Chemistry:Sodium benzoate

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Short description: Chemical compound
Sodium benzoate
Sodium benzoate
Powder of sodium benzoate
Sodium-benzoate-xtal-rod-micelle-b-3D-bs-17.png
Sodium-benzoate-xtal-rod-micelle-packing-3D-bs-17.png
Ball-and-stick model of packing in the crystal structure
Names
Preferred IUPAC name
Sodium benzoate
Other names
E211, benzoate of soda
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
RTECS number
  • DH6650000
UNII
Properties
C7H5NaO2
Molar mass 144.105 g·mol−1
Appearance white or colourless crystalline powder
Odor odorless
Density 1.497 g/cm3
Melting point 410 °C (770 °F; 683 K)
62.65 g/100 mL (0 °C)
62.84 g/100 mL (15 °C)
62.87 g/100 mL (30 °C)
74.2 g/100 mL (100 °C)[1]
Solubility soluble in liquid ammonia, pyridine[1]
Solubility in methanol 8.22 g/100 g (15 °C)
7.55 g/100 g (66.2 °C)[1]
Solubility in ethanol 2.3 g/100 g (25 °C)
8.3 g/100 g (78 °C)[1]
Solubility in 1,4-Dioxane 0.818 mg/kg (25 °C)[1]
Pharmacology
1=ATC code }} A16AX11 (WHO)
Hazards
GHS pictograms GHS07: Harmful[2]
GHS Signal word Warning
H319[2]
P305+351+338[2]
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
Flash point 100 °C (212 °F; 373 K)
500 °C (932 °F; 773 K)
Lethal dose or concentration (LD, LC):
4100 mg/kg (oral, rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references
Tracking categories (test):

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

Production

Sodium benzoate is commonly produced by the neutralization of sodium hydroxide (NaOH) with benzoic acid (C6H5COOH),[3] which is itself produced commercially by partial oxidation of toluene with oxygen.

Reactions

Sodium benzoate can be decarboxylated with strong base and heat, yielding benzene:[4]

[math]\ce{ C6H5COONa + NaOH -> C6H6 + Na2CO3 }[/math]

Natural occurrence

Many foods are natural sources of benzoic acid, its salts, and its esters.[5] 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]

Uses

As a preservative

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.[6][7] 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.[8] Sodium benzoate is also allowed as an animal food additive at up to 0.1%, per the Association of American Feed Control Officials.[9] Sodium benzoate has been replaced by potassium sorbate in the majority of soft drinks in the United Kingdom .[10]

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 disorders due to its ability to bind amino acids.[11][12] 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.[13][14][15] Total Positive and Negative Syndrome Scale scores dropped by 21% compared to placebo.

Sodium benzoate, along with phenylbutyrate, is used to treat hyperammonemia.[16][17]

Sodium benzoate, along with caffeine, is used to treat postdural puncture headache, respiratory depression associated with overdosage of narcotics,[18][19] and with ergotamine to treat vascular headache.[20]

Other uses

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.[citation needed]

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 anaerobic fermentation of glucose through phosphofructokinase decreases sharply,[21] which inhibits the growth and survival of microorganisms that cause food spoilage.

Health and safety

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.[22] The International Programme on Chemical Safety found no adverse effects in humans at doses of 647–825 mg/kg of body weight per day.[23][24]

Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice.[25]

The human body rapidly clears sodium benzoate by combining it with glycine to form hippuric acid which is then excreted.[24] The metabolic pathway for this begins with the conversion of benzoate by butyrate-CoA ligase into an intermediate product, benzoyl-CoA,[26] which is then metabolized by glycine N-acyltransferase into hippuric acid.[27]

Association with benzene in soft drinks & pepper sauces

Main page: Unsolved: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.[28] Most of the beverages that tested above the limit have been reformulated and subsequently tested below the safety limit.[28] 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"[29]) 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 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.[30][31][32] 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.[32] 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."[32]

