Sodium benzoate
Ball-and-stick model of part of the crystal structure
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Ball-and-stick model of packing in the crystal structure
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Names | |
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Preferred IUPAC name
Sodium benzoate | |
Other names
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.007.760 |
E number | E211 (preservatives) |
PubChem CID
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RTECS number
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UNII | |
CompTox Dashboard (EPA)
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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: | |
[2] | |
Warning | |
H319[2] | |
P305+P351+P338[2] | |
NFPA 704 (fire diamond) | |
Flash point | 100 °C (212 °F; 373 K) |
500 °C (932 °F; 773 K) | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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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).
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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]
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
In the 19th century, sodium benzoate as a food ingredient was investigated by
In pharmaceuticals
Sodium benzoate is used as a treatment for
Sodium benzoate, along with phenylbutyrate, is used to treat hyperammonemia.[16][17]
Sodium benzoate, along with
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.[21][22]
Mechanism of food preservation
The mechanism starts with the absorption of benzoic acid into the cell. If the
which inhibits the growth and survival of microorganisms that cause food spoilage.Health and safety
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
The human body rapidly clears sodium benzoate by combining it with
Association with benzene in soft drinks & pepper sauces
In combination with
ADHD and hyperactivity
Research published, including in 2007 for the UK's
Compendial status
- British Pharmacopoeia[35][36][37]
- European Pharmacopoeia[35]
- Food Chemicals Codex[35]
- Japanese Pharmacopoeia[38]
- United States Pharmacopeia[39]
See also
References
- ^ a b c d e "sodium benzoate". chemister.ru.
- ^ a b c Sigma-Aldrich Co., Sodium benzoate. Retrieved on 2014-05-23.
- ^ "International Programme on Chemical Safety". Inchem.org. Retrieved 9 February 2022.
- ^ Wertheim E (1942). Introductory Organic Chemistry with Certain Chapters of Biochemistry. The Blakistan Company. p. 236.
- S2CID 205692543.
- ^ "Sodium benzoate". PubChem. National Library of Medicine
- ^ "Robitussin (Guaifenesin)". Rxmed.com. Retrieved 14 January 2013.
- ^ "Code of Federal Regulations Title 21". www.accessdata.fda.gov.
- ^ AAFCO (2004). "Official Publication": 262.
{{cite journal}}
: Cite journal requires|journal=
(help) - PMID 24789520.
... the preservative used in the study, sodium benzoate, has been replaced by potassium sorbate in the majority of soft drinks.
- PMID 22642880.
- PMID 15050980.
- ^ Add-on Treatment of Benzoate for Schizophrenia A Randomized, Double-blind, Placebo-Controlled Trial of d-Amino Acid Oxidase Inhibitor December 2013
- ^ "Digest of Neurology and Psychiatry". Institute of Living. 16 April 2018 – via Google Books.
- ^ Mental Health Research Institute Staff Publications, University of Michigan. Mental Health Research Institute
- ^ "Cinnamon May Help Halt Parkinson's Disease Progression - News Releases - Rush University Medical Center".
- PMID 31643176.
- PMID 9952095.
- ^ mayoclinic.org, Caffeine And Sodium Benzoate (Injection Route)
- ^ ebi.ac.uk, CHEBI:32140 - sodium caffeine benzoate
- ^ Öztap S. "The pyrotechnic whistle and its applications" (PDF). Pyrotechnica. 11: 46–54.
- ISSN 0721-3115.
- PMID 6226283.
- ^ "CFR - Code of Federal Regulations Title 21". www.accessdata.fda.gov.
- ^ "Concise International Chemical Assessment Document 26: Benzoic acid and sodium benzoate". Inchem.org. Retrieved 14 January 2013.
- ^ S2CID 13639993.
- S2CID 2553612.)
{{cite journal}}
: CS1 maint: DOI inactive as of January 2024 (link - ^ "butyrate-CoA ligase". BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014. Substrate/Product
- ^ "glycine N-acyltransferase". BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014. Substrate/Product
- ^ United States Food and Drug Administration. 16 May 2007. Archived from the originalon 12 January 2017. Retrieved 7 November 2013.
- ^ "Is hot sauce good for your health?". 4 November 2016.
- ^ Food Standards Agency issues revised advice on certain artificial colours Archived 6 December 2011 at the Wayback Machine 6 September 2007
- ^ Food Colorings and Hyperactivity Archived 20 May 2023 at the Wayback Machine "Myomancy" 7 September 2007
- ^ a b c Agency revises advice on certain artificial colours Archived 12 April 2012 at the Wayback Machine, Food Standards Agency, 11 September 2007
- ^ Sigma Aldrich. "Sodium benzoate". Retrieved 17 July 2009.
- ^ Therapeutic Goods Administration. "Chemical Substances" (PDF). Archived from the original (PDF) on 15 June 2009. Retrieved 17 July 2009.
- ^ British Pharmacopoeia Commission Secretariat. "Index (BP)" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 2 March 2010.
- ^ "Japanese Pharmacopoeia 15th Edition". Archived from the original on 28 March 2010. Retrieved 2 March 2010.
- The United States Pharmacopeial Convention. "Revisions to USP 29–NF 24". Archived from the originalon 4 April 2009. Retrieved 17 July 2009.
External links
- International Programme on Chemical Safety - Benzoic Acid and Sodium Benzoate report
- Kubota K, Ishizaki T (1991). "Dose-dependent pharmacokinetics of benzoic acid following oral administration of sodium benzoate to humans". Eur. J. Clin. Pharmacol. 41 (4): 363–8. ureagenesis
- Safety data for sodium benzoate Archived 11 December 2011 at the Wayback Machine
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