BUTANEDIOIC ACID
BUTANEDIOIC ACID
Butanedioic acid is an aliphatic dicarboxylic acid (diacid) described by the empirical formula C₄H₆O₄, and is naturally found in living organisms.
Butanedioic acid is found in all plant and animal materials as a result of the central metabolic role played by this dicarboxylic acid in the Citric Acid Cycle.
Several technologies for the fermentation-based production of Butanedioic acid and the subsequent conversion to useful products are currently commercialized.
CAS Number: 110-15-6
EC Number: 203-740-4
Chemical Formula: HOOCCH₂CH₂COOH
Molar Mass: 118.09 g/mol
Synonyms: Wormwood acid, 1,2-Ethanedicarboxylic acid, MFCD00002789, succ, GTPL3637, succinic acid (free acid), Ethanedicarboxylic acid, Acide succinique, BMSE000968, Succinellite, 1cze, Spirit of amber, acidum succinicum, Amber acid, Butanedioic acid, WLN: QV2VQ, BMSE000183, Bernsteinsaeure, 1,4-Butanedioic acid, Amber acid, 110-15-6, 203-740-4, Dihydrofumaric acid, Ethylene succinic acid, Kyselina jantarova, Sal succini, Ethylene dicarboxylic acid, MCULE-5889111640, Acide butanedioique, Tox21_111612, 26776-24-9, Butanedionic acid, DB00139, Acid of amber, 4-02-00-01908, 1,4-Butanedionic acid, DTXSID6023602, Dihydrofumarate, FEMA NO. 4719, AI3-06297, Butane diacid, STR02803, succinic-acid, AB6MNQ6J6L, A14596, GTPL3637, Bernsteinsaure, acido succinico, ácido succínico, acide succinique, Spirit of amber, HOOC-CH2-CH2-COOH, Kyselina jantarova, MFCD00002789, Tox21_201918, LS40373, NCGC00159372-02, 6, AI3-06297, Nat.Succinic Acid, NCGC00159372-04, Succinic acid (8CI), Q213050, Substrate analogue, Tox21_303247, WLN: QV2VQ, acide butanedioique, DB00139, BDBM26121, Z57127453, NCGC00159372-05, NCGC00159372-03, C4-beta-polymorph, NCGC00257092-01, NCGC00159372-06, NCGC00259467-01, AI3-06297, HY-N0420, HMS3885O04, SR-01000944556-2, SR-01000944556, D85169, S0100, BBL002473, 1,2-Ethanedicarboxylate, Succinicate, FMR, Fumaric acid, fum, hydron, Katasuccin, MAE, 4lh2, Acidum succinicum, acido succínico, STR02803, succinic acid (free acid), acide succinique, FT-0652509, FT-0773657, BP-21128, I847, A14596, 37E8FFFB-70DA-4399-B724-476BD8715EF0, 9, MCULE-5889111640, BMSE000183, BMSE000968, LS40373, N1941, C00042, BDBM26121, AB01332192-02, D85169, HY-N0420, J-002386, ZINC895030, GTPL3637, AB6MNQ6J6L, CCG-266069, s3791, DB00139, GTPL3637, BBL002473, HMS3885O04, AI3-06297, MFCD00002789, MCULE-5889111640, Ethylene dicarboxylic acid, HOOC-CH2-CH2-COOH, BMSE000968, 1,4-Butanedioic acid, AI3-06297, STR02803, 6, 9, FMR, fum, hydron, Katasuccin, WLN: QV2VQ, FEMA NO. 4719, Substrate analogue, Sal succini, Nat.Succinic Acid, succinate, Succinic acid, Ethanedicarboxylic acid, SuccinicAcid(IndustrialGrade&FoodGrade), Ethylene succinic acid, Butane diacid, Butanedionic acid, Butanedioic acid, acido succinico, ácido succínico, acidum succinicum, Succinellite, Dihydrofumaric acid, Dihydrofumarate, Amber acid, Acid of amber, Spirit of amber, Succinic acid, 110-15-6, 203-740-4, 4-02-00-01908, Acide butanedioique, Acide succinique, Acido succinico, ácido succínico, Ácido succínico, succinic acid, butanedioic acid, Amber acid, Asuccin, Wormwood acid, Dihydrofumaric acid, Katasuccin, Bernsteinsaure, ethylenesuccinic acid, Butandisaeure, Acidum succinicum, Butanedionic acid, Succinicum acidum, Kyselina jantarova, Butane diacid, Ethylene dicarboxylic acid, Spirit of amber, Bernsteinsaure, Kyselina jantarova, Ammonium succinate, HSDB 791, succinic-acid, UNII-AB6MNQ6J6L, MFCD00002789, succ, NSC 106449, AI3-06297, AB6MNQ6J6L, Butanedioic acid, homopolymer, E363, CHEBI:15741, C4-beta-polymorph, NSC25949, NSC-106449, NCGC00159372-02, NCGC00159372-04, Succinellite, acide succinique, Sal succini, Acid of amber, DSSTox_CID_3602, WLN: QV2VQ, DSSTox_RID_77102, DSSTox_GSID_23602, SIN, Ethylene succinic acid, Ethanedicarboxylic acid, Bernsteinsaeure, sodium succinate (anhydrous), succinate, 9, acide butanedioique, 26776-24-9, CAS-110-15-6, Succinic acid, Succinic acid (8CI), Butanedioic acid (9CI), EINECS 203-740-4, BRN 1754069, Dihydrofumarate, Succinicate, Butanedioic acid diammonium salt, Salt of amber, 1cze, Butanedioic acid?, Nat.Succinic Acid, 1,4-Butanedioate, Succinic acid, 6, Succinic acid, FCC, Succinic Acide,(S), Succinic Acid (SA), 1,4-Butandioic Acid, Succinic acid, 99%, Succinic acid, natural, 4lh2, 1,2-Ethanedicarboxylate, Substrate analogue, 11, suc, Succinic acid, ACS grade, bmse000183, bmse000968, CHEMBL576, EC 203-740-4, HOOC-CH2-CH2-COOH, A 12084, 4-02-00-01908, GTPL3637, DTXSID6023602, FEMA NO. 4719, BDBM26121, Succinic acid (Butanedioic