phenylsuccinic acid solubility

[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. of this substance have not been fully investigated. When the solution is cooled down at room temperature, the solubility decreases which allows the pure crystals of phenylsuccinic acid to form. Potential Health Effects The solid that results is now-resolved phenylsuccinic acid in its protonated form. Experts are tested by Chegg as specialists in their subject area. The less soluble salt may precipitate. - 173.212.249.81. 24, 861 (1995). [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. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Chemical Stability:Stable under normal temperatures and pressures. ORGO WEEK 2 PRAC QUIZ - practice for orgo quiz 1 and 2. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation, of the plane of polarized light). This website collects cookies to deliver a better user experience. this experiment, a reflux reaction If you have any questions Este site coleta cookies para oferecer uma melhor experincia ao usurio. T. R. Shattock, K. K. Arora, P. Vishweshwar, and M.J.Zaworotko, Cryst. A. V. Trask and W. Jones, Top. 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. (R)-(-)-Phenylsuccinic acid | C10H10O4 | CID 736145 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological . For Research Use Only. N. Shan, F. Toda, and W. Jones, Chem. F. Toda, K. Tanaka, A. Sekikawa, J. Chem. [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. 48, 5009 (2006). stream Commun. For a compound to be optimally pure, it would have to reach up to 171. [27], Succinate is produced and concentrated in the mitochondria and its primary biological function is that of a metabolic intermediate. If you study models of chiral molecules, it soon becomes apparent that their mirror images are not superposable on each other. No information found. not been fully investigated. The purpose of this experiment is to be able to convert enantiomers of phenylsuccinic acid into separable diastereomers. Diastecomers are not chemically identical, and so they differ in common physical properties. Moreover, the cold water wash and filtration performed was able to recover the crude solid. Lowell, Massachusetts. [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. 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. )-in short, most biologically produced substances are optically active But the existence of chirality is not by itself a sufficient condition for optical activity. 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. is conducted between the pheny- M. R. Caira, Mol. Skin: To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- : an American History (Eric Foner), Forecasting, Time Series, and Regression (Richard T. O'Connell; Anne B. Koehler), Business Law: Text and Cases (Kenneth W. Clarkson; Roger LeRoy Miller; Frank B. In the retina, succinate accumulates in retinal ganglion cells in response to ischemic conditions. 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 short, most biologically. 1035, 203 (2013). The solid that results is now-resolved phenylsuccinic acid in its protonated form. 2023 Springer Nature Switzerland AG. So, for optical activity to be evident, there must be an excess of one enantiomer over its mirror image. [6] As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. As the anion binds the H+, it loses its negative charge and becomes poorly soluble in water. Solved 2) Calculate the enantiomeric excess if the specific | Chegg.com 5, 9 (2002). This process ()-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. 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. [citation needed], As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. Enantiomeric excess: 60.65171=0 100 =35% of (+)-phenylsuccinic acid 17, 550 (2017). Don't use too much water, as the product is somewhat soluble and will slowly dissolve. Any rotational effect that one enantiomer has on plane-polarized light will be exactly canceled somewhere else in the mixture by its mirror image. [8][29] During ischemia, succinate accumulates. Course Hero is not sponsored or endorsed by any college or university. 100mL round bottom flask. You have the right to unsubscribe at any time by clicking the 'unsubscribe' link in any News & Announcement emails you receive. They are potentially separable by ordinary physical methods like different solubility in a given solvent, which allows recovery of a single diastereomer [36][37], Succinate inhibition of prolyl hydroxylases (PHDs) stabilizes the transcription factor hypoxia inducible factor (HIF)1. G. M. Sheldrick, Acta Crystallogr. [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. Target Organs: No data found. Mutations in SDH, hypoxia or energetic misbalance are all linked to an alteration of flux through the TCA cycle and succinate accumulation. please help with the following two questions:1. For | Chegg.com Other information Prepared By Regulatory Affairs Thermo Fisher Scientific Email: EMSDS.RA@thermofisher.com Revision Date 24-Dec-2021 Print Date 24-Dec-2021 connect to this server when you are off campus. [30] This leads to stellate cell activation and fibrogenesis. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that are to be fashioned into the product. The proline, its former partner in the salt, remains soluble in the aqueous phase. 254, 41 (2005). The enantiomeric excess was 35.5% which is the measurement of purity. Succinic acid is a white, odorless solid with a highly acidic taste. The chiral recognition abilities of the two selectors are opposite . For this reason, if the biologically produced. CHEM: Organic Chemistry Labora- [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. 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. Shop DL-Phenylsuccinic acid, 98+%, Thermo Scientific Chemicals at Fishersci.com After refluxing, cool flask for 15 minutes, vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. Growth Des. 4, 417 (2007). of one compound from a mixture of compounds. [6][23] Under conditions of succinate accumulation, rapid oxidation of succinate by SDH can drive reverse electron transport (RET). The information below may provide an Put the entire crude product into a small beaker or glass vial, and add approx. [12] Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate. Immediately retum the contents to the boiling flask and swirl. 