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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL447868 ;
ChemSpider	5689 ;
DrugBank	DB01398 ;
ECHA InfoCard	100.000.181
EC Number	200-198-0;
KEGG	D00566 ;
PubChem CID	16760658;
RTECS number	VO5075000;
UNII	WIQ1H85SYP ;
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 Key: ABBQHOQBGMUPJH-UHFFFAOYSA-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/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)
Solubility	Soluble in glycerol, 1,4-Dioxane, alcohol
Solubility in methanol	26.28 g/100 g (15 °C); 34.73 g/100 g (67.2 °C)
Pharmacology
ATC code	N02BA04 (WHO)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Harmful
Eye hazards	Irritant
	GHS labelling:
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)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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]

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

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

^ ^a ^b ^c "sodium salicylate". chemister.ru. Archived from the original on 24 May 2014. Retrieved 8 April 2018.
^ 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.
^ Sigma-Aldrich Co., Sodium salicylate. Retrieved on 2014-05-26.
^ Lehman, J.W., Operational Organich Chemistry, 4th ed., New Jersey, Prentice Hall, 2009
^ "Sodium salicylate | 54-21-7". ChemicalBook. Archived from the original on 2024-09-02. Retrieved 2024-09-02.
^ EP0072095B1, Jansen, Gert & Wolff, Per, "Production of sodium salicylate", issued 1986-05-21
^ 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.
^ PubChem. "Salicylic Acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-08-08.
^ ^a ^b PubChem. "Sodium Salicylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-08-08.
^ "Sodium salicylate | 54-21-7". ChemicalBook. Archived from the original on 2024-09-02. Retrieved 2024-09-02.
^ 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.
^ 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.
^ 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.
^ 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.
^ Samson, James. "Vacuum Ultraviolet Spectroscopy" (PDF). Pied Publications. Archived from the original (PDF) on October 16, 2006. Retrieved July 26, 2012.
^ 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. hdl:2027.42/23492. ISSN 0003-2697.
^ 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.
^ "Sodium salicylate, 99% | Thermo Scientific Alfa Aesar | Fisher Scientific". www.fishersci.co.uk. Retrieved 2025-12-22.
^ PubChem. "Sodium Salicylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-12-22.
^ 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

[chemister-1] "sodium salicylate". chemister.ru. Archived from the original on 24 May 2014. Retrieved 8 April 2018.

[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". chem.sis.nlm.nih.gov. Archived from the original on 9 April 2018. Retrieved 8 April 2018.

[sigma-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". 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.

[:0-9] 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. hdl:2027.42/23492. 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.

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v t e Nonsteroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Grapiprant^‡ Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Meloxicam/rizatriptan Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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