Chemistry:Sodium salicylate

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Sodium salicylate
Names
Preferred IUPAC name
Sodium 2-hydroxybenzoate
Other names
Salsonin, Monosodium salicylate, Sodium o-hydroxybenzoate, Salicylic acid sodium salt, Monosodium 2-hydroxybenzoate, Diuratin, Enterosalicyl, Kerasalicyl, Alysine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
EC Number
  • 200-198-0
KEGG
RTECS number
  • VO5075000
UNII
Properties
C7H5NaO3
Molar mass 160.104 g/mol
Appearance White crystals
Melting point 200 °C (392 °F; 473 K)
25.08 g/100 g (-1.5 °C)
107.9 g/100 g (15 °C)
124.6 g/100 g (25 °C)
141.8 g/100 g (78.5 °C)
179 g/100 g (114 °C)[1]
Solubility Soluble in glycerol, 1,4-Dioxane, alcohol[1]
Solubility in methanol 26.28 g/100 g (15 °C)
34.73 g/100 g (67.2 °C)[1]
Pharmacology
1=ATC code }} N02BA04 (WHO)
Hazards
Main hazards Harmful
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H314, H331, H400
P210, P261, P273, P280, P305+351+338, P310
Eye hazard Irritant
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondFlammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
250 °C (482 °F; 523 K)
Lethal dose or concentration (LD, LC):
930 mg/kg (rats, oral)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

Sodium salicylate is a sodium salt of salicylic acid. It can be prepared from sodium phenoxide and carbon dioxide under higher temperature and pressure. Historically, it has been synthesized by refluxing methyl salicylate (wintergreen oil) with an excess of sodium hydroxide.[4]

Properties

Sodium salicylate is of the salicylate family. It is a shiny white powder with an aromatic flavor.[5] It has a molecular weight of 160.10 g/mol, and produces mildly alkaline solutions because it can donate 1 hydrogen-bond and accept 3.

Synthesis

Sodium salicylate is industrially prepared via the Kolbe-Schmitt process, by reacting sodium phenoxide with carbon dioxide at around 120 °C and 5 atm in a mixed alcohol solvent containing excess phenol.[6]

CA6HA5OA−NaA++COA2⟶HOCA6HA4COOA−NaA+

This reaction proceeds via a nucleophilic addition-elimination mechanism.[7]

Sodium salicylate can be prepared by neutralizing salicylic acid with a sodium base such as sodium hydroxide or sodium carbonate[8][9] or by refluxing methyl salicylate with sodium hydroxide.

Uses

It is used in medicine as an analgesic and antipyretic.[10] Sodium salicylate also acts as non-steroidal anti-inflammatory drug (NSAID), and induces apoptosis in cancer cells [11][12][13] and also necrosis.[14] It is also a potential replacement for aspirin for people sensitive to it. It may also be used as a phosphor for the detection of vacuum ultraviolet radiation and beta radiation.[15][16]

Sodium salicylate, alongside other salicylates, has historically been used to treat rheumatological disorders.[17][18]

Sodium salicylate can be found in cosmetics, personal care products, perfumes, and fragrances, often as a preservative.[19] Among 16 other salicylate salts in these products, it has been concluded to be safe.[20]

Mode of action

Sodium salicylate lends its analgesic effects to the inhibition of cyclooxygenase. This enzyme converts arachidonic acid to cyclic endoperoxides, which are precursors to prostaglandins, thus preventing the sensitization of pain receptors.[9]

