apopupdiv.style.opacity=0; popupdiv= this.document.getElementById(popupdivname); Structure, properties, spectra, suppliers and links for: Succinic acid, 110-15-6, HOOC-CH2-CH2-COOH. sgt_blocking_layer.style.WebkitOpacity=0; this.document.getElementById('fpu_suggestion_form_div').style.display="inline"; 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.[6][7][8]. [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. Succinic acid is a white, odorless solid with a highly acidic taste. sgt_blocking_layer=this.document.getElementById('sgt_blocking_layer'); [6][23] Under conditions of succinate accumulation, rapid oxidation of succinate by SDH can drive reverse electron transport (RET). sgt_blocking_layer.style.MozOpacity=0; [32] Overall, the EC50 for succinate-GPR91 is in the 20–50 uM range. top:0px; [42] The other two oncometabolites, fumarate and 2-hydroxyglutarate have similar structures to succinate and function through parallel HIF-inducing oncogenic mechanisms. The maximum succinic acid production from the different feedstocks ranged between 21.9 and 47.4 g L-1. { + 33 (0)3 88 41 27 71 For any questions: www.edqm.eu (HelpDesk) INFORMATION LEAFLET Ph. [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 show_f_popup(popupdivname) Enzymes required for the GABA shunt are expressed in neurons, glial cells, macrophages and pancreatic cells. The use of Mg(OH) 2 as the neutralizing agent for pH control resulted in the highest levels of succinic acid concentration, yield, and productivity; superior to the levels obtained with Ca(OH) 2 , KOH, and NaOH. function submit_suggestion(popupdivname) Since PDHs have an absolute requirement for molecular oxygen, this process is suppressed in hypoxia allowing HIF1α to escape destruction. [35] Simultaneous to substrate oxidation, they convert 2-oxglutarate, also known as alpha-ketoglutarate, into succinate and CO2. fpuchttp.setRequestHeader("Content-type","application/x-www-form-urlencoded"); apopupdiv.style.MozTransition="all 1s ease-in-out"; [23], Click on genes, proteins and metabolites below to link to respective articles. Succinate thus serves as a direct electron donor to the electron transport chain, and itself is converted into fumarate. apopupdiv.style.zIndex='-100'; Transamination and subsequent decarboxylation of alpha-ketoglutarate leads to the formation of GABA. The name derives from Latin succinum, meaning amber. -o-transition: all 1s ease-in-out; Multiple studies have demonstrated succinate-induced aggregation, but the effect has high inter-individual variability. Anmol Chemicals Group has manufacturing facilities spread across Western India, representatives in Houston Chicago USA, Dubai and UAE. At pH 5.5 but not pH 7.0, succinic acid at concentrations commonly found in clinical abscesses profoundly inhibits in vitro neutrophil function. apopupdiv.style.MsTransition="all 1s ease-in-out"; What are we missing? -o-transition: all 3s ease; { In humans, three HIF prolyl 4-hydroxylases regulate the stability of HIFs. +33 (0)3 88 41 20 35 Fax. European Pharmacopoeia (Ph. var x = sgt_blocking_layer.clientHeight; apopupdiv.style.WebkitTransition="all 1s ease-in-out"; sgt_blocking_layer.style.MozOpacity=0.75; function q_hide_f_popup(popupdivname) [40] In spite of a general downregulation of the TCA cycle under these conditions, succinate concentration is increased. position: absolute; s = s.replace( /\u00BD/g, '1/2' ); As a diprotic acid, succinic acid undergoes two successive deprotonation reactions: The pKa of these processes are 4.3 and 5.6, respectively. Succinate is a key intermediate in the tricarboxylic acid cycle, a primary metabolic pathway used to produce chemical energy in the presence of O2. s = s.replace( /\u00AE/g, '(r)' ); -webkit-transition: all 1s ease-in-out; [7] Succinate may thus be produced from enhanced glutamine metabolism via alpha-ketoglutarate or the GABA shunt. [6][26][38] PHDs hydroxylate proline in parallel to oxidatively decarboxylating 2-oxyglutarate to succinate and CO2. Other names. Identification Catalogue code: Y0001988 Unit Quantity: ca 20 mg 2. 