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May cause eye irritation. [15], Succinic acid is a precursor to some polyesters and a component of some alkyd resins. Consider a racemic chical compound (a sample in which there are exactly equal populations of both enantiomers). Add 1.15g of finely ground (s)-proline & a magnetic stir bar then mix contents for 2 minutes and reflux for 30 minutes. The phenylsuccinic acid gave up two positives, so it is a dianion. 4, 279 (1987). In the retina, succinate accumulates in retinal ganglion cells in response to ischemic conditions. o Likely reflux conflict of earlier step in result of failure to eliminate (R)-acid and The enantiomeric excess was 35.5% which is the measurement of purity. Commun. Conditions to Avoid:Incompatible materials, dust generation, excess heat, strong oxidants. This process [5] In an aqueous solution, succinic acid readily ionizes to form its conjugate base, succinate (/sksnet/). 4, 339 (2007). ), 2) Recovery of less soluble salt: Vacuum filter the contents of the flask using a medium Buchner funnel. [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. Add 2-propanol (approx. [39] Other inflammatory cytokines produced by activated macrophages such as tumor necrosis factor or interleukin 6 are not directly affected by succinate and HIF1. : 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. vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. Struct. Let aspirator run for several minutes after the second acetone wash. Poor filtrate into the organic hazardous waste container. [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. acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. Lexxus Pen Molecular Weight: 194.18. Let the clear solution rest at RT for about 20 min in order to allow for the crystallization of the desired compound. 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. Mutations in SDH, hypoxia or energetic misbalance are all linked to an alteration of flux through the TCA cycle and succinate accumulation. stream This is a preview of subscription content, access via your institution. T. R. Shattock, K. K. Arora, P. Vishweshwar, and M.J.Zaworotko, Cryst. [27], Succinate is produced and concentrated in the mitochondria and its primary biological function is that of a metabolic intermediate. Growth Des. 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. In The impact of chirality is assessed via comparison of structural features and properties of binary cocrystals. [33] Therapies targeting succinate to reduce cardiovascular risk and hypertension are currently under investigation.[28]. A strong acid (6 M HCI), added in excess to the salt, is poorly soluble in water. F. Toda and H. Miyamoto, Chem. Typi- cally, the less soluble diastere- omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. Diastecomers are not chemically identical, and so they differ in common physical properties. produced two diastereomers The phenylsuccinic acid Give the % of each enantiomer. Collect the purified crystals by vacuum filtration and rinse with 10mL of ice cold water. The less soluble salt may precipitate. Ingestion: Succinic acid (/ s k s n k /) is a dicarboxylic acid with the chemical formula (CH 2) 2 (CO 2 H) 2. The purpose of this experiment is to be able to convert enantiomers of phenylsuccinic Your email subscription to News & Announcements has been received. In humans, three HIF prolyl 4-hydroxylases regulate the stability of HIFs. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation, of the plane of polarized light). Curr. The 'Substance identity' section is calculated from substance identification information from all ECHA databases. [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. Dicarboxylic acids are ubiquitous in atmospheric aerosol particles, but their roles as surfactants in cloud condensation nuclei (CCN) activity remain unclear. A. V. Trask, N. Shan, W. D. S. Motherwell, et al., Chem. The phenylsuccinic acid is a proton donor making proline the proton acceptor. S. Mittapalli, M. K. C. Mannava, U. Article The pathway avoids the decarboxylation steps of the TCA cycle via the enzyme isocitrate lyase which cleaves isocitrate into succinate and glyoxylate. November 19th, 2018 Stir the mixture with a glass rod for 5 minutes. 1112, 1 (2016). When the solution is cooled down at room temperature, the solubility decreases which allows the pure crystals of phenylsuccinic acid to form. 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. Succinate thus serves as a direct electron donor to the electron transport chain, and itself is converted into fumarate. [11], Genetically engineered Escherichia coli and Saccharomyces cerevisiae are proposed for the commercial production via fermentation of glucose. 9, 1436 (2009). Think of a chinal center as an atom to which four different groups are covalently attached. Pharm. This property is a direct consequence of the configuration, or orientation of bonded atoms in space, around the chiral center. [42] The other two oncometabolites, fumarate and 2-hydroxyglutarate have similar structures to succinate and function through parallel HIF-inducing oncogenic mechanisms. Part of Springer Nature. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation of the plane of polarized light). Jump to main content Jump to site nav. Mass of product dissolved in acetone: 0 [ 1], Succinate can alternatively be formed by reverse activity of SDH. [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. 4036-30- (S)-(+)-Phenylsuccinic acid >99 223-719-3 Section 3 - Hazards Identification EMERGENCY OVERVIEW Appearance: almost white solid. They are potentially separable by ordinary physical methods like different solubility in a given solvent, which allows recovery of a single diastereomer ABC corresponds to the atomic number of the most characteristic element or the most characteristic organic group in the molecule. Chem. 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. [5], As a radical group it is called a succinyl (/sksnl/) group. [31] SDH mutations have also been identified in gastrointestinal stromal tumors, renal tumors, thyroid tumors, testicular seminomas and neuroblastomas. 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? 2-oxoglutarate-dependent dioxygenases bind substrates in a sequential, ordered manner. [35] Simultaneous to substrate oxidation, they convert 2-oxoglutarate, also known as alpha-ketoglutarate, into succinate and CO2. As a consequence, the mixture cases no net rotation, and appears optically inactive. [30], SUCNR1 is highly expressed on immature dendritic cells, where succinate binding stimulates chemotaxis. [5], Historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber. A 71, 3 (2015). [7] For dendritic cells, succinate functions as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production. Commun. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- Growth Des. If you study models of chiral molecules, it soon becomes apparent that their, mirror images are not superposable on each other. 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. In order to recrystallize the solid, boiling water was added to the solid until it fully dissolves to achieve a complete homoge-nous mixture. 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. This process produced two diastereomers where the more soluble compound was removed by the HCl. [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. It is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste. [24] Additionally, succinic acid produced during the fermentation of sugar provides a combination of saltiness, bitterness and acidity to fermented alcohols. Structure, properties, spectra, suppliers and links for: (+)-Phenylsuccinic acid, 4036-30-. Abstract. M. Yoshimura, M. Miyake, T. Kawato, et al., Cryst. ter. so they can be created by reacting Repeat a second time with 15 ml of acetone. The solid that results is now-resolved phenylsuccinic acid in its protonated form. 7, 1291 (2007). [9], Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. Both anions are colorless and can be isolated as the salts, e.g., Na(CH2)2(CO2H)(CO2) and Na2(CH2)2(CO2)2. Cloudflare has detected an error with your request. 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. [32] Overall, the EC50 for succinate-GPR91 is in the 2050 uM range. [10] Global production is estimated at 16,000 to 30,000 tons a year, with an annual growth rate of 10%. too much present in sample (soluble) Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA). Let aspirator run for sev- [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. )-in short, most biologically produced substances are optically active But the existence of chirality is not by itself a sufficient condition for optical activity. 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. [41], Succinate accumulation under hypoxic conditions has been implicated in the reperfusion injury through increased ROS production. Inhibition of KDMs and TET hydroxylases results in epigenetic dysregulation and hypermethylation affecting genes involved in cell differentiation. Given that enantiomers have identical physical properties, how can the mirror-image molecules become separated without the aid of some living thing? this experiment, a reflux reaction [12][13], Succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. [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. 20, 2372 (2002). You'll get a detailed solution from a subject matter expert that helps you learn core concepts. frothy The chiral recognition abilities of . Oxidative decarboxylation then generates a ferryl intermediate coordinated to succinate, which serves to oxidize the bound primary substrate. [30] This leads to stellate cell activation and fibrogenesis. Thus, succinate is thought to play a role in liver homeostasis. 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. 