Sodium benzoate

Sodium benzoate
Names
IUPAC name
sodium benzoate
Other names
E211, benzoate of soda
Identifiers
532-32-1 YesY
ChEBI CHEBI:113455 N
ChEMBL ChEMBL1356 YesY
ChemSpider 10305 YesY
Jmol 3D model Interactive image
PubChem 517055
RTECS number DH6650000
UNII OJ245FE5EU YesY
Properties
C7H5NaO2
Molar mass 144.10 g·mol−1
Appearance white or colorless crystalline powder
Odor odorless
Density 1.497 g/cm3
Melting point 410 °C (770 °F; 683 K)
62.69 g/100 mL (0 °C)
62.78 g/100 mL (15 °C)
62.87 g/100 mL (30 °C)
71.11 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 pictograms [2]
GHS signal word Warning
H319[2]
P305+351+338[2]
Xi
R-phrases R36
S-phrases S26
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special 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 YesYN ?)
Infobox references

Sodium benzoate has the chemical formula NaC7H5O2; it is a widely used food preservative, with an E number of E211. 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. Benzoic acid occurs naturally at low levels in cranberries, prunes, greengage plums, cinnamon, ripe cloves, and apples.

Uses

Preservative

Sodium benzoate is a preservative. As a food additive, sodium benzoate has the E number E211. It is bacteriostatic and fungistatic under acidic conditions. It is most widely used in acidic foods such as salad dressings (vinegar), carbonated drinks (carbonic acid), jams and fruit juices (citric acid), pickles (vinegar), and condiments. It is also used as a preservative in medicines and cosmetics.[3][4] Concentration as a food preservative is limited by the FDA in the U.S. to 0.1% by weight.[5] Sodium benzoate is also allowed as an animal food additive at up to 0.1%, according to AFCO's official publication.[6]

Pharmaceutical applications

Sodium benzoate is used as a treatment for urea cycle disorders due to its ability to bind amino acids.[7][8] 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.[9][10][11] Total Positive and Negative Syndrome Scale scores dropped by 21% compared to placebo.

Sodium benzoate is used to treat hyperammonemia.[12]

Sodium benzoate has been shown to halt the progression of Parkinson's in mice.[12]

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.

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

Production

Sodium benzoate is produced by the neutralization of benzoic acid with sodium hydroxide.[14] Sodium benzoate can also be prepared by adding benzoic acid to a hot concentrated solution of sodium carbonate until effervescence ceases. The solution is then evaporated, cooled and allowed to crystallize or evaporate to dryness, and then granulated.

Health and safety

In the United States, sodium benzoate is designated as generally recognized as safe (GRAS) by the Food and Drug Administration.[15] The International Programme on Chemical Safety found no adverse effects in humans at doses of 647–825 mg/kg of body weight per day.[16][17]

Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice.[18]

Association with benzene in soft drinks

In combination with ascorbic acid (vitamin C, E300), sodium benzoate and potassium benzoate may form benzene, a known carcinogen. When tested by the FDA, most beverages that contained both ascorbic acid and benzoate had benzene levels that were below those considered dangerous for consumption by the World Health Organization (5 ppb).[19] Most of the beverages that tested higher have been reformulated and subsequently tested below the safety limit.[19] Heat, light and shelf life can increase the rate at which benzene is formed.

Hyperactivity

Research published 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. The results were inconsistent regarding sodium benzoate, so the FSA recommended further study.[20][21][22] 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.[22] 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."[22]

Sodium benzoate may trigger or exacerbate symptoms or episodes of attention-deficit/hyperactivity disorder, or ADHD, according to the Mayo Clinic. The condition is most common in children but it can be present in adults as well, and affected individuals may be forgetful, have difficulty concentrating and following directions or display impulsiveness.[23]

In response to consumer insistence on a more natural product, the Coca Cola Company is in the process of phasing sodium benzoate out of Diet Coke. The company has stated it plans to remove sodium benzoate from its other products — including Sprite, Fanta, and Oasis — as soon as a satisfactory alternative is discovered.[24]

Compendial status

See also

References

  1. 1 2 3 4 5 http://chemister.ru/Database/properties-en.php?dbid=1&id=1004
  2. 1 2 3 Sigma-Aldrich Co., Sodium benzoate. Retrieved on 2014-05-23.
  3. ↑ "Skin Deep® Cosmetics Database | Environmental Working Group". Cosmeticsdatabase.com. Retrieved 2013-01-14.
  4. ↑ "Sodium benzoate in Robitussin cough". Rxmed.com. Retrieved 2013-01-14.
  5. ↑ CFR - Code of Federal Regulations Title 21
  6. ↑ AFCO (2004). "Official Publication": 262.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ Add-on Treatment of Benzoate for Schizophrenia A Randomized, Double-blind, Placebo-Controlled Trial of d-Amino Acid Oxidase Inhibitor December 2013
  10. ↑ Digest of Neurology and Psychiatry
  11. ↑ Mental Health Research Institute Staff Publications, University of Michigan. Mental Health Research Institute
  12. 1 2 Cinnamon May Be Used to Halt the Progression of Parkinson’s disease - Rush University, published in Journal of Neuroimmune Pharmacology Cinnamon Treatment Upregulates Neuroprotective Proteins Parkin and DJ-1 and Protects Dopaminergic Neurons in a Mouse Model of Parkinson’s Disease
  13. ↑ Krebs HA, Wiggins D, Stubbs M, Sols A, Bedoya F (September 1983). "Studies on the mechanism of the antifungal action of benzoate". Biochem. J. 214 (3): 657–63. PMC 1152300. PMID 6226283.
  14. ↑ "International Programme On Chemical Safety". Inchem.org. Retrieved 2013-01-14.
  15. ↑ CFR - Code of Federal Regulations Title 21
  16. ↑ "Concise International Chemical Assessment Document 26: Benzoic acid and sodium benzoate". Inchem.org. Retrieved 2013-01-14.
  17. ↑ 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.
  18. ↑ 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. PMID 4672555.
  19. 1 2 "Data on Benzene in Soft Drinks and Other Beverages". United States Food and Drug Administration. 16 May 2007. Retrieved 7 November 2013.
  20. ↑ Food Standards Agency issues revised advice on certain artificial colours 6 September 2007
  21. ↑ Food Colorings and Hyperactivity "Myomancy" 7 September 2007
  22. 1 2 3 Agency revises advice on certain artificial colours, Food Standards Agency, 11 September 2007
  23. ↑ http://www.livestrong.com/article/488257-the-dangers-of-sodium-benzoate/
  24. ↑ The Daily Mail DNA Damage Fear 24 May 2008
  25. 1 2 3 Sigma Aldrich. "Sodium benzoate". Retrieved 17 July 2009.
  26. ↑ Therapeutic Goods Administration. "Chemical Substances" (PDF). Retrieved 17 July 2009.
  27. ↑ British Pharmacopoeia Commission Secretariat. "Index (BP)" (PDF). Retrieved 2 March 2010.
  28. ↑ "Japanese Pharmacopoeia 15th Edition". Retrieved 2 March 2010.
  29. ↑ The United States Pharmacopeial Convention. "Revisions to USP 29–NF 24". Retrieved 17 July 2009.

External links

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