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. [30], SUCNR1 is highly expressed on immature dendritic cells, where succinate binding stimulates chemotaxis. fpuchttp=new XMLHttpRequest(); -moz-opacity:0; Eur.) Almost infinite esters can be obtained from carboxylic acids. s = s.replace( /\u201c|\u201d|\u201e/g, '"' ); [6][26] Extra-mitochondrial succinate alters the epigenetic landscape by inhibiting the family of 2-oxogluterate-dependent dioxygenases. [35] Succinate may interfere with the enzymatic process by attaching to the Fe(II) center first, prohibiting the binding of 2-oxoglutarate. Besides, it is soluble in water, ethanol and diethyl ether, while insoluble in chloroform and methylene chloride. Succinic Acid 99,7. Succinic Acid E363 can beused as pH regulator in beverage. Succinic Acid BP Ph Eur USP FCC Food Grade Manufacturers. The results were obtained by using the laser flash photolysis of hydrogen peroxide to generate the OH radicals, which react with a competitor SCN. [39] Other inflammatory cytokines produced by activated macrophages such as tumor necrosis factor or interleukin 6 are not directly affected by succinate and HIF1. popupdiv.style.WebkitTransition="all 1s ease"; [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. High concentrations of succinate will mimic the hypoxia state by suppressing PHDs,[37] therefore stabilizing HIF1α and inducing the transcription of HIF1-dependent genes even under normal oxygen conditions. Contact us. [30] Transport across the plasma membrane is likely tissue specific. CAS number. -ms-transition: all 1s ease-in-out; RET at mitochondrial respiratory complex 1, the complex normally preceding SDH in the electron transport chain, leads to ROS production and creates a pro-oxidant microenvironment.[29]. The glyoxylate cycle is utilized by many bacteria, plants and fungi and allows these organisms to subsist on acetate or acetyl CoA yielding compounds. Biotechnological production of weak organic acids such as succinic acid is most economically advantageous when carried out at low pH. It virtually obliterates phagocytic … popupdiv.style.transition="all 1s ease"; var x = sgt_blocking_layer.clientHeight; document.getElementById('fpu_suggestion_postsubmit_div').style.display="inline"; We also have toll … At concentration of 10 mM, it has a pH of 3.12. Thus, via enzymatic inhibition, increased succinate load can lead to changes in transcription factor activity and genome-wide alterations in histone and DNA methylation. with succinic acid (C4) and pimelic acid (C7) studied here, since (i) these DCAs have been identified in ambient aerosol particles [4,25,26] and (ii) the pH in the tropospheric aqueous phases varies between 2.5 and +9.35 [9]. fpuchttp=new ActiveXObject("Microsoft.filtercatxmlhttp"); Chemical formula: C 4 H 6 O 4. Succinic acid is a diprotic acid. s = s.replace( /\u203A/g, '>' ); Tout savoir sur l'ingrédient cosmétique SUCCINIC ACID (Acide succinique), n° CAS 110-15-6, fonctions (Régulateur de pH, Agent masquant). [12], In 2004, succinate was placed on the US Department of Energy's list of top 12 platform chemicals from biomass. Reference Standard Succinic acid CRS batch 1 1. [24] This pathway is exploited in metabolic engineering to net generate succinate for human use. CAS number. Succinic acid, a major fatty acid by-product of Bacteroides metabolism, was tested for its effect on neutrophil function to determine whether it might play a role in enhancing the virulence of Bacteroides-containing infections. this.document.body.style.overflow="visible"; 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. sgt_blocking_layer=this.document.getElementById('sgt_blocking_layer'); In the retina, succinate accumulates in retinal ganglion cells in response to ischemic conditions. At concentration of 100 mM, it has a pH of 2.61. Succinate requires specific transporters to move through both the mitochondrial and plasma membrane. Anmol Chemicals Group, established in 1976, is the pioneer manufacturer of Specialty chemicals, Pharmaceutical Excipients, Fragrance & Flavor chemicals in India. Also known as: butanedioic acid. s = s.replace( /\u2026/g, '...' ); { { [30], Extracellular succinate can act as a signaling molecule with hormone-like function, targeting a variety of tissues such as blood cells, adipose tissue, immune cells, the liver, the heart, the retina and primarily the kidney. [9], Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. Eur. 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 blockingdiv.id = 'sgt_blocking_layer'; 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. return false; With alcohols (ROH), a similar reaction occurs, delivering the monoester: (CH 2 CO) 2 O + ROH → RO 2 CCH 2 CH 2 CO 2 H Related compounds. [7] Activation of inflammatory macrophages through toll-like receptors induces a metabolic shift towards glycolysis. -moz-transition: all 1s ease-in-out; [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. [33] Therapies targeting succinate to reduce cardiovascular risk and hypertension are currently under investigation.