BUTANEDIOIC ACID
BUTANEDIOIC ACID
Butanedioic Acid = Succinic acid
CAS Number: 110-15-6
EC Number: 203-740-4
Linear Formula: HOOCCH2CH2COOH
Molecular Weight: 118.09
E number: E363
Butanedioic Acid (/səkˈsɪnɪk/) is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2.
The name of Succinic Acid 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.
Butanedioic Acid is marketed as food additive E363.
Butanedioic Acid, also called Succinic 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 was first obtained as a distillation product of amber (Latin: succinum), for which it is named.
The common method of synthesis of Butanedioic Acid is the catalytic hydrogenation of maleic acid or its anhydride, although other methods are being used and investigated.
Butanedioic Acid has uses in certain drug compounds, in agricultural and food production, and in manufacturing.
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.
General description of Butanedioic Acid:
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 Acids increasing demand many bio-based methods have been proposed for its synthesis as an efficient alternative.
Butanedioic Acids utility as a low shrinkage additive (LSA) in unsaturated polyester resin (UPR) has been investigated.
Applications of Butanedioic Acid:
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 is a naturally occurring four-carbon dicarboxylic acid with the molecular formula C4H6O4 that is produced by liquefied petroleum gas.
However, petroleum gas is expensive and thus Butanedioic Acid is generated by different microbes.
Butanedioic Acid is naturally formed by most living cells as an outcome of anaerobic digestion.
Butanedioic Acid is a common organic acid, which can be used in many food, chemical, and pharmaceutical industries as a precursor to generate many chemicals such as solvents, perfumes, lacquers, plasticizer, dyes, and photographic chemicals.
Butanedioic Acid is also used as an antibiotic and curative agent.
Butanedioic Acid also finds application as a surfactant, ion chelator, and as an additive in various industries.
What is 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.
How to Use Butanedioic Acid?
Ideally, it’s best to look for Butanedioic Acid in a lightweight serum or treatment; the molecule is too small to be able to effectively penetrate through heavy creams and oils.
Follow product directions when it comes to usage and application, particularly if Butanedioic Acid’s an anti-acne product.
Physical properties of Butanedioic Acid:
Butanedioic Acid is a white, odorless solid with a highly acidic taste.
In an aqueous solution, succinic acid readily ionizes to form its conjugate base, succinate (/ˈsʌksɪneɪt/).
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 succinic acid, is found.
As a radical group Butanedioic Acid is called a succinyl (/ˈsʌksɪnəl/) group.
Like most simple mono- and dicarboxylic acids, Butanedioic Acid is not harmful but can be an irritant to skin and eyes.
Butanedioic Acid 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 it 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.
Commercial production of Butanedioic Acid:
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.
Chemical reactions of Butanedioic Acid:
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.
Precursor to polymers, resins, and solvents:
Butanedioic Acid is a precursor to some polyesters and a component of some alkyd resins.
1,4-Butanediol (BDO) can be synthesized using succinic 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 succinic acid is called succination.
Oversuccination occurs when more than one succinate adds to a substrate.
Food and dietary supplement:
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.
Butanedioic Acid is a dicarboxylic acid that occurs naturally in plant and animal tissues.
Butanedioic Acid is also known as “Spirit of Amber.”
When Butanedioic Acid was first discovered, it was extracted from amber by pulverizing and distilling it using a sand bath.
Butanedioic Acid was primarily used externally for rheumatic aches and pains.
Almost infinite esters can be obtained from carboxylic acids.
Esters are produced by combining an acid with an alcohol and removal of a water molecule.
Carboxylic acid esters are used in a variety of direct and indirect applications.
Lower chain esters are used as flavoring base materials, plasticizers, solvent carriers and coupling agents.
Higher chain compounds are used as components in metalworking fluids, surfactants, lubricants, detergents, oiling agents, emulsifiers, wetting agents, textile treatments and emollients.
Esters are also used as intermediates for the manufacture of a variety of target compounds.
The almost infinite esters provide a wide range of viscosity, specific gravity, vapor pressure, boiling point, and other physical and chemical properties for the proper application selections.
Applications of Butanedioic Acid:
Butanedioic Acid is used as a flavoring agent for food and beverages.
Producing five heterocyclic compounds, Butanedioic Acid is used as an intermediate for dyes, perfumes, lacquers, photographic chemicals, alkyd resins, plasticizers, metal treatment chemicals, and coatings.
Butanedioic Acid is also used in the manufacture of medicines for sedatives, antispasmers, antiplegm, antiphogistic, anrhoers, contraceptives, and cancer-curing.
