Sodium salicylate

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
CAS Number	54-21-7  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL447868  Y
ChemSpider	5689  Y
DrugBank	DB01398  Y
ECHA InfoCard	100.000.181
EC Number	200-198-0
KEGG	D00566  Y
PubChem CID	16760658
RTECS number	VO5075000
UNII	WIQ1H85SYP  Y
CompTox Dashboard (EPA)	DTXSID5021708
InChI InChI=1S/C7H6O3.Na/c8-6-4-2-1-3-5(6)7(9)10;/h1-4,8H,(H,9,10);/q;+1/p-1 Y Key: ABBQHOQBGMUPJH-UHFFFAOYSA-M Y InChI=1/C7H6O3.Na/c8-6-4-2-1- 3-5(6)7(9)10;/h1-4,8H,(H,9,10); /q;+1/p-1/fC7H5O3.Na/q-1;m InChI=1/C7H6O3.Na/c8-6-4-2-1-3-5(6)7(9)10;/h1-4,8H,(H,9,10);/q;+1/p-1 Key: ABBQHOQBGMUPJH-REWHXWOFAO
SMILES [Na+].O=C([O-])c1ccccc1O
Properties
Chemical formula	C7H5NaO3
Molar mass	160.104 g/mol
Appearance	White crystals
Melting point	200 °C (392 °F; 473 K)
Solubility in water	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
ATC code	N02BA04 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Harmful
Eye hazards	Irritant
GHS labelling: [2]
Pictograms
Signal word	Warning
Hazard statements	H314, H331, H400
Precautionary statements	P210, P261, P273, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	1 1 0
Autoignition temperature	250 °C (482 °F; 523 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	930 mg/kg (rats, oral) [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

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]

${\displaystyle {\ce {C6H5O- Na+ + CO2 -> HOC6H4COO- Na+}}}$

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. "sodium salicylate". chemister.ru. Archived from the original on 24 May 2014. Retrieved 8 April 2018.
2. Sigma-Aldrich Co., Sodium salicylate. Retrieved on 2014-05-26.
3. Chambers, Michael. "ChemIDplus - 54-21-7 - ABBQHOQBGMUPJH-UHFFFAOYSA-M - Sodium salicylate [USP:JAN] - Similar structures search, synonyms, formulas, resource links, and other chemical information". chem.sis.nlm.nih.gov. Archived from the original on 9 April 2018. Retrieved 8 April 2018.
4. Lehman, J.W., Operational Organich Chemistry, 4th ed., New Jersey, Prentice Hall, 2009
5. "Sodium salicylate | 54-21-7". ChemicalBook. Archived from the original on 2024-09-02. Retrieved 2024-09-02.
6. EP0072095B1,Jansen, Gert&Wolff, Per,"Production of sodium salicylate",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) 12923. doi: 10.3390/ijms252312923 . ISSN   1422-0067. PMC   11640782 . PMID   39684634.
8. PubChem. "Salicylic Acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-08-08.
9. PubChem. "Sodium Salicylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-08-08.
10. "Sodium salicylate | 54-21-7". ChemicalBook. Archived from the original on 2024-09-02. Retrieved 2024-09-02.
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. Bibcode:2007PNAS..10412790R. doi: 10.1073/pnas.0701437104 . PMC   1937545 . PMID   17646662.
13. Stark, Lesley A.; et al. (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" (PDF). Pied Publications. Archived from the original (PDF) on October 16, 2006. Retrieved July 26, 2012.
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". www.fishersci.co.uk. Retrieved 2025-12-22.
19. PubChem. "Sodium Salicylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-12-22.
20. Johnson, Wilbur; Zhu, Jinqiu; Bergfeld, Wilma F.; Belsito, Donald V.; Hill, Ronald A.; Klaassen, Curtis D.; Liebler, Daniel C.; Marks, James G.; Shank, Ronald C.; Slaga, Thomas J.; Snyder, Paul W.; Fiume, Monice M.; Heldreth, Bart (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.

External links

• Chemicalland21
• Some synonyms
• Safety data for sodium salicylate at Oxford University Archived 2006-05-23 at the Wayback Machine
• Sodium salicylate, definitions at National Cancer Institute