You have the right to unsubscribe at any time by clicking the 'unsubscribe' link in any News & Announcement emails you receive. (R)-(-)-Phenylsuccinic acid | C10H10O4 - PubChem [30], Succinate signaling often occurs in response to hypoxic conditions. phenylsuccinic salt Organic Chemistry I Please note, if you are trying to access wiki.colby.edu or %PDF-1.4 To begin, dissolve 1 of racemic phenylsuccinic acid into 50mL of isopropanol in a Skin: Succinic acid (/ s k s n k /) is a dicarboxylic acid with the chemical formula (CH 2) 2 (CO 2 H) 2. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation of the plane of polarized light). An ideal solvent would completely precipitate one diastereomer while the other coe remained in the solution. 5.03E-005 mm Hg (25 deg C, Mod-Grain method) Water Solubility Estimate from Log Kow (WSKOW v1.41): Water Solubility at 25 deg C (mg/L): 4.234e+004 log Kow . As a consequence, the mixture cases no net rotation, and appears optically inactive. If you study models of chiral molecules, it soon becomes apparent that their mirror images are not superposable on each other. [32] Arg99, His103, Arg252, and Arg281 near the center of the receptor generate a positively charged binding site for succinate. Dehydration of succinic acid gives succinic anhydride. Since our excess is very low, our substance was nowhere near being pure. [citation needed], As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. If you study models of chiral molecules, it soon becomes apparent that their, mirror images are not superposable on each other. The pathway avoids the decarboxylation steps of the TCA cycle via the enzyme isocitrate lyase which cleaves isocitrate into succinate and glyoxylate. This process [5], Historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber. 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 . Copyright 2007-2023 Santa Cruz Biotechnology Inc. All Rights Reserved. Oversuccination occurs when more than one succinate adds to a substrate. )-in short, most biologically produced substances are optically active But the existence of chirality is not by itself a sufficient condition for optical activity. 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] Specific Gravity/Density:Not available. Share Improve this answer Follow edited Oct 28, 2019 at 15:24 Commun. Cross), Civilization and its Discontents (Sigmund Freud), Biological Science (Freeman Scott; Quillin Kim; Allison Lizabeth), Brunner and Suddarth's Textbook of Medical-Surgical Nursing (Janice L. Hinkle; Kerry H. Cheever). [6][38], Metabolic signaling involving succinate can be involved in inflammation via stabilization of HIF1-alpha or GPR91 signaling in innate immune cells. Resulting in observing another groups data: Such mirror images represent different stereoisomers , they are different molecules. comes insoluble in water. 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. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. Este site coleta cookies para oferecer uma melhor experincia ao usurio. [26] Alternative, succinate can be released into the extracellular milieu and the blood stream where it is recognized by target receptors. Eye: 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? PubMedGoogle Scholar. To place an order using RMB or to ship to mainland China, please visit www.scbio.cn, Click on image or enlarge button to enlarge. Who are the experts? To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- [35] Succinate may interfere with the enzymatic process by attaching to the Fe(II) center first, prohibiting the binding of 2-oxoglutarate. 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. 32% (R) - 67% (S), To comprehend the conver- G. M. Sheldrick, Acta Crystallogr. [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. [37] The oncogenic mechanism caused by mutated SHD is thought to relate to succinate's ability to inhibit 2-oxogluterate-dependent dioxygenases. Generated succinate is then available for either energy production or biosynthesis. 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. [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. The less soluble salt may precipitate. 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). Together, these three ions form a salt. RECEIVE -15-CRUZ CREDITS. acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. So, for optical activity to be evident, there must be an excess of one enantiomer over its mirror image. [7] For dendritic cells, succinate functions as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production. Alternate Names: Phenylsuccinic acid. Este site coleta cookies para oferecer uma melhor experincia ao usurio. Solved Suppose you want to purify (+)-phenylsuccinic acid - Chegg Google Scholar. The toxicological properties of this material have Two protons are transferred from the phenylsuccinic acid to the proline. 15, 2493 (2015). The phenylsuccinic acid is a proton donor making proline the proton acceptor. 5 mL of DI water. ORGO WEEK 2 PRAC QUIZ - practice for orgo quiz 1 and 2. 4, 417 (2007). Material Safety Data Sheet - Fisher Sci [25], Accumulation of fumarate can drive the reverse activity of SDH, thus enhancing succinate generation. Solubility:Not available. (S)-(&)-Phenylsuccinic acid | CAS 4036-30-0 - SCBT 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. GABA is then metabolized by GABA transaminase to succinic semialdehyde. [10] Global production is estimated at 16,000 to 30,000 tons a year, with an annual growth rate of 10%. [7] Succinate may thus be produced from enhanced glutamine metabolism via alpha-ketoglutarate or the GABA shunt. ;DgEvzv {M aK. [32] In inflammatory macrophages, succinate-induced stability of HIF1 results in increased transcription of HIF1-dependent genes, including the pro-inflammatory cytokine interleukin-1. S. Mittapalli, M. K. C. Mannava, U. RST is the consecutive number of the substance in the series ABC. S. L. Childs and K. I. Hardcastle, Cryst. RECEIVE -15-CRUZ CREDITS. The enantiomeric excess was 35.5% which is the measurement of purity. 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. The substance identifiers displayed in the InfoCard are the best available substance name, EC number, CAS number and/or the molecular and structural formulas. Vacuum filter and wash the solid with two 15mL volumes of cold water. process so the S configuration enantiomer will precipitate into the flask, leaving the R enan- CAS Number: 635-51-8. Cloudflare has detected an error with your request. This application requires Javascript. 