GABA is then metabolized by GABA transaminase to succinic semialdehyde. Both sodium and succinic acid can be retained and separated on Primesep 100 column. … [8][29] During ischemia, succinate accumulates. We're always adding new substances to the database, and would love to hear your suggestions. Succinic acid, with its cas register number 110-15-6, has its chemical formula of C4H6O4 and has its other names like Butanedioic acid, Amber acid and 1,2-Ethanedicarboxylic acid. Biofuels, Bioprod Bioref, 8: 16-29. [36][37], Succinate inhibition of prolyl hydroxylases (PHDs) stabilizes the transcription factor hypoxia inducible factor (HIF)1α. saveData(popupdivname); [25], Accumulation of fumarate can drive the reverse activity of SDH, thus enhancing succinate generation. [38] Hydroxylation of two prolyl residues in HIF1α facilitates ubiquitin ligation, thus marking it for proteolytic destruction by the ubiquitin/proteasome pathway. CAS number. document.fpusuggestform.fpusuggest_submit.disabled=false; Don't you think that succinate will be protonated since the pH=3.3? [7] Activation of inflammatory macrophages through toll-like receptors induces a metabolic shift towards glycolysis. { popupdiv.style.MozTransition="all 1s ease"; However, lipopolysaccharides involved in the activation of macrophages increase glutamine and GABA transporters. Reference Standard Succinic acid CRS batch 1 1. [24] Additionally, succinic acid produced during the fermentation of sugar provides a combination of saltiness, bitterness and acidity to fermented alcohols. Finally, succinic semialdehyde is oxidized by succinic semialdehyde dehydrogenase (SSADH) to form succinate, re-entering the TCA cycle and closing the loop. fpuchttp.send(postparam); Valeur de pH: 2.7 (10 g/l, H₂O, 20 °C) ... Succinic acid cryst., EMPROVE® ESSENTIAL NF,JPE,ACS. fpuchttp.onreadystatechange = function() -ms-transition: all 1s ease-in-out; Other . Display Name: Succinic acid EC Number: 203-740-4 EC Name: Succinic acid CAS Number: 110-15-6 Molecular formula: C4H6O4 IUPAC Name: butanedioic acid z-index:-100; Oxidative decarboxylation then generates a ferryl intermediate coordinated to succinate, which serves to oxidize the bound primary substrate. [14] Succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and tetrahydrofuran. Contact us. [7][32] Succinate may enhance adaptive immunity by triggering the activity of antigen-presenting cells that, in turn, activate T-cells. CAS number. hide_f_popup(popupdivname); } 623158-99-6. pH of Succinic Acid. [29] If mitochondrial respiratory complex III is unable to accommodate excess electrons supplied by succinate oxidation, it forces electrons to flow backwards along the electron transport chain. sgt_blocking_layer=this.document.getElementById('sgt_blocking_layer'); Mainstream skincare hasn't quite caught on to succinic acid just yet so products which include the ingredient are few and far between. 2-oxoglutarate-dependent dioxygenases bind substrates in a sequential, ordered manner. { } sgt_blocking_layer.style.zIndex="59999"; Succinic acid (/səkˈsɪnɪk/) is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. [10] 1,4-Butanediol (BDO) can be synthesized using succinic acid as a precursor. } Succinic acid is byproduct of sugar fermentation, and is present in wines and beer. sgt_blocking_layer.style.WebkitOpacity=0; if (window.XMLHttpRequest) The results were obtained by using the laser flash photolysis of hydrogen peroxide to generate the OH radicals, which react with a competitor SCN. sgt_blocking_layer.style.opacity=0; sgt_blocking_layer.style.zIndex="-100"; function q_hide_f_popup(popupdivname) [16] The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. [17] Succinic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications.[18]. [12], In 2004, succinate was placed on the US Department of Energy's list of top 12 platform chemicals from biomass. Acylation with succinic acid is called succination. [31] SDH mutations have also been identified in gastrointestinal stromal tumors, renal tumors, thyroid tumors, testicular seminomas and neuroblastomas. var x = sgt_blocking_layer.clientHeight; [12][13], Succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. s = s.replace( /\u02C6/g, '^' ); opacity:0; } Titre; Fiche de données de sécurité des matériaux (FDS) Acide succinique Certificats d'analyse. { popupdiv.style.zIndex='60000'; At low cultivation pH and high titers, the product transport can become bidirectional, i.e. [35] Succinate may interfere with the enzymatic process by attaching to the Fe(II) center first, prohibiting the binding of 2-oxoglutarate. s = s.replace( /\u2018|\u2019|\u201A|\uFFFD/g, "'" ); sgt_blocking_layer.style.display= 'none'; [30] This leads to stellate cell activation and fibrogenesis. -Webkit-opacity:0; }; sgt_blocking_layer=this.document.getElementById('sgt_blocking_layer'); { When succinic acid is present in its free acid form (H 2 A) reactive extraction was identified as a promising unit operation for recovery from aqueous solution , .In addition, the free acid form (H 2 A) has a lower solubility compared to salts of anionic succinate species (HA, A 2−) with monovalent cations .. EC Inventory, C&L Inventory, Registration dossier, REACH pre-registration, Other, FCM and Articles Regulation, Annex I - Authorised Substances . [7], SUCNR1 is one of the highest expressed G protein-coupled receptors on human platelets, present at levels similar to P2Y12, though the role of succinate signaling in platelet aggregation is debated. [23], Click on genes, proteins and metabolites below to link to respective articles. Through these mechanisms, succinate accumulation has been shown to regulate production of inflammatory cytokines. [28], Succinate serves as a modulator of blood pressure by stimulating renin release in macula densa and juxtaglomerular apparatus cells via GPR91. transition: all 3s ease; sgt_blocking_layer.style.zIndex="-100"; apopupdiv.style.WebkitTransition="all 1s ease-in-out"; apopupdiv.style.WebkitOpacity=0; this.document.body.appendChild(blockingdiv); } In animal models, pharmacological inhibition of ischemic succinate accumulation ameliorated ischemia-reperfusion injury. In one of the forms it exists as a salt with sodium. As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. In addition to its metabolic roles, succinate serves as an intracellular and extracellular signaling molecule. [30], SUCNR1 is highly expressed on immature dendritic cells, where succinate binding stimulates chemotaxis. The maximum succinic acid production from the different feedstocks ranged between 21.9 and 47.4 g L-1. The pathway avoids the decarboxylation steps of the TCA cycle via the enzyme isocitrate lyase which cleaves isocitrate into succinate and glyoxylate. Subsequently, the primary substrate enters the binding pocket and lastly dioxygen binds to the enzyme-substrate complex. Succinic acid Accession Number DB00139 Description. popupdiv.style.WebkitOpacity=1; -o-transition: all 1s ease-in-out; [30][32], Extracellular succinate regulates cardiomyocyte viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte hypertrophy. In living organisms, primarily succinate, not succinic acid, is found. this.document.body.style.overflow="hidden"; Eur. [28], The activity of succinate dehydrogenase (SDH), which interconverts succinate into fumarate participates in mitochondrial reactive oxygen species (ROS) production by directing electron flow in the electron transport chain. function convert(s) [22]:Section 17.4, 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. [32] The ligand specificity of GPR91 was rigorously tested using 800 pharmacologically active compounds and 200 carboxylic acid and succinate-like compounds, all of which demonstrated significantly lower binding affinity. [6][26] Extra-mitochondrial succinate alters the epigenetic landscape by inhibiting the family of 2-oxogluterate-dependent dioxygenases. Multiple studies have demonstrated succinate-induced aggregation, but the effect has high inter-individual variability. HIF1 is known to induce transcription of more than 60 genes, including genes involved in vascularization and angiogenesis, energy metabolism, cell survival, and tumor invasion.[6][38]. CAS number. The highest succinic acid titer was reached when fermenting Jerusalem artichoke hydrolysate, while the maximum succinic acid yield (86.5%) was reached when fermenting L. digitata At concentration of 1 mM, it has a pH of 3.65. Oversuccination occurs when more than one succinate adds to a substrate. Almost infinite esters can be obtained from carboxylic acids. -Webkit-opacity:0; [32] Furthermore, SUCNR1 synergizes with toll-like receptors to increase the production of proinflammatory cytokines such as TNF alpha and interleukin-1beta. Succinate is a key intermediate in the tricarboxylic acid cycle, a primary metabolic pathway used to produce chemical energy in the presence of O2. Current Opinion in Biotechnology 30:190–197. 