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This section provides an overview for acetoacetic acids as well as their applications and principles. Also, please take a look at the list of 11 acetoacetic acid manufacturers and their company rankings.
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Figure 1. Basic information on acetoacetic acid
Acetoacetic acid, a carboxylic acid compound with the chemical formula C4H6O3, is also known as 3-oxobutanoic acid. Typically unstable, it is often used in the form of its esters, such as ethyl acetoacetate or methyl acetoacetate. Ethyl acetoacetic acid, commonly handled, is classified as a flammable liquid and eye irritant under the GHS classification and as a Class 4 hazardous material under the Fire Service Law, but is exempt from several other regulations.
Acetoacetic acid is primarily used as a reaction intermediate in organic synthesis, obtained through the saponification of esters like methyl and ethyl acetoacetate. Biochemically, its concentration increases in the blood under certain conditions, such as in diabetics and during strenuous exercise while fasting. This increase is due to enhanced fatty acid breakdown, leading to the formation of acetoacetic acid, a condition known as ketosis, which can affect appetite and gastrointestinal function.
Figure 2. Reaction of acetoacetic acid
Acetoacetic acid melts at 97.7°F (36.5°C) and decomposes into acetone and carbon dioxide gas over time or when heated. Its acid form has a half-life of 140 minutes in water at 98.6°F (37°C), while its base form, as an anion, has a much slower half-life of 130 hours. It is a weak acid with a pKa of 3.58, similar to alkyl carboxylic acids.
Figure 3. Structure of acetoacetic acid
As a β-keto acid, acetoacetic acid exhibits keto-enol tautomerisation, with the enol form partially stabilized by conjugation and intramolecular hydrogen bonding. This equilibrium is highly solvent dependent, with the keto form predominating in polar solvents like water (98%) and the enol form more prevalent in non-polar solvents (25-49%).
Acetoacetic acid is produced by hydrolyzing diketene and can be synthesized from acetoacetic acid esters at 0 °C, decomposing rapidly into acetone and carbon dioxide for immediate use. Its esters are integral in acetoacetylation reactions, crucial for producing dyes such as arylide yellows and diarylides. Diketenes also react with alcohols and amines to yield corresponding acetoacetic acid derivatives.
Acetoacetic acid is measured in the urine of diabetic patients or those on ketogenic or low-carbohydrate diets to confirm diabetic ketoacidosis. A dipstick coated with nitroprusside changes color in the presence of acetoacetate, the conjugate base of acetoacetic acid, from pink to purple, facilitating visual assessment.
*Including some distributors, etc.
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MedChemExpress (MCE), is headquartered in Monmouth Junction, New Jersey, and is a supplier of research chemicals and biochemicals for laboratory and scientific use. The company’s product range includes biochemical assay reagents, isotope-labeled compounds, inhibitory antibodies, recombinant proteins, and fluorescent dyes. These products are used in various biopharmaceutical research and development fields, including areas such as infection, cardiovascular diseases, neurodegenerative diseases, diabetes, and autoimmune diseases. The company is ISO 19001 certified and provides testing services within the ISO 17025 framework, offering bulk and custom product services and support for metrological traceability.
GlpBio Technology, established in 2016 and headquartered in Montclair, California, is a supplier of life science products covering 20 popular research fields, including epigenetics, neuroscience, and cancer. Its product portfolio has over 20,000 life science reagents, including biochemicals, tag peptides, bioactive peptides, amino acids, and nature products. Its main clients include clinical diagnostic laboratories, government agencies, research institutes, universities, and pharmaceutical companies. The company regularly increases its products to meet the latest research needs and provides custom organic synthesis and analytical services.
Santa Cruz Biotechnology, Inc., established in 1991 and headquartered in Dallas, Texas, is an American manufacturer and supplier specializing in biological products for medical research. Initially providing antibodies to the research community, they expanded their offerings to include gene silencers like siRNA and shRNA (plasmid and lentiviral), targeting all known mouse and human genes. Over time, Santa Cruz Biotechnology provides over 175,000 research biochemicals under the brand ChemCruz, including protein-interacting inhibitors, substrates, and activators, tailored for studying protein functions. The company offers monoclonal primary antibodies, designed for various mammalian and non-mammalian protein targets, along with corresponding binding secondary antibodies.
Kanto Chemical Co. Inc., founded in 1944 and headquartered in Tokyo, Japan, is a reagent manufacturer with overseas affiliates in other countries, including China, France, USA, Taiwan, and Malaysia. Its product portfolio includes analytical reagents, ionic liquids, Iodine compounds, ultra-pure chemicals, and water analysis kits. The company is also developing regenerative medicine and genetics reagents and has over 50,000 products. It has several certifications, including ISO 9001, acquired in 1994, making it the first Japanese company in the reagent industry. Other certifications are ISO 14001, ISO 13485, and ISO/IEC 17025.
