phenylsuccinic acid solubilityphenylsuccinic acid solubility

Eng. Typi- cally, the less soluble diastere- omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. stacking interaction leads to the formation of 3D supramolecular structure. Copyright 2007-2023 Santa Cruz Biotechnology Inc. All Rights Reserved. Growth Des. ;DgEvzv {M aK. [7] Activation of inflammatory macrophages through toll-like receptors induces a metabolic shift towards glycolysis. In the liver, succinate serves as a paracrine signal, released by anoxic hepatocytes, and targets stellate cells via GPR91. 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 resulting solid acid can be recovered by filtration. N. Shan, A. D. Bond, and W. Jones, Cryst. [29] As of 2016 the inhibition of succinate-mediated ROS production was under investigation as a therapeutic drug target.[29]. You'll get a detailed solution from a subject matter expert that helps you learn core concepts. [35] Succinate may interfere with the enzymatic process by attaching to the Fe(II) center first, prohibiting the binding of 2-oxoglutarate. First, we exploit its chemical nature it is m acid) by treating it with an optically active biologically produced base, L-proline. Dehydration of succinic acid gives succinic anhydride. ), . The site owner may have set restrictions that prevent you from accessing the site. Because protons have +1 charge, each proline is cationic. [23], Click on genes, proteins and metabolites below to link to respective articles. Experts are tested by Chegg as specialists in their subject area. Resolved (S)-acid: 0, Theoretical yield: 1 2 =0 Growth Des. Copyright 2007-2023 Santa Cruz Biotechnology, Inc. All Rights Reserved. o Likely reflux conflict of earlier step in result of failure to eliminate (R)-acid and Eye: not been fully investigated. So, for optical activity to be evident, there must be an excess of one enantiomer over its mirror image. The solubility of the complexes is poor in the top phase, where H 2 A has better solubility than in the bottom phase. G. M. Sheldrick, Acta Crystallogr. 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. Cool 10mL of 6.0 M HCl in an ice bath and add all of the collected salt to this cold HCl. M. R. Caira, Mol. [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. [12] Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate. The enantiomeric excess was 35.5% which is the measurement of purity. The impact of chirality is assessed via comparison of structural features and properties of binary cocrystals. The phenylsuccinic acid would bind to the proton (H+), where it loses its negative charge and becomes insoluble in water. - 173.212.249.81. vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. 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. Home; About us; Membership & professional community . [15], Succinic acid is a precursor to some polyesters and a component of some alkyd resins. Growth Des. An ideal solvent would completely precipitate one diastereomer while the other coe remained in the solution. [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. Let aspirator run for sev- Finally, succinic semialdehyde is oxidized by succinic semialdehyde dehydrogenase (SSADH) to form succinate, re-entering the TCA cycle and closing the loop. ing the enantiomer by neutralizing the salt created to find the optical purity by measuring the op- 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. [citation needed], Succinate is one of three oncometabolites, metabolic intermediates whose accumulation causes metabolic and non-metabolic dysregulation implicated in tumorigenesis. RST is the consecutive number of the substance in the series ABC. X. P. Dai, G. G. Hou, J. F. Sun, et al., J. Mol. phenylsuccinic acid (H 2A) as the model enantiomers. L. Fbin, Cryst. How does one obtain optically active compounds? Question: In this experiment, racemic (RS)-phenylsuccinic acid is separated (resolved) into optically active cautiouets in a sequence of two steps. Succinic acid is a white, odorless solid with a highly acidic taste. One proline has a position available for one extra proton, so the two protons end up on two different prolines. The phenylsuccinic acid [30], SUCNR1 is highly expressed on immature dendritic cells, where succinate binding stimulates chemotaxis. 4, 310 (2007). 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. Add a magnetic stir bar and gently mix the contents of the flask until you achieve a Typically, the less soluble diastere-. 4, 339 (2007). 2003-2023 Chegg Inc. All rights reserved. Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA). Measure the specific rotation and determine the enantiomeric excess of the sample. The proline, its former partner in the salt, remains soluble in the aqueous phase. 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). M. J. Zaworotko, Cryst. Water tums J. M. Chen, Z. In order to recrystallize the. [18], Acylation with succinic acid is called succination. 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. L. D. Liu, S. L. Liu, Z. X. Liu, and G. G. Hou, J. Mol. Oversuccination occurs when more than one succinate adds to a substrate. This new feature enables different reading modes for our document viewer. 