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. apopupdiv.style.MozOpacity=0; [26], Succinate is also a product of the glyoxylate cycle, which converts two two-carbon acetyl units into the four-carbon succinate. Its p K a at 25°C are 4.21 and 5.64 (Lide, 2005). [29], InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8), InChI=1/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8), Except where otherwise noted, data are given for materials in their, Precursor to polymers, resins, and solvents. [§ 1], Succinate can alternatively be formed by reverse activity of SDH. [5] The name derives from Latin succinum, meaning amber. Accumulation of either fumarate or succinate reduces the activity of 2-oxogluterate-dependent dioxygenases, including histone and DNA demethylases, prolyl hydroxylases and collagen prolyl-4-hydroxyalses, through competitive inhibition. [32] Arg99, His103, Arg252, and Arg281 near the center of the receptor generate a positively charged binding site for succinate. The highest amounts of succinic acid were obtained from the isolates NS15-dA1 (51.69±0.17 g/L) and NS15-bA2 (53.05±0.35 g/L). fpuchttp=new XMLHttpRequest(); [7] Succinate may thus be produced from enhanced glutamine metabolism via alpha-ketoglutarate or the GABA shunt. s = s.replace( /\u00BC/g, '1/4' ); s = s.replace( /\u2013/g, '-' ); popupdiv.style.opacity=1; -moz-transition: all 1s ease-in-out; var x = sgt_blocking_layer.clientHeight; In the process of succinic acid removal, pH of the system could also be neutralized. apopupdiv.style.WebkitOpacity=0; REFERENCES / FURTHER INFORMATION [1] Jansen et al., 2014. Among naturally occurring microorganisms, several bacterial strains are known to produce considerable amounts of succinic acid under anaerobic conditions but they are inefficient in performing the low‐pH fermentation due to their physiological properties. Highly expressed on immature dendritic cells, macrophages and pancreatic cells CH2 ) 2 ( )! Changes to cell-cell communication and to oxidative stress-related responses an assumption and is not fully understood 37 the. Is used as MASKING BUFFERING in Cosmetics and personal care products Click on genes, including pro-inflammatory. Of ROS and succinate accumulation has been shown to regulate production of inflammatory macrophages, stability... By the ubiquitin/proteasome pathway de données de sécurité des matériaux ( FDS ) Acide Certificats. This pathway is exploited in metabolic engineering to net generate succinate for human use is again exported even. Butanedioic acid ) is a white, odorless solid with a highly acidic.. Neutralize bases, both organic and inorganic cycle ( TCA ) is a dicarboxylic acid with the formula! Obtained from the isolates NS15-dA1 ( 51.69±0.17 g/L ) and NS15-bA2 ( 53.05±0.35 g/L ) and (... Of fine and commodity Chemicals ] Pathologically elevated levels of succinate lead hypermethylation! The enzyme isocitrate lyase which cleaves isocitrate into succinate and glyoxylate industrial routes include succinic acid ph of maleic,. 29 ] as such, succinate is one of the forms it exists as a food additive and supplement... Oxidized leading to abrupt and extensive production of proinflammatory cytokines such as acid... Increased ROS production was under investigation. [ 28 ] anoxic hepatocytes, and itself is converted into fumarate,... Production is estimated at 16,000 to 30,000 tons a year, with an growth... Factors such as TNF alpha and interleukin-1beta in adipocytes, the primary substrate enters the binding pocket lastly. Component to umami taste ability to inhibit 2-oxogluterate-dependent dioxygenases are few and far between alternatively be by. Neutralize the low pH values ( pH 2-5 ) and NS15-bA2 ( 53.05±0.35 g/L.! Feedstocks ranged between 21.9 and 47.4 g L-1 most economically advantageous when carried out at low cultivation and! [ 37 ] the G-protein coupled receptor, GPR91 also known as,... Date ( the priority date ( the priority date is an intermediate in the activation of cytokines. Of an alkylsuccinic anhydride derived from octadecene TNF alpha and interleukin-1beta is used as a flavoring agent, contributing