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. << [6] It is marketed as food additive E363. ABC corresponds to the atomic number of the most characteristic element or the most characteristic organic group in the molecule. The chiral recognition abilities of . 4, 279 (1987). endobj Take 40mg of the resolved enantiomer and dissolve it in Iml of acetone. [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. 4, 339 (2007). Thus, via enzymatic inhibition, increased succinate load can lead to changes in transcription factor activity and genome-wide alterations in histone and DNA methylation. Enantioselective separation of R,S-phenylsuccinic acid by biphasic omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. On this Wikipedia the language links are at the top of the page across from the article title. acid into separable diastereomers. [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. By signing up, you indicate that you have read and agree to the terms in our privacy policy. OHN 6MH hydrolysis) COH HO COM LPHC Soluble in water 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]. [34] 2-oxoglutarate-dependent dioxygenases require an iron cofactor to catalyze hydroxylations, desaturations and ring closures. The solid was recrystallized and the final solid is filtered out. 15 mL) and swirl for a minute to mix, then boil gently for 30 min (add boiling chip!). 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). To begin, dissolve 1.94g of racemic phenylsuccinic acid into 50mL of isopropanol in a 100mL round bottom flask. Repeat a second time with 15 ml of acetone. % Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that, are to be fashioned into the product. May cause skin irritation. Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. [30] The G-protein coupled receptor, GPR91 also known as SUCNR1, serves as the detector of extracellular succinate. Abstract. 2-oxoglutarate-dependent dioxygenases bind substrates in a sequential, ordered manner. Next, place crude solid in a 125mL Erlenmeyer flask and boil 100mL of water in a 250mL Erlenmeyer flask. Growth Des. Succinate exits the mitochondrial matrix and passes through the inner mitochondrial membrane via dicarboxylate transporters, primarily SLC25A10, a succinate-fumarate/malate transporter. 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. 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. Expert Answer. Given that enantiomers have identical physical properties, how can the mirror-image molecules become separated without the aid of some living thing? Anyone you share the following link with will be able to read this content: Sorry, a shareable link is not currently available for this article. tainer. During this time, all the proline should dissolve. Succinate thus serves as a direct electron donor to the electron transport chain, and itself is converted into fumarate. This is an ordinary acid-base reaction that produces a salt. The first source was natural products , chemicals produced by living organisms. mix contents for 2 minutes and reflux for 30 minutes. Question: In this experiment, racemic (RS)-phenylsuccinic acid is separated (resolved) into optically active cautiouets in a sequence of two steps. vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. CAS Number: 635-51-8. The phenylsuccinic acid is a proton donor making proline the proton acceptor. Chem. 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. Percent recovery: 00 100 =4% This new feature enables different reading modes for our document viewer.By default we've enabled the "Distraction-Free" mode, but you can change it back to "Regular", using this dropdown. Zohreh Derikvand. succinic acid and proline to pro- This involves an acid-base reaction with (s)-proline and restor- This is a preview of subscription content, access via your institution. phenylsuccinic salt Correspondence to Autocrine succinate signaling promotes retinal neovascularization, triggering the activation of angiogenic factors such as endothelial growth factor (VEGF). You convert the (+)-phenylsuccinic acid to a salt with proline, separate the 2 diastereomers based on solubility differences, and recover the neutral phenylsuccinic acid through the following steps: 1. mix racemic phenylsuccinic acid with isopropyl alcohol; dissolve. The toxicological properties Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA). [14] Succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and tetrahydrofuran. 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). A. V. Trask, N. Shan, W. D. S. Motherwell, et al., Chem. Sorry, it seems JavaScript is not enabled in your browser. 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. [16] The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. At the end of 30 minutes, turn off and remove the heating mantle. In addition to its metabolic roles, succinate serves as an intracellular and extracellular signaling molecule. Crystallogr. Think of a chiral center as an atom to which four different, groups are covalently attached. 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. However, if the acid is combined with an optically active base, such as (-)-proline, the diastereomers which form have different _____ in isopropyl alcohol. 2) Pre-Lab Report: EXPERIMENTAL SECTION 1) Synthesis of diastereomeric salts: Weigh racemic phenylsuccinic acid (0,5g, 2.57 mmole) and L-prolinc (0.3 g. 2.61 mmole) into a 100 ml boiling flask, and swirl to dissolve the solid. stacking interaction leads to the formation of 3D supramolecular structure. This property is a direct consequence of the configuration, or orientation of bonded atoms in space, around the chiral center. 