Alternative name: Succinic Acid
Molecular Weight: 118.09g/mol
CAS Number: 110-15-6
Hazard: H315,H318,H335
Precaution: P261,P280,P305+P351+P338
This four carbon dicarboxylic acid has uses in a number of industries including polymers (clothing fibres), food, surfactants and detergents, flavors and fragrances and as a starting material for any number of chemicals including adipic acid, N-methyl pyrrolidinone, 2-pyrrolidinone, succinate salts, 1,4-butanediol, maleic anhydride, tetrahydrofuran and gamma-butyrolactone, which are used in the pharmaceutical industry.
Butanedioic Acid has many uses in the pharma industry – too many to mention, but some examples are as a starting material for active pharmaceutical ingredients (APIs), as an additive in formulation, succinic acid monoethyl ester has been used as an insulinotropic agent, and the compound has also been used as a cross linker in drug control release polymers.
Butanedioic Acid is a colorless crystalline solid with a melting point of 185-187° C.
Butanedioic Acid is soluble in water, slightly dissolves in ethanol, ether, acetone and glycerine.
Butanedioic Acid does not dissolve in benzene, carbon sulfide, carbon tetrachloride or oil ether.
Carboxylic acids can yield acyl halides, anhydrides, esters, amides, and nitriles for applications in the drug, agriculture, food products, and other industries.
Biosynthesis of Butanedioic Acid:
Succinate is a key intermediate in the tricarboxylic acid cycle, a primary metabolic pathway used to produce chemical energy in the presence of O2.
Succinyl-CoA + NDP + Pi → Succinate + CoA + NTP
Succinate + FAD → Fumarate + FADH2
SDH also participates in the mitochondrial electron transport chain, where it is known as respiratory complex II.
This enzyme complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of ubiquinone via the intermediate electron carriers FAD and three 2Fe-2S clusters.
Succinate thus serves as a direct electron donor to the electron transport chain, and itself is converted into fumarate.
Succinate can alternatively be formed by reverse activity of SDH.
Under anaerobic conditions certain bacteria such as A. succinogenes, A. succiniciproducens and M. succiniciproducens, run the TCA cycle in reverse and convert glucose to succinate through the intermediates of oxaloacetate, malate and fumarate.
This pathway is exploited in metabolic engineering to net generate succinate for human use.
Additionally, succinic acid produced during the fermentation of sugar provides a combination of saltiness, bitterness and acidity to fermented alcohols.
Accumulation of fumarate can drive the reverse activity of SDH, thus enhancing succinate generation.
Under pathological and physiological conditions, the malate-aspartate shuttle or the purine nucleotide shuttle can increase mitochondrial fumarate, which is then readily converted to succinate.
TYPE OF INGREDIENT: Butanedioic Acid is an antimicrobial and anti-inflammatory compound.
MAIN BENEFITS: Butanedioic Acid has antimicrobial, anti-inflammatory, and soothing effects.
Butanedioic Acid offers antioxidant protection as well as anti-aging properties, and hydrates.
WHO SHOULD USE IT: Because Butanedioic Acid has such a variety of benefits, it’s safe for all skin types, including sensitive skin, says Frieling.
HOW OFTEN CAN YOU USE IT: This depends on the particular product, but generally speaking, daily.
WORKS WELL WITH: Butanedioic Acid’s often paired with hyaluronic acid to boost the hydrating effects.
Butanedioic Acid also works well with other anti-acne ingredients, such as salicylic acid and sulfur, adds Curry.
DON’T USE WITH: There are no ingredients known to have a negative interaction with Butanedioic Acid.
Preferred IUPAC name:
Butanedioic acid
Physical properties of Butanedioic Acid:
At room temperature, pure Butanedioic Acid is a solid that forms colorless, odorless crystals.
Butanedioic Acid has a melting point of 185 °C and a boiling point of 235 °C.
Butanedioic Acid is a diprotic acid.
The carboxylate anion is called ‘succinate and esters of succinic acid are called alkyl succinates.
Biochemical role of Butanedioic Acid:
Succinate is a component of the citric acid cycle and is capable of donating electrons to the electron transfer chain via the following reaction:
succinate + FAD → fumarate + FADH2
This is catalysed by the enzyme succinate dehydrogenase (or complex II of the mitochondrial ETC).
The complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of ubiquinone. Intermediate electron carriers are FAD and three Fe2S2 clusters part of subunit B.
Mark Donnelly from Argonne National Laboratory developed one of the best strains (AFP 184) to convert raw hydrolysates from biomass to succinate.
History of Butanedioic Acid:
Spirit of amber was procured from amber by pulverising and distilling it using a sand bath.
