 from its other products - including [[Sprite]], [[Dr Pepper]], and [[Oasis]] - as soon as a satisfactory alternative is discovered.<ref>The Daily Mail [http://www.dailymail.co.uk/news/article-1021820/Diet-Coke-drop-additive-DNA-damage-fear.html DNA Damage Fear] [[24 May]] 2008</ref> ===Other Health Effects=== People who suffer from asthma, or who have recurrent [[urticaria]], may be sensitive to sodium benzoate and have allergic reactions. Sodium benzoate and [[tartrazine]] (E102) exacerbate the condition in between 10 and 40 percent of patients with chronic urticaria, and possibly a higher proportion still of aspirin sensitive individuals.<ref>E for additives, Maurice Hanssen with Jill Marsden, Thorsons 1987</ref> ==References== {{reflist}} ==External links== * [http://www.tradezone.com/tradesites/sodiumbenzoate.html Sodium Benzoate Material Safety Data Sheet] * [http://www.inchem.org/documents/cicads/cicads/cicad26.htm#SubSectionNumber:11.1.1 International Programme on Chemical Safety - Benzoic Acid and Sodium Benzoate report] * [http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=1804654&dopt=Abstract pharmokinetics of the high orally administered doses used to treat hyperammonaemia] * Andersen A. [http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=pubmed&list_uids=16835129&dopt=Books Final report on the safety assessment of benzaldehyde] ''Int J Toxicol'' 2006;25 Suppl 1:11-27. * [http://www.time.com/time/health/article/0,8599,1659835,00.html?imw=Y Sodium Benzoate A Cause of Hyper Kids (TIME.com)] [[Category:Benzoates]] [[Category:Sodium compounds]] [[Category:Antiseptics]] [[Category:Preservatives]] [[Category:Food additives]] [[ar:بنزوات صوديوم]] [[bs:Natrijum benzoat]] [[cs:Benzoát sodný]] [[de:Natriumbenzoat]] [[es:Benzoato de sodio]] [[fr:Benzoate de sodium]] [[it:Benzoato di sodio]] [[he:סודיום בנזואט]] [[nl:Natriumbenzoaat]] [[no:Natriumbenzoat]] [[pl:Benzoesan sodu]] [[pt:Benzoato de sódio]] [[ru:Бензоат натрия]] [[fi:Natriumbentsoaatti]] [[sv:Natriumbensoat]]