phenylsuccinic acid solubility

[32] Furthermore, SUCNR1 synergizes with toll-like receptors to increase the production of proinflammatory cytokines such as TNF alpha and interleukin-1beta. This is an ordinary acid-base reaction that produces a salt. Vacuum filtered and flushed with 30 mL of acetone: chunky powder, roux-like (S)- After refluxing, cool flask for 15 minutes, Este site coleta cookies para oferecer uma melhor experincia ao usurio. tiomer behind. Colby VPN to [27], Succinate is produced and concentrated in the mitochondria and its primary biological function is that of a metabolic intermediate. 1 0 obj Use a Pasteur pipet to drizzle 1-2 mL of ice-cold water over the entire surface of the solid to wash away as much 6 M HCl as possible. Kobra Moradifard, Derikvand, Z. Not Intended for Diagnostic or Therapeutic Use. D. K. Bucar, R. F. Henry, X. C. Lou, et al., Mol. Enantiomeric excess: of (+)-phenylsuccinic acid, To comprehend the conversion of an enantiomer to a di-astereomer, enantiomers are identical while diastereomers are not so they can be created by reacting a mixture of both enantiomers with another chiral molecule. Transamination and subsequent decarboxylation of alpha-ketoglutarate leads to the formation of GABA. Commun. To begin, dissolve 1 of racemic phenylsuccinic acid into 50mL of isopropanol in a Let Cool for 15 min: very chunky, wet-sand-like consistency, almost solid - slushy, succinic acid and proline to pro- Optically active reagents have long been important in studies of reaction mechanisms because they may offer glimpses at the molecular details of the process as the reaction proceeds. 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Moreover, the cold water wash and filtration performed was able to recover the crude solid. Mass of product dissolved in acetone: 0 indication of why you can't access this Colby College website. Phenylsuccinic acid [28], Succinate serves as a modulator of blood pressure by stimulating renin release in macula densa and juxtaglomerular apparatus cells via GPR91. Stir for 5 min to allow complete protonation. The phenylsuccinic acid is a proton donor making proline the proton acceptor. www.colby.edu/directory-profile-update-form you must use the Article tical rotation using polarimetry. Measure the specific rotation and determine the enantiomeric excess of the sample. Molecular Formula: C 10 H 10 O 4. volumes of cold water. . No information found. 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]. The difference, however, is subtle. Vacuum filter and wash the solid with two 15mL Pharmacol. CHEM: Organic Chemistry Labora- The acid and base are structurally more complex than HCl and NH3, but the concept is the same. First, we exploit its chemical nature it is m acid) by treating it with an optically active biologically produced base, L-proline. Cool 10mL of 6 M HCl in an ice bath and add all of the collected salt to this cold HCl. [10] 1,4-Butanediol (BDO) can be synthesized using succinic acid as a precursor. please help with the following two questions:1. For | Chegg.com Jump to main content Jump to site nav. Orgo I Lab 4 - orgo - Lexxus Pen Organic Chemistry I Lab Section 803 9 Appearance: almost white solid. 1112, 1 (2016). Experiment 4: Resolution of Phenylsuccinic Acid First, we exploit its chemical nature it is an acid) by treating it with an optically active biologically produced base, L-proline. This website collects cookies to deliver a better user experience. Soc. Eye: The reaction between the bis salt of proline and phenylsuccinic acid will give free phenyl succinic acid and proline hydrochloride as HCl is a much stronger acid than phenylsuccinic acid. Give the % of each enantiomer. 3) Recovery of resolved acid: Add all of the solid to 8 mL of ice-cold 6 M HCl in a small beaker or glass tube, place the sample in an ice bath. Experts are tested by Chegg as specialists in their subject area. Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA). Specific rotation is defined as [.." - r/le where "-the specific rotation (at 200C using the "D line" of a sodium lamp: units arc (deg x ml. [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. The chiral recognition abilities of the two selectors are opposite . Stir the mixture with a glass rod for 5 minutes. Struct. DL-Phenylsuccinic acid, 98+%, Thermo Scientific Chemicals Garcia, Jessica. This diethyl ester is a substrate in the Stobbe condensation. The possibility of why the specific rotation was so low was because the concentration might have been too low to consider in the first place. May cause irritation of the digestive tract. [5] The name derives from Latin succinum, meaning amber. InChI=1S/C10H10O4/c11-9(12)6-8(10(13)14)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,12)(H,13,14)/t8-/m0/s1, CSID:643286, http://www.chemspider.com/Chemical-Structure.643286.html (accessed 08:22, Mar 4, 2023), Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, Predicted data is generated using the US Environmental Protection Agencys EPISuite, Click to predict properties on the Chemicalize site, For medical information relating to Covid-19, please consult the. Insoluble in water. The toxicological RECEIVE -15-CRUZ CREDITS. DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. The Index number for each substance is in the form of a digit sequence of the type ABC-RST-VW-Y. connect to this server when you are off campus. Enantiomers are, distinguished from each other by designations like "R" or "S", "D" or "L", or by the direction of the rotation, Since the presence of optical activity is an indication of a particular configuration of atoms, any, change in optical activity that occurs during a chemical reaction offers a way to study the kind of, configurational change that accompanies the reaction. This website collects cookies to deliver a better user experience. Call us Toll Free at 1-800-457-3801. The enantiomeric excess was 35.5% which is the measurement of purity. Oxidative decarboxylation then generates a ferryl intermediate coordinated to succinate, which serves to oxidize the bound primary substrate. Succinate is also produced from butane via maleic anhydride. [30] Transport across the plasma membrane is likely tissue specific. [30], In adipocytes, the succinate-activated GPR91 signaling cascade inhibits lipolysis. process so the S configuration enantiomer will precipitate into the flask, leaving the R enan- Think of a chinal center as an atom to which four different groups are covalently attached. C. C. Seaton, CrystEngComm 13, 6583 (2011). N. J. Babu, L. S. Reddy, and A. Nangia, Mol. [35] Succinate may interfere with the enzymatic process by attaching to the Fe(II) center first, prohibiting the binding of 2-oxoglutarate. Most often, these pieces can attach to the enzyme only in one particular orientation. Purpose: produced substances are optically active. CAS Number: 4036-30-. RECEIVE -15-CRUZ CREDITS. [37] The oncogenic mechanism caused by mutated SHD is thought to relate to succinate's ability to inhibit 2-oxogluterate-dependent dioxygenases. A. V. Trask, N. Shan, W. D. S. Motherwell, et al., Chem. [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. The difference, however, is subtle Pure samples of mirror image molecules behave identically toward physical tests like melting and boiling points and solubility in given solvents The only way that these isomers differ physically is the direction in which they rotate plane-polarized light -their optical activity. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation of the plane of polarized light). [30] This leads to stellate cell activation and fibrogenesis. Since PHDs have an absolute requirement for molecular oxygen, this process is suppressed in hypoxia allowing HIF1 to escape destruction. X. P. Dai, G. G. Hou, J. F. Sun, et al., J. Mol. Collect the purified crystals by vacuum filtration and rinse with 10mL of ice cold water. the proton acceptor. o Likely reflux conflict of earlier step in result of failure to eliminate (R)-acid and Ingestion: Phenylsuccinic acid (H 2 A, racemate, purity 99 %) was purchased from DiBo (Shanghai, China) and polyethyleneglycol (PEG) was provided by Guangzhou (Guangdong, . Immediately retum the contents to the boiling flask and swirl. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from water. 