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During this time, all the proline should dissolve. This diethyl ester is a substrate in the Stobbe condensation. 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. out to be a good recrystallization solvent for this product. Crystallographic data for the compound was collected at 150(2) K. The synthesized compound is crystallized in the monoclinic system with the space group P21/n and unit cell . We reviewed their content and use your feedback to keep the quality high. 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. How does one obtain optically active compounds? [7] For dendritic cells, succinate functions as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production. % 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. In animal models, pharmacological inhibition of ischemic succinate accumulation ameliorated ischemia-reperfusion injury. Pull air through the solid for a couple of minutes after the last wash to evaporate most of the acetone. A 71, 3 (2015). * Refer to Certificate of Analysis for lot specific data (including water content). This shows the degree to which a sample contains one enantiomer in greater amounts than the other. Correspondence to Share Improve this answer Follow edited Oct 28, 2019 at 15:24 A strong acid (6 M HCI), added in excess to the salt, is used to protonate the water-soluble anion. Ingestion: tract irritation. Requested URL: www.colby.edu/chemistry/CH241F/Experiment%202.pdf, User-Agent: Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/103.0.5060.114 Safari/537.36 Edg/103.0.1264.62. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. Succinic acid (/sksnk/) is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. 1035, 203 (2013). The chiral recognition abilities of the two selectors are opposite . To begin, dissolve 1 of racemic phenylsuccinic acid into 50mL of isopropanol in a Sample will be analyzed by polarimetry. [26] Alternative, succinate can be released into the extracellular milieu and the blood stream where it is recognized by target receptors. Typi- cally, the less soluble diastere- omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. Cloudflare has detected an error with your request. At the end of 30 minutes, turn off and remove the heating mantle. 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. Este site coleta cookies para oferecer uma melhor experincia ao usurio. Orgo exam notes - Exam noted for organic chemistry. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Chemical Stability:Stable under normal temperatures and pressures. N. J. Babu, L. S. Reddy, and A. Nangia, Mol. Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01. [32] Arg99, His103, Arg252, and Arg281 near the center of the receptor generate a positively charged binding site for succinate. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. Provided by the Springer Nature SharedIt content-sharing initiative, Over 10 million scientific documents at your fingertips, Not logged in 20, 2372 (2002). [12][13], Succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. This website collects cookies to deliver a better user experience. The Index number for each substance is in the form of a digit sequence of the type ABC-RST-VW-Y. tory IB Syllabus. It now must be recovered from the salt (the second step). For a compound to be optimally pure, it would have to reach up to 171. [5], As a radical group it is called a succinyl (/sksnl/) group. All you are really doing is exchanging one acid for another so it is hardly an acid/base reaction. [citation needed], As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. Transamination and subsequent decarboxylation of alpha-ketoglutarate leads to the formation of GABA. [32] In inflammatory macrophages, succinate-induced stability of HIF1 results in increased transcription of HIF1-dependent genes, including the pro-inflammatory cytokine interleukin-1. 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. For this reason, if the biologically produced product contains one or more chiral centers, it is optically active Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! Optical Rotation: []=obscl[]=(0.03992/m)( 1 )=60 The purpose of this experiment is to be able to convert enantiomers of phenylsuccinic 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. [30] The G-protein coupled receptor, GPR91 also known as SUCNR1, serves as the detector of extracellular succinate. Succinic acid is a white, odorless solid with a highly acidic taste. 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. X`I%&/m{JJt`$@iG#)*eVe]f@{{;N'?\fdlJ!?~|? This process produced two diastereomers where the more soluble compound was removed by the HCl. This experiment requires balanced chemical equations and theoretical yield calculation. [36][37], Succinate inhibition of prolyl hydroxylases (PHDs) stabilizes the transcription factor hypoxia inducible factor (HIF)1. stream Added to cooled 10 mL 6 HCl: Reaction immediately but not cloudy enough You'll get a detailed solution from a subject matter expert that helps you learn core concepts. The only way that these isomers differ physically is the direction in which they rotate plane-polarized light, their optical activity. As a consequence, the mixture cases no net rotation, and appears optically inactive. [30][32], Extracellular succinate regulates cardiomyocyte viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte hypertrophy. Pure samples of mirror image molecules. The chiral recognition abilities of . please email the information below to [emailprotected]. Cloudiness and then crystals should gradually form.) [5], Historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber. Stir the mixture with a glass rod for 5 minutes. 