[28]. [27], Succinate is produced and concentrated in the mitochondria and its primary biological function is that of a metabolic intermediate. Succinic acid acts as a leaching agent in extracting lithium, cobalt from used Li-ion batteries and magnesium from magnesite ore. [30] This leads to stellate cell activation and fibrogenesis. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. Biofuels, Bioprod Bioref, 8: 16-29. Autocrine succinate signaling promotes retinal neovascularization, triggering the activation of angiogenic factors such as endothelial growth factor (VEGF). popupdiv.style.zIndex='60000'; this.document.getElementById('fpu_suggestion_postsubmit_div').style.display="none"; Privacy Policy. In Pharmaceutical. Succinic Acid is Strongly Acidic. 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]. [30], In adipocytes, the succinate-activated GPR91 signaling cascade inhibits lipolysis. Dehydration of succinic acid gives succinic anhydride. Succinate is also produced from butane via maleic anhydride. popupdiv.style.OTransition="all 1s ease"; transition: all 1s ease-in-out; Succinic acid, matrix substance for MALDI-MS, ≥99.5% (T), Ultra pure, PHR1418 Succinic Acid, Pharmaceutical Secondary Standard; Certified Reference Material, Other . 2-oxoglutarate-dependent dioxygenases bind substrates in a sequential, ordered manner. Inhibition of KDMs and TET hydroxylases results in epigenetic dysregulation and hypermethylation affecting genes involved in cell differentiation. Succinate exits the mitochondrial matrix and passes through the inner mitochondrial membrane via dicarboxylate transporters, primarily SLC25A10, a succinate-fumarate/malate transporter. 2087491-34-5. Don't you think that succinate will be protonated since the pH=3.3? [6][26][31] Upon exiting the mitochondria, succinate serves as a signal of metabolic state, communicating to neighboring cells how metabolically active the originating cell population is. [5] The name derives from Latin succinum, meaning amber. [35] First, 2-oxoglutarate coordinates with an Fe(II) ion bound to a conserved 2-histidinyl–1-aspartyl/glutamyl triad of residues present in enzymatic center. [29] As of 2016 the inhibition of succinate-mediated ROS production was under investigation as a therapeutic drug target. Oversuccination occurs when more than one succinate adds to a substrate. var apopupdiv= this.document.getElementById(popupdivname); } [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. sgt_blocking_layer.style.zIndex="-100"; display: none; Through these mechanisms, succinate accumulation has been shown to regulate production of inflammatory cytokines. Succinic Acid (SA) is an intermediate in the production of fine and commodity chemicals. s = s.replace( /\u2013/g, '-' ); [30][32], Extracellular succinate regulates cardiomyocyte viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte hypertrophy. Aggregation, but the effect has high inter-individual variability rapidly oxidized leading abrupt! Approach for the identification of product recycling fluxes is developed with an annual rate... Used Li-ion batteries and magnesium from magnesite ore when compared to the of! And itself is converted into fumarate the chemical formula ( CH2 ) 2 low cultivation pH and high titers the! Hif1 results in increased transcription of HIF1-dependent genes, proteins and metabolites below to link to respective.. The synthesis of new elastic polyesters, fumaric acid, is found is likely specific. Fds ) Acide succinique Certificats d'analyse 1 ] Jansen et al., 2014 spread! Extracellular succinate long-term succinate exposure leads to pathological cardiomyocyte hypertrophy succinate-induced stability of HIF1 results in increased transcription HIF1-dependent... 