132926
Acetylsalicylic acid
99%
Synonym(s):
2-Acetoxybenzoic acid, O-Acetylsalicylic acid, ASA, Aspirin
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About This Item
Linear Formula:
2-(CH3CO2)C6H4CO2H
CAS Number:
Molecular Weight:
180.16
Beilstein:
779271
EC Number:
MDL number:
UNSPSC Code:
12352103
Assay
99%
mp
134-136 °C (lit.)
SMILES string
CC(=O)Oc1ccccc1C(O)=O
InChI
1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
InChI key
BSYNRYMUTXBXSQ-UHFFFAOYSA-N
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Biochem/physiol Actions
Blocks the production of prostaglandins by inhibiting cyclooxygenase (prostaglandin H synthase), with greater selectivity toward the COX-1 isoform. The antithrombotic effect is due to the inhibition of COX-1 in platelets that blocks thromboxane production and platelet aggregation. Chemopreventive against colorectal and other solid tumors.
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Niels Hulsman et al.
Journal of medicinal chemistry, 50(10), 2424-2431 (2007-04-20)
Hybrid drug 1 (NO-ASA) continues to attract intense research from chemists and biologists alike. It consists of ASA and a -ONO2 group connected through a spacer and is in preclinical development as an antitumor drug. We report that, contrary to
Carlos A Velázquez et al.
Journal of medicinal chemistry, 51(6), 1954-1961 (2008-03-05)
The carboxylic acid group of the anti-inflammatory (AI) drugs aspirin and indomethacin was covalently linked to the 1-(2-carboxypyrrolidin-1-yl)diazen-1-ium-1,2-diolate ion via a one-carbon methylene spacer to obtain two new hybrid prodrugs. The aspirin prodrug ( 23) was a 2.2-fold more potent
Morshed A Chowdhury et al.
Bioorganic & medicinal chemistry letters, 20(4), 1324-1329 (2010-01-26)
A new group of hybrid nitric oxide (NO) releasing anti-inflammatory (AI) coxib prodrugs (NO-coxibs) wherein the para-tolyl moiety present in celecoxib was replaced by a N-(4-nitrooxybutyl)piperidyl 15a-b, or N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridyl 17a-b, NO-donor moiety was synthesized. All compounds released a low amount
Hiroko Sano et al.
Bioorganic & medicinal chemistry letters, 16(11), 3068-3072 (2006-03-04)
Indole- and indoline-type basic COX-1-selective competitive inhibitors, 5-amino-1-(3,5-dimethylbenzoyl)-1H-indole (1) and 5-amino-1-(3,5-dimethylphenyl)-2,3-dihydro-1H-indole (2), were found to possess anti-angiogenic activity estimated as a tube formation-inhibition using human umbilical vein endothelial cells (HUVECs).
Carlos A Velázquez et al.
Bioorganic & medicinal chemistry, 15(14), 4767-4774 (2007-05-19)
A novel group of O2-acetoxymethyl-protected diazeniumdiolate-based non-steroidal anti-inflammatory prodrugs (NONO-NSAIDs) were synthesized by esterifying the carboxylate group of aspirin, ibuprofen, or indomethacin with O2-acetoxymethyl 1-[N-(2-hydroxyethyl)-N-methylamino]diazeniumdiolate. The resulting nitric oxide (*NO)-releasing prodrugs (7-9) did not exhibit in vitro cyclooxygenase (COX) inhibitory
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