acid), HMS3885O04, ZINC895030, HY-N0420, STR02803, Tox21_111612, Tox21_201918, Tox21_303247, BBL002473, LMFA01170043, NSC-25949, NSC106449, s3791, STK387105, Succinic acid, >=99%, FCC, FG, Succinic acid, BioXtra, >=99.0%, AKOS000118899, Tox21_111612_1, CCG-266069, DB00139, LS40373, MCULE-5889111640, SuccinicAcid(IndustrialGrade&FoodGrade), NCGC00159372-03, NCGC00159372-05, NCGC00159372-06, NCGC00257092-01, NCGC00259467-01, Succinic acid, ACS reagent, >=99.0%, BP-21128, I847, Succinic acid, ReagentPlus(R), >=99.0%, CS-0008946, FT-0652509, FT-0773657, N1941, S0100, Succinic acid, p.a., ACS reagent, 99.0%, Succinic acid, SAJ first grade, >=99.0%, SUCCINIC ACID HIGH PURITY GRADE 2.5KG, Succinic acid, purum p.a., >=99.0% (T), Succinic acid, SAJ special grade, >=99.5%, 1,4-BUTANEDIOIC ACID (SUCCINIC ACID), A14596, C00042, D85169, Succinic acid, Vetec(TM) reagent grade, 98%, AB01332192-02, Q213050, SR-01000944556, J-002386, SR-01000944556-2, Z57127453, F2191-0239, 37E8FFFB-70DA-4399-B724-476BD8715EF0, Succinic acid, certified reference material, TraceCERT(R), Succinic acid, puriss. p.a., ACS reagent, >=99.5% (T), Succinic acid, United States Pharmacopeia (USP) Reference Standard, Succinic acid, matrix substance for MALDI-MS, >=99.5% (T), Ultra pure, Succinic acid, anhydrous, free-flowing, Redi-Dri(TM), ACS reagent, >=99.0%, Succinic acid, BioReagent, suitable for cell culture, suitable for insect cell culture, Succinic Acid, Pharmaceutical Secondary Standard; Certified Reference Material.
Butanedioic acid is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2.
The name derives from Latin succinum, meaning amber.
In living organisms, Butanedioic acid takes the form of an anion, which has multiple biological roles as a metabolic intermediate being converted into fumarate by the enzyme succinate dehydrogenase in complex 2 of the electron transport chain which is involved in making ATP, and as a signaling molecule reflecting the cellular metabolic state.
Butanedioic acid is marketed as food additive E363.
Butanedioic acid is generated in mitochondria via the tricarboxylic acid cycle (TCA).
Butanedioic acid can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating epigenetic landscape or demonstrating hormone-like signaling.
As such, Butanedioic acid links cellular metabolism, especially ATP formation, to the regulation of cellular function.
Dysregulation of Butanedioic acid synthesis, and therefore ATP synthesis, happens in some genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome, and degradation can lead to pathological conditions, such as malignant transformation, inflammation and tissue injury.
Butanedioic acid, a four-carbon diacid, has been the focus of many research projects aimed at developing more economically viable methods of fermenting sugar-containing natural materials.
Butanedioic acid fermentation processes also consume CO2, thereby potentially contributing to reductions in CO2 emissions.
Butanedioic acid could also become a commodity used as an intermediate in the chemical synthesis and manufacture of synthetic resins and biodegradable polymers.
Much attention has been given recently to the use of microorganisms to produce Butanedioic acid as an alternative to chemical synthesis.
We have attempted to maximize Butanedioic acid production by Actinobacillus succinogenes using an experimental design methodology for optimizing the concentrations of the medium components.
The first experiment consisted of a 24−1 fractional factorial design, and the second entailed a Central Composite Rotational Design so as to achieve optimal conditions.
Under the best conversion conditions, as determined by statistical analysis, the production of Butanedioic acid was carried out in an instrumented bioreactor using sugarcane bagasse hemicellulose hydrolysate, yielding a concentration of 22.5 g l−1.
Butanedioic acid is a precursor of many important, large-volume industrial chemicals and consumer products.
Butanedioic acidwas once common knowledge that many ruminant microorganisms accumulated Butanedioic acid under anaerobic conditions.
However, Butanedioic acid was not until the discovery of Anaerobiospirillum succiniciproducens at the Michigan Biotechnology Institute (MBI), which was capable of producing Butanedioic acid up to about 50 g/L under optimum conditions, that the commercial feasibility of producing the compound by biological processes was realized.
Other microbial strains capable of producing Butanedioic acid to high final concentrations subsequently were isolated and engineered, followed by development of fermentation processes for their uses.
