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Sodium benzoate

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Sodium benzoate
Sodium benzoate
Powder of sodium benzoate


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
ECHA InfoCard 100.007.760 Edit this at Wikidata
E number E211 (preservatives)
RTECS number
  • DH6650000
UNII
  • InChI=1S/C7H6O2.Na/c8-7(9)6-4-2-1-3-5-6;/h1-5H,(H,8,9);/q;+1/p-1 checkY
    Key: WXMKPNITSTVMEF-UHFFFAOYSA-M checkY
  • InChI=1/C7H6O2.Na/c8-7(9)6-4-2-1-3-5-6;/h1-5H,(H,8,9);/q;+1/p-1
    Key: WXMKPNITSTVMEF-REWHXWOFAY
  • [Na+].[O-]C(=O)c1ccccc1
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
A16AX11 (WHO)
Hazards
GHS labelling:
GHS07: Exclamation mark[2]
Warning
H319[2]
P305+P351+P338[2]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
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 checkY☒N ?)

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

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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

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

Natural occurrence

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Sodium benzoate is not a naturally occurring substance. However 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

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As a preservative

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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

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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

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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.[21][22]

Mechanism of food preservation

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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,[23] which inhibits the growth and survival of microorganisms that cause food spoilage.

Health and safety

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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.[24] The International Programme on Chemical Safety found no adverse effects in humans at doses of 647–825 mg/kg of body weight per day.[25][26]

Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice.[27]

The human body rapidly clears sodium benzoate by combining it with glycine to form hippuric acid which is then excreted.[26] The metabolic pathway for this begins with the conversion of benzoate by butyrate-CoA ligase into an intermediate product, benzoyl-CoA,[28] which is then metabolized by glycine N-acyltransferase into hippuric acid.[29]

Association with benzene in soft drinks and pepper sauces

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Main article: 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.[30] Most of the beverages that tested above the limit have been reformulated and subsequently tested below the safety limit.[30] 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"[31]) so the observation about beverages applies to pepper sauces containing sodium benzoate, like Texas Pete.

ADHD and hyperactivity

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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.[32][33][34] 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.[34] 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."[34]

Compendial status

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See also

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References

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  1. ^ a b c d e "sodium benzoate". chemister.ru.
  2. ^ a b c Sigma-Aldrich Co., Sodium benzoate. Retrieved on 2014-05-23.
  3. ^ "International Programme on Chemical Safety". Inchem.org. Retrieved 9 February 2022.
  4. ^ Wertheim E (1942). Introductory Organic Chemistry with Certain Chapters of Biochemistry. The Blakistan Company. p. 236.
  5. ^ del Olmo A, Calzada J, Nuñez M (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. S2CID 205692543.
  6. ^ "Sodium benzoate". PubChem. National Library of Medicine
  7. ^ "Robitussin (Guaifenesin)". Rxmed.com. Retrieved 14 January 2013.
  8. ^ "Code of Federal Regulations Title 21". www.accessdata.fda.gov.
  9. ^ AAFCO (2004). "Official Publication": 262. {{cite journal}}: Cite journal requires |journal= (help)
  10. ^ Saltmarsh M (15 March 2015). "Recent trends in the use of food additives in the United Kingdom". Journal of the Science of Food and Agriculture. 95 (4): 649–652. Bibcode:2015JSFA...95..649S. doi:10.1002/jsfa.6715. ISSN 1097-0010. PMID 24789520. ... 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, Crespo PS, Santer R, Servais A, Valayannopoulos V, Lindner M, Rubio V, Dionisi-Vici C (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. PMC 3488504. 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 – via Google Books.
  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".
  17. ^ PHENYLBUTYRATE, SODIUM BENZOATE. National Institute of Diabetes and Digestive and Kidney Diseases. 2012. PMID 31643176.
  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. ^ Öztap S. "The pyrotechnic whistle and its applications" (PDF). Pyrotechnica. 11: 46–54.
  22. ^ Verbovytskyy Y, Juknelevicius D (2023). "Pyrotechnic whistles: An overview". Propellants, Explosives, Pyrotechnics. 48 (6): e202300044. doi:10.1002/prep.202300044. ISSN 0721-3115.
  23. ^ 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. PMC 1152300. PMID 6226283.
  24. ^ "CFR - Code of Federal Regulations Title 21". www.accessdata.fda.gov.
  25. ^ "Concise International Chemical Assessment Document 26: Benzoic acid and sodium benzoate". Inchem.org. Retrieved 14 January 2013.
  26. ^ a b 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.
  27. ^ Bedford PG, Clarke EG (January 1972). "Experimental benzoic acid poisoning in the cat". Vet. Rec. 90 (3): 53–8. doi:10.1136/vr.90.3.53 (inactive 1 November 2024). PMID 4672555. S2CID 2553612.{{cite journal}}: CS1 maint: DOI inactive as of November 2024 (link)
  28. ^ "butyrate-CoA ligase". BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014. Substrate/Product
  29. ^ "glycine N-acyltransferase". BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014. Substrate/Product
  30. ^ a b "Data on Benzene in Soft Drinks and Other Beverages". United States Food and Drug Administration. 16 May 2007. Archived from the original on 12 January 2017. Retrieved 7 November 2013.
  31. ^ "Is hot sauce good for your health?". 4 November 2016.
  32. ^ Food Standards Agency issues revised advice on certain artificial colours Archived 6 December 2011 at the Wayback Machine 6 September 2007
  33. ^ Food Colorings and Hyperactivity Archived 20 May 2023 at the Wayback Machine "Myomancy" 7 September 2007
  34. ^ a b c Agency revises advice on certain artificial colours Archived 12 April 2012 at the Wayback Machine, Food Standards Agency, 11 September 2007
  35. ^ a b c Sigma Aldrich. "Sodium benzoate". Retrieved 17 July 2009.
  36. ^ Therapeutic Goods Administration. "Chemical Substances" (PDF). Archived from the original (PDF) on 15 June 2009. Retrieved 17 July 2009.
  37. ^ British Pharmacopoeia Commission Secretariat. "Index (BP)" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 2 March 2010.
  38. ^ "Japanese Pharmacopoeia 15th Edition". Archived from the original on 28 March 2010. Retrieved 2 March 2010.
  39. ^ The United States Pharmacopeial Convention. "Revisions to USP 29–NF 24". Archived from the original on 4 April 2009. Retrieved 17 July 2009.
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