Sorbic Acid

Base Information

• Chemical Name: Sorbic Acid
• CAS No.: 110-44-1
• Deprecated CAS: 91751-55-2,1197240-56-4,22500-92-1
• Molecular Formula: C6H8O2
• Molecular Weight: 112.128
• Hs Code.: 29161930
• European Community (EC) Number: 203-768-7,640-983-9
• ICSC Number: 1284
• UNII: X045WJ989B
• DSSTox Substance ID: DTXSID3021277
• Nikkaji Number: J394.115I,J628.002A,J2.449J
• Wikipedia: Sorbic_acid
• Wikidata: Q407131
• NCI Thesaurus Code: C82293
• RXCUI: 1311139
• Metabolomics Workbench ID: 533
• ChEMBL ID: CHEMBL250212
• Mol file: 110-44-1.mol

Synonyms:Acid, Hexadienoic;Acid, Propenylacrylic;Acid, Sorbic;Hexadienoic Acid;Potassium Sorbate;Propenylacrylic Acid;Sodium Sorbate;Sorbate, Potassium;Sorbate, Sodium;Sorbic Acid

Chemical Property of Sorbic Acid

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.01 mm Hg ( 20 °C)
• Melting Point: 132-135 ºC
• Refractive Index: 1.4600 (estimate)
• Boiling Point: 233 ºC at 760 mmHg
• PKA: 4.76(at 25℃)
• Flash Point: 127 ºC
• PSA: 37.30000
• Density: 1.024 g/cm³
• LogP: 1.20330
• Storage Temp.: 2-8°C
• Solubility.: ethanol: 0.1 g/mL, clear
• Water Solubility.: 1.6 g/L (20 ºC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 123

Purity/Quality:

99.5% ^*data from raw suppliers

Sorbic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC=CC=CC(=O)O
• Isomeric SMILES: C/C=C/C=C/C(=O)O
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Natural Origin and Synthesis: Sorbic acid (SA), also known as 2,4-hexadienoic acid, is a natural organic compound derived from the berries of the mountain rowan tree. Despite its natural origin, sorbic acid has been predominantly produced by chemical synthesis to meet the high demand for use as a preservative in food and wine since the 1930s.
• Application as a Preservative: Sorbic acid and its salt, sorbate, have been used as food preservatives since the 1940s to prevent spoilage caused by yeast, fungi, molds, and some bacteria. It can be directly added to food products, sprayed onto surfaces, sprinkled in powder form, dipped into sorbate solutions, or incorporated into packaging materials.
• Safety and Allergies: Sorbic acid is generally regarded as safe and nontoxic as a preservative but may cause allergic reactions or intolerance, particularly in large amounts.
• Functional Properties: Besides its use as a food preservative, sorbic acid is employed as a mold and yeast inhibitor, fungistatic agent, and alkyd coating to improve the gloss and milling characteristics of cold rubber. Its salts are utilized when greater water solubility is required.
• Regulatory Status: Sorbic acid and its salts (potassium and calcium) are classified as food preservatives (E 200, E 202, E 203) in Europe and are widely applied to extend the shelf life of food products.
• Stability and Processing: Sorbic acid is stable when stored at room temperature for extended periods but undergoes autoxidation in aqueous solutions and foods, leading to the formation of carbonyls and other compounds.; Heat treatment during processing does not significantly affect its stability or degradation.
• Industrial Applications: Sorbic acid and its potassium salt serve as alternatives to parabens in the food and pharmaceutical industries, where they are widely used for antimicrobial preservation in various formulations, including aqueous solutions, emulsions, suspensions, gels, and ointments, typically in concentrations ranging from 0.1% to 0.2%.

Technology Process of Sorbic Acid

There total 123 articles about Sorbic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Sorbyl alcohol (17102-64-6) → sorbic Acid (110-44-1,91751-55-2)

Guidance literature:

With Acetobacter aceti MIM₂₀₀₀/28; In phosphate buffer; ethanol; for 2h; pH=6.8;

DOI:10.1016/j.tet.2008.07.011

Reference yield: 98.0%

C12H22O2Si → sorbic Acid (110-44-1,91751-55-2)

Guidance literature:

C₁₂H₂₂O₂Si; carbon tetrabromide; In methanol; at 20 ℃; for 0.5h; Irradiation;

In methanol; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2005.07.049

Reference yield: 97.0%

trans,trans-2,4-Hexadienal (142-83-6,4488-48-6) → sorbic Acid (110-44-1,91751-55-2)

Guidance literature:

With C₄H₁₁FeMo₆NO₂₄^(3-)*3C₁₆H₃₆N⁽¹⁺⁾; water; oxygen; sodium carbonate; at 50 ℃; for 8h; under 760.051 Torr; Green chemistry;

DOI:10.1002/anie.201612225

upstream raw materials:

Ketene

trans-Crotonaldehyde

tetrachloromethane

N-Bromosuccinimide

Downstream raw materials:

(2E,4E)-hexa-2,4-dienoic acid n-propyl ester

ethyl hexa-2,4-dienoate

(2E,4E)-ethyl hexa-2,4-dienoate

sorbicillin

Refernces

• 1、 Surovtseva,Orlov,Morozova,Krylov,Belov. "Palladium η3-allyl complex with sorbic acid: Kinetics and mechanism of protodemetalation in aqueous solutions". . p. 855 - 857. Retrieved 2006.
• 2、 Hattori, Tetsutaro,Suzuki, Yutaka,Miyano, Sotaro. "Lewis acid-mediated carboxylation of aryl- and allylsilanes with carbon dioxide". . p. 454 - 455. Retrieved 2003.
• 3、 Hattori, Tetsutaro,Suzuki, Yutaka,Ito, Yuuichi,Hotta, Daido,Miyano, Sotaro. "Synthesis of 3,6-dihydro-2H-pyran-2-ones via cationic palladium(II) complex-catalyzed tandem [2+2] cycloaddition-allylic rearrangement of ketene with α,β-unsaturated aldehydes and ketones". . p. 5215 - 5223. Retrieved 2002.
• 4、 Pini, Elena,Bertacche, Vittorio,Molinari, Francesco,Romano, Diego,Gandolfi, Raffaella. "Direct conversion of polyconjugated compounds into their corresponding carboxylic acids by Acetobacter aceti". . p. 8638 - 8641. Retrieved 2008.
• 5、 Hoberg, Heinz,Schaefer, Dietmar. "SORBINSAEURE AUS PIPERYLEN UND CO2 DURCH C-C-VERKNUEPFUNG AN NICKEL(0)". . p. C15 - C17. Retrieved 1983.
• 6、 Zhao, Hua,Kanpadee, Naphatsawan,Jindarat, Chanida. "Ether-functionalized ionic liquids for nonaqueous biocatalysis: Effect of different cation cores". . p. 104 - 112. Retrieved 2019.
• 7、 Gandon, Vincent,Masson, Géraldine,Mati?i?, Mateja,Neuville, Luc,Van Elslande, Elsa,Varlet, Thomas. "Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition". supporting information. p. 11611 - 11619. Retrieved 2021/08/16.