Biosynth is a Swiss manufacturer of life science reagents established in 1966 and headquartered in Staad. The company sources and manufactures biochemical products such as carbohydrates, nucleosides, and enzyme substrates, as well as various peptides and biologics. They also operate as a contract manufacturer offering custom synthesis and manufacturing services for their clients in the pharmaceutical, diagnostic, food, and agrochemical sectors. Biosynth has regional sales offices and specialized facilities in Europe and North America, including in the Netherlands, United Kingdom, and United States.
Toronto Research Chemicals Inc., founded in 1982 and based in Toronto, Canada, is a manufacturer of biochemicals and is a subsidiary of LGC Standards. The ISO 9001-certified company has an extensive catalog of over 350,000 products, including metabolites, impurities, and natural products APIs, which are used in several applications like environmental analysis, forensic science, and medicinal R&D. The company supports the scientific community across more than 120 countries and has 19 production laboratories. In 2019, it was bought by LGC, which provides components to customers in the pharmaceutical, clinical diagnostics, and food markets, among others.
Millipore Sigma, formerly known as Sigma-Aldrich, was created in 175 through the merger of Sigma Chemical Company and Aldrich Chemical company and today is a subsidiary of Merck. Millipore Sigma is a life science and biotechnology company serving the industry with several products and services. Some of their product categories include peptide synthesis materials, biochemicals, building blocks, catalysts, chemical biology, chemical synthesis, flavors & fragrances, formulation, lab chemicals, lab safety, APIs, and stable isotopes. Services include characterization, contract manufacturing, custom products, software, support, testing, and mRNA development & manufacturing.
Nacalai Tesque Inc., founded in 1846 and headquartered in Kyoto, Japan, is a manufacturer of research chemicals, fine chemicals, diagnostics, and the related instruments. Some of its products include cytokines, nucleic acid electrophoresis, cell dissociation reagents, and sialic acid-related products, and it also offers custom and bulk service for bulk reagents and cell culture media. The company has more than 50 domestic distributors and several worldwide, including Asia, the Middle East, Oceania, Europe, and Africa. It is ISO 9001 and ISO 9002 certified, while the Kyoto South brand and Tesque factory are ISO 14001 certified.
Alfa Aesar is based in Lancashire, United Kingdom. Alfa Aesar is part of Thermo Fisher Scientific, is a manufacturer and supplier of chemicals, metals, and life science products for research and development. Alfa Aesar’s product lines include chemicals, life science, materials & metals, catalysts, and analytical & lab ware. Chemical offerings include inorganic compounds, organic compounds, organometallic, and solvents. Life sciences include biotechnology products, cellular & molecular biology, genomics, and immunology. Materials & metal include alloys, carbon, etchants, and more. Catalysts include ferrocenes, fuel cell products, and precious metals & catalysts. Alfa Aesar also offers custom manufacturing options.
Carl Roth GmbH + Co. KG, established in 1879 and headquartered in Karlsruhe, Germany, is a manufacturer, distributor, and supplier of laboratory equipment, life science products, and chemicals. Their extensive product range encompasses analytical instruments, biological safety cabinets, heating mantles, pH meters, centrifuges, thermometers, and various chemicals. Their products support and facilitate laboratory research, analysis, and experimentation across various industries such as pharmaceutical, chemical, and environmental sectors. The company is certified according to DIN EN ISO 9001:2015 and DIN EN ISO 14001:2015.
Starsky international holdings Co., Ltd., established in 1984 and headquartered in Shanghai, China, is a manufacturer of organic and inorganic chemicals. The company provides APIs, organic and inorganic chemicals, food additives, fragrances and catalysts with customized service based on customers’ demands. It has two production facilities and complies with quality standards including ISO 9001 and 14001, GMP and Kosher. With independent export rights, the company exports its products to over 100 countries including USA, England, France, Germany and Thailand.
Number of Employees
Newly Established Company
Company with a History
*Including some distributors, etc.
*Including some distributors, etc.
| Country | Number of Companies | Share (%) |
|---|---|---|
|
United States of America
|
3 | 33.3% |
|
Japan
|
2 | 22.2% |
|
Switzerland
|
1 | 11.1% |
|
Canada
|
1 | 11.1% |
|
United Kingdom
|
1 | 11.1% |
|
Germany
|
1 | 11.1% |
