2-(acetyloxy)benzoic acid

• ChemBase ID: 821
• Molecular Formular: C9H8O4
• Molecular Mass: 180.15742
• Monoisotopic Mass: 180.04225874
• SMILES: O(c1c(cccc1)C(=O)O)C(=O)C
• Canonical SMILES: CC(=O)Oc1ccccc1C(=O)O
• InChI: InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
• InChIKey: BSYNRYMUTXBXSQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(acetyloxy)benzoic acid
• IUPAC Traditional name: aspirin
• Brand Name: Acetophen; Acetosal; Acetosalin; Acetylin; Acetylsal; Acimetten; Acisal; Acylpyrin; Adiro; Asagran; Asatard; Ascoden-30; Aspalon; Aspec; Aspergum; Aspirdrops; Aspirine; Aspro; Asteric; Bayer Extra Strength Aspirin For Migraine Pain; Benaspir; Bi-prin; Bialpirina; Bialpirinia; Bufferin; Caprin; Cemirit; Claradin; Clariprin; Colfarit; Contrheuma retard; Coricidin; Crystar; Decaten; Delgesic; Dolean pH 8; Duramax; ECM; Easprin; Ecolen; Ecotrin; Empirin; Endydol; Entericin; Enterophen; Enterosarein; Enterosarine; Entrophen; Extren; Globentyl; Globoid; Helicon; Idragin; Levius; Measurin; Micristin; Neuronika; Novid; Nu-seals; Nu-seals aspirin; Persistin; Pharmacin; Pirseal; Polopiryna; Premaspin; Rheumintabletten; Rhodine; Rhonal; Salacetin; Salcetogen; Saletin; Solfrin; Solprin; Solprin acid; Solpyron; Spira-Dine; St. Joseph; St. Joseph Aspirin for Adults; Supac; Tasprin; Temperal; Triaminicin; Triple-sal; Vanquish; Xaxa; Yasta; Aspirin; 8-hour Bayer; A.S.A. Empirin; Acenterine; Acesal; Acetal; Aceticyl; Acetisal; Acetol; Acetonyl
• Synonyms: Aspirin; o-Acetoxybenzoic acid; O-Acetylsalicylic acid; o-Carboxyphenyl acetate; Salicylic acid acetate; Salicylic acid, acetate; Kyselina 2-acetoxybenzoova; Kyselina acetylsalicylova; Acetylsalicylic acid; 2-Acetoxybenzenecarboxylic acid; 2-Acetoxybenzoic acid; 2-Carboxyphenyl acetate; A.S.A.; Acetosalic acid; Acetoxybenzoic acid; Acetylsalicylsaure (GERMAN); Acetylsalicylate; Acetysalicylic acid; Acide acetylsalicylique (FRENCH); Acido acetilsalicilico; Acido O-acetil-benzoico; Acidum acetylsalicylicum; Acetilum acidulatum; Acetilsalicilico; ASA; O-accetylsalicylic acid; Aspirin (Acetylsalicylic acid); 2-(Acetyloxy)benzoic Acid; Acylpyrin; Angettes; Aspro; Aspirin; Acetylsalicylic acid; Acetylsalicylic acid; 2-acetyloxybenzoic acid; Aspirin; Acetal; O-Acetylsalicylic acid; 乙酰水杨酸; 阿司匹林; 2-乙酰氧基苯甲酸; O-乙酰基水杨酸; 阿斯匹林; 乙酰水杨酸; O-乙酰基水杨酸

Database IDs

• CAS Number: 50-78-2; 105-57-7
• EC Number: 200-064-1
• MDL Number: MFCD00002430
• Beilstein Number: 779271
• Merck Index: 14851
• PubChem SID: 24278218; 46505803; 24890723; 24890623; 24891140; 160964284
• PubChem CID: 2244
• CHEBI ID: 15365
• ATC CODE: N02BA01; B01AC06; A01AD05
• CHEMBL: 25
• Chemspider ID: 2157
• DrugBank ID: DB00945
• KEGG ID: D00109
• Unique Ingredient Identifier: R16CO5Y76E
• Wikipedia Title: Aspirin
• Medline Plus: a682878

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4147992
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.83532584
• LogD (pH = 7.4): -2.1610374
• Log P: 1.2380897
• Molar Refractivity: 44.4466 cm^3
• Polarizability: 17.147835 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.43
• LOG S: -2.09
• Solubility (Water): 1.46e+00 g/l

