phenylsuccinic acid solubility

X`I%&/m{JJt`$@iG#)*eVe]f@{{;N'?\fdlJ!?~|? Allow the flask to air-cool about 10 min. 7, 1291 (2007). [12][13], Succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. ing the enantiomer by neutralizing the salt created to find the optical purity by measuring the op- "R}~Q:~pgg'"l/O:OV~ @zo7g;)K;=d'}z8}7w7?Iuw?w~ik=w= f.y_j6}Y23 > qB-i%mSiGt{ogo&wMuv!v?qB&p4.IR)>~O4v{x?StuS)F;Nf-iLn)&}tfi7|y]6X4o72{d4j>:h_h=^NC{ ? P4%W,w& y${N~`__/ 1CUoOv|q,foCwa ToC)x;2W`tF2 b2~P2hMD>? Curr. 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. Crystallogr. Question: In this experiment, racemic (RS)-phenylsuccinic acid is separated (resolved) into optically active cautiouets in a sequence of two steps. 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. RECEIVE -15-CRUZ CREDITS. 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. . [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. Abstract. N. J. Babu, L. S. Reddy, and A. Nangia, Mol. ), 2) Recovery of less soluble salt: Vacuum filter the contents of the flask using a medium Buchner funnel. 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. In addition to its metabolic roles, succinate serves as an intracellular and extracellular signaling molecule. [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. Such mirror images represent different stereoisomers , they are different molecules. Let the clear solution rest at RT for about 20 min in order to allow for the crystallization of the desired compound. [37][41] Loss-of-function mutations in the genes encoding succinate dehydrogenase, frequently found in hereditary paraganglioma and pheochromocytoma, cause pathological increase in succinate. Allow to fully dry & poor the filtrate into the aqueous hazardous waste container. [27] The GABA shunt serves as an alternate route to convert alpha-ketoglutarate into succinate, bypassing the TCA cycle intermediate succinyl-CoA and instead producing the intermediate GABA. Succinate thus serves as a direct electron donor to the electron transport chain, and itself is converted into fumarate. ACD/Labs Percepta Platform - PhysChem Module, US Environmental Protection Agencys EPISuite, Compounds with the same molecular formula, Search Google for structures with same skeleton, CAUTION: May irritate eyes, skin, and respiratory tract. N. Shan, F. Toda, and W. Jones, Chem. 32% (R) - 67% (S), To comprehend the conver- 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. endobj [40] In spite of a general downregulation of the TCA cycle under these conditions, succinate concentration is increased. Lab Section 803 9:00am Measure the specific rotation and determine the enantiomeric excess of the sample. 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. 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. ter. Phenylsuccinic acid | C10H10O4 - PubChem Phenylsuccinic acid | C10H10O4 | CID 95459 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. [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. 7, 4 (2007). In this experiment, a reflux reaction is conducted between the pheny-succinic acid and proline to produce salt. [8][29] During ischemia, succinate accumulates. 4, 339 (2007). You'll get a detailed solution from a subject matter expert that helps you learn core concepts. The information below may provide an 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. [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 tract irritation. PubMedGoogle Scholar. Part of Springer Nature. L. D. Liu, S. L. Liu, Z. X. Liu, and G. G. Hou, J. Mol. 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. [35] Succinate may interfere with the enzymatic process by attaching to the Fe(II) center first, prohibiting the binding of 2-oxoglutarate. At the end of 30 minutes, turn off and remove the heating mantle. 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. * Refer to Certificate of Analysis for lot specific data (including water content). RST is the consecutive number of the substance in the series ABC. For this reason, if the biologically produced. tory IB Syllabus. Pharm. This experiment requires balanced chemical equations and theoretical yield calculation. Santa Cruz Biotechnology, Inc. is a world leader in the development of products for the biomedical research market. Swirl and pour as fast as possible into a clean Buchner funnel. The chiral recognition abilities of . [32] Arg99, His103, Arg252, and Arg281 near the center of the receptor generate a positively charged binding site for succinate. Experiment 4: Resolution of Phenylsuccinic Acid May cause skin irritation. This process produced two diastereomers where the more soluble compound was removed by the HCl. [30] The G-protein coupled receptor, GPR91 also known as SUCNR1, serves as the detector of extracellular succinate. Alternate Names: Phenylsuccinic acid. In the retina, succinate accumulates in retinal ganglion cells in response to ischemic conditions. It is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste. Give the % of each enantiomer. 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. Share Improve this answer Follow edited Oct 28, 2019 at 15:24 Chem. [7] Activation of inflammatory macrophages through toll-like receptors induces a metabolic shift towards glycolysis. This is an ordinary acid-base reaction that produces a salt. Chem. Multiple studies have demonstrated succinate-induced aggregation, but the effect has high inter-individual variability. Resulting in observing another groups data: Dicarboxylic acids are ubiquitous in atmospheric aerosol particles, but their roles as surfactants in cloud condensation nuclei (CCN) activity remain unclear. In stream www.colby.edu/directory-profile-update-form you must use the tical while diastereomers are not Consider a racemic chical compound (a sample in which there are exactly equal populations of both enantiomers). of one compound from a mixture of compounds. 