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Sodium benzoate

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Sodium benzoate
Sodium benzoate
Ball-and-stick model of the benzoate anion
Ball-and-stick model of the benzoate anion
The sodium cation
The sodium cation
Names
IUPAC name
sodium benzoate
Other names
E211, benzoate of soda
Identifiers
3D model (JSmol)
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
NaC6H5CO2
Molar mass 144.11 g/mol
Appearance white or colorless crystalline powder
Odor odorless
Density 1.497 g/cm3
Melting point 300 °C (572 °F; 573 K)
62.9g/100ml [1]
Solubility 1.33g/100ml ethanol [1]
Hazards
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
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).
checkY verify (what is checkY☒N ?)

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.

Uses

Sodium benzoate is a preservative. 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.[2][3] As a food additive, sodium benzoate has the E number E211.

It 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 also one of the fastest burning rocket fuels and provides a lot of thrust and smoke. It does have its downsides: there is a high danger of explosion when the fuel is sharply compressed because of the fuel's sensitivity to impact.

Sodium benzoate is produced by the neutralization of benzoic acid with sodium hydroxide.[4] Benzoic acid is detectable at low levels in cranberries, 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. The International Programme on Chemical Safety found no adverse effects in humans at doses of 647–825 mg/kg of body weight per day.[5][6]

Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice.[7] Sodium benzoate is, however, allowed as an animal food additive at up to 0.1%, according to AFCO's[specify] official publication.[8]

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 anaerobic fermentation of glucose through phosphofructokinase is decreased by 95%,[9] thereby inhibiting the growth and survival of micro-organisms that cause food spoilage.

Production

Sodium benzoate is 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.

Safety and health

Main article: Benzene in soft drinks

In combination with ascorbic acid (vitamin C, E300), sodium benzoate and potassium benzoate form benzene, a known carcinogen. However, in most beverages that contain both, the benzene levels are below those considered dangerous for consumption.[10] Heat, light and shelf life can affect 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 (E211) may be linked to hyperactive behaviour. The results were inconsistent regarding sodium benzoate, so the FSA recommended further study.[11][12][13]

The report's author, Professor 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."[13]

Two mixtures of additives were tested in the research:[13]

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 observed effects were not consistent. The Food Standards Agency concluded that the observed increases in hyperactive behavior, if real, were more likely to be linked to the colours tested.

On 10 April 2008, the Foods Standard Agency called for a voluntary removal of the colours (but not sodium benzoate) by 2009.[14] In addition, it recommended there should be action to phase them out in food and drink in the European Union (EU) over a specified period.[15]

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 E211 from its other products — including Sprite, Fanta, and Oasis — as soon as a satisfactory alternative is discovered.[16]

Schizophrenia

Recent research shows that sodium benzoate may be beneficial as an add-on therapy (1 gram/day) in schizophrenia. Total PANSS scores dropped by 21% compared to placebo.

Compendial status

See also

References

  1. ^ a b "SODIUM BENZOATE - Emerald Performance Materials" (PDF).
  2. ^ "Skin Deep® Cosmetics Database | Environmental Working Group". Cosmeticsdatabase.com. Retrieved 14 January 2013.
  3. ^ "Sodium benzoate in Robitussin cough". Rxmed.com. Retrieved 14 January 2013.
  4. ^ "International Programme On Chemical Safety". Inchem.org. Retrieved 14 January 2013.
  5. ^ "Concise International Chemical Assessment Document 26: Benzoic acid and sodium benzoate". Inchem.org. Retrieved 14 January 2013.
  6. ^ 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.
  7. ^ Bedford PG, Clarke EG (1972). "Experimental benzoic acid poisoning in the cat". Vet. Rec. 90 (3): 53–8. doi:10.1136/vr.90.3.53. PMID 4672555. {{cite journal}}: Unknown parameter |month= ignored (help)
  8. ^ AFCO (2004). "Official Publication": 262. {{cite journal}}: Cite journal requires |journal= (help)
  9. ^ Krebs HA, Wiggins D, Stubbs M, Sols A, Bedoya F (1983). "Studies on the mechanism of the antifungal action of benzoate". Biochem. J. 214 (3): 657–63. PMC 1152300. PMID 6226283. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  10. ^ "FDA, 2006. "Data on Benzene in Soft Drinks and Other Beverages, " United States Food and Drug Administration". Fda.gov. Retrieved 14 January 2013.
  11. ^ Food Standards Agency issues revised advice on certain artificial colours 6 September 2007
  12. ^ Food Colorings and Hyperactivity "Myomancy" 7 September 2007
  13. ^ a b c Agency revises advice on certain artificial colours Food Standards Agency 11 September 2007
  14. ^ BBC Europe-wide food colour ban call 10 April 2008
  15. ^ FSA Board discusses colours advice 10 April 2008
  16. ^ The Daily Mail DNA Damage Fear 24 May 2008
  17. ^ a b c Sigma Aldrich. "Sodium benzoate". Retrieved 17 July 2009. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)
  18. ^ Therapeutic Goods Administration. "Chemical Substances" (PDF). Retrieved 17 July 2009. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)
  19. ^ British Pharmacopoeia Commission Secretariat. "Index (BP)" (PDF). Retrieved 2 March 2010. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)
  20. ^ "Japanese Pharmacopoeia 15th Edition". Retrieved 2 March 2010. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)
  21. ^ The United States Pharmacopeial Convention. "Revisions to USP 29–NF 24". Retrieved 17 July 2009. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)

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