Acetylsalicylic acid (C9H8O4) or aspirin is a commonly used medication for relieving pain, reducing fever, and preventing blood clotting. It belongs to the class of drugs known as nonsteroidal anti-inflammatory drugs (NSAIDs).
| IUPAC Name | 2-acetoxybenzoic acid |
| Molecular Formula | C9H8O4 |
| CAS Number | 50-78-2 |
| Synonyms | Aspirin, ASA, acetylsalicylate, etc. |
| InChI | InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12) |
Acetylsalicylic Acid Properties
Acetylsalicylic Acid Formula
The chemical formula of acetylsalicylic acid is C9H8O4. It consists of nine carbon atoms, eight hydrogen atoms, and four oxygen atoms.
Acetylsalicylic Acid Molar Mass
The molar mass of acetylsalicylate is calculated by adding up the atomic masses of its constituent elements. It is approximately 180.16 grams per mole (g/mol).
Acetylsalicylic Acid Boiling Point
Acetylsalicylate has a boiling point of about 140 degrees Celsius (°C). At this temperature, the compound transitions from a liquid to a gaseous state.
Acetylsalicylic Acid Melting Point
The melting point of acetylsalicylate is around 135 degrees Celsius (°C). When heated to this temperature, it changes from a solid to a liquid.
Acetylsalicylic Acid Density g/mL
The density of acetylsalicylate is typically reported as approximately 1.40 grams per milliliter (g/mL). This value indicates the mass of the compound per unit volume.
Acetylsalicylic Acid Molecular Weight
The molecular weight of acetylsalicylate is approximately 180.16 grams per mole (g/mol). It represents the sum of the atomic weights of all the atoms in one molecule of the compound.
Acetylsalicylic Acid Structure
The structure of acetylsalicylate consists of a benzene ring with a carboxylic acid group (-COOH) and an acetyl group (-COCH3) attached. This structure gives it its unique properties and pharmacological effects.
Acetylsalicylic Acid Solubility
Acetylsalicylate is sparingly soluble in water, with a solubility of about 1-2 grams per 100 milliliters (g/100 mL) of water at room temperature. However, it is more soluble in organic solvents like ethanol and acetone.
These properties of acetylsalicylate play a crucial role in its pharmaceutical applications, such as its use as a pain reliever, fever reducer, and anti-inflammatory agent.
| Appearance | White crystalline powder |
| Specific Gravity | 1.40 |
| Color | Colorless |
| Odor | Odorless |
| Molar Mass | 180.16 g/mol |
| Density | 1.40 g/mL |
| Melting Point | 135 °C |
| Boiling Point | 140 °C |
| Flash Point | Not applicable |
| Water Solubility | Sparingly soluble |
| Solubility | Soluble in organic solvents |
| Vapor Pressure | Not available |
| Vapor Density | Not available |
| pKa | 3.5 (carboxylic acid group) |
| pH | 2.4 (when dissolved in water) |
Acetylsalicylic Acid Safety and Hazards
Acetylsalicylate should be handled with caution due to its potential safety hazards. It may cause irritation to the skin, eyes, and respiratory system upon contact or inhalation. Ingesting high doses can lead to gastrointestinal disturbances and even toxicity. Individuals with a history of bleeding disorders or stomach ulcers should exercise extra care when using this compound. As with any medication, allergic reactions are possible, and immediate medical attention should be sought if symptoms such as difficulty breathing or swelling occur. It is important to follow recommended dosages and consult a healthcare professional before using acetylsalicylate, especially in combination with other medications.
| Hazard Symbols | GHS07 |
| Safety Description | Causes eye and skin irritation. Harmful if swallowed or inhaled. |
| UN IDs | UN 2811 (Solid) |
| HS Code | 2918.11.00 |
| Hazard Class | 6.1 (Toxic substances) |
| Packing Group | III |
| Toxicity | Moderate toxicity with potential gastrointestinal effects. |
These risk and safety properties outline the potential hazards associated with acetylsalicylate and provide guidance for its safe handling, transportation, and storage. It is important to adhere to proper safety measures and regulations when dealing with this substance to minimize any potential risks to human health and the environment.
Acetylsalicylic Acid Synthesis Methods
Various methods allow for the synthesis of acetylsalicylate.
