E363 (Succinic acid)

E363 (Succinic acid)

CAS NO.: 110-15-6
EC/LIST NO.: 203-740-4

E363 (Succinic acid) (/səkˈsɪnɪk/) is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2.
The name derives from Latin succinum, meaning amber. 
In living organisms, E363 (Succinic 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.
E363 (Succinic 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.

E363 (Succinic 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. 
E363 (Succinic acid) fermentation processes also consume CO2, thereby potentially contributing to reductions in CO2 emissions. 
E363 (Succinic 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 E363 (Succinic acid) as an alternative to chemical synthesis. 
We have attempted to maximize E363 (Succinic 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 E363 (Succinic acid) was carried out in an instrumented bioreactor using sugarcane bagasse hemicellulose hydrolysate, yielding a concentration of 22.5 g l−1.

E363 (Succinic acid) is a precursor of many important, large-volume industrial chemicals and consumer products. 
E363 (Succinic acid)was once common knowledge that many ruminant microorganisms accumulated E363 (Succinic acid) under anaerobic conditions. 
However, it was not until the discovery of Anaerobiospirillum succiniciproducens at the Michigan Biotechnology Institute (MBI), which was capable of producing E363 (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 E363 (Succinic 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 E363 (Succinic acid) from fermentation broths were simultaneously established along with new applications of E363 (Succinic acid), e.g., production of biodegradable deicing compounds and solvents. 
Several technologies for the fermentation-based production of E363 (Succinic 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 E363 (Succinic acid)

E363 (Succinic 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. 
E363 (Succinic acid) is also used in foods as a sequestrant, buffer, and a neutralizing agent. E363 (Succinic acid) is a normal intermediary metabolite and a constituent of the citric acid cycle, and found naturally in human urine

E363 (Succinic acid)" is distributed widely through the natural world, where it is contained in bivalves, fossils, seaweed, lichen, bacteria and so on. 
E363 (Succinic acid) was discovered in the year 1550 when Dr.Agricola with Germany distilled amber. 
"E363 (Succinic acid)" is useful, non-toxic, stable and harmless to the human body. 
E363 (Succinic acid) is generated in a citric acid cycle (E363 (Succinic acid) dehydrate enzyme) and a E363 (Succinic acid)-glycine cycle through the process of metabolism and eventually becomes energy. E363 (Succinic acid) is industrially produced by hydrogenation of Maleic Anhydride. 
E363 (Succinic acid) of NIPPON SHOKUBAI has not only been used as food additives but also biodegradable polymers, bath additives, plating agents, photochemicals and so on

E363 (Succinic acid) is a precursor of many important, large-volume industrial chemicals and consumer products. 
E363 (Succinic acid) was once common knowledge that many ruminant microorganisms accumulated E363 (Succinic acid) under anaerobic conditions. 
However, it was not until the discovery of Anaerobiospirillum succiniciproducens at the Michigan Biotechnology Institute (MBI), which was capable of producing E363 (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 E363 (Succinic 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 E363 (Succinic acid) from fermentation broths were simultaneously established along with new applications of E363 (Succinic acid), e.g., production of biodegradable deicing compounds and solvents. 
Several technologies for the fermentation-based production of E363 (Succinic 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 E363 (Succinic acid).

E363 (Succinic 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. 
E363 (Succinic acid) is an intermediate metabolite in the citric acid cycle. 
E363 (Succinic acid) has a role as a nutraceutical, a radiation protective agent, an anti-ulcer drug, a micronutrient and a fundamental metabolite. 
E363 (Succinic acid) is an alpha,omega-dicarboxylic acid, a C4-dicarboxylic acid and a lipid. 
E363 (Succinic acid) is a conjugate acid of a succinate

E363 (Succinic 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  . 
E363 (Succinic acid) is a diprotic acid. Its pKa at 25°C are 4.21 and 5.64   . 
This means that at pH 3.50, most E363 (Succinic 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

E363 (Succinic acid), an organic acid is an important building block that has a wide range of synthetic applications. 
Presently it is synthesized from petrochemical compounds. 
Due to its increasing demand many bio-based methods have been proposed for its synthesis as an efficient alternative. 
E363 (Succinic acid)s utility as a low shrinkage additive (LSA) in unsaturated polyester resin (UPR) has been investigated.

E363 (Succinic 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 E363 (Succinic 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)

E363 (Succinic 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-E363 (Succinic acid)). 
Looking for more natural ingredients, the cosmetics market now has access to a new affordable plant-based ingredient.

E363 (Succinic 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. 
E363 (Succinic 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, E363 (Succinic acid) has been recognized as a safe substance for years (1). 
Studies also proved its antioxidant properties (2) especially for cosmetics. 
E363 (Succinic acid) is also a fully safe intermediate to manufacture derivatives like emollients, surfactants and emulsifiers used in cosmetic formulations.

E363 (Succinic 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 E363 (Succinic acid) sustainably.

While it has only recently become a 'buzzy' ingredient in skincare, succinic has been around for a while.

E363 (Succinic acid) works by helping to peel away dead skin cells from pores to keep them clear.
E363 (Succinic acid) is used to target blemishes, heal scarring, and improve signs of ageing, and it is most often likened to salicylic acid. 
Unlike salicylic, however, "it doesn’t encourage a lot of exfoliation," notes Rock. 
For this reason, it's not really comparable to stronger acids that encourage rapid exfoliation and skin turnover.

E363 (Succinic acid) is a white, odorless solid with a highly acidic taste.
In an aqueous solution, E363 (Succinic acid) readily ionizes to form its conjugate base, succinate (/ˈsʌksɪneɪt/). 
As a diprotic acid, E363 (Succinic 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 E363 (Succinic acid), is found. 

As a radical group it is called a succinyl (/ˈsʌksɪnəl/) group. 

Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes.

Historically, E363 (Succinic 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

E363 (Succinic 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 E363 (Succinic acid) gives succinic anhydride.
Succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and tetrahydrofuran

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

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 %

E363 (Succinic 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. 
E363 (Succinic acid) is a colourless crystalline solid, soluble in water, with a melting point of 185–187° C (365–369° F).

E363 (Succinic acid) is a precursor to some polyesters and a component of some alkyd resins.
E363 (Succinic acid)) can be synthesized using E363 (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.
E363 (Succinic acid) also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications. 

Acylation with E363 (Succinic acid) is called succination. 
Oversuccination occurs when more than one succinate adds to a substrate

As a food additive and dietary supplement, E363 (Succinic acid) is generally recognized as safe by the U.S. Food and Drug Administration.
E363 (Succinic acid) is used primarily as an acidity regulator[20] in the food and beverage industry. 
E363 (Succinic acid) is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste.
As an excipient in pharmaceutical products, it 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 E363 (Succinic acid) (Succinate) assay kit is suitable for the specific assay of E363 (Succinic acid) in wine, cheese, eggs, sauce and other food products.

E363 (Succinic 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. 
E363 (Succinic 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).

E363 (Succinic 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.

E363 (Succinic acid) (succinate) is a dicarboxylic acid. 
E363 (Succinic 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 (PMID 16143825 ). 
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 (PMID: 26971832 ). 
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. 
E363 (Succinic 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. 
E363 (Succinic acid)s oncogenic action appears to due to its 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, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation.

IUPAC NAME :

1,4-Butanedioic acid
 
Butanedioic Acid
 
Butanedioic acid
 
butanedioic acid

Butanedionic acid
 
Ethanedicarboxylic acid
 
Succinic

SYNONYMS:

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