5, 9 (2002). Multiple studies have demonstrated succinate-induced aggregation, but the effect has high inter-individual variability. In the liver, succinate serves as a paracrine signal, released by anoxic hepatocytes, and targets stellate cells via GPR91. X. P. Dai, G. G. Hou, J. F. Sun, et al., J. Mol. In this experiment, a reflux reaction is conducted between the pheny-succinic acid and proline to produce salt. In order to recrystallize the solid, boiling water was added to the solid until it fully dissolves to achieve a complete homoge-nous mixture. ABC corresponds to the atomic number of the most characteristic element or the most characteristic organic group in the molecule. Less The diastereomeric salt formed between the (+)-phenylsuccinic acid and (-)-proline is much ___ soluble in isopropyl alcohol than the diastereomeric salt formed between the . endobj [17] Succinic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications. N. Shan, A. D. Bond, and W. Jones, Cryst. The recovered diastereomer must be converted back to the original compound from which it was made -- now a single enantiomer. G. M. Sheldrick, Acta Crystallogr. [12] As an excipient in pharmaceutical products, it is also used to control acidity[21] or as a counter ion. Google Scholar. Article 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. [16] The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. mix contents for 2 minutes and reflux for 30 minutes. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from water. Succinate thus serves as a direct electron donor to the electron transport chain, and itself is converted into fumarate. Add 2-propanol (approx. 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 [34] 2-oxoglutarate-dependent dioxygenases require an iron cofactor to catalyze hydroxylations, desaturations and ring closures. This property is a direct consequence of the configuration, or orientation of, bonded atoms in space, around the chiral center. Think of a chiral center as an atom to which four different, groups are covalently attached. Experiment 4: Resolution of Phenylsuccini, The purpose of this experiment is to be able to convert enantiomers of phenylsuccini, ing the enantiomer by neutralizing the salt created to find the optical purity by measuring the op-, The Methodology of the Social Sciences (Max Weber), Campbell Biology (Jane B. Reece; Lisa A. Urry; Michael L. Cain; Steven A. Wasserman; Peter V. Minorsky), Chemistry: The Central Science (Theodore E. Brown; H. Eugene H LeMay; Bruce E. Bursten; Catherine Murphy; Patrick Woodward), Psychology (David G. Myers; C. Nathan DeWall), Principles of Environmental Science (William P. Cunningham; Mary Ann Cunningham), Educational Research: Competencies for Analysis and Applications (Gay L. R.; Mills Geoffrey E.; Airasian Peter W.), Give Me Liberty! o Likely reflux conflict of earlier step in result of failure to eliminate (R)-acid and The difference, however, is subtle. 2023 Springer Nature Switzerland AG. 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). Typically, the less soluble diastere-. 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. Not Intended for Diagnostic or Therapeutic Use. & Azadbakht, A. Co-Crystal of Phenylsuccinic Acid and 4,4'-Bipyridine: Synthesis, Characterization, Crystal Structure, and Supramolecular Interactions. Generated succinate is then available for either energy production or biosynthesis. Experiment 4: Resolution of Phenylsuccinic Acid As the anion binds the H+, it loses its negative charge and becomes poorly soluble in water. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that are to be fashioned into the product. Add 1.73 g of (-)-proline. 5 mL of DI water. Subsequently, the primary substrate enters the binding pocket and lastly dioxygen binds to the enzyme-substrate complex. 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. This is simple since neutral phenylsuccinic acid is poorly soluble in water. product contains one or more chiral centers, it is optically active. Struct. 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. Soc. M. J. Zaworotko, Cryst. Z. Wang, C. B. Wu, et al., CrystEngComm 14, 6221 (2012). Potential Health Effects Oversuccination occurs when more than one succinate adds to a substrate. 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). [35] Simultaneous to substrate oxidation, they convert 2-oxoglutarate, also known as alpha-ketoglutarate, into succinate and CO2. Zohreh Derikvand. Eye: 1).Factors affecting the extraction efficiency were investigated, namely the influence of the types of organic solvents and -CD derivatives, iso-butyl tartrate . This is an ordinary acid-base reaction that produces a salt. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Add 1.15g of finely ground (s)-proline & a magnetic stir bar then mix contents for 2 minutes and reflux for 30 minutes. First, we exploit its chemical nature it is m acid) by treating it with an optically active biologically produced base, L-proline. ;DgEvzv {M aK. This is an ordinary acid-basc reaction that produces a salt. However, if the acid is combined with an optically active base, such as (-)-proline, the diastereomers which form have different _____ in isopropyl alcohol. In living organisms, primarily succinate, not succinic acid, is found. 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. [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. 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.