4 0 obj * Refer to Certificate of Analysis for lot specific data (including water content). A key candidate transporter is INDY (I'm not dead yet), a sodium-independent anion exchanger, which moves both dicarboxylate and citrate into the bloodstream. Please note, if you are trying to access wiki.colby.edu or These must be removed to get a good optical activity measurement. [36] Pathologically elevated levels of succinate lead to hypermethylation, epigenetic silencing and changes in neuroendocrine differentiation, potentially driving cancer formation. Given that enantiomers have identical physical properties, how can the mirror-image molecules become separated without the aid of some living thing? Soluble in acetone, alcohols, and methanol. ), . Accumulation of either fumarate or succinate reduces the activity of 2-oxoglutarate-dependent dioxygenases, including histone and DNA demethylases, prolyl hydroxylases and collagen prolyl-4-hydroxylases, through competitive inhibition. When the solution is cooled down at room temperature, the solubility decreases which allows the pure crystals of phenylsuccinic acid to form. It washes away in the acidic water, leaving nearly pure phenylsuccinic acid as the solid.) Typi- In the liver, succinate serves as a paracrine signal, released by anoxic hepatocytes, and targets stellate cells via GPR91. One proline has a position available for one extra proton, so the two protons end up on two different prolines. 8, 4533 (2008). DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. Mutations in SDH, hypoxia or energetic misbalance are all linked to an alteration of flux through the TCA cycle and succinate accumulation. The chiral recognition abilities of . In order to recrystallize the. This is an ordinary acid-basc reaction that produces a salt. Commun. X`I%&/m{JJt`$@iG#)*eVe]f@{{;N'?\fdlJ!?~|? 2003-2023 Chegg Inc. All rights reserved. Less The diastereomeric salt formed between the (+)-phenylsuccinic acid and (-)-proline is much ___ soluble in isopropyl alcohol than the diastereomeric salt formed between the . Chem. Pharm. Determine the mass of purified crystals and prepare a solution to analyze by polarimetry, first measure about 0.4g of your (S)-phenylsuccinic acid and then dissolve in exactly 10mL of HPLC-grade acetone. Resulting in observing another groups data: [6][26][38] PHDs hydroxylate proline in parallel to oxidatively decarboxylating 2-oxyglutarate to succinate and CO2. N. Shan, A. D. Bond, and W. Jones, Cryst. The first source was natural products chemicals produced by living organisms. Let aspirator run for sev- [37][41] Loss-of-function mutations in the genes encoding succinate dehydrogenase, frequently found in hereditary paraganglioma and pheochromocytoma, cause pathological increase in succinate. T. Friscic, L. Fabian, J. C. Burley, et al., Chem. This property is a direct consequence of the configuration, or orientation of bonded atoms in space, around the chiral center. Experimental Procedure: The impact of chirality is assessed via comparison of structural features and properties of binary cocrystals. Growth Des. [citation needed], As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. Growth Des. The 'Substance identity' section is calculated from substance identification information from all ECHA databases. [9], Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. [34] 2-oxoglutarate-dependent dioxygenases require an iron cofactor to catalyze hydroxylations, desaturations and ring closures. Chronic: Abstract A new co-crystal compound of 4,4'-bipyridine and phenylsuccinic acid was synthesized and characterized by elemental analysis, infrared and ultraviolet-visible spectroscopy, and X-ray single crystal diffraction. L. D. Liu, S. L. Liu, Z. X. Liu, and G. G. Hou, J. Mol. These chemicals are invariably synthesized by catalysts called, enzymes, which are large chiral molecules specially designed to carry out a particular chemical, transformation. The less soluble salt may precipitate. S. Mittapalli, M. K. C. Mannava, U. [30] Depending on the cell type, GPR91 can interact with multiple G proteins, including Gs, Gi and Gq, and enabling a multitude of signaling outcomes. [12] As an excipient in pharmaceutical products, it is also used to control acidity[21] or as a counter ion. Other information Prepared By Regulatory Affairs Thermo Fisher Scientific Email: EMSDS.RA@thermofisher.com Revision Date 24-Dec-2021 Print Date 24-Dec-2021 1035, 203 (2013). Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! Once it was cooled, the purified crystals are collected via vacuum filtration and the final product came out to be 0.399g, thus our concentration being 0.0399g. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Chemical Stability:Stable under normal temperatures and pressures. 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. 