Optically active reagents have long been important, in studies of reaction mechanisms because they may offer glimpses at the molecular details of the process, How does one obtain optically active compounds? 4, 279 (1987). Kobra Moradifard, Derikvand, Z. 4036-30- (S)-(+)-Phenylsuccinic acid >99 223-719-3 Section 3 - Hazards Identification EMERGENCY OVERVIEW Appearance: almost white solid. Both anions are colorless and can be isolated as the salts, e.g., Na(CH2)2(CO2H)(CO2) and Na2(CH2)2(CO2)2. %PDF-1.4 Added to cooled 10 mL 6 HCl: Reaction immediately but not cloudy enough Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! [42] The other two oncometabolites, fumarate and 2-hydroxyglutarate have similar structures to succinate and function through parallel HIF-inducing oncogenic mechanisms. Who are the experts? N. Shan, A. D. Bond, and W. Jones, Cryst. Space available to draw mechanisms. In humans, three HIF prolyl 4-hydroxylases regulate the stability of HIFs. The calculated specific rotation came out to be 60.65, meaning that it was not optimally pure but the fact that it was positive meaning that it was more of an S enan-tiomer than an R which was preferred. Neutral phenylsuccinic - 173.212.249.81. Single crystal structures, thermal analysis, powder X-ray analysis and equilibrium solubility in water and ethanol of the cocrystals were measured. Mutations in SDH, hypoxia or energetic misbalance are all linked to an alteration of flux through the TCA cycle and succinate accumulation. We reviewed their content and use your feedback to keep the quality high. May cause skin irritation. Potential Health Effects If you have any questions When the solution is completely ho-mogenous, remove the flask from the hot plate and allow to cool. [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. Vis x dm) r=the observed angular rotation of planc-polarized light in degrees 1 - cell path length in decimeters (1 dm - 10 cm; use I dm in equation) c-concentration of compound in g'mL of solution The published specific rotation of (+-phenylsuccinic acid is +173.3" (Shiraiwa, T., Sado, Y, Fujii, S. Nakamura, M., Kurokawo, H., Bull. o Likely reflux conflict of earlier step in result of failure to eliminate (R)-acid and 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. In animal models, pharmacological inhibition of ischemic succinate accumulation ameliorated ischemia-reperfusion injury. 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]. Chem. Succinate thus serves as a direct electron donor to the electron transport chain, and itself is converted into fumarate. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. C. C. Seaton, CrystEngComm 13, 6583 (2011). Oversuccination occurs when more than one succinate adds to a substrate. Remove the beaker from the ice bath and quickly dry off the outside with a paper towel to prevent water from contaminating the crystals. With the product collected, specific rotation was calculated where polarimetry is used to calculate the alpha observed in degrees. Also calculate the samples enantiomeric excess. Calculate the exact concentration which will be needed to calculate specific rotation. [41], Succinate accumulation under hypoxic conditions has been implicated in the reperfusion injury through increased ROS production. [ 1], Succinate can alternatively be formed by reverse activity of SDH. 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. tory IB Syllabus. [30] Stimulation of GPR91 triggers at least two signaling pathways in the heart: a MEK1/2 and ERK1/2 pathway that activates hypertrophic gene expression and a phospholipase C pathway which changes the pattern of Ca2+ uptake and distribution and triggers CaM-dependent hypertrophic gene activation. Experimental Procedure: 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 . Upon reperfusion, succinate is rapidly oxidized leading to abrupt and extensive production of ROS. The substance identifiers displayed in the InfoCard are the best available substance name, EC number, CAS number and/or the molecular and structural formulas. Google Scholar. [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. This involves an acid-base reaction with (s)-proline and restor- The phenylsuccinic acid is a proton donor making proline the proton acceptor. Santa Cruz Biotechnology, Inc. is a world leader in the development of products for the biomedical research market. Other information Prepared By Regulatory Affairs Thermo Fisher Scientific Email: EMSDS.RA@thermofisher.com Revision Date 24-Dec-2021 Print Date 24-Dec-2021 Skin: Next, place crude solid in a 125mL Erlenmeyer flask and boil 100mL of water in a 250mL Erlenmeyer flask. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation of the plane of polarized light). 1).Factors affecting the extraction efficiency were investigated, namely the influence of the types of organic solvents and -CD derivatives, iso-butyl tartrate . 5 mL of DI water. [40] In spite of a general downregulation of the TCA cycle under these conditions, succinate concentration is increased. [7][32] Succinate may enhance adaptive immunity by triggering the activity of antigen-presenting cells that, in turn, activate T-cells. Exact concentration: 0 10 mL=0. [27], Succinate is produced and concentrated in the mitochondria and its primary biological function is that of a metabolic intermediate. Water tums Solubility: Not available. Scratch inside this test tube several minutes until the contents begin to get cloudy. To get rid of 2-propanol and any unreacted phenylsuccinic acid, wash the crystals with 10 mL of acetone. 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. this experiment, a reflux reaction [33] Therapies targeting succinate to reduce cardiovascular risk and hypertension are currently under investigation.[28]. So, for optical activity to be evident, there must be an excess of one enantiomer over its mirror image. [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. [39] Other inflammatory cytokines produced by activated macrophages such as tumor necrosis factor or interleukin 6 are not directly affected by succinate and HIF1. Call us Toll Free at 1-800-457-3801. For a compound to be optimally pure, it would have to reach up to 171. please email the information below to [emailprotected]. phenylsuccinic acid would bind to the proton (H+), where it loses its negative charge and be- 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. 4, 417 (2007). 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. solid. Commun. Garcia, Jessica. After refluxing, cool flask for 15 minutes, We reviewed their content and use your feedback to keep the quality high. For this reason, if the biologically produced. Insoluble in water. This work presents more extensive results of separation of phenylsuccinic acid enantiomers by biphasic recognition chiral extraction (BRCE), which is an important intermediate of N-methyl--phensuximide and antitumor agents (in Fig. [16] The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. of this substance have not been fully investigated. The acid and base are structurally more complex than HCl and NH3, but the concept is the same. (R)-(-)-Phenylsuccinic acid | C10H10O4 | CID 736145 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological . 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. https://doi.org/10.1134/S1063774519070125, DOI: https://doi.org/10.1134/S1063774519070125. Nonsuperposable mirror image molecules are called enantiomers. Enzymes required for the GABA shunt are expressed in neurons, glial cells, macrophages and pancreatic cells. Growth Des. J. M. Chen, Z. Sample will be analyzed by polarimetry. Lett. A suitable solvent is found by trial and error. Mass of product dissolved in acetone: 0 configuration enantiomer, the other diastereomer must be more soluble during the filtration Dehydration of succinic acid gives succinic anhydride. Course Hero is not sponsored or endorsed by any college or university. [36][37], Succinate inhibition of prolyl hydroxylases (PHDs) stabilizes the transcription factor hypoxia inducible factor (HIF)1. Struct. This process Resulting in observing another groups data: 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). tainer. Succinate and fumarate inhibit the TET (ten-eleven translocation) family of 5-methylcytosine DNA modifying enzymes and the JmjC domain-containing histone lysine demethylase (KDM). [10] Global production is estimated at 16,000 to 30,000 tons a year, with an annual growth rate of 10%. G. M. Sheldrick, Acta Crystallogr. S. Mittapalli, M. K. C. Mannava, U. Optical Rotation: []=obscl[]=(0.03992/m)( 1 )=60 connect to this server when you are off campus. As a consequence, the mixture cases no net rotation, and appears optically inactive. Growth Des. Conditions to Avoid:Incompatible materials, dust generation, excess heat, strong oxidants. Your email subscription to News & Announcements has been received. Collect the purified crystals by vacuum filtration and rinse with 10mL of ice cold water. Lowell, Massachusetts. These chemicals are invariably synthesized by catalysts called, enzymes, which are large chiral molecules specially designed to carry out a particular chemical, transformation. To begin, dissolve 1 of racemic phenylsuccinic acid into 50mL of isopropanol in a Less The diastereomeric salt formed between the (+)-phenylsuccinic acid and (-)-proline is much ___ soluble in isopropyl alcohol than the diastereomeric salt formed between the . [5], Historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber. [35] First, 2-oxoglutarate coordinates with an Fe(II) ion bound to a conserved 2-histidinyl1-aspartyl/glutamyl triad of residues present in the enzymatic center. 15 mL) and swirl for a minute to mix, then boil gently for 30 min (add boiling chip!). endobj Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity [36] Pathologically elevated levels of succinate lead to hypermethylation, epigenetic silencing and changes in neuroendocrine differentiation, potentially driving cancer formation. Think of a chiral center as an atom to which four different, groups are covalently attached. The information below may provide an [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. 1 0 obj Such mirror images represent different stereoisomers they are different molecules. The phenylsuccinic acid is a proton donor making proline the proton acceptor. Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that are to be fashioned into the product.

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