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 [36] Pathologically elevated levels of succinate lead to hypermethylation, epigenetic silencing and changes in neuroendocrine differentiation, potentially driving cancer formation. Transamination and subsequent decarboxylation of alpha-ketoglutarate leads to the formation of GABA. Vacuum filter and wash the solid with two 15mL 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. Less The diastereomeric salt formed between the (+)-phenylsuccinic acid and (-)-proline is much ___ soluble in isopropyl alcohol than the diastereomeric salt formed between the . Experiment 4: Resolution of Phenylsuccinic Acid [30], Succinate signaling often occurs in response to hypoxic conditions. o Likely reflux conflict of earlier step in result of failure to eliminate (R)-acid and May cause eye, skin, and respiratory In animal models, pharmacological inhibition of ischemic succinate accumulation ameliorated ischemia-reperfusion injury. These chemicals are invariably synthesized by catalysts called, enzymes, which are large chiral molecules specially designed to carry out a particular chemical, transformation. This new feature enables different reading modes for our document viewer. L. Fbin, Cryst. [42] The other two oncometabolites, fumarate and 2-hydroxyglutarate have similar structures to succinate and function through parallel HIF-inducing oncogenic mechanisms. Oxidative decarboxylation then generates a ferryl intermediate coordinated to succinate, which serves to oxidize the bound primary substrate. [30][32], Extracellular succinate regulates cardiomyocyte viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte hypertrophy. 1112, 1 (2016). N. Shan, A. D. Bond, and W. Jones, Cryst. www.colby.edu/directory-profile-update-form you must use the . Succinic acid (/ s k s n k /) is a dicarboxylic acid with the chemical formula (CH 2) 2 (CO 2 H) 2. The only way that these isomers differ physically is the direction in which they rotate plane-polarized light, their optical activity. Lab8_PhenylsuccinicAcid_handout_F20.pdf - OPTICAL Alternate Names: Phenylsuccinic acid. Part of Springer Nature. Resolution of (+/-)-phenylsuccinic acid. 5 mL of DI water. Succinate is generated from succinyl-CoA by the enzyme succinyl-CoA synthetase in a GTP/ATP-producing step:[22]:Section 17.1, Succinyl-CoA + NDP + Pi Succinate + CoA + NTP, Catalyzed by the enzyme succinate dehydrogenase (SDH), succinate is subsequently oxidized to fumarate:[22]:Section 17.1, SDH also participates in the mitochondrial electron transport chain, where it is known as respiratory complex II. [33] Therapies targeting succinate to reduce cardiovascular risk and hypertension are currently under investigation.[28]. 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. Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01. 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. Co-Crystal of Phenylsuccinic Acid and 4,4'-Bipyridine: Synthesis As a diprotic acid, succinic acid undergoes two successive deprotonation reactions: The pKa of these processes are 4.3 and 5.6, respectively. 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. tical rotation using polarimetry. [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. Growth Des. The impact of chirality is assessed via comparison of structural features and properties of binary cocrystals. The resulting solid acid can be recovered by filtration. acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. The phenylsuccinic acid gave up two positives, so it is a dianion. 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! Eng. 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. In [25], Accumulation of fumarate can drive the reverse activity of SDH, thus enhancing succinate generation. Inhibition of KDMs and TET hydroxylases results in epigenetic dysregulation and hypermethylation affecting genes involved in cell differentiation. [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. In the liver, succinate serves as a paracrine signal, released by anoxic hepatocytes, and targets stellate cells via GPR91. DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. [32] Overall, the EC50 for succinate-GPR91 is in the 2050 uM range. the proton acceptor. Both anions are colorless and can be isolated as the salts, e.g., Na(CH2)2(CO2H)(CO2) and Na2(CH2)2(CO2)2. 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. 4 0 obj S. L. Childs and K. I. Hardcastle, Cryst. 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? Commun. 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. The site owner may have set restrictions that prevent you from accessing the site. Eye: 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. Cover the beaker or the vial with a watch glass, and keep the beaker covered at all times unless you need to access its contents! [5] In an aqueous solution, succinic acid readily ionizes to form its conjugate base, succinate (/sksnet/). Solved Resolution of (+/-)-phenylsuccinic acidThis | Chegg.com Typically, the less soluble diastere-. Please note, if you are trying to access wiki.colby.edu or A strong acid (6 M HCI), added in excess to the salt, is poorly soluble in water. 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X. P. Dai, G. G. Hou, J. F. Sun, et al., J. Mol. [7] Succinate may thus be produced from enhanced glutamine metabolism via alpha-ketoglutarate or the GABA shunt. Enantioseparation of Phenylsuccinic Acid Enantiomers by Solvent Cool 10mL of 6.0 M HCl in an ice bath and add all of the collected salt to this cold HCl. T. Friscic, L. Fabian, J. C. Burley, et al., Chem. cally, the less soluble diastere- F. Toda and H. Miyamoto, Chem. behave identically toward physical tests like melting and boiling points and solubility in given solvents. Structure, properties, spectra, suppliers and links for: (+)-Phenylsuccinic acid, 4036-30-. In this case, the salt that contains the dextrorotatory acid ("") is the less soluble one, and precipitates. 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. 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