phenylsuccinic acid solubility

Let the clear solution rest at RT for about 20 min in order to allow for the crystallization of the desired compound. 4, 417 (2007). ORGO WEEK 2 PRAC QUIZ - practice for orgo quiz 1 and 2. Measure the specific rotation and determine the enantiomeric excess of the sample. Alternate Names: Phenylsuccinic acid. >> Soc. Lexxus Pen 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. [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 recovered diastereomer must be converted back to the original compound from which it was made -- now a single enantiomer. [28], Succinate serves as a modulator of blood pressure by stimulating renin release in macula densa and juxtaglomerular apparatus cells via GPR91. %PDF-1.4 Give the % of each enantiomer. These chemicals are invariably synthesized by catalysts called, enzymes, which are large chiral molecules specially designed to carry out a particular chemical, transformation. X. P. Dai, G. G. Hou, J. F. Sun, et al., J. Mol. Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA). 100mL round bottom flask. InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8), InChI=1/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8), Except where otherwise noted, data are given for materials in their, Precursor to polymers, resins, and solvents. [15], Succinic acid is a precursor to some polyesters and a component of some alkyd resins. [9], Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. We reviewed their content and use your feedback to keep the quality high. [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. 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. At the end of 30 minutes, turn off and remove the heating mantle. Molecular Formula: C 10 H 10 O 4. Because protons have +1 charge, each proline is cationic. [26], Succinate is also a product of the glyoxylate cycle, which converts two two-carbon acetyl units into the four-carbon 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)/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. [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. Calculate the exact concentration which will be needed to calculate specific rotation. 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. You have the right to unsubscribe at any time by clicking the 'unsubscribe' link in any News & Announcement emails you receive. 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. produced substances are optically active. [8] ROS then trigger the cellular apoptotic machinery or induce oxidative damage to proteins, membranes, organelles etc. Add 1 of finely ground (s)-proline & a magnetic stir bar then RECEIVE -15-CRUZ CREDITS. The information below may provide an % Any rotational effect that one enantiomer has on plane-polarized light will be exactly canceled somewhere else in the mixture by its mirror image. Transamination and subsequent decarboxylation of alpha-ketoglutarate leads to the formation of GABA. 7, 1291 (2007). out to be a good recrystallization solvent for this product. Struct. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from water. S. L. Childs and K. I. Hardcastle, Cryst. Structure, properties, spectra, suppliers and links for: (+)-Phenylsuccinic acid, 4036-30-. Conditions to Avoid:Incompatible materials, dust generation, excess heat, strong oxidants. mix contents for 2 minutes and reflux for 30 minutes. duce salt. 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. [36][37], Succinate inhibition of prolyl hydroxylases (PHDs) stabilizes the transcription factor hypoxia inducible factor (HIF)1. process so the S configuration enantiomer will precipitate into the flask, leaving the R enan- 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 . [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. 5, 9 (2002). Generated succinate is then available for either energy production or biosynthesis. Optical Rotation: []=obscl[]=(0.03992/m)( 1 )=60 Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Chemical Stability:Stable under normal temperatures and pressures. is a proton donor making proline The site owner may have set restrictions that prevent you from accessing the site. 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. Molecular Weight: 194.18. Vacuum filtered and flushed with 30 mL of acetone: chunky powder, roux-like (S)- Shop DL-Phenylsuccinic acid, 98+%, Thermo Scientific Chemicals at Fishersci.com Learn more about Institutional subscriptions. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that are to be fashioned into the product. In the retina, succinate accumulates in retinal ganglion cells in response to ischemic conditions. Zohreh Derikvand. Ingestion: Please note, if you are trying to access wiki.colby.edu or [32] In inflammatory macrophages, succinate-induced stability of HIF1 results in increased transcription of HIF1-dependent genes, including the pro-inflammatory cytokine interleukin-1. Insoluble in water. Experiment 4: Resolution of Phenylsuccinic Acid [29] As of 2016 the inhibition of succinate-mediated ROS production was under investigation as a therapeutic drug target.