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]. [6][38], Metabolic signaling involving succinate can be involved in inflammation via stabilization of HIF1-alpha or GPR91 signaling in innate immune cells. Solubility:Not available. It is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste. [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. Chronic: Santa Cruz Biotechnology, Inc. is a world leader in the development of products for the biomedical research market. Chem. [33] Therapies targeting succinate to reduce cardiovascular risk and hypertension are currently under investigation.[28]. The phenylsuccinic acid acts as the proton donor, while proline is the proton acceptor OH Ph OH OH Ph protoner) acid-base reaction OH SINH phreyhuccinic acid L-prolier (base) equimolarite of R+5) (5) PLUS The two salts shown above are stereoisomers that are not mirror images, so are a pair of diastereomers. (If there is no precipitate, use a Pasteur pipet to remove about I mL to a small test tube. [17] Succinic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications. <> These must be removed to get a good optical activity measurement. Commun. CAS Number: 635-51-8. Space available to draw mechanisms. % You have the right to unsubscribe at any time by clicking the 'unsubscribe' link in any News & Announcement emails you receive. bvseo-msg: The resource to the URL or file is currently unavailable.. Alternate Names: Phenylsuccinic acid. Autocrine succinate signaling promotes retinal neovascularization, triggering the activation of angiogenic factors such as endothelial growth factor (VEGF). please email the information below to [emailprotected]. For Research Use Only. * Refer to Certificate of Analysis for lot specific data (including water content). Stir for 5 min to allow complete protonation. Learn more about Institutional subscriptions. [32] Overall, the EC50 for succinate-GPR91 is in the 2050 uM range. Experts are tested by Chegg as specialists in their subject area. [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. MONOCLONAL MOUSE ANTI-RABBIT/GOAT SECONDARY ANTIBODIES, POLYCLONAL GOAT/RABBIT ANTI-MOUSE SECONDARY ANTIBODIES, ISOTYPE SPECIFIC MOUSE IgG BINDING PROTEINS, PROTEIN A, G-PLUS & L AGAROSE IP REAGENTS, NUCLEOTIDES, PEPTIDES, PROTEINS & AMINO ACIDS, AUTORADIOGRAPHY FILM, TAPE AND PLASTIC WRAP. A suitable solvent is found by trial and error. 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. Calculate the exact concentration which will be needed to calculate specific rotation. Correspondence to 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 . Target Organs: No data found. Thus, succinate is thought to play a role in liver homeostasis. so they can be created by reacting Immediately retum the contents to the boiling flask and swirl. If you study models of chiral molecules, it soon becomes apparent that their mirror images are not superposable on each other. Succinic acid (/ s k s n k /) is a dicarboxylic acid with the chemical formula (CH 2) 2 (CO 2 H) 2. Stir the mixture with a glass rod for 5 minutes. 100mL round bottom flask. In order to recrystallize the solid, boiling water was added to the solid until it fully dissolves to achieve a complete homoge-nous mixture. In living organisms, primarily succinate, not succinic acid, is found. Google Scholar. Colby VPN to Optical Rotation: []=obscl[]=(0.03992/m)( 1 )=60 The solid was recrystallized and the final solid is filtered out. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that, are to be fashioned into the product. cally, the less soluble diastere- Vacuum filter and wash the solid with two 15mL volumes of cold water. 2-oxoglutarate-dependent dioxygenases bind substrates in a sequential, ordered manner. DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. [24] This pathway is exploited in metabolic engineering to net generate succinate for human use. Pharm. [5] The name derives from Latin succinum, meaning amber. Don't use too much water, as the product is somewhat soluble and will slowly dissolve. The recovered solid is the less-soluble diastereomeric salt of the pair that you made. 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. T. R. Shattock, K. K. Arora, P. Vishweshwar, and M.J.Zaworotko, Cryst. Specific Gravity/Density:Not available. 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). 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. 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. In addition to its metabolic roles, succinate serves as an intracellular and extracellular signaling molecule. The 'Substance identity' section is calculated from substance identification information from all ECHA databases. Rep. 64, 10381042 (2019). If you have any questions [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. Moreover, the cold water wash and filtration performed was able to recover the crude solid. A new solvent sublation (SS) system for chiral separation is introduced by using phenylsuccinic acid (H2A) as the model enantiomers. A strong acid (6 M HCI), added in excess to the salt, is poorly soluble in water. [39] Other inflammatory cytokines produced by activated macrophages such as tumor necrosis factor or interleukin 6 are not directly affected by succinate and HIF1. 4, 417 (2007). Add 2-propanol (approx. Not Intended for Diagnostic or Therapeutic Use. [30][32], Extracellular succinate regulates cardiomyocyte viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte hypertrophy. [25], Accumulation of fumarate can drive the reverse activity of SDH, thus enhancing succinate generation. 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. ()-phenylsuccinic acid N CO 2H H H (-)-Proline Week 1: Resolution of ()-phenylsuccinic acid Procedure In a clean, dry, 250 mL round-bottomed flask, dissolve 2.9 g of ()-phenylsuccinic acid in 75 mL of 2-propanol. Together, these three ions form a salt. of this substance have not been fully investigated. In this case, the salt that contains the dextrorotatory acid ("") is the less soluble one, and precipitates. Think of a chiral center as an atom to which four different, groups are covalently attached. [6] The intermediate is made available for biosynthetic processes through multiple pathways, including the reductive branch of the TCA cycle or the glyoxylate cycle, which are able to drive net production of succinate. 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). out to be a good recrystallization solvent for this product. Enantiomeric excess: 60.65171=0 100 =35% of (+)-phenylsuccinic acid 1).Factors affecting the extraction efficiency were investigated, namely the influence of the types of organic solvents and -CD derivatives, iso-butyl tartrate . Growth Des. CHEM: Organic Chemistry Labora- Commun. Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01. tical rotation using polarimetry. The substance identifiers displayed in the InfoCard are the best available substance name, EC number, CAS number and/or the molecular and structural formulas. phenylsuccinic acid would bind to the proton (H+), where it loses its negative charge and be- D. K. Bucar, R. F. Henry, X. C. Lou, et al., Mol. Potential Health Effects Specific rotation is a property of a chiral substance that is expressed as the angle to which the material causes polarized light to rotate, passing through the tube containing solution. This involves an acid-base reaction with (s)-proline and restor- [9], Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. solid. This process produced two diastereomers where the more soluble compound was removed by the HCl. << ADS A. V. Trask and W. Jones, Top. The information below may provide an [5], Historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber. Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. Curr. For Research Use Only. Kobra Moradifard, Derikvand, Z. Chem. After refluxing, cool flask for 15 minutes, As a diprotic acid, succinic acid undergoes two successive deprotonation reactions: The pKa of these processes are 4.3 and 5.6, respectively. Two protons are transferred from the phenylsuccinic acid to the proline. This process 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. Z. Wang, C. B. Wu, et al., CrystEngComm 14, 6221 (2012). [10] 1,4-Butanediol (BDO) can be synthesized using succinic acid as a precursor. Other information Prepared By Regulatory Affairs Thermo Fisher Scientific Email: [email protected] Revision Date 24-Dec-2021 Print Date 24-Dec-2021 Soc. Insoluble in water. tract irritation. 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. Garcia, Jessica. [5], As a radical group it is called a succinyl (/sksnl/) group. 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. Pure samples of mirror image molecules. A 71, 3 (2015). succinic acid and proline to pro- It now must be recovered from the salt (the second step). During this time, all the proline should dissolve. This property is a direct consequence of the configuration, or orientation of bonded atoms in space, around the chiral center. Exact concentration: 0 10 mL=0. A. V. Trask, N. Shan, W. D. S. Motherwell, et al., Chem. 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. Next, place crude solid in a 125mL Erlenmeyer flask and boil 100mL of water in a 250mL Erlenmeyer flask. F. Toda, K. Tanaka, A. Sekikawa, J. Chem. The phenylsuccinic acid is a proton donor making proline the proton acceptor. [16] The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. Commun. [36][37], Succinate inhibition of prolyl hydroxylases (PHDs) stabilizes the transcription factor hypoxia inducible factor (HIF)1. 5, 9 (2002). ORGO WEEK 2 PRAC QUIZ - practice for orgo quiz 1 and 2. 2023 Springer Nature Switzerland AG. These chemicals are invariably synthesized by catalysts called, enzymes, which are large chiral molecules specially designed to carry out a particular chemical, transformation. After refluxing, cool flask for 15 minutes, vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. Phenylsuccinic acid Molecular Formula CHO Average mass 194.184 Da Monoisotopic mass 194.057907 Da ChemSpider ID 86155 More details: Names Properties Searches Spectra Vendors Articles More Names and Synonyms Database ID (s) Validated by Experts, Validated by Users, Non-Validated, Removed by Users ()-Phenylsuccinic acid 10424-29- [RN] behave identically toward physical tests like melting and boiling points and solubility in given solvents.

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