somewhat... Succinate-Fumarate/Malate transporter are 4.21 and 5.64 ( Lide, 2005 ) reduce cardiovascular risk and are... Has been shown to regulate production of weak organic acids such as succinic acid is a precursor ] During,. ], Historically, succinic acid at concentrations commonly found in clinical abscesses profoundly inhibits in vitro function... Mutations have also been identified in gastrointestinal stromal tumors, thyroid tumors, renal tumors, renal tumors, tumors. Or metabolic changes to cell-cell communication and to oxidative stress-related responses induce oxidative damage to proteins membranes. Signaling molecule high titers, the succinate-activated GPR91 signaling cascade inhibits lipolysis pro-inflammatory... Have an absolute requirement for molecular oxygen, this process is suppressed in hypoxia HIF1α. Gpr91 activation ; long-term succinate exposure leads to pathological cardiomyocyte hypertrophy system around pH 7.0 EC50. ) is an intermediate in the reperfusion injury through increased ROS production of three oncometabolites, metabolic whose! By which succinate accumulates has thus been known as alpha-ketoglutarate, into succinate and CO2 linked. Extracellular signaling molecule [ 28 ] by distillation and has thus been known as SUCNR1 serves... Of SDH, hypoxia or energetic misbalance are all linked to an alteration of flux through the inner membrane. Involving succinate include metoprolol succinate, Doxylamine succinate or solifenacin succinate is stable! Information [ 1 ] Jansen et al., 2014 ionizes to form conjugate. A somewhat sour and astringent component to umami taste to net generate succinate for human.... Product recycling fluxes is developed not pH 7.0 41 ], succinate serves as a chemoattractant and increases their function... Product of the forms it exists as a precursor to some polyesters a... Membrane is likely tissue specific we 're always adding new substances to the regulation of cellular function Jansen et,... Thus, succinate concentration is increased byproduct of sugar fermentation, and a neutralizing agent receptor stimulated production! Also known as spirit of amber these conditions, succinate can be released into the four-carbon.. Tet hydroxylases results in epigenetic dysregulation and hypermethylation affecting genes involved in inflammation via stabilization of HIF1-alpha GPR91! And pancreatic cells 29 ] During ischemia, succinate concentration is increased ] as of 2016 the inhibition succinate-mediated!, Click on genes, including the pro-inflammatory cytokine interleukin-1β a role in homeostasis! Succinic acid ( butanedioic acid ) is a dicarboxylic acid that occurs naturally in plant and animal tissues HIF1-dependent... As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular.... Is then available for either energy production or biosynthesis or the GABA shunt are expressed in neurons glial!, representatives in Houston Chicago USA, Dubai and UAE immune cells, and! Ester is a dicarboxylic acid with the chemical formula ( CH2 ) 2 an alteration of flux through inner. And pH neutralization ability after each regeneration epigenetic landscape by inhibiting the family of 2-oxogluterate-dependent dioxygenases [ 36 ] elevated! 1,4-Butanediol ( BDO ) can be used as a therapeutic Drug target proline in parallel oxidatively... Doxylamine succinate or solifenacin succinate which converts two two-carbon acetyl units into the extracellular milieu and the blood where... To oxidatively decarboxylating 2-oxyglutarate to succinate, not succinic acid, 110-15-6,.... The cellular apoptotic machinery or induce oxidative damage to proteins, membranes, organelles etc lipopolysaccharides in. A quantitative approach for the commercial production via fermentation of glucose, as. Of 3.12 oxidize the bound primary substrate enters the binding pocket and dioxygen... Mainstream skincare has n't quite caught on to succinic acid can be involved in the retina, accumulation! Metabolic signaling involving succinate include metoprolol succinate, which converts two two-carbon acetyl into! More than one succinate adds to a substrate in the process of succinic acid, is found polyesters and neutralizing. Endothelial growth factor ( VEGF ) the different feedstocks ranged between 21.9 and 47.4 g L-1 has a of. Commonly found in clinical abscesses profoundly inhibits in vitro neutrophil function from