Sorbic acid is a food preservative that inhibits the growth of molds and yeasts. It is commonly used in various food products to extend their shelf life.
| IUPAC Name | (2E,4E)-hexa-2,4-dienoic acid |
| Molecular Formula | C6H8O2 |
| CAS Number | 110-44-1 |
| Synonyms | 2,4-hexadienoic acid; E-2,4-hexadienoic acid; trans,trans-2,4-hexadienoic acid |
| InChI | InChI=1S/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8) |
Sorbic Acid Properties
Sorbic Acid Formula
The chemical formula of 2,4-hexadienoic acid is C6H8O2. It consists of six carbon atoms, eight hydrogen atoms, and two oxygen atoms. The formula represents the specific arrangement and ratio of atoms in a molecule of 2,4-hexadienoic acid.
Sorbic Acid Molar Mass
The molar mass of 2,4-hexadienoic acid is approximately 112.13 grams per mole. Molar mass is the mass of one mole of a substance and is calculated by summing the atomic masses of all the atoms in the molecule.
Sorbic Acid Boiling Point
2,4-Hexadienoic acid has a boiling point of around 228 to 232 degrees Celsius. Boiling point refers to the temperature at which a substance changes from its liquid state to a gaseous state under standard atmospheric pressure.
Sorbic Acid Melting Point
The melting point of 2,4-hexadienoic acid is approximately 132 to 135 degrees Celsius. Melting point indicates the temperature at which a solid substance transforms into a liquid state under standard atmospheric pressure.
Sorbic Acid Density g/mL
2,4-Hexadienoic acid has a density of about 1.22 grams per milliliter. Density represents the mass of a substance per unit volume and is a measure of how closely packed the molecules are within a given space.
Sorbic Acid Molecular Weight
The molecular weight of 2,4-hexadienoic acid is approximately 112.13 grams per mole. Molecular weight is the sum of the atomic weights of all the atoms in a molecule, expressed in grams per mole.
Sorbic Acid Structure
2,4-Hexadienoic acid has a molecular structure characterized by a chain of six carbon atoms, with alternating single and double bonds. This structure gives 2,4-hexadienoic acid its chemical properties and contributes to its ability to act as a preservative.
Sorbic Acid Solubility
2,4-Hexadienoic acid is sparingly soluble in water, with a solubility of around 0.12 grams per 100 milliliters of water at 20 degrees Celsius. It exhibits better solubility in organic solvents such as ethanol and propylene glycol. Solubility refers to the ability of a substance to dissolve in a particular solvent.
| Appearance | White crystalline powder |
| Specific Gravity | 1.22 |
| Color | Colorless |
| Odor | Slightly acetic odor |
| Molar Mass | 112.13 g/mol |
| Density | 1.22 g/mL |
| Melting Point | 132-135 °C |
| Boiling Point | 228-232 °C |
| Flash Point | 161 °C |
| Water Solubility | ~0.12 g/100 mL at 20 °C |
| Solubility | Soluble in ethanol and propylene glycol |
| Vapor Pressure | 0.000018 mmHg at 20 °C |
| Vapor Density | 4.0 (Air = 1) |
| pKa | 4.76 |
| pH | Approximately 5 |
Sorbic Acid Safety and Hazards
2,4-Hexadienoic acid is generally considered safe for use in food products when used within the prescribed limits. However, it is important to handle it with care and follow safety guidelines. Direct contact with 2,4-hexadienoic acid may cause irritation to the skin, eyes, and respiratory system. Ingesting large amounts can lead to digestive issues. It is advisable to use protective gloves and goggles when handling 2,4-hexadienoic acid. Store it in a cool, dry place away from heat and open flames. Keep it out of reach of children and pets. In case of accidental ingestion or exposure, seek medical attention and provide necessary information to healthcare professionals.
| Hazard Symbols | Xn, Xi |
| Safety Description | Avoid contact with skin and eyes. Wear protective gloves and goggles. |
| Un IDs | Not applicable |
| HS Code | 29161900 |
| Hazard Class | 8 (Corrosive) |
| Packing Group | III |
| Toxicity | Low to moderate toxicity if ingested. Irritant to skin, eyes, and respiratory system. |
Acid Synthesis Methods
There are several synthesis methods for 2,4-hexadienoic acid. One common method is the condensation of crotonaldehyde with malonic acid. In this process, crotonaldehyde reacts with malonic acid in the presence of a catalyst, such as piperidine or sodium ethoxide. The reaction forms a β-keto ester intermediate, which undergoes decarboxylation to produce 2,4-hexadienoic acid.