24, 861 (1995). High concentrations of succinate will mimic the hypoxia state by suppressing PHDs,[37] therefore stabilizing HIF1 and inducing the transcription of HIF1-dependent genes even under normal oxygen conditions. stream Not Intended for Diagnostic or Therapeutic Use. Enantioseparation of Phenylsuccinic Acid Enantiomers Using Aqueous Two 2. the phenylsuccinic acid will precipitate and can be filtered out while the proline is very soluble in water HCl can also be added to (-)-phenylsuccinic acid to release it from any salt which may have formed specific rotation = alpha (observed rotation in degrees)/ l (dm)*c (g/ml) optical purity aka = enantiomeric excess This is a preview of subscription content, access via your institution. Stir for 5 min to allow complete protonation. If you study models of chiral molecules, it soon becomes apparent that their, mirror images are not superposable on each other. May cause skin irritation. A 71, 3 (2015). Note that the two diastercomeric salts (S.S) and (R.S) differ in their mions (phenylsuccinate), which are nonsuper-posable mirror images, but have identical cations (L-proline). Next, place crude solid in a 125mL Erlenmeyer flask and boil 100mL of water in a 250mL Erlenmeyer flask. Caution! Lexxus Pen Proceed to measure the specific rotation of the sample and calculate the enantiomeric excess 4) Recrystallization: The recovered acid contains contaminants- possibly some left-over proline and some HCl or some of the enantiomeric succinic acid. [7] Activation of inflammatory macrophages through toll-like receptors induces a metabolic shift towards glycolysis. The solubility of the complexes is poor in the top phase, where H 2 A has better solubility than in the bottom phase. Skin: Growth Des. On this Wikipedia the language links are at the top of the page across from the article title. RST is the consecutive number of the substance in the series ABC. [32] Overall, the EC50 for succinate-GPR91 is in the 2050 uM range. Molecular Formula: C 10 H 10 O 4. 1).Factors affecting the extraction efficiency were investigated, namely the influence of the types of organic solvents and -CD derivatives, iso-butyl tartrate . Eng. 4, 339 (2007). Enantiomers are distinguished from cach other by designations like "R" or "S", "D" or "L", or by the direction of the rotation they cause ("+" or "-") Since the presence of optical activity is an indication of a particular configuration of atoms, any change in optical activity that occurs during a chemical reaction offers a way to study the kind of configurational change that accompanies the reaction. Lab8_PhenylsuccinicAcid_handout_F20.pdf - OPTICAL The experiments were carried out in a traditional SS apparatus but with collaborative chiral selectors: dibenzoyl-L-tartaric acid (L-DBTA) in the organic phase and hydroxypropyl-b-cyclodextrin (HP-b-CD) in the aqueous phase. This process produced two diastereomers where the more soluble compound was removed by the HCl. Este site coleta cookies para oferecer uma melhor experincia ao usurio. [15], Succinic acid is a precursor to some polyesters and a component of some alkyd resins. This process produced two diastereomers where the more soluble compound was removed by the HCl. Struct. 5, 9 (2002). (S)-(&)-Phenylsuccinic acid | CAS 4036-30-0 - SCBT Who are the experts? GABA is then metabolized by GABA transaminase to succinic semialdehyde. tainer. Share Improve this answer Follow edited Oct 28, 2019 at 15:24 [40] In spite of a general downregulation of the TCA cycle under these conditions, succinate concentration is increased. This new feature enables different reading modes for our document viewer. [30][32], Extracellular succinate regulates cardiomyocyte viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte hypertrophy. 100mL round bottom flask. This specificity of attachment means that the atoms of the product always end up being connected to each other in only one of several possible ways. In this experiment, 2-propanol is the suitable solvent that will selectively precipitate most of one diastercomer and leave most of the other diastercomer in the solution. PDF Material Safety Data Sheet - Cole-Parmer Heat and gently swirl the mixture on the hot plate until all the solid dissolves (add a little more water if the entire solid is not in solution just as the solution begins to gently boil). OPTICAL RESOLUTION OF 2-PHENYLSUCCINIC ACID (From R. Stephani and V. Cesare, Journal of Chemical Education 74, 1226, 1997) 1) Background: The purposes of this experiment are to show how enantiomers can be separated if they are converted into a mixture of diastereomers and to understand how careful choice of solvent can permit selective precipitation of one compound from a mixture of compounds. this experiment, a reflux reaction Subsequently, the primary substrate enters the binding pocket and lastly dioxygen binds to the enzyme-substrate complex. OPTICAL RESOLUTION OF 2-PHENYLSUCCINIC ACID (From R. Stephani and V. Cesare, Journal of Chemical Education 74.1226, 1997 1) Background: The purposes of this experiment are to show how enantiomers can be separated if they are converted into a mixture of diastereomers and to understand how careful choice of solvent can permit selective precipitation of one compound from a mixture of compounds. In order to recrystallize the solid, boiling water was added to the solid until it fully dissolves to achieve a complete homoge-nous mixture. We reviewed their content and use your feedback to keep the quality high. [7][32] Succinate may enhance adaptive immunity by triggering the activity of antigen-presenting cells that, in turn, activate T-cells. May cause eye, skin, and respiratory Pharm. 4,4-Bipyridine and 1,2-bis(4-pyridyl)ethane were combined with achiral, racemic mixture or pure enantiomers of selected carboxylic acids with similar constituents (p-toluic acid, rac-2-phenylbutyric acid, racemic or S-phenylsuccinic acid). Molecular Weight: 194.18. endobj 3) Recovery of resolved acid: Add all of the solid to 8 mL of ice-cold 6 M HCl in a small beaker or glass tube, place the sample in an ice bath. The name derives from Latin succinum, meaning amber.In living organisms, 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 . [42] The other two oncometabolites, fumarate and 2-hydroxyglutarate have similar structures to succinate and function through parallel HIF-inducing oncogenic mechanisms. The solid that results is now-resolved phenylsuccinic acid in its protonated form. Material Safety Data Sheet - Fisher Sci It was concluded that the aqueous solubility of the cocrystals is inversely related to their melting points and this trend can be linked to some packing features. Because protons have +1 charge, each proline is cationic. [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. They are potentially separable by ordinary physical methods like different solubility in a given solvent, which allows recovery of a single diastereomer If you study models of chiral molecules, it soon becomes apparent that their mirror images are not superposable on each other. PubMedGoogle Scholar. Melting point-solubility-structure correlations in chiral and racemic Chem. The solid was recrystallized and the final solid is filtered out. Learn more about Institutional subscriptions. Add 1 of finely ground (s)-proline & a magnetic stir bar then 20, 2372 (2002). This involves an acid-base reaction with (s)-proline and restoring the enantiomer by neutralizing the salt created to find the optical purity by measuring the optical rotation using polarimetry. Filtration permits discard of the more soluble salt, which cames away one enantiomer () of the phenylsuccinic acid Once the less soluble diastereomeric salt has been isolated, only a single enantiomer of phenylsuccinic acid remains. Succinic acid is a white, odorless solid with a highly acidic taste. Correspondence to N. Shan, F. Toda, and W. Jones, Chem. The phenylsuccinic acid 17, 550 (2017). Phenylsuccinic acid | C10H10O4 | ChemSpider The toxicological properties of this material have Vacuum filter and wash the solid with two 15mL volumes of cold water. 48, 5009 (2006). Santa Cruz Biotechnology, and the Santa Cruz Biotechnology, Inc. logo, Santa Cruz Animal Health, San Juan Ranch, Supplement of Champions, the San Juan Ranch logo, UltraCruz, ChemCruz, ImmunoCruz, ExactaCruz, and EZ Touch are registered trademarks of Santa Cruz Biotechnology, Inc. All trademarks are the property of their respective owners. [30] In the second step of mitochondrial export, succinate readily crosses the outer mitochondrial membrane through porins, nonspecific protein channels that facilitate the diffusion of molecules less than 1.5 kDa. Commun. The experiments were carried out in a traditional SS apparatus but with collaborative chiral selectors: dibenzoyl-L-tartaric acid (L-DBTA) in the organic phase and hydroxypropyl--cyclodextrin (HP--CD) in the aqueous phase. phenylsuccinic salt The proline, its former partner in the salt, remains soluble in the aqueous phase. This application requires Javascript. OPTICAL RESOLUTION OF 2-PHENYLSUCCINIC ACID, (From R. Stephani and V. Cesare, Journal of Chemical Education, The purposes of this experiment are to show how enantiomers can be separated if they are converted into a, mixture of diastereomers and to understand how careful choice of solvent can permit selective precipitation. The recovered solid is the less-soluble diastereomeric salt of the pair that you made. Enzymes required for the GABA shunt are expressed in neurons, glial cells, macrophages and pancreatic cells. Growth Des. Melting point-solubility-structure correlations in chiral and racemic Once the contents of the flask are near room temperature, take it to a sink and run cold water over the outside for one minute while swirling (NO WATER INSIDE! [6][26] Extra-mitochondrial succinate alters the epigenetic landscape by inhibiting the family of 2-oxogluterate-dependent dioxygenases. In addition to its metabolic roles, succinate serves as an intracellular and extracellular signaling molecule. The interactive pathway map can be edited at WikiPathways: Learn how and when to remove this template message, JmjC domain-containing histone lysine demethylase, Institute for Occupational Safety and Health, "Product Information Sheet: Succinic Acid", "Succinate, an intermediate in metabolism, signal transduction, ROS, hypoxia, and tumorigenesis", "Ischaemic accumulation of succinate controls reperfusion injury through mitochondrial ROS", Ullmann's Encyclopedia of Industrial Chemistry, "NNFCC Renewable Chemicals Factsheet: Succinic Acid", "Succinate production in Escherichia coli", "Industrial Systems Biology of Saccharomyces cerevisiae Enables Novel Succinic Acid Cell Factory", "Top Value Added Chemicals from Biomass, Volume 1: Results of Screening for Potential Candidates from Sugars and Synthesis Gas", "1,4-Butanediol (BDO) Market Analysis By Application (Tetrahydrofuran, Polybutylene Teraphthalate, Gamma-Butyrolactone & Polyurethanes), And Segment Forecasts To 2020", "Design and Applications of Biodegradable Polyester Tissue Scaffolds Based on Endogenous Monomers Found in Human Metabolism", "Succinic acid in the FDA SCOGS Database", "Overview of pharmaceutical excipients used in tablets and capsules", "Differential effects of complex II on mitochondrial ROS production and their relation to cardioprotective pre- and postconditioning", "Improved Succinate Production by Metabolic Engineering", "Intermediates of Metabolism: From Bystanders to Signalling Molecules", "The succinate receptor as a novel therapeutic target for oxidative and metabolic stress-related conditions", "Succinate metabolism: a new therapeutic target for myocardial reperfusion injury", "GPR91: expanding the frontiers of Krebs cycle intermediates", "Insight into SUCNR1 (GPR91) structure and function", "Inhibition of -KG-dependent histone and DNA demethylases by fumarate and succinate that are accumulated in mutations of FH and SDH tumor suppressors", "Oncometabolites: linking altered metabolism with cancer", "Inhibition of hypoxia-inducible factor (HIF) hydroxylases by citric acid cycle intermediates: possible links between cell metabolism and stabilization of HIF", "Succinate is a danger signal that induces IL-1 via HIF-1", "Metabolic reprogramming in macrophages and dendritic cells in innate immunity", "Oncometabolites: Unconventional triggers of oncogenic signalling cascades", "Succinate dehydrogenase and fumarate hydratase: linking mitochondrial dysfunction and cancer", Flame Retardant Finishing of Cotton Fleece Fabric: Part IV-Bifunctional Carboxylic Acids, Calculator: Water and solute activities in aqueous succinic acid, ScienceDirect: Succinic Acid - Production of organic acids and enzymes / biocatalysts from food waste, PubChem: Compound Summary for Succinic Acid, https://en.wikipedia.org/w/index.php?title=Succinic_acid&oldid=1135423431, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Short description is different from Wikidata, Articles with unsourced statements from January 2021, Articles lacking reliable references from March 2017, Creative Commons Attribution-ShareAlike License 3.0, This page was last edited on 24 January 2023, at 15:55.

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