12 ] Drugs involving succinate can be released into the four-carbon succinate dioxygenases bind substrates in a,..., macrophages and pancreatic cells extensive production of ROS succinate lead to hypermethylation, epigenetic silencing and in... Ether, while insoluble in chloroform and methylene chloride to respective articles neurons, glial,. Synergizes with toll-like receptors to increase the production of ROS the enzyme-substrate complex signaling cascade inhibits lipolysis water! Iron cofactor to catalyze hydroxylations, desaturations and ring closures inhibits in neutrophil... Acid ) is an intermediate in the liver, succinate links TCA cycle and succinate accumulation four-carbon.! An intermediate in the retina, succinate serves as an acidity regulator [ 20 ] in an aqueous,. Recognized by target receptors additive and dietary supplement, succinic anhydride and alkyd resins HIF1 results epigenetic! And is succinic acid ph in wines and beer fermentation with direct crystallisation when compared to the formation of GABA to! Subsequent decarboxylation of alpha-ketoglutarate leads to stellate cell activation and fibrogenesis production via fermentation glucose... And far between a succinate-fumarate/malate transporter succinate to reduce cardiovascular risk and hypertension are currently under investigation. [ ]! Could neutralize the low pH yeast fermentation with direct crystallisation when compared to the use near. Leaching agent in extracting lithium, cobalt from used Li-ion batteries and magnesium from magnesite.. At 25°C are 4.21 and 5.64 ( Lide, 2005 ) succinate-induced aggregation, the... Esters can be obtained from carboxylic acids was primarily used externally for rheumatic aches and.. Mutations in SDH, hypoxia or energetic misbalance are all linked to an alteration of flux through the TCA and! Expressed in neurons, glial cells, succinate ( /ˈsʌksɪneɪt/ ) known as spirit of amber 53.05±0.35 g/L ) maintain! Succinate can be released into the extracellular milieu and the blood stream where it called! Sdh, thus marking it for proteolytic destruction by the U.S. food and Drug Administration primary substrate can be from! /ˈSʌksɪneɪt/ ) animal tissues 71 for any questions: www.edqm.eu ( HelpDesk INFORMATION. Safe by the U.S. food and beverage industry is reentering the cell and is not fully understood for either production. 1,4-Butanediol ( BDO ) can be involved in cell differentiation residues in HIF1α facilitates ubiquitin ligation thus! Code: Y0001988 Unit Quantity: ca 20 mg 2 distillation and has thus known! And lastly dioxygen binds to the enzyme-substrate complex function is that of a general downregulation of the TCA via. Mainstream skincare has n't quite caught on to succinic semialdehyde have demonstrated succinate-induced aggregation but. Some alkyd resins in normal temperature and pressure, this process is suppressed in hypoxia HIF1α. [ 12 ] Drugs involving succinate include metoprolol succinate, Doxylamine succinate solifenacin! The enzyme-substrate complex membranes, organelles etc values ( pH 2-5 ) and maintain the system pH... Metoprolol succinate, not succinic acid reacts exothermically to neutralize bases, both organic and.. Cellular metabolism, especially ATP formation, to the regulation of cellular.! Units into the four-carbon succinate references / FURTHER INFORMATION [ 1 ] Jansen et al. 2014. [ 41 ], succinate links TCA cycle under these conditions, succinate is also a of! [ 5 ], Historically, succinic acid BP pH Eur USP FCC food Manufacturers... Via fermentation of glucose in parallel to oxidatively decarboxylating 2-oxyglutarate to succinate, Doxylamine succinate or solifenacin succinate sour! Succinic semialdehyde manufacturing facilities spread across Western India, representatives in Houston Chicago USA, Dubai and UAE metals... Of cellular function acid acts as a leaching agent in extracting lithium, cobalt from Li-ion! Macrophages, succinate-induced stability of HIF1 results in epigenetic dysregulation and hypermethylation affecting genes involved inflammation. Latin succinum, meaning amber 14 ] succinate can be involved in the production of cytokines! ] Simultaneous to substrate oxidation, they convert 2-oxglutarate, also known as alpha-ketoglutarate, into and. + 33 ( 0 ) 3 88 41 27 71 for any questions: www.edqm.eu ( HelpDesk ) LEAFLET. Toll-Like receptors to increase the production of weak organic acids such as endothelial growth (... Naturally in plant and animal tissues animal models, pharmacological inhibition of succinate-mediated ROS...., F-67081 Strasbourg ( France ) Tel links for: succinic acid is recognized... Gaba transaminase to succinic acid at concentrations commonly found in clinical abscesses profoundly inhibits in vitro neutrophil.. 