Butanedioic Acid was chiefly used externally for rheumatic aches and pains, and internally in inveterate gleets.
Other names:
Succinic acid
1,4-Butanedioic acid
Butanedioic Acid, also referred to as butanedioic acid, is an organic acid, which can be synthesized by various microorganisms from different carbon sources.
Butanedioic Acid is a dicarboxylic acid and an intermediate in Kreb’s cycle.
CAS Number: 110-15-6
CHEBI: 15741
ChEMBL: ChEMBL576
ChemSpider: 1078
DrugBank: DB00139
ECHA InfoCard: 100.003.402
E number: E363 (antioxidants, …)
IUPHAR/BPS: 3637
PubChem CID: 1110
UNII: AB6MNQ6J6L
CompTox Dashboard (EPA): DTXSID6023602
Butanedioic Acid accounts for up to the 90% of the nonvolatile acids produced during alcoholic fermentation.
The content of Butanedioic 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 Acids 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 its undissociated form; monodissociated succinate ion accounts only for approximately 16%, while the dissociation of the second carboxylic group is practically negligible.
Chemical formula: C4H6O4
Molar mass: 118.088 g·mol−1
Density: 1.56 g/cm3
Melting point: 184–190 °C (363–374 °F; 457–463 K)
Boiling point: 235 °C (455 °F; 508 K)
Solubility in water : 58 g/L (20 °C) or 100 mg/mL
Solubility in Methanol: 158 mg/mL
Solubility in Ethanol: 54 mg/mL
Solubility in Acetone: 27 mg/mL
Solubility in Glycerol: 50 mg/mL
Solubility in Ether: 8.8 mg/mL
Acidity (pKa): pKa1 = 4.2
pKa2: = 5.6
Magnetic susceptibility (χ): -57.9·10−6 cm3/mol
Succinate is also a product of the glyoxylate cycle, which converts two two-carbon acetyl units into the four-carbon succinate.
The glyoxylate cycle is utilized by many bacteria, plants and fungi and allows these organisms to subsist on acetate or acetyl CoA yielding compounds.
The pathway avoids the decarboxylation steps of the TCA cycle via the enzyme isocitrate lyase which cleaves isocitrate into succinate and glyoxylate.
Succinate is the re-entry point for the gamma-aminobutyric acid (GABA) shunt into the TCA cycle, a closed cycle which synthesizes and recycles GABA.
The GABA shunt serves as an alternate route to convert alpha-ketoglutarate into succinate, bypassing the TCA cycle intermediate succinyl-CoA and instead producing the intermediate GABA.
Transamination and subsequent decarboxylation of alpha-ketoglutarate leads to the formation of GABA. GABA is then metabolized by GABA transaminase to succinic semialdehyde.
Finally, succinic semialdehyde is oxidized by succinic semialdehyde dehydrogenase (SSADH) to form succinate, re-entering the TCA cycle and closing the loop.
Enzymes required for the GABA shunt are expressed in neurons, glial cells, macrophages and pancreatic cells.
Cellular metabolism of Butanedioic Acid:
Succinate is produced and concentrated in the mitochondria and its primary biological function is that of a metabolic intermediate.
All metabolic pathways that are interlinked with the TCA cycle, including the metabolism of carbohydrates, amino acids, fatty acids, cholesterol, and heme, rely on the temporary formation of succinate.
The intermediate is made available for biosynthetic processes through multiple pathways, including the reductive branch of the TCA cycle or the glyoxylate cycle, which are able to drive net production of succinate.
In rodents, mitochondrial concentrations are approximately ~0.5 mM while plasma concentration are only 2–20 μM.
Mechanism of action:
Succinate is an essential component of the Krebs or citric acid cycle and serves an electron donor in the production of fumaric acid and FADH2.
Butanedioic Acid also has been shown to be a good “natural” antibiotic because of its relative acidic or caustic nature (high concentrations can even cause burns).
Succinate supplements have been shown to help reduce the effects of hangovers by activating the degradation of acetaldehyde – a toxic byproduct of alcohol metabolism – into CO2 and H2O through aerobic metabolism.
Butanedioic Acid has been shown to stimulate neural system recovery and bolster the immune system.
Claims have also been made that Butanedioic Acid boosts awareness, concentration and reflexes.
Quality Level: 200
grade: ACS reagent
assay: ≥99.0%
impurities:
≤0.001% N compounds
≤0.01% insolubles
ign. residue: ≤0.02%
bp: 235 °C (lit.)
mp: 184-186 °C (lit.)
solubility: water: soluble 83 g/L at 25 °C
anion traces:
chloride (Cl-): ≤0.001%
phosphate (PO43-): ≤0.001%
sulfate (SO42-): ≤0.003%
Butanedioic Acid is an important chemical and raw material widely used in medicine, food, biodegradable materials, fine chemicals, and other industrial fields.