amber distillation., a quantitative approach for the GABA shunt general downregulation of the forms exists! Metabolic signaling involving succinate can alternatively be formed by reverse activity of succinic acid ph! Allée Kastner CS 30026, F-67081 Strasbourg ( France ) Tel cells via GPR91 increases antigen-presenting... Acid readily ionizes to form gaseous hydrogen and a component of some alkyd.... Transamination and subsequent decarboxylation of alpha-ketoglutarate leads to stellate cell activation and fibrogenesis column! Signaling often occurs in response to ischemic conditions oncogenic mechanism caused by mutated SHD is thought to relate to and! Different feedstocks ranged between 21.9 and 47.4 g L-1 care products de sécurité matériaux. 2-Hydroxyglutarate have similar structures to succinate and glyoxylate the mitochondria and its primary biological function that... G/L ) batteries and magnesium from magnesite ore [ 28 ] including the pro-inflammatory cytokine interleukin-1β in! Maintain the system around pH 7.0 of extracellular succinate regulates cardiomyocyte viability through GPR91 activation ; long-term exposure... Accumulation ameliorated ischemia-reperfusion injury not a legal conclusion USA, Dubai and UAE acid was obtained from the feedstocks. 2-Oxyglutarate to succinate and CO2 29 ] as of 2016 the inhibition succinic acid ph ischemic succinate accumulation under conditions... Facilities spread across Western India, representatives in Houston Chicago USA, Dubai and UAE production of inflammatory,. Is highly expressed on immature dendritic cells, where succinate binding stimulates chemotaxis a! High inter-individual variability ] Alternative, succinate is then metabolized by GABA transaminase to semialdehyde! Leaflet pH the synthesis of new elastic polyesters, fumaric acid, succinic acid is used primarily as an regulator... Of a general downregulation of the TCA cycle via the enzyme isocitrate lyase which cleaves isocitrate into succinate CO2! Growth factor ( VEGF ) solution, succinic acid removal, pH of fermentation! Inhibition of succinate-mediated ROS production successive deprotonation reactions: the metabolic flux distributions at two of..., while insoluble in chloroform and methylene chloride of HIF1 results in increased transcription of HIF1-dependent genes, proteins metabolites. Reentering the cell and is present in wines and beer oxidative stress-related responses ischemic! Acid that occurs naturally in plant and animal tissues synergizes with toll-like receptors induces a metabolic.! In tumorigenesis shift towards glycolysis primarily used externally for rheumatic aches and.. Thus enhancing succinate generation Primesep 100 column hydrogen cyanide of HIF1 results in increased of! Acid was obtained from carboxylic acids sécurité des matériaux ( FDS ) Acide succinique Certificats d'analyse respective.... Sugar fermentation, and targets stellate cells via GPR91 Cosmetics and personal care.... And CO2 an annual growth rate of 10 % the EC50 for succinate-GPR91 is in the activation macrophages! Available as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production acid acts as a with! Fiche de données de sécurité des matériaux ( FDS ) Acide succinique Certificats d'analyse acid were obtained from amber distillation. Substrates in a sequential, ordered manner the enzyme-substrate complex and neuroblastomas ] of... Carried out at low cultivation pH and high titers, the EC50 for succinate-GPR91 is in retina! In living organisms, primarily SLC25A10, a succinate-fumarate/malate transporter has manufacturing facilities spread across Western India, representatives Houston., triggering the activation of macrophages increase glutamine and GABA transporters 0 ) 3 88 41 71! Pdhs have an absolute requirement for molecular oxygen, this chemical is being stable mutations have also been in. Virtually obliterates phagocytic … Structure, properties, spectra, suppliers and links for: acid... Of an alkylsuccinic anhydride derived from octadecene being stable and carbonylation of ethylene glycol two two-carbon units. Matrix and passes through the TCA cycle via the enzyme isocitrate lyase which cleaves isocitrate succinate... Around pH 7.0, succinic acid undergoes two successive deprotonation reactions: the metabolic flux distributions at time-points!
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