Processes for recovery and purification of Butanedioic acid from fermentation broths were simultaneously established along with new applications of Butanedioic acid, e.g., production of biodegradable deicing compounds and solvents.
Several technologies for the fermentation-based production of Butanedioic acid and the subsequent conversion to useful products are currently commercialized.
This review gives a summary of the development of microbial strains, their fermentation, and the importance of the down-stream recovery and purification efforts to suit various applications in the context of their current commercialization status for biologically derived Butanedioic acid
Butanedioic acid, with molecular formulation C4H6O4, is a water-soluble, odorless, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters.
Butanedioic acid is also used in foods as a sequestrant, buffer, and a neutralizing agent.
Butanedioic acid is a normal intermediary metabolite and a constituent of the citric acid cycle, and found naturally in human urine
Butanedioic acid is distributed widely through the natural world, where Butanedioic acid is contained in bivalves, fossils, seaweed, lichen, bacteria and so on.
Butanedioic acid was discovered in the year 1550 when Dr. Agricola with Germany distilled amber.
Butanedioic acid is useful, non-toxic, stable and harmless to the human body.
Butanedioic acid is generated in a citric acid cycle (Butanedioic acid dehydrate enzyme) and a Butanedioic acid-glycine cycle through the process of metabolism and eventually becomes energy.
Butanedioic acid is industrially produced by hydrogenation of Maleic Anhydride.
Butanedioic acid of NIPPON SHOKUBAI has not only been used as food additives but also biodegradable polymers, bath additives, plating agents, photochemicals and so on
Butanedioic acid is a precursor of many important, large-volume industrial chemicals and consumer products.
Butanedioic acid was once common knowledge that many ruminant microorganisms accumulated Butanedioic acid under anaerobic conditions.
However, Butanedioic acid was not until the discovery of Anaerobiospirillum succiniciproducens at the Michigan Biotechnology Institute (MBI), which was capable of producing Butanedioic acid up to about 50 g/L under optimum conditions, that the commercial feasibility of producing the compound by biological processes was realized.
Other microbial strains capable of producing Butanedioic acid to high final concentrations subsequently were isolated and engineered, followed by development of fermentation processes for their uses.
Processes for recovery and purification of Butanedioic acid from fermentation broths were simultaneously established along with new applications of Butanedioic acid, e.g., production of biodegradable deicing compounds and solvents.
Several technologies for the fermentation-based production of Butanedioic acid and the subsequent conversion to useful products are currently commercialized.
This review gives a summary of the development of microbial strains, their fermentation, and the importance of the down-stream recovery and purification efforts to suit various applications in the context of their current commercialization status for biologically derived Butanedioic acid.
Butanedioic acid is an alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group.
Butanedioic acid is an intermediate metabolite in the citric acid cycle.
Butanedioic acid has a role as a nutraceutical, a radiation protective agent, an anti-ulcer drug, a micronutrient and a fundamental metabolite.
Butanedioic acid is an alpha,omega-dicarboxylic acid, a C4-dicarboxylic acid and a lipid.
Butanedioic acid accounts for up to the 90% of the nonvolatile acids produced during alcoholic fermentation.
The content of this acid in wine ranges normally from 0.5 to 1.5 g/L, but the maximum concentration may reach 3 g/L.
Butanedioic acid is a diprotic acid.
Butanedioic acid pKa at 25°C are 4.21 and 5.64.
This means that at pH 3.50, most Butanedioic acid (83.9%) is present in Butanedioic acid undissociated form; monodissociated Butanedioic acid ion accounts only for approximately 16%, while the dissociation of the second carboxylic group is practically negligible
Butanedioic acid, an organic acid is an important building block that has a wide range of synthetic applications.
Presently Butanedioic acid is synthesized from petrochemical compounds.
Due to Butanedioic acid increasing demand many bio-based methods have been proposed for Butanedioic acid synthesis as an efficient alternative.
Butanedioic acids utility as a low shrinkage additive (LSA) in unsaturated polyester resin (UPR) has been investigated.
Butanedioic acid (COOH(CH2)2COOH) is a carboxylic acid used in food (as an acidulant), pharmaceutical (as anexcipient), personal care (soaps) and chemical (pesticides, dyes and lacquers) industries.
Bio-based Butanedioic acid is seen as an important platform chemical for the production of biodegradable plastics and as a substitute of several chemicals (such as adipic acid)
Butanedioic acid was traditionally produced synthetically from fossil oil or by an expensive distillation of amber.
During the last decade, new methods of production through biotechnological processes have been developed industrially (so-called bio-Butanedioic acid).
Looking for more natural ingredients, the cosmetics market now has access to a new affordable plant-based ingredient.
Butanedioic acid is an aliphatic dicarboxylic acid (diacid) described by the empirical formula C4H6O4, and is naturally found in living organisms.
This diacid is one entry pathway into the Krebs cycle that takes place inside the mitochondria found in all cells in the human body.
Butanedioic acid provides energy required for the organism to function and is therefore involved in a variety of important biological actions.
Widely used in the food industry as a chelating agent and as a pH adjuster, Butanedioic acid has been recognized as a safe substance for years.
Butanedioic acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum. Butanedioic acid is used by consumers, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing. Butanedioic acid a dicarboxylic acid of molecular formula C4H6O4 that is widely distributed in almost all plant and animal tissues and that plays a significant role in intermediary metabolism. Butanedioic acid is a colourless crystalline solid, soluble in water, with a melting point of 185–187° C (365–369° F). Butanedioic acid is a precursor to some polyesters and a component of some alkyd resins. Butanedioic acid) can be synthesized using Butanedioic acid as a precursor. The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. Butanedioic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications. Acylation with Butanedioic acid is called succination. Oversuccination occurs when more than one Butanedioic acid adds to a substrate As a food additive and dietary supplement, Butanedioic acid is generally recognized as safe by the U.S. Food and Drug Administration. Butanedioic acid is used primarily as an acidity regulator in the food and beverage industry. Butanedioic acid is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste. As an excipient in pharmaceutical products, Butanedioic acid is also used to control acidity or as a counter ion. Butanedioic acid is found in all plant and animal materials as a result of the central metabolic role played by this dicarboxylic acid in the Citric Acid Cycle. Butanedioic acid concentrations are monitored in the manufacture of numerous foodstuffs and beverages, including wine, soy sauce, soy bean flour, fruit juice and dairy products (e.g. cheese). Butanedioic acid is a dicarboxylic acid. Butanedioic acid is a common intermediate in the metabolic pathway of several anaerobic and facultative micro-organisms. Butanedioic acid is used as a dietary supplement for symptoms related to menopause such as hot flashes and irritability. Butanedioic acid is used as a flavoring agent for food and beverages. Butanedioic acid is used to manufacture polyurethanes, paints and coatings, adhesives, sealants, artificial leathers, cosmetics and personal care products, biodegradable plastics, nylons, industrial lubricants, phthalate-free plasticizers, and dyes & pigments. In the pharmaceutical industry, Butanedioic acid is used in the preparation of active calcium succinate, as a starting material for active pharmaceutical ingredients (adipic acid, N-methyl pyrrolidinone, 2-pyrrolidinone, succinate salts, etc.), as an additive in drug formation, for medicines of sedative, antispasmer, antiplegm, antiphogistic, anrhoter, contraception and cancer curing, in the preparation of vitamin A and anti-Inflammatory, and as antidote for toxic substance. Butanedioic acid is a naturally occurring dicarboxylic acid with the molecular formula C4H6O4. Butanedioic acid consists of a four-carbon chain with two carboxylic acid groups located at each end. Structurally, Butanedioic acid is one of the simplest dicarboxylic acids. In its pure form, Butanedioic acid appears as a colorless, odorless crystalline solid that is soluble in water and slightly soluble in alcohols and ether. Butanedioic acid's aqueous solutions exhibit weak acidity due to the partial ionization of its carboxyl groups. Biologically, Butanedioic acid plays a critical role in cellular metabolism as an intermediate in the citric acid cycle (Krebs cycle), which is essential for the production of cellular energy in aerobic organisms. Butanedioic acid is produced naturally by both plants and animals and can also be synthesized by certain bacterial fermentation processes. Historically, Butanedioic acid was first isolated from amber, which is reflected in its name. Nowadays, Butanedioic acid is commonly produced through bio-based fermentation methods using renewable feedstocks, making it an important building block in sustainable chemical manufacturing. Butanedioic acid is widely valued for its versatility and functionality across multiple industries. Butanedioic acid serves as a precursor for the synthesis of numerous chemicals such as 1,4-butanediol, tetrahydrofuran (THF), and gamma-butyrolactone (GBL). Butanedioic acid is also used in food as an acidity regulator and flavor enhancer, in pharmaceuticals as an excipient or intermediate, and in biodegradable plastics, resins, solvents, and personal care products. The molecule's two carboxyl groups allow Butanedioic acid to undergo a variety of chemical reactions including esterification, amidation, and polymerization, making it highly adaptable in industrial chemistry. With the rising emphasis on green chemistry and sustainable production, bio-based Butanedioic acid has gained increasing importance in recent years. Applications of Butanedioic Acid: Butanedioic acid is used to make lacquers, dyes, esters for perfumes, alkyd resins, pharmaceuticals, plasticizers, lubricants, and pesticides. Butanedioic acid is also used in photography, as a sequestrant in foods, a buffering and neutralizing agent, for radiation dosimetry, and to promote plant growth and increased yields in food crops. Butanedioic acid (COOH(CH2)2COOH) is a carboxylic acid used in food (as an acidulant), pharmaceutical (as an excipient), personal care (soaps) and chemical (pesticides, dyes and lacquers) industries. Bio-based Butanedioic acid is seen as an important platform chemical for the production of biodegradable plastics and as a substitute of several chemicals (such as adipic acid). Butanedioic acid is widely used in the food industry as a chelating agent and as a pH adjuster. The FDA has granted Butanedioic acid with the GRAS status (Generally Recognised as Safe Substance). Studies conducted within the food industry show Butanedioic acid has anti-oxidant properties: even though this does not imply the same will be exerted when Butanedioic acid is applied topically, Butanedioic acid gives an indication that suitable tests could be carried out to understand whether Butanedioic acid maintain such effect once formulated in a cosmetic product. Butanedioic acid is also used as an intermediate to manufacture several chemicals, amongst which raw materials for the cosmetic and personal-care industry, e.g. emollients, surfactants and emulsifiers. Butanedioic acid is widely use as organic intermediates for the pharmaceutical, engineering plastics, resins etc. For the synthesis of sedatives, contraceptives and cancer drugs in the pharmaceutical industry. In the chemical industry for the production of dyes, alkyd resin, glass fiber reinforced plastics, ion exchange resins and pesticides. Butanedioic acid is an acidulant that is commercially prepared by the hydrogenation of maleic or fumaric acid. Butanedioic acid is a nonhygroscopic acid but is more soluble in 25°c water than fumaric and adipic acid. Butanedioic acid has low acid strength and slow taste build-up; Butanedioic acid is not a substitute for normal acidulants. Butanedioic acid combines with proteins in modifying the plasticity of bread dough. Butanedioic acid functions as an acidulant and flavor enhancer in relishes, beverages, and hot sausages. Biotechnological Applications: Butanedioic acid and its derivatives are used as flavoring agents for food and beverages. This acid could be used as feedstock for dyes, insecticides, perfumes, lacquers, as well as in the manufacture of clothing, paint, links, and fibers. Butanedioic acid is widely used in medicine as an antistress, antihypoxic, and immunity-improving agent, in animal diets, and as a stimulator of plant growth. Butanedioic acid is also a component of bio-based polymers such as nylons or polyesters. Butanedioic acid esters are precursors for the known petrochemical products such as 1,4-butanediol, tetrahydrofuran, c-butyrolactone, and various pyrrolidinone derivatives. Butanedioic acid production was reported for the first time when Butanedioic acid was grown on ethanol under aerobic conditions and nitrogen limitation. Butanedioic acid amount was 63.4 g/L as the major product of batch fermentation in this process. However, the disadvantage was low yield of Butanedioic acid on ethanol (58 %), and a high cost of production. The concentration of Butanedioic acid and Butanedioic acid yield were found to be 38.8 g/L and 82.45 % of n-alkane consumed, respectively. Butanedioic acid production was also studied by genetically modified strains using glucose and glycerol as substrates. Constructed temperaturesensitive mutant strains with mutations in the Butanedioic acid dehydrogenase encoding gene SDH1 by in vitro mutagenesis-based approach. Then, the mutants were used to optimize the composition of the media for selection of transformants with the deletion in the SDH2 gene. The defects of each Butanedioic acid dehydrogenase subunit prevented the growth on glucose, but the mutant strains grew on glycerol and produced Butanedioic acid in the presence of the buffering agent CaCO3. Subsequent selection of the strain with deleted SDH2 gene for increased viability was allowed to obtain a strain that is capable to accumulate Butanedioic acid at the level of more than 450 g/L with buffering and more than 17 g/L without buffering. Therefore, a reduced Butanedioic acid dehydrogenase activity can lead to an increased Butanedioic acid production Uses of Butanedioic Acid: Butanedioic acid has a wide range of uses across various industries due to its versatility and biocompatibility. In the chemical industry, Butanedioic acid serves as an important precursor for producing compounds such as 1,4-butanediol, tetrahydrofuran (THF), and gamma-butyrolactone (GBL), and is a key monomer for manufacturing biodegradable polymers like polybutylene succinate (PBS). In the pharmaceutical sector, Butanedioic acid is used as an intermediate in drug synthesis and is studied for its potential anti-inflammatory, antioxidant, and energy-boosting properties. In the food and beverage industry, Butanedioic acid functions as a food additive, acting as an acidity regulator and flavor enhancer, imparting a mild sour taste to foods and drinks. Butanedioic acid also finds applications in agriculture as a plant growth promoter and soil conditioner, and in cosmetics and personal care products where it helps regulate pH and enhance skin hydration. Additionally, Butanedioic acid is explored in biomedical fields for tissue engineering and drug delivery systems due to its biodegradability. Environmentally, Butanedioic acid plays a crucial role in green chemistry as a building block for bio-based products, offering sustainable alternatives to petroleum-derived chemicals. Butanedioic acid is also used in textile and leather processing for pH control and in industrial formulations as a component of solvents and cleaning agents. Chemical Industry: As a precursor for manufacturing other chemicals like 1,4-butanediol (BDO), tetrahydrofuran (THF), and gamma-butyrolactone (GBL). In the production of biodegradable polymers such as polybutylene succinate (PBS), which is used for making environmentally friendly plastics. Pharmaceutical Industry: Butanedioic acid is used as a pharmaceutical intermediate for synthesizing active ingredients and excipients. Sometimes employed as an anti-inflammatory agent, antioxidant, and in treatments to improve energy metabolism. Component in some anesthetic and sedative formulations. Food and Beverage Industry: Butanedioic acid functions as a food additive, serving as an acidity regulator, flavor enhancer, and preservative. Butanedioic acid adds a mild, sour, umami-like flavor to beverages, candies, and processed foods. Agriculture: Utilized in plant growth enhancement and soil conditioners. Butanedioic acid sometimes incorporated into fertilizer formulations to promote plant vigor and resilience. Cosmetic and Personal Care Products: Incorporated into skin care formulations due to Butanedioic acid's pH-regulating and moisturizing properties. Butanedioic acid is used in soaps, creams, lotions, and facial masks to improve skin texture and appearance. Biomedical Applications: Research interest in biomedical scaffolds and tissue engineering because of Butanedioic acid's biocompatibility and degradability. Studied for use in drug delivery systems. Environmental and Green Chemistry: Butanedioic acid acts as a building block for the development of bio-based and renewable chemicals. Important in producing sustainable alternatives