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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, succinate, 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.
CAS Number: 110-15-6
EC Number: 203-740-4
IUPAC Name: butanedioic acid
Chemical Formula: C4H6O4
Other 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, Butanedioic acid, 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, Biosuccinium™, Succinic acid, Succinic Acid 99,7, 110-15-6, 2087491-34-5, 2087491-34-5, 623158-99-6, 623158-99-6, 1,2-Ethanedicarboxylic acid, 1,4-Butanedioic 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, 110-15-6, Amber acid, Asuccin, Wormwood acid, Dihydrofumaric acid, Katasuccin, Bernsteinsaure, ethylenesuccinic acid, 1,2-Ethanedicarboxylic acid, 1,4-Butanedioic acid, Wormwood, 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, 1,2-Ethanedicarboxylic acid, 1,4-Butanedioic acid, 110-15-6, 203-740-4, 4-02-00-01908, Acide butanedioique, Acide succinique, Acido succinico, ácido succínico, Ácido succínico, acidum succinicum, Bernsteinsaeure, Bernsteinsäure, Butanedioic acid, HOOC-CH2-CH2-COOH, Kyselina jantarova, MFCD00002789, QV2VQ, Succinic acid, Succinic acid, Янтарная кислота, 14493-42-6, 152556-05-3, 21668-90-6, 61128-08-3, acidum succinicum, amber acid, asuccin, Bernsteinsaeure, Bernsteinsaure, Butandisaeure, BUTANE DIACID, BUTANEDIOICACID, CpeE protein, DB00139, Dihydrofumaric acid, Ethanedicarboxylic acid, Ethylene dicarboxylic acid, Ethylene succinic acid, FMR, fum, Fumaric acid, hydron, Katasuccin, Kyselina jantarova, MAE, Maleic acid, Sal succini, STR02803, Succinellite, succinic acid(free acid), SUCCINIC-D4 ACID, succunic acide, Wormwood acid
Butanedioic acid is marketed as food additive E363.
Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA).
Succinate 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, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function.
Dysregulation of succinate 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.
The optimal concentrations of nutrients predicted by the model were: NaHCO3, 10.0 g l−1; MgSO4, 3.0 g l−1; yeast extract, 2.0 g l−1; KH2PO4.
5.0 g l−1; these were experimentally validated.
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 is a conjugate acid of a succinate
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 succinate 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.
Studies also proved Butanedioic acid antioxidant properties especially for cosmetics.
Butanedioic acid is also a fully safe intermediate to manufacture derivatives like emollients, surfactants and emulsifiers used in cosmetic formulations.
Butanedioic acid is a naturally occurring ingredient in amber and sugar cane as well as apple cider vinegar, and is found in living organisms.
The process of fermentation obtains Butanedioic acid sustainably.
While Butanedioic acid has only recently become a 'buzzy' ingredient in skincare, succinic has been around for a while.
Butanedioic acid works by helping to peel away dead skin cells from pores to keep them clear.
Butanedioic acid is used to target blemishes, heal scarring, and improve signs of ageing, and Butanedioic acid is most often likened to salicylic acid.
Unlike salicylic, however, "it doesn’t encourage a lot of exfoliation," notes Rock.
For this reason, Butanedioic acid not really comparable to stronger acids that encourage rapid exfoliation and skin turnover.
Butanedioic acid is a white, odorless solid with a highly acidic taste.
In an aqueous solution, Butanedioic acid readily ionizes to form Butanedioic acid conjugate base, succinate.
As a diprotic acid, Butanedioic acid undergoes two successive deprotonation reactions:
(CH2)2(CO2H)2 → (CH2)2(CO2H)(CO2)− + H+
(CH2)2(CO2H)(CO2)− → (CH2)2(CO2)22− + H+
The pKa of these processes are 4.3 and 5.6, respectively.
Both anions are colorless and can be isolated as the salts, e.g., Na(CH2)2(CO2H)(CO2) and Na2(CH2)2(CO2)2.
In living organisms, primarily succinate, not Butanedioic acid, is found.
As a radical group Butanedioic acid is called a succinyl group.
Like most simple mono- and dicarboxylic acids, Butanedioic acid is not harmful but can be an irritant to skin and eyes.
