Aspirin

Base Information

• Chemical Name: Aspirin
• CAS No.: 50-78-2
• Deprecated CAS: 11126-35-5,11126-37-7,2349-94-2,26914-13-6,98201-60-6,2087491-38-9,11126-37-7,2349-94-2,26914-13-6
• Molecular Formula: C9H8O4
• Molecular Weight: 180.16
• Hs Code.: 3004.90
• European Community (EC) Number: 200-064-1
• ICSC Number: 0822
• NSC Number: 755899,406186,27223
• UN Number: 2811
• UNII: R16CO5Y76E
• DSSTox Substance ID: DTXSID5020108
• Nikkaji Number: J2.300K
• Wikipedia: Aspirin
• Wikidata: Q18216
• NCI Thesaurus Code: C287
• RXCUI: 1191
• Pharos Ligand ID: NNQ793F142LD
• Metabolomics Workbench ID: 37905
• ChEMBL ID: CHEMBL25
• Mol file: 50-78-2.mol

Synonyms:2-(Acetyloxy)benzoic Acid;Acetylsalicylic Acid;Acetysal;Acid, Acetylsalicylic;Acylpyrin;Aloxiprimum;Aspirin;Colfarit;Dispril;Easprin;Ecotrin;Endosprin;Magnecyl;Micristin;Polopirin;Polopiryna;Solprin;Solupsan;Zorprin

Chemical Property of Aspirin

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0.000124mmHg at 25°C
• Melting Point: 134-136 °C(lit.)
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 321.4 °C at 760 mmHg
• PKA: 3.5(at 25℃)
• Flash Point: 131.1 °C
• PSA: 63.60000
• Density: 1.35
• LogP: 1.31010
• Storage Temp.: Store at RT.
• Solubility.: H2O: 10 mg/mL at 37 °C
• Water Solubility.: 3.3 g/L (20 ºC)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 180.04225873
• Heavy Atom Count: 13
• Complexity: 212
• Transport DOT Label: Poison

Purity/Quality:

Above 99% ^*data from raw suppliers

Acetylsalicylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Antithrombotic Agents, Antiinflammatory Agents, Salicylates
• Canonical SMILES: CC(=O)OC1=CC=CC=C1C(=O)O
• Recent ClinicalTrials: Postpartum Low-Dose Aspirin After Preeclampsia for Optimization of Cardiovascular Risk (PAPVASC)
• Recent EU Clinical Trials: The safety of ticagrelor monotherapy after primary percutaneous coronary intervention for ST-elevation myocardial infarction and the effect on intramyocardial haemorrhage
• Recent NIPH Clinical Trials: J-FAPP Study V
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. Ingestion of large amounts could cause effects on the blood and central nervous system.
• Effects of Long Term Exposure: Animal tests show that this substance possibly causes toxic effects upon human reproduction.
• Uses: 1.Acetylsalicylic acid is the raw material for rodenticide intermediates 4-hydroxycoumarin. 2.Used to make outdoor structural members and equipment parts exposed in highlights, such as the automobile body, agricultural machinery parts, meters and electric lamps, road marking, etc. 3.It is the earliest applied, the most popular and the most common antipyretic analgesics anti-rheumatism medicine, has aspects of pharmacological effects as antipyretic-analgesic and anti-inflammatory, anti-platelet aggregation and works quickly and effectively. Overdosage can be easily diagnosed and treated, with rare allergic reactions. Often used to cold fever, headache, neuralgia, joint ache, muscle pain, rheumatic fever, acute wet sex arthritis, rheumatoid arthritis and toothache, etc. Listed in National Essential Medicine List. Acetylsalicylic acid also works as an intermediate of other medicines. Acetylsalicylic acid's original use as an analgesic, an antipyretic, and to reduce inflammation continues to this day. More recently there is some evidence that aspirin lessens the chance of heart attacks as a result of its effect as a blood "thinner." Analgesic; antipyretic; anti-inflammatory; antithrombotic antifungal Axepim Cephalosporin antibiotic Acetylsalicylic acid is the prototypical analgesic used in the treatment of mild to moderate pain. Acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Acetylsalicylic acid also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. Along with sodium salicylate (sc-3520), aspirin has been shown to block the long terminal repeat from the human immunodeficiency virus and the Ig κ enhancer from NFκB dependent transcription.
• Production method: Acetylsalicylic acid: add acetic anhydride (feeding ratio is 0.7889 times of the total salicylic acid) in reaction vessel, and then add two thirds of salicylic acid, stir it and temperature rises. React 40-60min in 81-82℃. Cool it to 81-82 ℃ and keep the temperature for 2h. When free salicylic acid is qualified, cool it to 13 ℃, precipitation crystallization, rejection filter, dry it in 65-70℃ air flow, then we get acetylsalicylic acid.
• Description: Acetylsalicylic acid is a white crystalline powder commonly known by its common name as aspirin or ASA. Aspirin is the most widely used medication in the world.
• Physical properties: Acetylsalicylic acid, an acetyl derivative of salicylic acid, is a white, crystalline, weakly acidic substance, with a melting point of 136 °C , and a boiling point of 140 °C . Synthesis The synthesis of aspirin is classified as an esterification reaction. Salicylic acid is treated with acetic anhydride, an acid derivative, causing a chemical reaction that turns salicylic acid's hydroxyl group into an ester group (R-OH → R-OCOCH3). This process yields aspirin and acetic acid, which is considered a byproduct of this reaction. Polymorphism Polymorphism, or the ability of a substance to form more than one crystal structure, is important in the development of pharmaceutical ingredients. Many drugs are receiving regulatory approval for only a single crystal form or polymorph. For a long time, only one crystal structure for aspirin was known. That aspirin might have a second crystalline form was suspected since the 1960s. The elusive second polymorph was first discovered by Vishweshwar and coworkers in 2005 , and fine structural details were given by Bond et al. .
• Indications: Acetylsalicylic acid is available as capsules, tablets, enteric-coated tablets (Ecotrin), timed-release tablets (ZORprin), buffered tablets (Ascriptin, Bufferin), and as rectal suppositories. Sodium salicylate is available generically. Other salicylates include choline salicylate (Arthropan), choline magnesium trisalicylate (Trilisate), and magnesium salicylate (Momentum).
• Biological Functions: Acetylsalicylic acid is one of the most important NSAIDs because it decreases pain at predominantly peripheral sites with little cortical interaction and thus has few CNS effects. The prototypical COX-2 inhibitors are celecoxib (Celebrex) and its chemical cousin, rofecoxib (Vioxx). In addition to a role in inflammatory processes,COX-2 seems to play a role in colon cancer and Alzheimer’s disease, providing potential additional uses for COX-2-selective drugs.
• Clinical Use: Acetylsalicylic acid?is used in the treatment of a number of conditions, including fever, pain, rheumatic fever, and inflammatory diseases, such as rheumatoid arthritis, pericarditis, and Kawasaki disease.PainAsprin 325 MG for pain In most cases, Acetylsalicylic acid?is considered inferior to ibuprofen for the alleviation of pain, because Acetylsalicylic acid?is more likely to cause gastrointestinal bleeding . Acetylsalicylic acid?is generally ineffective for those pains caused by muscle cramps, bloating, gastric distension, or acute skin irritation.HeadacheAcetylsalicylic acid, either by itself or in combined formulation, effectively treats some types of headache, but its efficacy may be questionable for others.Acetylsalicylic acid?or other overthe- counter analgesics are widely recognized as effective for the treatment of tension headache. Acetylsalicylic acid, especially as a component of an acetaminophen/Acetylsalicylic acid/caffeine formulation (e.g., Excedrin Migraine), is considered a first - line therapy in the treatment of migraine, and comparable to lower doses of sumatriptan.FeverLike its ability to control pain, Acetylsalicylic acid's ability to control fever is due to its action on the prostaglandin system through its irreversible inhibition of COX .Heart attacks and strokesFor a subset of the population, Acetylsalicylic acid?may help prevent heart attacks and strokes. In lower doses, Acetylsalicylic acid?has been known to prevent the progression of existing cardiovascular disease, and reduce the frequency of these events for those with a history of them . ( This is known as secondary prevention.)Post-surgeryAfter percutaneous coronary interventions (PCIs), such as the placement of a coronary artery stent, a US Agency for Healthcare Research and Quality guideline recommends that Acetylsalicylic acid?be taken indefinitely.Frequently, Acetylsalicylic acid?is combined with an ADP receptor inhibitor, such as clopidogrel, prasugrel or ticagrelor to prevent blood clots. This is called dual anti-platelet therapy (DAPT).
• Drug interactions: Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect, increased risk of nephrotoxicity and hyperkalaemia. Analgesics: avoid concomitant use of 2 or more NSAIDs - increased side effects; avoid with ketorolac - increased risk of side effects and haemorrhage. Antibacterials: possibly increased risk of convulsions with quinolones. Anticoagulants: effects of coumarins enhanced; possibly increased risk of bleeding with edoxaban, heparins and coumarins. Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine. Antidiabetic agents: effects of sulphonylureas enhanced. Antiepileptics: possibly increased phenytoin concentration. Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir. Ciclosporin: may potentiate nephrotoxicity. Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib. Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect, hyperkalaemia with potassium-sparing diuretics; increased risk of toxicity of acetazolamide with high dose aspirin. Lithium: excretion decreased. Pentoxifylline: increased risk of bleeding. Tacrolimus: increased risk of nephrotoxicity.