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 solid that results is now-resolved phenylsuccinic acid in its protonated form. Remove the beaker from the ice bath and quickly dry off the outside with a paper towel to prevent water from contaminating the crystals. 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. Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! Keep adding hot water until the solid fully dissolves. 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. Nonsuperposable mirror image molecules are called enantiomers. Abstract A new co-crystal compound of 4,4'-bipyridine and phenylsuccinic acid was synthesized and characterized by elemental analysis, infrared and ultraviolet-visible spectroscopy, and X-ray single crystal diffraction. Enantiomeric excess: 60.65171=0 100 =35% of (+)-phenylsuccinic acid a mixture of both enantiomers Moreover, the cold water wash and filtration performed was able to recover the crude solid. Lett. Solubility: Not available. In order to recrystallize the. Specific Gravity/Density:Not available. Since PHDs have an absolute requirement for molecular oxygen, this process is suppressed in hypoxia allowing HIF1 to escape destruction. In living organisms, primarily succinate, not succinic acid, is found. phenylsuccinic acid would bind to the proton (H+), where it loses its negative charge and be- Chem. The substance identifiers displayed in the InfoCard are the best available substance name, EC number, CAS number and/or the molecular and structural formulas. Stir for 5 min to allow complete protonation. 5, 9 (2002). These chemicals are invariably synthesized by catalysts called I enzymes, which are large chiral molecules specially designed to carry out a particular chemical transformation. Once the water is boiling, add hot water to the 125mL flask with the solid. The phenylsuccinic acid would bind to the proton (H+), where it loses its negative charge and becomes insoluble in water. Cloudiness and then crystals should gradually form.) Other information Prepared By Regulatory Affairs Thermo Fisher Scientific Email: EMSDS.RA@thermofisher.com Revision Date 24-Dec-2021 Print Date 24-Dec-2021 Soc. 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. Pharmacol. Phenylsuccinic acid (H 2 A, racemate, purity 99 %) was purchased from DiBo (Shanghai, China) and polyethyleneglycol (PEG) was provided by Guangzhou (Guangdong, . Write a review Ask a question. 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. please email the information below to [emailprotected]. Specific Gravity/Density:Not available. At the end of 30 minutes, turn off and remove the heating mantle. Pharm. ORGO WEEK 2 PRAC QUIZ - practice for orgo quiz 1 and 2. Not Intended for Diagnostic or Therapeutic Use. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. 8, 4533 (2008). 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. succinic acid and proline to pro- These must be removed to get a good optical activity measurement. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from water. N. Shan, A. D. Bond, and W. Jones, Cryst. . Orgo exam notes - Exam noted for organic chemistry. This diethyl ester is a substrate in the Stobbe condensation. [29] As of 2016 the inhibition of succinate-mediated ROS production was under investigation as a therapeutic drug target.[29]. Eye: 48, 5009 (2006). Any rotational effect that one enantiomer has on plane-polarized light will be exactly canceled somewhere else in the mixture by its mirror image. First, we exploit its chemical nature it is m acid) by treating it with an optically active biologically produced base, L-proline. This application requires Javascript. 24, 861 (1995). Dehydration of succinic acid gives succinic anhydride. 15 mL) and swirl for a minute to mix, then boil gently for 30 min (add boiling chip!). After refluxing, cool flask for 15 minutes, vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. * Refer to Certificate of Analysis for lot specific data (including water content). This experiment requires balanced chemical equations and theoretical yield calculation. Pull air through the solid for a couple of minutes after the last wash to evaporate most of the acetone. 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. 254, 41 (2005). Scratch inside this test tube several minutes until the contents begin to get cloudy. Shop DL-Phenylsuccinic acid, 98+%, Thermo Scientific Chemicals at Fishersci.com 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. tical rotation using polarimetry. An ideal solvent would completely precipitate one diastereomer while the other coe remained in the solution. This involves an acid-base reaction with (s)-proline and restor- ), . This property is a direct consequence of the configuration, or orientation of, bonded atoms in space, around the chiral center. The answer lies in converting the mixture of enantiomers into different compounds - a pair of diastereomers (stereoisomers that are not mitror images of each other). [17] Succinic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications.