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Key Documents

A5376

Sigma-Aldrich

Acetylsalicylic acid

≥99.0%

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:
12352106
PubChem Substance ID:
NACRES:
NA.21

biological source

synthetic

Quality Level

Assay

≥99.0%

form

powder

color

white

pKa (25 °C)

3.5

mp

134-136 °C (lit.)

solubility

H2O: 10 mg/mL at 37 °C(lit.)
H2O: 3 mg/mL at 25 °C(lit.)
ethanol: 50 mg/mL
aqueous base: decomposes

ε (extinction coefficient)

190 at 298 nm in aqueous base at 1 mM
409 at 231 nm in aqueous base at 1 mM
466 at 230 nm in aqueous acid at 1 mM
68 at 278 nm in aqueous acid at 1 mM

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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General description

Acetylsalicylic acid is an organic compound commonly referred to as aspirin. It works by blocking the production of compounds in the body that cause pain, swelling, and fever. Acetylsalicylic acid also serves a vital function in preventing blood clots from forming in the arteries. In research, acetylsalicylic acid is studied for its role in oxidative stress, and in cancer research as a biomarker.

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

482.0 °F

Flash Point(C)

250 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Seung-Hwan Jung et al.
Redox biology, 37, 101751-101751 (2020-10-21)
Treatment with nonsteroidal anti-inflammatory drugs (NSAIDs) is associated with various side effects, including cardiovascular and hepatic disorders. Studies suggest that mitochondrial damage and oxidative stress are important mediators of toxicity, yet the underlying mechanisms are poorly understood. In this study
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
Christina Perneby et al.
Thrombosis and haemostasis, 95(4), 652-658 (2006-04-08)
Aspirin is widely used, but dosages in different clinical situations and the possible importance of "aspirin resistance" are debated. We performed an open cross-over study comparing no treatment (baseline) with three aspirin dosage regimens--37.5 mg/day for 10 days, 320 mg/day
Katarzyna Palus et al.
PloS one, 10(11), e0143661-e0143661 (2015-11-26)
This experiment was designed to establish the localization and neurochemical phenotyping of sympathetic neurons supplying prepyloric area of the porcine stomach in a physiological state and during acetylsalicylic acid (ASA) induced gastritis. In order to localize the sympathetic perikarya the
Gregg W Stone et al.
Lancet (London, England), 382(9892), 614-623 (2013-07-31)
The relation between platelet reactivity and stent thrombosis, major bleeding, and other adverse events after coronary artery implantation of drug-eluting stents has been incompletely characterised. We aimed to determine the relation between platelet reactivity during dual therapy with aspirin and

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