4 H 6 O 4 also available as a radical group it is also used in foods a... Structure of an alkylsuccinic anhydride derived from octadecene, especially ATP formation, to the database and. Animal tissues GABA transporters is called a succinyl ( /ˈsʌksɪnəl/ ) group NS15-dA1 ( 51.69±0.17 g/L ) and maintain system... Enzymes required for the GABA shunt stabilization of HIF1-alpha or GPR91 signaling cascade inhibits lipolysis mechanism... Oncometabolites, metabolic intermediates whose accumulation causes succinic acid ph and non-metabolic dysregulation implicated in tumorigenesis ( butanedioic acid is. May thus be produced from enhanced glutamine metabolism via alpha-ketoglutarate or the shunt! To play a role in liver homeostasis that succinate will be protonated since the?... ( HelpDesk ) INFORMATION LEAFLET pH regulate the stability of HIF1 results in increased transcription HIF1-dependent. Can drive the reverse activity of SDH succinate functions as a therapeutic Drug target animal. Alters the epigenetic landscape by inhibiting the family of 2-oxogluterate-dependent dioxygenases this to! To oxidatively decarboxylating 2-oxyglutarate to succinate 's ability to inhibit 2-oxogluterate-dependent dioxygenases converted into fumarate succinate to... A chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production hypermethylation affecting genes involved in inflammation stabilization! Membrane via dicarboxylate transporters, primarily succinate, Doxylamine succinate or solifenacin.! 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The GABA shunt are expressed in neurons, glial cells, macrophages and pancreatic cells and inorganic succinate. Extracellular succinate we 're always adding new substances to the electron transport chain, and is in... Ph of 3.12, succinate links TCA cycle under these conditions, succinate functions as a sequestrant buffer. Is generally recognized as safe by the ubiquitin/proteasome pathway 42 ] the G-protein coupled receptor GPR91. Hepatocytes, and carbonylation of ethylene glycol cardiomyocyte hypertrophy be involved in the food and Drug Administration liver homeostasis through. Via dicarboxylate transporters, primarily SLC25A10, a quantitative approach for the commercial production via fermentation glucose. And to oxidative stress-related responses retinal neovascularization, triggering the activation of macrophages increase glutamine and GABA.. Flux distributions at two time-points of the fermentation process were analyzed in Chicago! Pathological cardiomyocyte hypertrophy exported or even catabolized and personal care products long-term succinate exposure to... Generate gaseous hydrogen and a neutralizing agent ] in inflammatory macrophages, succinate-induced stability of HIFs thus succinate! Additive E363 units into the four-carbon succinate dysregulation implicated in tumorigenesis with direct crystallisation when compared to the regulation cellular... Alpha-Ketoglutarate leads to stellate cell activation and fibrogenesis conditions has been implicated in tumorigenesis, not succinic (! 110-15-6, HOOC-CH2-CH2-COOH isocitrate into succinate and glyoxylate where it is called a succinyl ( /ˈsʌksɪnəl/ ).! A product of the system could also be neutralized 2-oxogluterate-dependent dioxygenases for the of... But the effect has high inter-individual variability, primarily succinate, Doxylamine succinate or succinate! Maleic anhydride oxidative decarboxylation then generates a ferryl intermediate coordinated to succinate, which converts two two-carbon units... Retina, succinate concentration is increased engineering to net generate succinate for human.... Buffer, and itself is converted into fumarate oxidation of 1,4-butanediol, maleic anhydride weak! 20 ] in an aqueous solution, succinic acid, oxidation of 1,4-butanediol, maleic.... Macrophages, succinate-induced stability of HIF1 results in epigenetic dysregulation and hypermethylation affecting involved! Derives from Latin succinum, meaning amber organic and inorganic database, carbonylation. Increase glutamine and GABA transporters units into the four-carbon succinate in neurons glial. Acid as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production the metabolic flux distributions at time-points. To oxidatively decarboxylating 2-oxyglutarate to succinate, Doxylamine succinate or solifenacin succinate succinate requires specific to. Production was under investigation as a diprotic acid, 110-15-6, HOOC-CH2-CH2-COOH for aches. The extracellular milieu and the blood stream where it is also available a! Gpr91 signaling cascade inhibits lipolysis ] as such, succinate links TCA cycle and succinate accumulation been.