References

  1. ↑ 1.0 1.1 1.2 "sodium salicylate". http://chemister.ru/Database/properties-en.php?dbid=1&id=2993. 
  2. ↑ Chambers, Michael. "ChemIDplus - 54-21-7 - ABBQHOQBGMUPJH-UHFFFAOYSA-M - Sodium salicylate [USP:JAN - Similar structures search, synonyms, formulas, resource links, and other chemical information."]. https://pubchem.ncbi.nlm.nih.gov/#tab/sidsrcname=ChemIDplus&query=54-21-7&input_type=text. 
  3. ↑ Sigma-Aldrich Co., Sodium salicylate. Retrieved on 2014-05-26.
  4. ↑ Lehman, J.W., Operational Organich Chemistry, 4th ed., New Jersey, Prentice Hall, 2009
  5. ↑ "Sodium salicylate | 54-21-7" (in en). https://m.chemicalbook.com/ChemicalProductProperty_EN_CB1255762.htm. 
  6. ↑ , Gert & Per Wolff"Production of sodium salicylate" patent EP0072095B1, issued 1986-05-21
  7. ↑ Kojčinović, Aleksa; Likozar, Blaž; Grilc, Miha (2024-12-01). "Mechanism, Kinetics and Modelling of Phenol Carboxylation Reactions with CO2". International Journal of Molecular Sciences 25 (23). doi:10.3390/ijms252312923. ISSN 1422-0067. PMID 39684634. 
  8. ↑ PubChem. "Salicylic Acid" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/338. 
  9. ↑ 9.0 9.1 PubChem. "Sodium Salicylate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/16760658. 
  10. ↑ "Sodium salicylate | 54-21-7" (in en). https://m.chemicalbook.com/ChemicalProductProperty_EN_CB1255762.htm. 
  11. ↑ Klampfer, Lidija; Jörg Cammenga; Hans-Georg Wisniewski; Stephen D. Nimer (1999-04-01). "Sodium Salicylate Activates Caspases and Induces Apoptosis of Myeloid Leukemia Cell Lines". Blood 93 (7): 2386–94. doi:10.1182/blood.V93.7.2386. PMID 10090950. 
  12. ↑ Rae, Colin; Susana Langa; Steven J. Tucker; David J. MacEwan (2007-07-31). "Elevated NF-κB responses and FLIP levels in leukemic but not normal lymphocytes: reduction by salicylate allows TNF-induced apoptosis". Proceedings of the National Academy of Sciences of the USA 104 (31): 12790–5. doi:10.1073/pnas.0701437104. PMID 17646662. Bibcode: 2007PNAS..10412790R. 
  13. ↑ Stark, Lesley A. (May 2007). "Aspirin activates the NF-κB signalling pathway and induces apoptosis in intestinal neoplasia in two in vivo models of human colorectal cancer". Carcinogenesis 28 (5): 968–76. doi:10.1093/carcin/bgl220. PMID 17132819. 
  14. ↑ Schwenger, Paul; Edward Y. Skolnik; Jan Vilcek (1996-04-05). "Inhibition of Tumor Necrosis Factor-induced p42/p44 Mitogen-Activated Protein Kinase Activation by Sodium Salicylate". The Journal of Biological Chemistry 271 (14): 8089–94. doi:10.1074/jbc.271.14.8089. PMID 8626494. 
  15. ↑ Samson, James. "Vacuum Ultraviolet Spectroscopy". Pied Publications. http://www.mcphersoninc.com/detectors/Sodium%20Salicylate.pdf. 
  16. ↑ Chamberlain, John P. (1979-09-15). "Fluorographic detection of radioactivity in polyacrylamide gols with the water-soluble fluor, sodium salicylate". Analytical Biochemistry 98 (1): 132–135. doi:10.1016/0003-2697(79)90716-4. ISSN 0003-2697. 
  17. ↑ Hedner, T.; Everts, B. (1998). "The early clinical history of salicylates in rheumatology and pain". Clinical Rheumatology 17 (1): 17–25. doi:10.1007/BF01450953. ISSN 0770-3198. PMID 9586674. 
  18. ↑ "Sodium salicylate, 99% | Thermo Scientific Alfa Aesar | Fisher Scientific" (in en). https://www.fishersci.co.uk/shop/products/sodium-salicylate-99-thermo-scientific/11468916. 
  19. ↑ PubChem. "Sodium Salicylate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/16760658. 
  20. ↑ Johnson, Wilbur; Zhu, Jinqiu; Bergfeld, Wilma F.; Belsito, Donald V.; Hill, Ronald A.; Klaassen, Curtis D.; Liebler, Daniel C.; Marks, James G. et al. (2025). "Amended Safety Assessment of Salicylic Acid and Salicylates as Used in Cosmetics". International Journal of Toxicology 44 (4_suppl): 5S–57S. doi:10.1177/10915818251389456. ISSN 1092-874X. PMID 41243163. 



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