Salsalate

Base Information

• Chemical Name: Salsalate
• CAS No.: 552-94-3
• Deprecated CAS: 2087491-28-7
• Molecular Formula: C14H10O5
• Molecular Weight: 258.23
• Hs Code.: 29182300
• European Community (EC) Number: 209-027-4
• NSC Number: 755823,49171
• UNII: V9MO595C9I
• DSSTox Substance ID: DTXSID1023572
• Nikkaji Number: J2.069I
• Wikipedia: Salsalate
• Wikidata: Q1320691
• NCI Thesaurus Code: C62636
• RXCUI: 36108
• Metabolomics Workbench ID: 43535
• ChEMBL ID: CHEMBL154111
• Mol file: 552-94-3.mol

Synonyms:Arcylate;Argesic;benzoic acid, 2-hydroxy-, 2-carboxyphenyl ester;Disalcid;disalicylic acid;Mono-Gesic;Salflex;salicyl salicylate;salicylsalicylic acid;Saloxium;salsalate;Salsitab

Chemical Property of Salsalate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.88E-10mmHg at 25°C
• Melting Point: 148-151°C
• Refractive Index: 1.4825 (estimate)
• Boiling Point: 482.9 °C at 760 mmHg
• PKA: pKa 3.5 (Uncertain);9.8 (Uncertain)
• Flash Point: 188 °C
• PSA: 83.83000
• Density: 1.404 g/cm³
• LogP: 2.30960
• Storage Temp.: room temp
• Sensitive.: Moisture Sensitive
• Solubility.: DMSO: ≥15mg/mL
• Water Solubility.: HYDROLYSIS
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 258.05282342
• Heavy Atom Count: 19
• Complexity: 341

Purity/Quality:

99.5% ^*data from raw suppliers

Salsalate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-50-22
• Safety Statements: 37/39-26-61

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiinflammatory Agents
• Canonical SMILES: C1=CC=C(C(=C1)C(=O)OC2=CC=CC=C2C(=O)O)O
• Recent ClinicalTrials: Omega-3 Fatty Acid Lipidomics in Diabetes Peripheral Neuropathy
• Description: Salsalate, or salicylsalicylic acid, (pKa 3.5 [COOH], 9.8 [AR-OH]) is a dimer of salicylic acid. It is insoluble in gastric juice but is soluble in the small intestine, where it is partially hydrolyzed to two molecules of salicylic acid and absorbed. On a molar basis, it produces 15% less salicylic acid than aspirin. It does not cause GI blood loss and can be given to aspirin-sensitive patients. Salsalate is available as capsules and tablets.
• Uses: Nonacetylated aspirin analog. Analgesic, anti-inflammatory. Nonacetylated (e.g., sodium salicylate) and acetylated (aspirin) forms of salicylate are widely used to target inflammation in the treatment of insulin resistance, type 2 diabetes, or rheumatic pain. Sasapyrine is a dimeric prodrug comprising two esterified salicylate moieties. It is advantageous over sodium salicylate because it is insoluble at the acid pH of the stomach and passes suspended but undissolved into the small intestine, sparing the gastric mucosa direct contact. Salicylsalicylic acid is used in organic synthesis and functions as a plant hormone, as a key ingredient in topical anti-acne products.

Technology Process of Salsalate

There total 35 articles about Salsalate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.08%

salicylic acid (69-72-7,25496-36-0,8052-31-1) → 2-hydroxy-benzoic acid, 2-carboxyphenyl ester (552-94-3)

Guidance literature:

With diethylamine; In water; 1,2-dichloro-ethane; at 0 - 25 ℃; for 12h; Temperature; Large scale;

Reference yield:

acetylsalicylsalicylic acid (530-75-6) → 2-hydroxy-benzoic acid, 2-carboxyphenyl ester (552-94-3) + aspirin (50-78-2,98201-60-6)

Guidance literature:

In water; at 40 ℃; Rate constant; ionic strength 0.5; effect of pH;

DOI:10.1248/cpb.33.2158

Reference yield:

aspirin (50-78-2,98201-60-6) → 2-hydroxy-benzoic acid, 2-carboxyphenyl ester (552-94-3) + acetylsalicylsalicylic acid (530-75-6) + salicylic acid (69-72-7,25496-36-0,8052-31-1)

Guidance literature:

With magnesium stearate; at 60 ℃; Product distribution;

DOI:10.1002/jps.2600711004

upstream raw materials:

1,4-dioxane

1-methyl-4-nitrosobenzene

disalicylide

pyridine

Downstream raw materials:

acetylsalicylsalicylic acid

2-salicyloyloxy-benzoyl chloride

1,9,17-trioxa-[2.2.2]orthocyclophane-2,10,18-trione

C₄₇H₆₃N₃O₉S₂

Refernces

• 1、 Kawamura, Yasuhiko,Sato, Yoshinori,Horie, Tokunaru,Tsukayama, Masao. "Dehydration induced by intramolecular redox character of a stable allylidenetributylphosphorane". . p. 7893 - 7896. Retrieved 2007/10/03.
• 2、 Sunada,Iba,Ogawa,Arakawa,Masuyama,Hara,Otsuka. "Hydrolysis of acetylsalicylsalicylic acid and salicylsalicylic acid in aqueous solution". . p. 2158 - 2161. Retrieved 2007/10/02.