However, traditional methods for purifying Butanedioic Acid from fermentation broth are costly, poorly efficient, and harmful to the environment.
In this study, an efficient method for purifying Butanedioic Acid from the fermentation broth of Escherichia coli NZN111 was developed through crystallization and co-crystallization with urea.
First, the filtrate was collected by filtering the fermentation broth, and pH was adjusted to 2.0 by supplementing sulfuric acid.
Crystallization was carried out at 8°C for 4 h to obtain Butanedioic Acid crystals.
The recovery rate and purity of Butanedioic Acid were 73.4% and over 99%, respectively.
Then, urea was added to the remaining solution with a mass ratio of urea to residual Butanedioic Acid of 4:1 (murea/mSA).
The second crystallization was carried out at pH 2 and 4°C for 12 h to obtain Butanedioic Acid-urea co-crystal.
The recovery rate of Butanedioic Acid residue was 92.0%.
The Butanedioic Acid-urea crystal was further mixed with phosphorous acid (4.2% of the mass of Butanedioic Acid co-crystal) and maintained at 195°C for 6 h to synthesize succinimide, and the yield was >80%.
This novel and efficient purification process was characterized by the significantly reduced urea consumption, and high Butanedioic Acid recovery (totally 95%), and high succinimide synthesis yield (80%).
Thus, this study potentially provided a novel and efficient strategy for the industrial production of Butanedioic Acid and succinimide.
cation traces:
Fe: ≤5 ppm
heavy metals (as Pb): ≤5 ppm
SMILES string: OC(=O)CCC(O)=O
InChI: 1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
InChI key: KDYFGRWQOYBRFD-UHFFFAOYSA-N
CAS number: 110-15-6
EC number: 203-740-4
Hill Formula: C₄H₆O₄
Chemical formula: HOOCCH₂CH₂COOH
Molar Mass: 118.09 g/mol
HS Code: 2917 19 80
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
About Butanedioic Acid Helpful information:
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.
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.
Article service life of Butanedioic Acid:
ECHA has no public registered data on the routes by which Butanedioic Acid is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses of Butanedioic Acid 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. This substance is used in the following areas: printing and recorded media reproduction, health services and scientific research and development. This substance is used for the manufacture of: plastic products. Other release to the environment of this substance 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).
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.
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, scientific research and development and printing and recorded media reproduction.
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.
Manufacture of Butanedioic Acid:
Release to the environment of Butanedioic Acid can occur from industrial use: manufacturing of the substance.
Product Number: S0100
Purity / Analysis Method: >99.0%(T)
Molecular Formula / Molecular Weight: C4H6O4 = 118.09
Physical State (20 deg.C): Solid
CAS RN: 110-15-6
Reaxys Registry Number: 1754069
PubChem Substance ID: 87575714
SDBS (AIST Spectral DB): 3001
Merck Index (14): 8869
MDL Number: MFCD00002789
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 succinic 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 succinic 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 succinic 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 succinic acid.
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
Kyselina jantarova
Butane diacid
Ethylene dicarboxylic acid
Spirit of amber
Bernsteinsaure [German]
Kyselina jantarova [Czech]
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
Succinicum acidum
NSC-106449
NCGC00159372-02