One commonly used method for synthesizing acetylsalicylate involves esterifying salicylic acid with acetic anhydride in the presence of a catalyst like sulfuric acid or phosphoric acid. The reaction yields acetylsalicylate and acetic acid as byproducts, and the filtration process collects them after cooling the reaction mixture.
Another method utilizes acetic acid instead of acetic anhydride. A mixture of salicylic acid and acetic acid undergoes heating with an acid catalyst, typically sulfuric acid. The reaction proceeds to form acetylsalicylate and water. Upon cooling, one isolates the solid product from the resulting mixture.
The Kolbe-Schmitt reaction offers an alternative route for preparing acetylsalicylate. Sodium phenolate, obtained from the reaction of salicylic acid with sodium hydroxide, undergoes treatment with carbon dioxide under high pressure and temperature. The resulting salicylate is then acidified to yield acetylsalicylate.
These synthesis methods provide routes to produce acetylsalicylate on an industrial scale, ensuring a stable and reliable supply for various applications in the pharmaceutical industry. It is important to note that these processes require expertise and adherence to safety protocols to ensure efficient and safe production.
Acetylsalicylic Acid Uses
Acetylsalicylate finds a wide range of uses due to its beneficial properties. Here are some key applications:
- Pain relief: Acetylsalicylate relieves mild to moderate pain, such as headaches, toothaches, and muscle aches.
- Fever reduction: Acetylsalicylate reduces fever effectively, making it a preferred choice for managing febrile conditions.
- Anti-inflammatory effects: Acetylsalicylate possesses anti-inflammatory properties, making it useful in reducing inflammation associated with conditions like arthritis and sports injuries.
- Blood clot prevention: As a blood-thinning agent, acetylsalicylate helps prevent the formation of blood clots, lowering the risk of heart attacks and strokes.
- Cardiovascular health: Healthcare professionals may recommend regular low-dose intake of acetylsalicylate for individuals at high risk of cardiovascular diseases to improve their cardiovascular health.
- Antiplatelet therapy: Antiplatelet therapy utilizes acetylsalicylate to actively inhibit platelet aggregation and actively decrease the chances of blood clot formation in conditions such as atrial fibrillation and after stent placement.
- Transient ischemic attack (TIA) prevention: Acetylsalicylate may be prescribed for preventing transient ischemic attacks, which are brief episodes of reduced blood flow to the brain.
- Rheumatic fever prophylaxis: In individuals at risk, acetylsalicylate is actively used for prophylaxis against rheumatic fever in certain cases.
These diverse applications demonstrate the broad utility of acetylsalicylate in managing pain, inflammation, fever, and cardiovascular conditions. However, it is crucial to consult a healthcare professional before using acetylsalicylate to ensure appropriate dosage and suitability for specific conditions.
Questions:
Q: How many pi bonds are present in acetylsalicylic acid?
A: Acetylsalicylate contains two pi bonds.
Q: Which parts of acetylsalicylic acid are rigid?
A: The benzene ring and the carboxylic acid group in acetylsalicylic acid are considered rigid.
Q: How many sigma bonds are present in acetylsalicylic acid?
A: Acetylsalicylate has 20 sigma bonds.
Q: How many sigma bonds are present in acetylsalicylic acid, and what parts are rigid?
A: Acetylsalicylate consists of 20 sigma bonds, with the benzene ring and carboxylic acid group being rigid portions.
Q: What is acetylsalicylic acid?
A: Acetylsalicylate, commonly known as aspirin, is a medication used for pain relief, reducing fever, and preventing blood clotting.
Q: What is the pH of a 0.10 M aqueous solution of acetylsalicylic acid?
A: The pH of a 0.10 M aqueous solution of acetylsalicylate cannot be determined without additional information.
Q: What is acetylsalicylic acid used for?
A: Acetylsalicylate is used as an analgesic (pain reliever), antipyretic (fever reducer), anti-inflammatory agent, and antiplatelet medication.
Q: What is the serum acetylsalicylic acid range?
A: The serum acetylsalicylate range may vary depending on the specific medical condition being treated. It is determined by healthcare professionals through individualized monitoring.
Q: Can acetylsalicylic acid cause tinnitus?
A: Yes, in rare cases, acetylsalicylate can cause tinnitus (ringing in the ears) as a side effect. If experiencing such symptoms, it is advisable to consult a healthcare professional.