PROPERTIES

Physical Property

• Solubility: 3 mg/mL (20°C) in water; 4.6 mg/mL; aqueous base: decomposes; DMSO; Ethanol; ethanol: soluble50 mg/mL; H2O: soluble10 mg/mL at 37 °C; H2O: soluble3 mg/mL at 25 °C; Water
• Apperance: white crystalline; White Solid
• Melting Point: 134-136 °C; 134-136 °C(lit.); 134-136°C; 135 °C; 136°C (276.8°F); 136-140°C
• Boiling Point: 140 °C (decomposes); 140°C (284°F) (decomposes)
• Flash Point: 250 °C; 250°C(482°F); 482 °F
• Auto Ignition Point: 490 °C
• Density: 1.40 g/cm^3; 1.400; 1350 kg/m3 at 20 °C
• Vapor Pressure: 2.52E-05 mm Hg at 25 deg. C (calculated)
• Absorption Wavelength: ε1mM/230 nm, aqueous acid 466; ε1mM/231 nm, aqueous base 409; ε1mM/278 nm, aqueous acid 68; ε1mM/298 nm, aqueous base 190
• Hydrophobicity(logP): 1.4
• pKa: 3.5

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: VO0700000
• European Hazard Symbols: Toxic (T); X; Harmful (Xn)
• UN Number: 2811
• German water hazard class: 1
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: 22-36/37/38; R:25-68
• Safety Statements: 26; 26-36/37; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Target: Others
• Admin Routes: Most commonly oral, also rectal, lysine acetylsalicylate may be given IV or IM
• Bioavailability: Rapidly and completely absorbed
• Excretion: Renal
• Half Life: 300–650 mg dose: 3.1–3.2 h; 1 g dose: 5 h; 2 g dose: 9 h
• Metabolism: Hepatic
• Protein Bound: 99.6%
• Legal Status: GSL (UK); OTC (US); unscheduled (Australia)
• Pregnancy Category: C (Australia); D (US)
• Gene Information: human ... ITGA2B(3674), ITGB3(3690), PTGS1(5742), PTGS2(5743); human ... ITGA2B(3674), PTGS1(5742), PTGS2(5743)

Product Information

• Purity: ≥99%; ≥99.0%; ≥99.0% (HPLC); 97%; 99%
• Grade: analytical standard; purum
• Salt Data: Free Base
• Packaging: vial of 500 mg
• Suitability: meets USP testing specifications; plant cell culture tested
• Ignition Residue: ≤0.1%
• Pharmacopeia Traceability: traceable to BP 617; traceable to PhEur A0200000; traceable to USP 1044006
• Linear Formula: 2-(CH3CO2)C6H4CO2H

DETAILS

MP Biomedicals - 02150245

Crystalline

DrugBank - DB00945

• Drug Groups: approved
• Description: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and 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. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5)
• Indication: For use in the temporary relief of various forms of pain, inflammation associated with various conditions (including rheumatoid arthritis, juvenile rheumatoid arthritis, systemic lupus erythematosus, osteoarthritis, and ankylosing spondylitis), and is also used to reduce the risk of death and/or nonfatal myocardial infarction in patients with a previous infarction or unstable angina pectoris.
• Pharmacology: Acetylsalicylic acid is an analgesic, antipyretic, antirheumatic, and anti-inflammatory agent. Acetylsalicylic acid's mode of action as an antiinflammatory and antirheumatic agent may be due to inhibition of synthesis and release of prostaglandins. Acetylsalicylic acid appears to produce analgesia by virtue of both a peripheral and CNS effect. Peripherally, acetylsalicylic acid acts by inhibiting the synthesis and release of prostaglandins. Acting centrally, it would appear to produce analgesia at a hypothalamic site in the brain, although the mode of action is not known. Acetylsalicylic acid also acts on the hypothalamus to produce antipyresis; heat dissipation is increased as a result of vasodilation and increased peripheral blood flow. Acetylsalicylic acid's antipyretic activity may also be related to inhibition of synthesis and release of prostaglandins.
• Toxicity: Oral, mouse: LD₅₀ = 250 mg/kg; Oral, rabbit: LD₅₀ = 1010 mg/kg; Oral, rat: LD₅₀ = 200 mg/kg. Effects of overdose include: tinnitus, abdominal pain, hypokalemia, hypoglycemia, pyrexia, hyperventilation, dysrhythmia, hypotension, hallucination, renal failure, confusion, seizure, coma, and death.
• Affected Organisms: Humans and other mammals
• Biotransformation: Acetylsalicylic acid is rapidly hydrolyzed primarily in the liver to salicylic acid, which is conjugated with glycine (forming salicyluric acid) and glucuronic acid and excreted largely in the urine.
• Absorption: Absorption is generally rapid and complete following oral administration but may vary according to specific salicylate used, dosage form, and other factors such as tablet dissolution rate and gastric or intraluminal pH.
• Half Life: The plasma half-life is approximately 15 minutes; that for salicylate lengthens as the dose increases: doses of 300 to 650 mg have a half-life of 3.1 to 3.2 hours; with doses of 1 gram, the half-life is increased to 5 hours and with 2 grams it is increased to about 9 hours.
• Protein Binding: High (99.5%) to albumin. Decreases as plasma salicylate concentration increases, with reduced plasma albumin concentration or renal dysfunction, and during pregnancy.
• References: Macdonald S: Aspirin use to be banned in under 16 year olds. BMJ. 2002 Nov 2;325(7371):988. [Pubmed] ; Sneader W: The discovery of aspirin: a reappraisal. BMJ. 2000 Dec 23-30;321(7276):1591-4. [Pubmed] ; Aukerman G, Knutson D, Miser WF: Management of the acute migraine headache. Am Fam Physician. 2002 Dec 1;66(11):2123-30. [Pubmed] ; Randomised trial of intravenous streptokinase, oral aspirin, both, or neither among 17,187 cases of suspected acute myocardial infarction: ISIS-2. ISIS-2 (Second International Study of Infarct Survival) Collaborative Group. Lancet. 1988 Aug 13;2(8607):349-60. [Pubmed] ; Dorsch MP, Lee JS, Lynch DR, Dunn SP, Rodgers JE, Schwartz T, Colby E, Montague D, Smyth SS: Aspirin resistance in patients with stable coronary artery disease with and without a history of myocardial infarction. Ann Pharmacother. 2007 May;41(5):737-41. Epub 2007 Apr 24. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - A6810