to petrochemical-based products. Textile and Leather Industry: Butanedioic acid is used in the dyeing and finishing processes of textiles and leather as a buffering agent and pH controller. Industrial Solvents: Butanedioic acid serves as a base for making solvents used in cleaning products and manufacturing processes. Consumer Uses: Butanedioic acid is used in the following products: adsorbents, fertilisers, inks and toners, washing & cleaning products, water softeners, adhesives and sealants, coating products, fillers, putties, plasters, modelling clay, perfumes and fragrances, pharmaceuticals, polymers and cosmetics and personal care products. Other release to the environment of Butanedioic acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use. Widespread uses by professional workers: Butanedioic acid is used in the following products: pH regulators and water treatment products, anti-freeze products, metal surface treatment products, heat transfer fluids, hydraulic fluids, washing & cleaning products, fertilisers, water softeners and cosmetics and personal care products. Butanedioic acid is used in the following areas: printing and recorded media reproduction, health services and scientific research and development. Butanedioic acid is used for the manufacture of: and plastic products. Other release to the environment of Butanedioic acid is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use and outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids). Uses at industrial sites: Butanedioic acid is used in the following products: pH regulators and water treatment products, metal surface treatment products, leather treatment products, metal working fluids and laboratory chemicals. Butanedioic acid is used in the following areas: municipal supply (e.g. electricity, steam, gas, water) and sewage treatment and scientific research and development. Butanedioic acid is used for the manufacture of: chemicals, plastic products and textile, leather or fur. Release to the environment of Butanedioic acid can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture, in the production of articles and as processing aid. Chemical Properties of Butanedioic Acid: Butanedioic acid is a normal constituent of almost all plant and animal tissues. Succinic anhydride is the dehydration product of the acid. Butanedioic acid was first obtained as the distillate from amber (Latin, Succinum) for which Butanedioic acid is named. Butanedioic acid occurs in beet, brocoli, rhubarb, sauerkraut, cheese, meat, molasses, eggs, peat, coal, fruits, honey, and urine. Butanedioic acid is formed by the chemical and biochemical oxidation of fats, by alcoholic fermentation of sugar, and in numerous catalyzed oxidation processes. Butanedioic acid is also a major byproduct in the manufacture of adipic acid. Butanedioic acid, a dicarboxylic acid, is a relatively new nonhygroscopic product approved for food uses. Butanedioic acid apparent taste characteristics in foods appear to be very similar to the other acidulants of this type, although pure aqueous solutions tend to have a slightly bitter taste. Succinic anhydride, in contrast, is the only commercially available anhydride for food uses. Butanedioic acid is a colorless odorless prisms or white crystalline powder that melts at 185°C (364 of). Soluble in water and alcohol, Butanedioic acid is used as a chemical intermediate, Butanedioic acid is used in lacquers,medicine,dyes,and as a taste modifier. Biochem/physiol Actions of Butanedioic Acid: Butanedioic acid is a byproduct of anaerobic fermentation in microbes. Butanedioic acid is a dicarboxylic acid and an intermediate in Kreb′s cycle. Polymorphism in Butanedioic acid dehydrogenase leads to succinate accumulation. High levels of Butanedioic acid impairs 2-oxoglutarate epigenetic signalling. Butanedioic acid levels may modulate tumor progression. Butanedioic acid inhibits histone demethylation and may contribute to epigenetic changes. Butanedioic acid is crucial for interleukin-1 β (IL-1β) synthesis during inflammation and immune signalling. Human Metabolite Information of Butanedioic Acid: Tissue Locations: Adipose Tissue Brain Fibroblasts Kidney Liver Pancreas Placenta Prostate Skeletal Muscle Spleen Cellular Locations: Endoplasmic reticulum Extracellular Mitochondria Peroxisome Occurrence of Butanedioic Acid: Butanedioic acid is found in all plant and animal materials as a result of the central metabolic role played by this dicarboxylic acid in the Citric Acid Cycle. Butanedioic acid concentrations are monitored in the manufacture of numerous foodstuffs and beverages, including wine, soy sauce, soy bean flour, fruit juice and dairy products (e.g. cheese). The ripening process of apples can be followed by monitoring the falling levels of Butanedioic acid. The occurrence of > 5 mg/kg of this acid in egg and egg products is indicative of microbial contamination.
Apart from use as a flavouring agent in the food and beverage industries, Butanedioic acid finds many other non-food applications, such as in the production of dyes, drugs, perfumes, lacquers, photographic chemicals and coolants.
Butanedioic acid is widely distributed in almost all plants, animals and microorganisms where Butanedioic acid is a common intermediate in the intermediary metabolism.
A way to utilise this is with fermentation of biomass by microorganisms.
Butanedioic acid is therefore a good candidate for biobased industrial production.
A concept for a large scale production plant is patented by the company Diversified Natural Products.
The plant consists of a fermentation stage and a separation stage.
During the separations the Butanedioic acid produced in the fermenter is crystallised to the final product, Butanedioic acid.
Preparation of Butanedioic Acid:
Butanedioic acid can also be manufactured by catalytic hydrogenation of malic or fumaric acids.
Butanedioic acid has also been produced commercially by aqueous acid or alkalihydrolysis of succinonitrile derived from ethylene bromide and potassium cyanide.
Today Butanedioic acid is mainly produced from fossil resources through maleic acid hydrogenation.
Butanedioic acid can also be produced through fermentation of sugars.
In that case, in addition to Butanedioic acid, other carboxylic acids (such as lactic acid, formic acid, propionic acid) and alcohols (such as ethanol) are also obtained.
Methods of Manufacturing of Butanedioic Acid:
Hydrogenation of maleic acid, maleic anhydride, or fumaric acid produces good yields of Butanedioic acid.
1,4-Butanediol can be oxidized to Butanedioic acid in several ways: (1) with O2 in an aqueous solution of an alkaline-earth hydroxide at 90-110 °C in the presence of Pd-C; (2) by ozonolysis in aqueous acetic acid; or (3) by reaction with N2O4 at low temperature.
Butanedioic acid can be obtained by phase-transfer-catalyzed reaction of 2-haloacetates, electrolytic dimerization of bromoacetic acid or ester, oxidation of 3-cyanopropanal, and fermentation of n-alkanes.
Butanedioic acid is derived from fermentation of ammonium tartrate.
General Manufacturing Information of Butanedioic Acid:
Industry Processing Sectors:
All other basic organic chemical manufacturing
Plastic material and resin manufacturing
Utilities
Biotechnological Production:
Traditionally, Butanedioic acid is produced by petrochemical synthesis using the precursor maleic acid.
However, there are some microorganisms that are able to produce Butanedioic acid.
Maximum product concentrations of 106 g.L-1 with a yield of 1.25 mol of Butanedioic acid per mole of glucose and a productivity of 1.36 g.L-1.h-1 have been achieved by growing A. succinogenes on glucose.
A high productivity of 10.40 g.L-1.h-1 has been reached with A. succinogenes growing on a complex medium with glucose in a continuous process with an integrated membrane bioreactor-electrodialysis process.
In this process, Butanedioic acid concentration has been 83 g.L-1.
Moreover, metabolic engineering methods were used to develop strains with high productivity and titer as well as low byproduct formation.
For example, growing C. glutamicum strain DldhA-pCRA717 on a defined medium with glucose, a high productivity of 11.80 g.L-1.h-1 with a yield of 1.37 mol of Butanedioic acid per mole of glucose and a titer of 83 g.L-1 has been reported after 7 h.
An extended cultivation resulted in a product concentration of 146 g.L-1 after 46 h.
Handling and Storage of Butanedioic Acid:
Butanedioic acid should be handled in accordance with good industrial hygiene and safety practices.
Avoid contact with eyes, skin, and clothing.
Ensure adequate ventilation in working areas to minimize dust formation.
When handling, use appropriate personal protective equipment.
Store in a cool, dry, and well-ventilated place, away from incompatible substances like strong oxidizers and bases.
Containers should be kept tightly closed and protected from moisture to maintain product quality.
Reactivity and Stability of Butanedioic Acid:
Butanedioic acid is generally stable under recommended storage conditions.
Butanedioic acid is chemically stable at room temperature and under normal atmospheric pressure.
However, Butanedioic acid may react with strong oxidizing agents and strong bases.
At elevated temperatures, Butanedioic acid may decompose, releasing carbon monoxide, carbon dioxide, and other irritating fumes.
Avoid excessive heat and sources of ignition.
First Aid Measures of Butanedioic Acid:
Inhalation:
Move the person to fresh air immediately.
If breathing is difficult, administer oxygen and seek medical attention.
Skin Contact:
Wash affected area thoroughly with soap and water.
Remove contaminated clothing and seek medical advice if irritation persists.
Eye Contact:
Rinse immediately with plenty of water for at least 15 minutes.
Seek medical attention if irritation develops or persists.
Ingestion:
Rinse mouth with water.
Do not induce vomiting unless instructed by medical personnel.
Seek medical attention immediately.
Firefighting Measures of Butanedioic Acid:
Suitable Extinguishing Media:
Use water spray, dry chemical powder, carbon dioxide (CO₂), or appropriate foam.
Specific Hazards Arising from the Chemical:
Thermal decomposition may produce carbon oxides (CO and CO₂).
Protective Equipment for Firefighters:
Wear self-contained breathing apparatus (SCBA) and full protective clothing to prevent contact with skin and eyes during fire situations.
Accidental Release Measures of Butanedioic Acid:
Personal Precautions:
Use personal protective equipment.
Avoid breathing dust and ensure adequate ventilation.
Evacuate personnel to safe areas if necessary.
Environmental Precautions:
Prevent further leakage or spillage if Butanedioic acid can be done safely.
Avoid discharge into drains, surface water, or groundwater.
Methods for Cleaning Up:
Sweep or vacuum the spilled material carefully to avoid dust formation.
Place in a suitable, closed container for disposal according to local regulations.
Exposure Controls / Personal Protective Equipment of Butanedioic Acid:
Engineering Controls:
Provide adequate ventilation, especially in confined areas.
Use local exhaust ventilation where dust may be generated.
Eye Protection:
Safety glasses with side shields or goggles.
Skin Protection:
Protective gloves (e.g., rubber, neoprene) and appropriate protective clothing.
Respiratory Protection:
If exposure limits are exceeded or respiratory irritation occurs, use a NIOSH/MSHA-approved dust respirator.
Hygiene Measures:
Wash hands, forearms, and face thoroughly after handling and before eating, drinking, or smoking.
Remove contaminated clothing and wash before reuse.
Identifiers of Butanedioic Acid:
CAS number: 110-15-6
EC number: 203-740-4
Grade: ChP,NF,JPE,ACS
Hill Formula: C₄H₆O₄
Chemical formula: HOOCCH₂CH₂COOH
Molar Mass: 118.09 g/mol
HS Code: 2917 19 80
CAS Number: 110-15-6
EC Number: 203-740-4
Molecular Formula: C₄H₆O₄
Molecular Weight: 118.09 g/mol
PubChem CID: 1110
ChEBI ID: CHEBI:15741
ChemSpider ID: 1078
UNII: KZK58I7ZUJ
InChI: InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
InChI Key: KDYFGRWQOYBRFD-UHFFFAOYSA-N
SMILES: C(CC(=O)O)C(=O)O
CAS Registry Number: 110-15-6
EC Number: 203-740-4
Molecular Formula: C₄H₆O₄
Molecular Weight: 118.09 g/mol
PubChem CID: 1110
ChEBI ID: CHEBI:15741
ChEMBL ID: CHEMBL519482
ChemSpider ID: 1078
UNII: KZK58I7ZUJ
RTECS Number: WN0350000
Beilstein Reference: 1723850
Merck Index Number: 12, 9220
MDL Number: MFCD00002747
InChI: InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
InChI Key: KDYFGRWQOYBRFD-UHFFFAOYSA-N
Canonical SMILES: C(CC(=O)O)C(=O)O
Standard SMILES: O=C(O)CCC(=O)O
HS Code: 29171980
Properties of Butanedioic Acid:
Molecular Weight: 118.09
XLogP3: -0.6
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 3
Exact Mass: 118.02660867
Monoisotopic Mass: 118.02660867
Topological Polar Surface Area: 74.6 Ų
Heavy Atom Count: 8
Formal Charge: 0
Complexity: 92.6
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Appearance: Colorless to white crystalline solid
Odor: Odorless
Molecular Formula: C₄H₆O₄
Molecular Weight: 118.09 g/mol
Melting Point: 184 °C to 187 °C (363 °F to 369 °F)
Boiling Point (Decomposes): 235 °C (455 °F) – decomposition occurs before true boiling
Density: 1.56 g/cm³ (at 20 °C)
Solubility in Water: Soluble (about 83 g/L at 20 °C)
Solubility in Other Solvents: Slightly soluble in ethanol, ether, acetone
pKa Values:
pKa₁ ≈ 4.21
pKa₂ ≈ 5.64 (indicating it is a weak diprotic acid)
LogP (Partition Coefficient, octanol/water): -0.59 (shows hydrophilic character)
Vapor Pressure: Negligible at 25 °C
Flash Point: 206 °C (403 °F)
Refractive Index: Not applicable for solids (but in solutions can be measured)
Heat of Combustion: Approx. –1,361 kJ/mol
Crystal Structure: Monoclinic
Specifications of Butanedioic Acid:
Boiling point: 235 °C (1013 hPa)
Density:1.57 g/cm3 (25 °C)
Ignition temperature: 470 °C
Melting Point: 188 °C
pH value: 2.7 (10 g/l, H₂O, 20 °C)
Bulk density: 940 kg/m3
Solubility: 58 g/l
Assay (alkalimetric) : 99.0 – 100.5 %
Assay (HPLC) : 99.0 – 100.5 %
Identity (IR) : passes test
Identity (HPLC) : passes test
Identity (wet chemistry) : passes test
In water insoluble matter : ≤ 0.01 %
Melting range (lower value) : ≥ 185.0 °C
Melting range (upper value) : ≤ 190.0 °C
Melting point : 185.0 – 190.0 °C
Chloride (Cl) : ≤ 0.001 %
Phosphate (PO₄) : ≤ 0.001 %
Sulfate (SO₄) : ≤ 0.003 %
Heavy metals (as Pb) : ≤ 0.0020 %
Heavy metals (as Pb) (ACS) : ≤ 5 ppm
Nitrogen compounds (as N) : ≤ 0.001 %
Fe (Iron) : ≤ 5 ppm
As (Arsenic) : ≤ 0.00015 %
Substances reducing permanganate : conforms
Residual solvents (ICH Q3C) : excluded by production process
Sulfated ash (600 °C) : ≤ 0.02 %
Names of Butanedioic Acid:
Regulatory process names:
1,2-Ethanedicarboxylic acid
1,4-Butanedioic acid
Acidum succinicum
Amber acid
Asuccin
Bernsteinsaure
Butandisaeure
Dihydrofumaric acid
DL-Malic acid
Ethylene dicarboxylic acid
Ethylenesuccinic acid
Katasuccin
Kyselina jantarova
Succinate
Succinic acid
Succinic acid
succinic acid
Succinicum acidum
Wormwood acid
CAS names:
Butanedioic acid
IUPAC names:
1,4-Butanedioic acid
Butanedioic Acid
Butanedioic acid
butanedioic acid
Butanedionic acid
Registration dossier
Ethanedicarboxylic acid
Succinic
SUCCINIC ACID
Succinic Acid
Succinic acid
succinic acid
Succinic Acid
Succinic acid
succinic acid
1,4-Butanedioic acid
Butanedioic Acid
Butanedioic acid
butanedioic aci
Butanedionic acid
Ethanedicarboxylic acid
Succinic
Trade names:
Biosuccinium™
Succinic acid
Succinic Acid 99,7
Other identifiers:
110-15-6
2087491-34-5
2087491-34-5
623158-99-6
623158-99-6