Sodium salicylate

Sodium salicylate
IUPAC name Sodium salicylate
Other names Salsonin, Monosodium salicylate, Sodium o-hydroxybenzoate, Sodium 2-hydroxybenzoate, Salicylic acid sodium salt, Monosodium 2-hydroxybenzoate, Diuratin, ...
Identifiers
CAS number	54-21-7 Y
PubChem	5900
ChemSpider	5689 Y
UNII	WIQ1H85SYP Y
EC number	200-198-0
DrugBank	DB01398
KEGG	D00566
RTECS number	VO5075000
Jmol-3D images	Image 1
SMILES [Na+].O=C([O-])c1ccccc1O
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
Properties
Molecular formula	C7H5NaO3
Molar mass	160.11 g/mol
Appearance	White crystals
Melting point	200 °C
Solubility in water	~ 660 g/l at 20 °C
Hazards
R-phrases	R22, R36/37/38
S-phrases	S24/25, S26, S36/37/39
Main hazards	Harmful
NFPA 704	1 1 0
Autoignition temperature	> 250 °C
Y salicylate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Sodium salicylate is a sodium salt of salicylic acid. It can be prepared from sodium phenolate and carbon dioxide under higher temperature and pressure. Historically, it has been synthesized from methyl salicylate (found in wintergreen plants or the bark of sweet birch tree) by reacting it with an excess of sodium hydroxide and heating it under reflux.^[1]

Properties

Sodium salicylate is of the salicylate family and this compound is known to trigger Reye's Syndrome in children and adults, usually following a viral infection such as influenza or chicken pox. Products containing such salicylates should not be given to children under the age of 19.^{[citation needed]}

Uses

It is used in medicine as an analgesic and antipyretic. Sodium salicylate also acts as non-steroidal anti-inflammatory drug (NSAID), and induces apoptosis in cancer cells ^[2][3][4] and also necrosis.^[5] It is also a potential replacement for aspirin for people sensitive to it.

References

1. ^ Lehman, J.W., Operational Organich Chemistry, 4th ed., New Jersey, Prentice Hall, 2009
2. ^ 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. PMID 10090950. http://bloodjournal.hematologylibrary.org/cgi/content/full/93/7/2386. Retrieved 2011-02-21. 
3. ^ 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. PMC 1937545. PMID 17646662. http://www.pnas.org/content/104/31/12790. Retrieved 2011-02-21. 
4. ^ Stark, Lesley A.; et al (2007-05). "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. http://carcin.oxfordjournals.org/content/28/5/968. Retrieved 2011-02-21. 
5. ^ 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. http://www.jbc.org/content/271/14/8089. Retrieved 2011-02-21. 

External links

• Chemicalland21
• Some synonyms
• Safety data for sodium salicylate at Oxford University
• Sodium salicylate, definitions at National Cancer Institute