Application
用于植物细胞程序性凋亡研究。
Biochem/physiol Actions
通过抑制环加氧酶（前列腺素 H 合成酶）来阻断前列腺素的生成，对 COX-1 亚型具有较高的选择性。可抑制血小板中的 COX-1，从而阻断血栓素的生成和血小板凝集，因此具有抗血栓形成的作用。针对结直肠和其他实体瘤的化学防治剂。

Sigma Aldrich - A2093

Biochem/physiol Actions
通过抑制环加氧酶（前列腺素 H 合成酶）来阻断前列腺素的生成，对 COX-1 亚型具有较高的选择性。可抑制血小板中的 COX-1，从而阻断血栓素的生成和血小板凝集，因此具有抗血栓形成的作用。针对结直肠和其他实体瘤的化学防治剂。

Sigma Aldrich - A3160

Biochem/physiol Actions
通过抑制环加氧酶（前列腺素 H 合成酶）来阻断前列腺素的生成，对 COX-1 亚型具有较高的选择性。可抑制血小板中的 COX-1，从而阻断血栓素的生成和血小板凝集，因此具有抗血栓形成的作用。针对结直肠和其他实体瘤的化学防治剂。
包装
棕色螺纹盖样品瓶包装

Sigma Aldrich - A5376

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
通过抑制环加氧酶（前列腺素 H 合成酶）来阻断前列腺素的生成，对 COX-1 亚型具有较高的选择性。可抑制血小板中的 COX-1，从而阻断血栓素的生成和血小板凝集，因此具有抗血栓形成的作用。针对结直肠和其他实体瘤的化学防治剂。
包装
1 kg in poly bottle
100, 250, 500 g in poly bottle

Sigma Aldrich - 239631

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.

Sigma Aldrich - 132926

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.

Sigma Aldrich - 01459

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.

Sigma Aldrich - 01478

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.

Toronto Research Chemicals - A187780

Analgesic; antipyretic; anti-inflammatory; antithrombotic.

REFERENCES

• Macdonald S: Aspirin use to be banned in under 16 year olds. BMJ. 2002 Nov 2;325(7371):988. Pubmed
• Sneader W: The discovery of aspirin: a reappraisal. BMJ. 2000 Dec 23-30;321(7276):1591-4. Pubmed
• Aukerman G, Knutson D, Miser WF: Management of the acute migraine headache. Am Fam Physician. 2002 Dec 1;66(11):2123-30. Pubmed
• Randomised trial of intravenous streptokinase, oral aspirin, both, or neither among 17,187 cases of suspected acute myocardial infarction: ISIS-2. ISIS-2 (Second International Study of Infarct Survival) Collaborative Group. Lancet. 1988 Aug 13;2(8607):349-60. Pubmed
• Dorsch MP, Lee JS, Lynch DR, Dunn SP, Rodgers JE, Schwartz T, Colby E, Montague D, Smyth SS: Aspirin resistance in patients with stable coronary artery disease with and without a history of myocardial infarction. Ann Pharmacother. 2007 May;41(5):737-41. Epub 2007 Apr 24. Pubmed
• Hart, E.R., et al.: J. Pharmacol. Exp. Ther., 89, 205 (1947)
• Florey, K., et al.: Anal. Profiles Drug Subs., 8, 1 (1947)