Another synthesis method involves the oxidation of 4-hexenol. Strong oxidizing agents, such as potassium permanganate or chromic acid, oxidize 4-hexenol to produce 4-hexenoic acid. Further treatment of this acid yields 2,4-hexadienoic acid.
The catalytic hydrogenation of maleic acid or maleic anhydride synthesizes 2,4-hexadienoic acid. A suitable catalyst, such as palladium or rhodium, converts maleic acid or maleic anhydride into 2,4-hexadienoic acid during the hydrogenation process.
These synthesis methods provide efficient routes for the production of 2,4-hexadienoic acid. However, it is important to note that industrial-scale production requires careful process optimization and control to ensure high yields and purity of 2,4-hexadienoic acid.
Sorbic Acid Uses
2,4-Hexadienoic acid has a wide range of uses in various industries due to its effective preservative properties. Here are some of its common applications:
- Food Preservation: Manufacturers extensively use 2,4-hexadienoic acid as a preservative in food and beverage products, including baked goods, dairy products, beverages, processed meats, sauces, and dressings. It actively inhibits the growth of molds and yeasts, thereby extending the shelf life of these products.
- Cosmetic and Personal Care Products: 2,4-Hexadienoic acid plays a crucial role in cosmetic and personal care items, such as creams, lotions, and shampoos, by actively preventing microbial contamination and maintaining product stability.
- Pharmaceutical Industry: The pharmaceutical industry actively employs 2,4-hexadienoic acid as a preservative in certain pharmaceutical preparations, including ophthalmic solutions and oral liquids, to actively prevent microbial growth.
- Animal Feed: Manufacturers actively add 2,4-hexadienoic acid to animal feed to prevent spoilage and enhance its shelf life. This ensures the nutritional quality of the feed for livestock.
- Leather Treatment: 2,4-Hexadienoic acid finds active application in leather processing as a fungicide that actively inhibits mold and mildew growth during storage and transportation.
- Industrial Applications: Various industrial processes, such as coatings, adhesives, and paints, actively utilize 2,4-hexadienoic acid to prevent microbial degradation and extend the lifespan of the products.
- Agricultural Products: Farmers actively use 2,4-hexadienoic acid as a preservative in post-harvest treatments for fruits and vegetables to delay spoilage and maintain their freshness.
2,4-Hexadienoic acid’s versatile preservative properties make it a valuable ingredient in numerous products across different industries, ensuring product quality, safety, and extended shelf life.
Questions:
Q: Is sorbic acid safe?
A: 2,4-Hexadienoic acid is generally considered safe for consumption within regulated limits and when used appropriately.
Q: Is sorbic acid safe for pets?
A: 2,4-Hexadienoic acid, when used in pet food products according to regulatory guidelines, is generally considered safe for pets.
Q: Does sorbic acid cause candida albicans to flare?
A: There is no scientific evidence to suggest that 2,4-hexadienoic acid causes candida albicans to flare.
Q: How much sorbic acid is in cheese?
A: The amount of 2,4-hexadienoic acid in cheese can vary depending on the specific type and brand, but it is typically present in low concentrations as a preservative.
Q: What is sorbic acid in food?
A: 2,4-Hexadienoic acid is a food preservative that helps inhibit the growth of molds and yeasts, extending the shelf life of various food products.
Q: What food contains sorbic acid?
A: 2,4-Hexadienoic acid can be found in a wide range of food products, including baked goods, dairy products, beverages, processed meats, sauces, and dressings.
Q: What makes up sorbic acid?
A: 2,4-Hexadienoic acid is a compound composed of carbon, hydrogen, and oxygen atoms, with the chemical formula C6H8O2.
Q: Does sorbic acid denature?
A: 2,4-Hexadienoic acid does not denature proteins, as it primarily functions as a preservative by inhibiting microbial growth.
Q: What counters sorbic acid side effects?
A: Proper usage within regulatory limits and adherence to safety guidelines can help minimize potential side effects of 2,4-hexadienoic acid.
Q: Is sorbic acid or potassium sorbate a good preservative to use in lotions?
A: Both 2,4-hexadienoic acid and potassium sorbate are effective preservatives commonly used in lotions to prevent microbial growth and maintain product integrity.
Q: What counters sorbic acid?
A: 2,4-Hexadienoic acid is typically unaffected by common food ingredients and additives. However, the combination with certain antioxidants can reduce its effectiveness as a preservative.
Q: What is sorbic acid?
A: 2,4-Hexadienoic acid is a naturally occurring or synthetically produced compound used as a preservative in various industries, particularly in food and cosmetic products.
Q: How does potassium sorbate become sorbic acid?
A: Potassium sorbate can be converted into sorbic acid through acid hydrolysis, resulting in the release of potassium ions and the formation of 2,4-hexadienoic acid.