Sodium benzoate

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Sodium benzoate
Sodium benzoate
Powder of sodium benzoate
Identifiers
CAS number 532-32-1 YesY
PubChem 517055
ChemSpider 10305 YesY
UNII OJ245FE5EU YesY
ChEMBL CHEMBL1356 YesY
RTECS number DH6650000
Jmol-3D images Image 1
Properties
Molecular formula 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)
Solubility in water 62.69 g/100 mL (0 °C)
62.78 g/100 mL (15 °C)
62.6 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]
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)[2]
GHS signal word Warning
GHS hazard statements H319[2]
GHS precautionary statements P305+351+338[2]
EU classification Irritant 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
Flash point 100 °C (212 °F; 373 K)
LD50 4100 mg/kg (oral, rat)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Sodium benzoate has the chemical formula NaC7H5O2; it is a widely used food preservative, with E number 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[edit]

Preservative[edit]

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 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[edit]

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][citation needed] Total Positive and Negative Syndrome Scale scores dropped by 21% compared to placebo.

Sodium benzoate is used to treat hyperammonemia.[10]

Sodium benzoate has been shown to halt the progression of Parkinson's in mice.[10]

Other uses[edit]

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. The fuel is one of the fastest-burning rocket fuels and provides a lot of thrust and smoke.[citation needed] It is sensitive to impact and can explode when sharply compressed.[citation needed]

Mechanism of food preservation[edit]

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[11] which inhibits the growth and survival of micro-organisms that cause food spoilage.

Production[edit]

Sodium benzoate is produced by the neutralization of benzoic acid with sodium hydroxide.[12] 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[edit]

In the United States, sodium benzoate is designated as generally recognized as safe (GRAS) by the Food and Drug Administration.[13] The International Programme on Chemical Safety found no adverse effects in humans at doses of 647–825 mg/kg of body weight per day.[14][15]

Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice.[16]

Association with benzene in soft drinks[edit]

In combination with ascorbic acid (vitamin C, E300), sodium benzoate and potassium benzoate 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).[17] Most of the beverages that tested higher have been reformulated and subsequently tested below the safety limit.[17] Heat, light and shelf life can increase the rate at which benzene is formed.

Hyperactivity[edit]

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.[18][19][20] 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.[20] 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."[20]

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.[21]

Compendial status[edit]

See also[edit]

References[edit]

  1. ^ a b c d e http://chemister.ru/Database/properties-en.php?dbid=1&id=1004
  2. ^ a b c 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". p. 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. ^ a b 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
  11. ^ 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. 
  12. ^ "International Programme On Chemical Safety". Inchem.org. Retrieved 2013-01-14. 
  13. ^ CFR - Code of Federal Regulations Title 21
  14. ^ "Concise International Chemical Assessment Document 26: Benzoic acid and sodium benzoate". Inchem.org. Retrieved 2013-01-14. 
  15. ^ 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. 
  16. ^ 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. 
  17. ^ a b "Data on Benzene in Soft Drinks and Other Beverages". United States Food and Drug Administration. 16 May 2007. Retrieved 7 November 2013. 
  18. ^ Food Standards Agency issues revised advice on certain artificial colours 6 September 2007
  19. ^ Food Colorings and Hyperactivity "Myomancy" 7 September 2007
  20. ^ a b c Agency revises advice on certain artificial colours, Food Standards Agency, 11 September 2007
  21. ^ The Daily Mail DNA Damage Fear 24 May 2008
  22. ^ a b c Sigma Aldrich. "Sodium benzoate". Retrieved 17 July 2009. 
  23. ^ Therapeutic Goods Administration. "Chemical Substances" (PDF). Retrieved 17 July 2009. 
  24. ^ British Pharmacopoeia Commission Secretariat. "Index (BP)". Retrieved 2 March 2010. 
  25. ^ "Japanese Pharmacopoeia 15th Edition". Retrieved 2 March 2010. 
  26. ^ The United States Pharmacopeial Convention. "Revisions to USP 29–NF 24". Retrieved 17 July 2009. 

External links[edit]