NCGC00159372-04
Succinellite
ethylenedicarboxylic acid
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 [NF]
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 (Beilstein Handbook Reference)
GTPL3637
DTXSID6023602
FEMA NO. 4719
BDBM26121
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
98-EP2269610A2
98-EP2269983A1
98-EP2269984A1
98-EP2269986A1
98-EP2269988A2
98-EP2269989A1
98-EP2269990A1
98-EP2270002A1
98-EP2270003A1
98-EP2270006A1
98-EP2270008A1
98-EP2270011A1
98-EP2270505A1
98-EP2272516A2
98-EP2272537A2
98-EP2272827A1
98-EP2275401A1
98-EP2275411A2
98-EP2275412A1
98-EP2275413A1
98-EP2275414A1
98-EP2277507A1
98-EP2277848A1
98-EP2277858A1
98-EP2277866A1
98-EP2277867A2
98-EP2280003A2
98-EP2280006A1
98-EP2280010A2
98-EP2281559A1
98-EP2281563A1
98-EP2281819A1
98-EP2284146A2
98-EP2284147A2
98-EP2284149A1
98-EP2284160A1
98-EP2284165A1
98-EP2284169A1
98-EP2284178A2
98-EP2284179A2
98-EP2286795A1
98-EP2287153A1
98-EP2287155A1
98-EP2287156A1
98-EP2287160A1
98-EP2287161A1
98-EP2287162A1
98-EP2289510A1
98-EP2289518A1
98-EP2289876A1
98-EP2289879A1
98-EP2289883A1
98-EP2289890A1
98-EP2292227A2
98-EP2292231A1
98-EP2292234A1
98-EP2292592A1
98-EP2292611A1
98-EP2292617A1
98-EP2292619A1
98-EP2295401A2
98-EP2295402A2
98-EP2295406A1
98-EP2295416A2
98-EP2295424A1
98-EP2295426A1
98-EP2295427A1
98-EP2295433A1
98-EP2295437A1
98-EP2298731A1
98-EP2298734A2
98-EP2298735A1
98-EP2298742A1
98-EP2298746A1
98-EP2298747A1
98-EP2298748A2
98-EP2298757A2
98-EP2298758A1
98-EP2298759A1
98-EP2298768A1
98-EP2298772A1
98-EP2298775A1
98-EP2301544A1
98-EP2301922A1
98-EP2301924A1
98-EP2301931A1
98-EP2301937A1
98-EP2301940A1
98-EP2305219A1
98-EP2305248A1
98-EP2305257A1
98-EP2305633A1
98-EP2305636A1
98-EP2305641A1
98-EP2305646A1
98-EP2305651A1
98-EP2305653A1
98-EP2305655A2
98-EP2305657A2
98-EP2305659A1
98-EP2305663A1
98-EP2305664A1
98-EP2305673A1
98-EP2305675A1
98-EP2305676A1
98-EP2305679A1
98-EP2308839A1
98-EP2308849A1
98-EP2308850A1
98-EP2308851A1
98-EP2308854A1
98-EP2308857A1
98-EP2308861A1
98-EP2308869A1
98-EP2308872A1
98-EP2308873A1
98-EP2308875A1
98-EP2311807A1
98-EP2311808A1
98-EP2311809A1
98-EP2311810A1
98-EP2311811A1
98-EP2311814A1
98-EP2311818A1
98-EP2311829A1
98-EP2311831A1
98-EP2311834A1
98-EP2311837A1
98-EP2311842A2
98-EP2314295A1
98-EP2314574A1
98-EP2314575A1
98-EP2314576A1
98-EP2314581A1
98-EP2314585A1
98-EP2314586A1
98-EP2314588A1
98-EP2314593A1
98-EP2316457A1
98-EP2316458A1
98-EP2316459A1
98-EP2316825A1
98-EP2316826A1
98-EP2316827A1
98-EP2316828A1
98-EP2316829A1
98-EP2316831A1
98-EP2316834A1
98-EP2316835A1
98-EP2316836A1
98-EP2371797A1
98-EP2371798A1
98-EP2371800A1
98-EP2371802A1
98-EP2371804A1
98-EP2371805A1
98-EP2372017A1
98-EP2374454A1
98-EP2374780A1
98-EP2374781A1
98-EP2380874A2
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%
47632-EP2281817A1
47632-EP2311811A1
AB01332192-02
196539-EP2270007A1
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 [RN]
203-740-4 [EINECS]
4-02-00-01908 [Beilstein]
Acide butanedioique [French]
Acide succinique [French] [ACD/IUPAC Name]
Acido succinico [Italian]
ácido succínico [Spanish]
Ácido succínico [Portuguese]
acidum succinicum [Latin]
Bernsteinsaeure [German]
Bernsteinsäure [German] [ACD/IUPAC Name]
Butanedioic acid [ACD/Index Name]
HOOC-CH2-CH2-COOH [Formula]
Kyselina jantarova [Czech]
MFCD00002789 [MDL number]
QV2VQ [WLN]
Succinic acid [ACD/IUPAC Name] [Wiki]
Succinic acid
Ηλεκτρικό οξύ [Modern Greek (1453-)]
Янтарная кислота [Russian]
コハク酸 [Japanese]
琥珀酸 [Chinese]
14493-42-6 [RN]
152556-05-3 [RN]
21668-90-6 [RN]
61128-08-3 [RN]
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 [Wiki]
hydron [Wiki]
Katasuccin
Kyselina jantarova
MAE
Maleic acid [Wiki]
Sal succini
STR02803
Succinellite
Succinic acid 100 µg/mL in Acetonitrile
succinic acid(free acid)
Succinic acid, ACS grade
SUCCINIC-D4 ACID
succunic acide
Wormwood acid