Compendial status

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 "sodium benzoate". https://chemister.ru/Database/properties-en.php?dbid=1&id=1004. 
  2. ↑ 2.0 2.1 2.2 Sigma-Aldrich Co., Sodium benzoate. Retrieved on 2014-05-23.
  3. ↑ "International Programme on Chemical Safety". Inchem.org. https://inchem.org/documents/cicads/cicads/cicad26.htm#SectionNumber:4.1. 
  4. ↑ Wertheim, Edgar (1942). Introductory Organic Chemistry with Certain Chapters of Biochemistry. The Blakistan Company. p. 236. https://archive.org/details/introductoryorga00wert/mode/1up. 
  5. ↑ del Olmo, Ana; Calzada, Javier; Nuñez, Manuel (20 November 2015). "Benzoic acid and its derivatives as naturally occurring compounds in foods and as additives: Uses, exposure, and controversy". Critical Reviews in Food Science and Nutrition 57 (14): 3084–3103. doi:10.1080/10408398.2015.1087964. PMID 26587821. 
  6. ↑ "Sodium benzoate". PubChem. https://pubchem.ncbi.nlm.nih.gov/compound/Sodium-benzoate.  National Library of Medicine
  7. ↑ "Robitussin (Guaifenesin)". Rxmed.com. https://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20(General%20Monographs-%20R)/ROBITUSSIN.html. 
  8. ↑ "Code of Federal Regulations Title 21". https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=184.1733. 
  9. ↑ AAFCO (2004). Official Publication. p. 262. 
  10. ↑ Saltmarsh, Mike (2015-03-15). "Recent trends in the use of food additives in the United Kingdom". Journal of the Science of Food and Agriculture 95 (4): 649–652. doi:10.1002/jsfa.6715. ISSN 1097-0010. PMID 24789520. Bibcode: 2015JSFA...95..649S. "... the preservative used in the study, sodium benzoate, has been replaced by potassium sorbate in the majority of soft drinks.". 
  11. ↑ Häberle, J; Boddaert, N; Burlina, A; Chakrapani, A; Dixon, M; Huemer, M; Karall, D; Martinelli, D et al. (2012). "Suggested guidelines for the diagnosis and management of urea cycle disorders". Orphanet Journal of Rare Diseases 7: 32. doi:10.1186/1750-1172-7-32. PMID 22642880. 
  12. ↑ Wilcken, B (2004). "Problems in the management of urea cycle disorders". Molecular Genetics and Metabolism 81 (Suppl 1): S86–91. doi:10.1016/j.ymgme.2003.10.016. PMID 15050980. 
  13. ↑ Add-on Treatment of Benzoate for Schizophrenia A Randomized, Double-blind, Placebo-Controlled Trial of d-Amino Acid Oxidase Inhibitor December 2013
  14. ↑ "Digest of Neurology and Psychiatry". Institute of Living.. 16 April 2018. https://books.google.com/books?id=BKwHAAAAIAAJ&q=benzoic+acid+schizophrenia. 
  15. ↑ Mental Health Research Institute Staff Publications, University of Michigan. Mental Health Research Institute
  16. ↑ "Cinnamon May Help Halt Parkinson's Disease Progression - News Releases - Rush University Medical Center". https://www.rush.edu/news/press-releases/cinnamon-may-help-halt-parkinsons-disease-progression. 
  17. ↑ PHENYLBUTYRATE, SODIUM BENZOATE. National Institute of Diabetes and Digestive and Kidney Diseases. 2012. https://livertox.nih.gov/PhenylbutyrateSodiumBenzoate.htm. 
  18. ↑ Yücel, A; Ozyalçin, S; Talu, GK; Yücel, EC; Erdine, S (1999). "Intravenous administration of caffeine sodium benzoate for postdural puncture headache". Reg Anesth Pain Med 24 (1): 51–4. doi:10.1097/00115550-199924010-00010. PMID 9952095. 
  19. ↑ mayoclinic.org, Caffeine And Sodium Benzoate (Injection Route)
  20. ↑ ebi.ac.uk, CHEBI:32140 - sodium caffeine benzoate
  21. ↑ Krebs H. A.; Wiggins D.; Stubbs M.; Sols A.; Bedoya F. (September 1983). "Studies on the mechanism of the antifungal action of benzoate". Biochemical Journal 218 (3): 657–663. doi:10.1042/bj2140657. PMID 6226283. 
  22. ↑ "CFR - Code of Federal Regulations Title 21". https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?CFRPart=184. 
  23. ↑ "Concise International Chemical Assessment Document 26: Benzoic acid and sodium benzoate". Inchem.org. https://www.inchem.org/documents/cicads/cicads/cicad26.htm. 
  24. ↑ 24.0 24.1 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. 
  25. ↑ "Experimental benzoic acid poisoning in the cat". Vet. Rec. 90 (3): 53–8. January 1972. doi:10.1136/vr.90.3.53. PMID 4672555. 
  26. ↑ "butyrate-CoA ligase". BRENDA. Technische Universität Braunschweig.. https://www.brenda-enzymes.org/php/result_flat.php4?ecno=6.2.1.2&Suchword=&organism%5B%5D=Homo+sapiens&show_tm=0.  Substrate/Product
  27. ↑ "glycine N-acyltransferase". BRENDA. Technische Universität Braunschweig.. https://www.brenda-enzymes.org/php/result_flat.php4?ecno=2.3.1.13&Suchword=&organism%5B%5D=Homo+sapiens&show_tm=0.  Substrate/Product
  28. ↑ 28.0 28.1 "Data on Benzene in Soft Drinks and Other Beverages". United States Food and Drug Administration. 16 May 2007. https://www.fda.gov/food/foodborneillnesscontaminants/chemicalcontaminants/ucm055815.htm. 
  29. ↑ "Is hot sauce good for your health?". 4 November 2016. https://www.ahchealthenews.com/2016/11/04/hot-sauce-good-health/. 
  30. ↑ Food Standards Agency issues revised advice on certain artificial colours 6 September 2007
  31. ↑ Food Colorings and Hyperactivity "Myomancy" 7 September 2007
  32. ↑ 32.0 32.1 32.2 Agency revises advice on certain artificial colours , Food Standards Agency, 11 September 2007
  33. ↑ 33.0 33.1 33.2 Sigma Aldrich. "Sodium benzoate". 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. 
  34. ↑ Therapeutic Goods Administration. "Chemical Substances". https://www.tga.gov.au/docs/pdf/aan/aanchem.pdf. 
  35. ↑ British Pharmacopoeia Commission Secretariat. "Index (BP)". https://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. 
  36. ↑ "Japanese Pharmacopoeia 15th Edition". https://jpdb.nihs.go.jp/jp15e/. 
  37. ↑ The United States Pharmacopeial Convention. "Revisions to USP 29–NF 24". https://www.usp.org/USPNF/revisions/usp29nf24firstSupplement04.html. 

External links

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