[29]. 48, 5009 (2006). CAS Number: 4036-30-. Copyright 2007-2023 Santa Cruz Biotechnology, Inc. All Rights Reserved. [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. [30], Succinate signaling often occurs in response to hypoxic conditions. A new solvent sublation (SS) system for chiral separation is introduced by using phenylsuccinic acid (H2A) as the model enantiomers. 24, 861 (1995). Water tums Phenylsuccinic acid (H 2 A, racemate, purity 99 %) was purchased from DiBo (Shanghai, China) and polyethyleneglycol (PEG) was provided by Guangzhou (Guangdong, . Through these mechanisms, succinate accumulation has been shown to regulate production of inflammatory cytokines. phenylsuccinic acid (H 2A) as the model enantiomers. [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. Keep adding hot water until the solid fully dissolves. Not Intended for Diagnostic or Therapeutic Use. 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. [32] Furthermore, SUCNR1 synergizes with toll-like receptors to increase the production of proinflammatory cytokines such as TNF alpha and interleukin-1beta. Repeat a second time with 15 ml of acetone. In addition to its metabolic roles, succinate serves as an intracellular and extracellular signaling molecule. 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. DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. https://doi.org/10.1134/S1063774519070125. S. Fernandez-Lopez, H. S. Kim, E. C. Choi, et al., Nature 412, 452 (2001). X`I%&/m{JJt`$@iG#)*eVe]f@{{;N'?\fdlJ!?~|? 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. As the anion binds the H+, it loses its negative charge and becomes poorly soluble in water. 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. sion of an enantiomer to a di- Este site coleta cookies para oferecer uma melhor experincia ao usurio. Growth Des. Since our excess is very low, our substance was nowhere near being pure. Skin: ADS T. R. Shattock, K. K. Arora, P. Vishweshwar, and M.J.Zaworotko, Cryst. eral minutes after the second acetone wash. Poor filtrate into the organic hazardous waste con- Dehydration of succinic acid gives succinic anhydride. J. M. Chen, Z. [14] Succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and tetrahydrofuran. Added to cooled 10 mL 6 HCl: Reaction immediately but not cloudy enough Succinate is also produced from butane via maleic anhydride. The toxicological properties Growth Des. 4 0 obj After refluxing, cool flask for 15 minutes, vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. Think of a chinal center as an atom to which four different groups are covalently attached. If you study models of chiral molecules, it soon becomes apparent that their, mirror images are not superposable on each other. An ideal solvent would completely precipitate one diastereomer while the other coe remained in the solution. Such mirror images represent different stereoisomers they are different molecules. Let aspirator run for sev- acid into separable diastereomers. Nonsuperposable mirror image molecules are called enantiomers. Este site coleta cookies para oferecer uma melhor experincia ao usurio. Stir for 5 min to allow complete protonation. [26] As such, succinate links TCA cycle dysfunction or metabolic changes to cell-cell communication and to oxidative stress-related responses. As a consequence, the mixture cases no net rotation, and appears optically inactive. 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. In this study, we investigated CCN activity of inorganic salt (sodium chloride and ammonium sulfate) and dicarboxylic acid (including malonic acid (MA), phenylmalonic acid (PhMA), succinic acid (SA), phenylsuccinic acid (PhSA . [12] As an excipient in pharmaceutical products, it is also used to control acidity[21] or as a counter ion. N. Shan, F. Toda, and W. Jones, Chem. is conducted between the pheny- The proline, its former partner in the salt, remains soluble in the aqueous phase. [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 Next, place crude solid in a 125mL Erlenmeyer flask and boil 100mL of water in a 250mL Erlenmeyer flask. The phenylsuccinic acid is a proton donor making proline the proton acceptor. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- [30] The G-protein coupled receptor, GPR91 also known as SUCNR1, serves as the detector of extracellular succinate. The purpose of this experiment is to be able to convert enantiomers of phenylsuccinic Molecular Formula: C 10 H 10 O 4. 15 mL) and swirl for a minute to mix, then boil gently for 30 min (add boiling chip!). Experimental Procedure: [12][13], Succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. [8][29] During ischemia, succinate accumulates. Subsequently, the primary substrate enters the binding pocket and lastly dioxygen binds to the enzyme-substrate complex. 