Technology Process of Aspirin

There total 97 articles about Aspirin 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: 100.0%

acetic anhydride (108-24-7) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → aspirin (50-78-2,98201-60-6)

Guidance literature:

In neat (no solvent); Molecular sieve; Microwave irradiation; Green chemistry;

DOI:10.3762/bjoc.12.214

Reference yield: 100.0%

methylene-benzo[1,3]dioxin-4-one (302353-24-8) → aspirin (50-78-2,98201-60-6)

Guidance literature:

With water; at 25 ℃; for 1h; pH=7;

DOI:10.1016/S0040-4039(01)00996-0

Reference yield: 95.7%

acetic acid (64-19-7,77671-22-8) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → aspirin (50-78-2,98201-60-6)

Guidance literature:

at 80 - 90 ℃;

upstream raw materials:

acetic anhydride

salicylic acid

benzene

(2-acetoxy-benzoic acid )-acetic acid-anhydride

Downstream raw materials:

methyl acetylsalicylate

acetylsalicylsalicylic acid

(2-acetoxy-benzoyl)-carbonic acid ethyl ester

4-Methylacetanilide

Refernces

• 1、 Everett,Naylor,Patel,Stratford,Wardman. "Bioreductively-activated prodrugs for targeting hypoxic tissue: Elimination of aspirin from 2-nitroimidazole derivatives". . p. 1267 - 1272. Retrieved 1999.
• 2、 Bamoharram, Fatemeh F.,Heravi, Majid M.,Roshani, Mina,Gharib, Ali,Jahangir, Manouchehr. "Catalytic method for synthesis of aspirin by a green, efficient and recyclable solid acid catalyst (Preyssler's anion) at room temperature". . p. 1017 - 1020. Retrieved 2007.
• 3、 Tyagi, Beena,Mishra, Manish Kumar,Jasra, Raksh Vir. "Solvent free synthesis of acetyl salicylic acid over nano-crystalline sulfated zirconia solid acid catalyst". . p. 41 - 45. Retrieved 2010.
• 4、 Sha, Jing-Quan,Yang, Xi-Ya,Sun, Long-Jiang,Li, Shu-Xian,Sheng, Ning,Li, Ji-Shen. "Construction and catalytic activities of polyoxometalate-based compound containing helical chains". . p. 392 - 403. Retrieved 2017.
• 5、 Bayer & Co.. "-". . p. 376. Retrieved 1900.
• 6、 Liu, Yanfei,Long, Shuo,Zhang, Shanshan,Tan, Yifu,Wang, Ting,Wu, Yuwei,Jiang, Ting,Liu, Xiaoqin,Peng, Dongming,Liu, Zhenbao. "Synthesis and antioxidant activities of berberine 9-: O -benzoic acid derivatives". . p. 17611 - 17621. Retrieved 2021/05/29.
• 7、 Cho, Hanna,Cho, Kyungseon,Kim, Mi-Jin,Kim, Nam Doo,Lee, In-Kyu,Park, Sungmi,Shin, Injae,Sim, Taebo,Yoo, Eun Kyung,Yoon, Hojong. "Identification of Novel Resorcinol Amide Derivatives as Potent and Specific Pyruvate Dehydrogenase Kinase (PDHK) Inhibitors". . . Retrieved 2019/10/08.