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). To begin, dissolve 1.94g of racemic phenylsuccinic acid into 50mL of isopropanol in a 100mL round bottom flask. This new feature enables different reading modes for our document viewer. 15 mL) and swirl for a minute to mix, then boil gently for 30 min (add boiling chip!). 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. tical while diastereomers are not The solid that results is now-resolved phenylsuccinic acid in its protonated form. 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. 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. Abstract. . Take 40mg of the resolved enantiomer and dissolve it in Iml of acetone. [ 1], Succinate can alternatively be formed by reverse activity of SDH. Scratch inside this test tube several minutes until the contents begin to get cloudy. Vacuum filtered and flushed with 30 mL of acetone: chunky powder, roux-like (S)- behave identically toward physical tests like melting and boiling points and solubility in given solvents. N. J. Babu, L. S. Reddy, and A. Nangia, Mol. These must be removed to get a good optical activity measurement. For Research Use Only. This involves an acid-base reaction with (s)-proline and restor- T. Friscic, L. Fabian, J. C. Burley, et al., Chem. [39] Other inflammatory cytokines produced by activated macrophages such as tumor necrosis factor or interleukin 6 are not directly affected by succinate and HIF1. Chem. 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. 100mL round bottom flask. Given that enantiomers have identical physical properties, how can the mirror-image molecules become separated without the aid of some living thing? Struct. [7] The mechanism by which succinate accumulates in immune cells is not fully understood. www.colby.edu/directory-profile-update-form you must use the [42] The other two oncometabolites, fumarate and 2-hydroxyglutarate have similar structures to succinate and function through parallel HIF-inducing oncogenic mechanisms. The enantiomeric excess (ee) can be calculated with the expression above, where []mixture and []pureenantiomer are the specific rotations of th. This experiment requires balanced chemical equations and theoretical yield calculation. 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. 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 Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Chemical Stability:Stable under normal temperatures and pressures. Diastecomers are not chemically identical, and so they differ in common physical properties. Keep adding hot water until the solid fully dissolves. [24][27] In rodents, mitochondrial concentrations are approximately ~0.5 mM[6] while plasma concentration are only 220 M. Target Organs: No data found. Add 1.73 g of (-)-proline. 4036-30- (S)-(+)-Phenylsuccinic acid >99 223-719-3 Section 3 - Hazards Identification EMERGENCY OVERVIEW Appearance: almost white solid. Other information Prepared By Regulatory Affairs Thermo Fisher Scientific Email: EMSDS.RA@thermofisher.com Revision Date 24-Dec-2021 Print Date 24-Dec-2021 The toxicological properties In the liver, succinate serves as a paracrine signal, released by anoxic hepatocytes, and targets stellate cells via GPR91. [30], SUCNR1 is highly expressed on immature dendritic cells, where succinate binding stimulates chemotaxis. acid into separable diastereomers. It now must be recovered from the salt (the second step). "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>? 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. S. Fernandez-Lopez, H. S. Kim, E. C. Choi, et al., Nature 412, 452 (2001). The 'Substance identity' section is calculated from substance identification information from all ECHA databases. Pharm. 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. The solid that results is now-resolved phenylsuccinic acid in its protonated form. 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. 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 . [23], Click on genes, proteins and metabolites below to link to respective articles. First, we exploit its chemical nature it is m acid) by treating it with an optically active biologically produced base, L-proline. May cause eye irritation. 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. 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. ing the enantiomer by neutralizing the salt created to find the optical purity by measuring the op- [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. [6][26][38] PHDs hydroxylate proline in parallel to oxidatively decarboxylating 2-oxyglutarate to succinate and CO2. [16] The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. - 173.212.249.81. Both anions are colorless and can be isolated as the salts, e.g., Na(CH2)2(CO2H)(CO2) and Na2(CH2)2(CO2)2. Phenylsuccinic acid (H 2 A, racemate, purity 99 %) was purchased from DiBo (Shanghai, China) and polyethyleneglycol (PEG) was provided by Guangzhou (Guangdong, . This website collects cookies to deliver a better user experience. produced two diastereomers 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. Mutations in SDH, hypoxia or energetic misbalance are all linked to an alteration of flux through the TCA cycle and succinate accumulation. volumes of cold water. Growth Des. 2003-2023 Chegg Inc. All rights reserved. [27], Succinate is produced and concentrated in the mitochondria and its primary biological function is that of a metabolic intermediate. Orgo exam notes - Exam noted for organic chemistry. Exact concentration: 0 10 mL=0. endobj Purpose: Growth Des. 1 0 obj At the end of 30 minutes, turn off and remove the heating mantle. C. C. Seaton, CrystEngComm 13, 6583 (2011). The recovered diastereomer must be converted back to the original compound from which it was made -- now a single enantiomer. Part of Springer Nature. [7][32] Succinate may enhance adaptive immunity by triggering the activity of antigen-presenting cells that, in turn, activate T-cells. After refluxing, cool flask for 15 minutes, vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. Less The diastereomeric salt formed between the (+)-phenylsuccinic acid and (-)-proline is much ___ soluble in isopropyl alcohol than the diastereomeric salt formed between the . Safety Data Sheet 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. In living organisms, primarily succinate, not succinic acid, is found. The toxicological
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