Historically, Butanedioic acid was obtained from amber by distillation and has thus been known as spirit of amber.
Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol.
Succinate is also produced from butane via maleic anhydride.
Global production is estimated at 16,000 to 30,000 tons a year, with an annual growth rate of 10%.
Genetically engineered Escherichia coli and Saccharomyces cerevisiae are proposed for the commercial production via fermentation of glucose
Butanedioic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2.
This diethyl ester is a substrate in the Stobbe condensation.
Dehydration of Butanedioic acid gives succinic anhydride.
Succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and tetrahydrofuran
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, also called 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 succinate 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.
Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate.
The Butanedioic acid (Succinate) assay kit is suitable for the specific assay of Butanedioic acid in wine, cheese, eggs, sauce and other food products.
Butanedioic acid (or succinate) 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 (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 may be used in the following processes:
As a leaching agent in extracting lithium (Li), cobalt from used Li-ion batteries and magnesium from magnesite ore.
Synthesis of new elastic polyesters.
As a cocrystallising agent in the synthesis of cocrystals with organic molecules.
Butanedioic acid (succinate) is a dicarboxylic acid.
Butanedioic acid is an important component of the citric acid or TCA cycle and is capable of donating electrons to the electron transfer chain.
Succinate is found in all living organisms ranging from bacteria to plants to mammals.
In eukaryotes, succinate is generated in the mitochondria via the tricarboxylic acid cycle (TCA).
Succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. g. malate.
Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space.
Succinate has multiple biological roles including roles as a metabolic intermediate and roles as a cell signalling molecule.
Succinate can alter gene expression patterns, thereby modulating the epigenetic landscape or Butanedioic acid can exhibit hormone-like signaling functions.
As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function.
Succinate can be broken down or metabolized into fumarate by the enzyme succinate dehydrogenase (SDH), which is part of the electron transport chain involved in making ATP.
Dysregulation of succinate synthesis, and therefore ATP synthesis, can happen in a number of genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome.
Succinate has been found to be associated with D-2-hydroxyglutaric aciduria, which is an inborn error of metabolism.
Butanedioic acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite.
High levels of this organic acid can be found in tumors or biofluids surrounding tumors.
Butanedioic acids oncogenic action appears to due to Butanedioic acid ability to inhibit prolyl hydroxylase-containing enzymes.
In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth.
The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha).
Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, that hydroxylate HIF-alpha and lead to Butanedioic acid degradation.
Biotechnological Applications of Butanedioic acid:
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.
Succinate 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 succinate 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 succinate dehydrogenase subunit prevented the growth on glucose, but the mutant strains grew on glycerol and produced succinate 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 succinate at the level of more than 450 g/L with buffering and more than 17 g/L without buffering.
Therefore, a reduced succinate dehydrogenase activity can lead to an increased succinate production
Able to produce Butanedioic acid at low pH values.
High amounts of succinate can be achieved by genetic engineering.
Uses of Butanedioic acid:
Found in fossils, fungi, and lichens.
Present in nearly all plant and animal tissues.
Butanedioic acid is used to make lacquers, dyes, esters for perfumes, alkyd resins, pharmaceuticals, plasticizers, lubricants, and pesticides.
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.
Organic synthesis, manufacture of lacquers, dyes esters for perfumes, photography, in foods as sequestrant, buffer, neutralizing agent
Uses of Butanedioic acid range from scientific applications such as radiation dosimetry and standard buffer solutions to applications in agriculture, food, medicine, plastics, cosmetics, textiles, plating, and waste-gas scrubbing
Butanedioic acid is used as starting material in the manufacture of alkyd resins, dyes, pharmaceuticals, and pesticides.
Reaction with glycols gives polyesters; esters formed by reaction with monoalcohols are important plasticizers and lubricants.
In the growing of food, Butanedioic acid is a biogenic stimulant leading to faster plant growth and increased yields.
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.
Butanedioic acid was identified in essential oil from Saxifraga stolonifera and has antibacterial activity.
Consumer Uses of Butanedioic acid:
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.
Adhesives and sealants,
Water treatment products.
Widespread uses by professional workers of Butanedioic acid:
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 of Butanedioic acid:
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.
Adsorbents and absorbents,
Corrosion inhibitors and anti-scaling agents,
Intermediates,
Plasticizers,
Processing aids, not otherwise listed.
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,C02H(CH2)2C02H, also known as butanedioic acid,butane diacid, and amber 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.
Biotechnological Production of Butanedioic acid:
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, the product 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.
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 succinate dehydrogenase leads to succinate accumulation.
High levels of succinate impairs 2-oxoglutarate epigenetic signalling.
Succinate levels may modulate tumor progression.
Succinate inhibits histone demethylation and may contribute to epigenetic changes.
Succinate is crucial for interleukin-1 β (IL-1β) synthesis during inflammation and immune signalling.
Human Metabolite Information of Butanedioic acid:
Tissue Locations of Butanedioic acid:
Adipose Tissue
Brain
Fibroblasts
Kidney
Liver
Pancreas
Placenta
Prostate
Skeletal Muscle
Spleen
Cellular Locations of Butanedioic acid:
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 succinate 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.
Reactivity Profile of Butanedioic acid:
Butanedioic acid reacts exothermically to neutralize bases, both organic and inorganic.
Can react with active metals to form gaseous hydrogen and a metal salt.
Such reactions are slow in the dry, but systems may absorb water from the air to allow corrosion of iron, steel, and aluminum parts and containers.
Reacts slowly with cyanide salts to generate gaseous hydrogen cyanide.
Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide.
May generate flammable and/or toxic gases and heat with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides.
May react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.
Can be oxidized exothermically by strong oxidizing agents and reduced by strong reducing agents.
May initiate polymerization reactions.
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.
Manufacture of Butanedioic acid:
Release to the environment of Butanedioic acid can occur from industrial use: manufacturing of Butanedioic acid.
General Manufacturing Information of Butanedioic acid:
Industry Processing Sectors:
All other basic organic chemical manufacturing
Plastic material and resin manufacturing
Utilities
Formulation or re-packing of Butanedioic acid:
Butanedioic acid is used in the following products: washing & cleaning products, water softeners, cosmetics and personal care products, non-metal-surface treatment products, inks and toners, paper chemicals and dyes and polymers.
Release to the environment of Butanedioic acid can occur from industrial use: formulation of mixtures.
Handling and Storage of Butanedioic acid:
Nonfire Spill Response:
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container.
Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material.
Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal.
Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution.
Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and keep Butanedioic acid away from oxidizing materials.
Storage Conditions of Butanedioic acid:
Keep tightly closed.
Safety Profile of Butanedioic acid:
Moderately toxic by subcutaneous route.
A severe eye irritant.
Mutation data reported.
When heated to decomposition Butanedioic acid emits acrid smoke and irritating fumes.
First Aid of Butanedioic acid:
EYES: First check the victim for contact lenses and remove if present.
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center.
Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician.
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing.
Gently wash all affected skin areas thoroughly with soap and water.
If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.
INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air.
If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital.
Provide proper respiratory protection to rescuers entering an unknown atmosphere.
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.
INGESTION: DO NOT INDUCE VOMITING.
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center.
Be prepared to transport the victim to a hospital if advised by a physician.
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body.
DO NOT INDUCE VOMITING.
IMMEDIATELY transport the victim to a hospital.
Fire Fighting of Butanedioic acid:
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher.
Accidental Release Measures of Butanedioic acid:
Disposal Methods of Butanedioic acid:
The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination.
Recycle any unused portion of the material for Butanedioic acid approved use or return Butanedioic acid to the manufacturer or supplier.
Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision.
Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Incineration: Butanedioic acid should be combined with paper or other flammable material.
An alternate procedure is to dissolve Butanedioic acid in a flammable solvent and spray the solutions into the fire chamber.
Preventive Measures of Butanedioic acid:
The scientific literature for the use of contact lenses in industry is conflicting.
The benefit or detrimental effects of wearing contact lenses depend not only upon Butanedioic acid, but also on factors including the form of Butanedioic acid, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses.
However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye.
In those specific cases, contact lenses should not be worn.
In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
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
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
Complexity: 92.6
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
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 %
