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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:
50-78-2
Molecular Weight:
180.16
Beilstein:
779271
EC Number:
200-064-1
MDL number:
MFCD00002430
UNSPSC Code:
12352106
PubChem Substance ID:
24278218
NACRES:
NA.21
Pricing and availability is not currently available.

biological source

synthetic

Quality Level

200

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

Gene Information

human ... ITGA2B(3674) , ITGB3(3690) , PTGS1(5742) , PTGS2(5743)

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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
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF3892V
WXBF2976V
WXBF2042V
WXBD9906V
WXBF0972V

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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
Connie N Hess et al.
Journal of the American College of Cardiology, 66(7), 777-787 (2015-08-14)
Bleeding limits anticoagulant treatment in patients with acute coronary syndromes (ACS). We investigated whether background concomitant antiplatelet therapy influences the effects of apixaban after ACS. This study examined high-risk ACS patients who were treated with aspirin or aspirin plus clopidogrel
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
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
View All Related Papers

Questions

1–7 of 7 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. could you please tell me what is the stability of aspirin (cat #5376) once recnstituted in PBS please?

    1 answer

    1. Aqueous solutions of acetylsalicylic acid will readily hydrolyze to form salicylic acid. Solutions are most stable at pH 2 - 3, but to assure full activity, solutions should be freshly prepared. Please see the link below to review a publication on the compound stability:
      https://intapi.sciendo.com/pdf/10.1515/cipms-2016-0009

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  4. How should solutions of Product A5376, Acetylsalicylic acid, be prepared and stored?

    1 answer

    1. Acetylsalicylic acid is slightly soluble in water, with a limit of solubility reported as approximately 3 mg/ml at 25 Deg C.  It is also soluble in ethanol at 50 mg/ml and will dissolve in solutions of alkali hydroxides and carbonates with decomposition.  Aqueous solutions of acetylsalicylic acid are most stable at pH 2 - 3, but to assure full activity, fresh solutions are recommended.

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  5. How does aspirin act as an anticlotting agent?

    1 answer

    1. There may be multiple modes of action which result in the anticlotting properties of aspirin. Some studies have indicated a decrease in thrombin levels and others reduced clotting properties of fibrinogen.

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  6. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  7. Is Product A5376, Acetylsalicylic acid, offered by Sigma-Aldrich different from that found in aspirin tablets from the drug store?

    1 answer

    1. The active ingredient acetylsalicylic acid offered by Sigma-Aldrich is the same chemical as found in aspirin tablets. However, chemicals for pharmaceutical use are manufactured, tested, and packaged under the regulation of the FDA, but chemicals sold for research use do not have the same regulatory oversight.

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