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. Commun. Cool 10mL of 6 M HCl in an ice bath and add all of the collected salt to this cold HCl. University of Massachusetts Lowell. A 71, 3 (2015). 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. 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). A suitable solvent is found by trial and error. Moreover, the cold water wash and filtration performed was able to recover the crude solid. This process produced two diastereomers where the more soluble compound was removed by the HCl. 1 0 obj Space available to draw mechanisms. Growth Des. 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. acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. First, we exploit its chemical nature it is an acid) by treating it with an optically active biologically produced base, L-proline. "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>? The toxicological RECEIVE -15-CRUZ CREDITS. 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. 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. [16] The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. connect to this server when you are off campus. Filtration permits discard of the more soluble salt, which cames away one enantiomer () of the phenylsuccinic acid Once the less soluble diastereomeric salt has been isolated, only a single enantiomer of phenylsuccinic acid remains. 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. The enantiomeric excess was 35.5% which is the measurement of purity. A strong acid (6 M HCI), added in excess to the salt, is used to protonate the water-soluble anion. Eng. comes insoluble in water. The resulting solid acid can be recovered by filtration. ()-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. Stir the mixture with a glass rod for 5 minutes. 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. 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. tory IB Syllabus. [30], In adipocytes, the succinate-activated GPR91 signaling cascade inhibits lipolysis. Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. [citation needed], As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. Growth Des. [6][26][38] PHDs hydroxylate proline in parallel to oxidatively decarboxylating 2-oxyglutarate to succinate and CO2. )-in short, most biologically produced substances are optically active But the existence of chirality is not by itself a sufficient condition for optical activity. (R)-(-)-Phenylsuccinic acid | C10H10O4 | CID 736145 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological . This is an ordinary acid-basc reaction that produces a salt. [18], Acylation with succinic acid is called succination. was removed by the HCl. Your email subscription to News & Announcements has been received. This process Typically, the less soluble diastere-. /Producer(Sub Systems, Inc.)/CreationDate(D:20211226231644+05'00')/ModDate(D:20211226231644+05'00')/Creator(Sub Systems, Inc.) [24] Additionally, succinic acid produced during the fermentation of sugar provides a combination of saltiness, bitterness and acidity to fermented alcohols. 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. [38] Hydroxylation of two prolyl residues in HIF1 facilitates ubiquitin ligation, thus marking it for proteolytic destruction by the ubiquitin/proteasome pathway. [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. 7, 880 (2005). In order to recrystallize the solid, boiling water was added to the solid until it fully dissolves to achieve a complete homoge-nous mixture. Chem. Two protons are transferred from the phenylsuccinic acid to the proline. This enzyme complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of ubiquinone via the intermediate electron carriers FAD and three 2Fe-2S clusters. Course Hero is not sponsored or endorsed by any college or university. Experts are tested by Chegg as specialists in their subject area. The solid that results is now-resolved phenylsuccinic acid in its protonated form. [23], Click on genes, proteins and metabolites below to link to respective articles. This website collects cookies to deliver a better user experience. ing the enantiomer by neutralizing the salt created to find the optical purity by measuring the op- [34] 2-oxoglutarate-dependent dioxygenases require an iron cofactor to catalyze hydroxylations, desaturations and ring closures. Collect the purified crystals by vacuum filtration and rinse with 10mL of ice cold water. [29] If mitochondrial respiratory complex III is unable to accommodate excess electrons supplied by succinate oxidation, it forces electrons to flow backwards along the electron transport chain. : 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. A. V. Trask, N. Shan, W. D. S. Motherwell, et al., Chem.