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. No information found. (If there is no precipitate, use a Pasteur pipet to remove about I mL to a small test tube. (2018). T. R. Shattock, K. K. Arora, P. Vishweshwar, and M.J.Zaworotko, Cryst. Not Intended for Diagnostic or Therapeutic Use. The proline, its former partner in the salt, remains soluble in the aqueous phase. This process produced two diastereomers where the more soluble compound was removed by the HCl. [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. Finally, succinic semialdehyde is oxidized by succinic semialdehyde dehydrogenase (SSADH) to form succinate, re-entering the TCA cycle and closing the loop. [ 1], Succinate can alternatively be formed by reverse activity of SDH. Stir the mixture with a glass rod for 5 minutes. tainer. Pure samples of mirror image molecules. Since PHDs have an absolute requirement for molecular oxygen, this process is suppressed in hypoxia allowing HIF1 to escape destruction. [36] Additionally, succinate-promoted activation of HIF-1 generates a pseudo-hypoxic state that can promote tumorneogensis by transcriptional activation of genes involved in proliferation, metabolism and angiogenesis. ABC corresponds to the atomic number of the most characteristic element or the most characteristic organic group in the molecule. [30] In general, leakage from the mitochondria requires succinate overproduction or underconsumption and occurs due to reduced, reverse or completely absent activity of SDH or alternative changes in metabolic state. 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). 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. [30], In adipocytes, the succinate-activated GPR91 signaling cascade inhibits lipolysis. connect to this server when you are off campus. Growth Des. [32] In inflammatory macrophages, succinate-induced stability of HIF1 results in increased transcription of HIF1-dependent genes, including the pro-inflammatory cytokine interleukin-1. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity 2003-2023 Chegg Inc. All rights reserved. J. M. Chen, Z. Rep. 64, 10381042 (2019). B. R. Khandavilli, et al., Cryst. 20, 2372 (2002). eral minutes after the second acetone wash. Poor filtrate into the organic hazardous waste con- [24] Additionally, succinic acid produced during the fermentation of sugar provides a combination of saltiness, bitterness and acidity to fermented alcohols. S. Fernandez-Lopez, H. S. Kim, E. C. Choi, et al., Nature 412, 452 (2001). [citation needed], Succinate is a key intermediate in the tricarboxylic acid cycle, a primary metabolic pathway used to produce chemical energy in the presence of O2. Soc. Orgo exam notes - Exam noted for organic chemistry. Caution! Given that enantiomers have identical physical properties, how can the mirror-image molecules become separated without the aid of some living thing? For Research Use Only. Provided by the Springer Nature SharedIt content-sharing initiative, Over 10 million scientific documents at your fingertips, Not logged in << duce salt. Oversuccination occurs when more than one succinate adds to a substrate. [6][22]:Section 17.1 All metabolic pathways that are interlinked with the TCA cycle, including the metabolism of carbohydrates, amino acids, fatty acids, cholesterol, and heme, rely on the temporary formation of succinate. Organic Chemistry I A strong acid (6 M HCI), added in excess to the salt, is used to protonate the water-soluble anion. The resulting solid acid can be recovered by filtration. Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01. DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. 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 electron transport chain which is involved in making ATP, and as a signaling molecule reflecting the cellular metabolic state. The toxicological /Producer(Sub Systems, Inc.)/CreationDate(D:20211226231644+05'00')/ModDate(D:20211226231644+05'00')/Creator(Sub Systems, Inc.) The enantiomeric excess (ee) can be calculated with the expression above, where []mixture and []pureenantiomer are the specific rotations of th. This property is a direct consequence of the configuration, or orientation of, bonded atoms in space, around the chiral center. Single crystal structures, thermal analysis, powder X-ray analysis and equilibrium solubility in water and ethanol of the cocrystals were measured. 2-oxoglutarate-dependent dioxygenases bind substrates in a sequential, ordered manner. phenylsuccinic acid would bind to the proton (H+), where it loses its negative charge and be- 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), CSID:86155, http://www.chemspider.com/Chemical-Structure.86155.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. Specific Gravity/Density:Not available. May cause eye, skin, and respiratory in short, most biologically. This is a preview of subscription content, access via your institution. Some substance identifiers may have been claimed confidential, or may . Growth Des. Molecular Formula: C 10 H 10 O 4. Proline likewise gains 18+, but this gives ita net + charge, making it very soluble in water. [6] As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. [5], Historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber. In animal models, pharmacological inhibition of ischemic succinate accumulation ameliorated ischemia-reperfusion injury. [12] Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate. properties of this substance have not been fully investigated. 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. These must be removed to get a good optical activity measurement. Course Hero is not sponsored or endorsed by any college or university. Put the entire crude product into a small beaker or glass vial, and add approx. F. Toda and H. Miyamoto, Chem. was removed by the HCl. Japan (1987), 60, 824-827). phenylsuccinic salt ), . 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. Soc. The solid was recrystallized and the final solid is filtered out. CHEM: Organic Chemistry Labora- During this time, all the proline should dissolve. Please note, if you are trying to access wiki.colby.edu or [23], Click on genes, proteins and metabolites below to link to respective articles. Any rotational effect that one enantiomer has on plane-polarized light will be exactly canceled somewhere else in the mixture by its mirror image. [17] Succinic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications. Mutations in SDH, hypoxia or energetic misbalance are all linked to an alteration of flux through the TCA cycle and succinate accumulation. 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.