phenylsuccinic acid solubility

Let aspirator run for several minutes after the second acetone wash. Poor filtrate into the organic hazardous waste container. [16] The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. [12] As an excipient in pharmaceutical products, it is also used to control acidity[21] or as a counter ion. Rep. 64, 10381042 (2019). https://doi.org/10.1134/S1063774519070125. [30] This leads to stellate cell activation and fibrogenesis. To get rid of 2-propanol and any unreacted phenylsuccinic acid, wash the crystals with 10 mL of acetone. 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. 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. In humans, three HIF prolyl 4-hydroxylases regulate the stability of HIFs. [6] As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. cally, the less soluble diastere- Learn more about Institutional subscriptions. This is an ordinary acid-basc reaction that produces a salt. The solid that results is now-resolved phenylsuccinic acid in its protonated form. Succinate requires specific transporters to move through both the mitochondrial and plasma membrane. Think of a chinal center as an atom to which four different groups are covalently attached. Take 40mg of the resolved enantiomer and dissolve it in Iml of acetone. Moreover, the cold water wash and filtration performed was able to recover the crude solid. Vacuum filter and wash the solid with two 15mL Such mirror images represent different stereoisomers they are different molecules. [12][13], Succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. Add 1.15g of finely ground (s)-proline & a magnetic stir bar then mix contents for 2 minutes and reflux for 30 minutes. [26], Succinate is also a product of the glyoxylate cycle, which converts two two-carbon acetyl units into the four-carbon succinate. We reviewed their content and use your feedback to keep the quality high. 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! 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. Add 1.73 g of (-)-proline. Succinic acid is a white, odorless solid with a highly acidic taste. [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. 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]. Dicarboxylic acids are ubiquitous in atmospheric aerosol particles, but their roles as surfactants in cloud condensation nuclei (CCN) activity remain unclear. This involves an acid-base reaction with (s)-proline and restor- [37] The oncogenic mechanism caused by mutated SHD is thought to relate to succinate's ability to inhibit 2-oxogluterate-dependent dioxygenases. The first source was natural products chemicals produced by living organisms. Finally, succinic semialdehyde is oxidized by succinic semialdehyde dehydrogenase (SSADH) to form succinate, re-entering the TCA cycle and closing the loop. Succinic acid (/sksnk/) is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. 5, 9 (2002). 2-oxoglutarate-dependent dioxygenases bind substrates in a sequential, ordered manner. Other information Prepared By Regulatory Affairs Thermo Fisher Scientific Email: EMSDS.RA@thermofisher.com Revision Date 24-Dec-2021 Print Date 24-Dec-2021 Exact concentration: 0 10 mL=0. solid. 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. Inhalation: 1 0 obj 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. If you study models of chiral molecules, it soon becomes apparent that their, mirror images are not superposable on each other. Organic Chemistry I Chem. 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 phenylsuccinic acid gave up two positives, so it is a dianion. Show transcribed image text. 1112, 1 (2016). Transamination and subsequent decarboxylation of alpha-ketoglutarate leads to the formation of GABA. 15 mL) and swirl for a minute to mix, then boil gently for 30 min (add boiling chip!). To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- Appearance: almost white solid. (R)-(-)-Phenylsuccinic acid | C10H10O4 | CID 736145 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological . Este site coleta cookies para oferecer uma melhor experincia ao usurio. Article This experiment requires balanced chemical equations and theoretical yield calculation. stream bvseo-msg: The resource to the URL or file is currently unavailable.. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from water. Not Intended for Diagnostic or Therapeutic Use. These chemicals are invariably synthesized by catalysts called, enzymes, which are large chiral molecules specially designed to carry out a particular chemical, transformation. 24, 861 (1995). Percent recovery: 00 100 =4% The enantiomeric excess (ee) can be calculated with the expression above, where []mixture and []pureenantiomer are the specific rotations of th. Proline likewise gains 18+, but this gives ita net + charge, making it very soluble in water. %PDF-1.4 with another chiral molecule. [5], As a radical group it is called a succinyl (/sksnl/) group. ter. Nonsuperposable mirror image molecules are called enantiomers. not been fully investigated. Growth Des. You'll get a detailed solution from a subject matter expert that helps you learn core concepts. 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. As a diprotic acid, succinic acid undergoes two successive deprotonation reactions: The pKa of these processes are 4.3 and 5.6, respectively. tiomer behind. Allow to fully dry & poor the filtrate into the aqueous hazardous waste container. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. Copyright 2007-2023 Santa Cruz Biotechnology, Inc. All Rights Reserved. 1).Factors affecting the extraction efficiency were investigated, namely the influence of the types of organic solvents and -CD derivatives, iso-butyl tartrate . In the liver, succinate serves as a paracrine signal, released by anoxic hepatocytes, and targets stellate cells via GPR91. tract irritation. Soc. During this time, all the proline should dissolve. 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. In the retina, succinate accumulates in retinal ganglion cells in response to ischemic conditions. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Chemical Stability:Stable under normal temperatures and pressures. Remove the beaker from the ice bath and quickly dry off the outside with a paper towel to prevent water from contaminating the crystals. 9, 1436 (2009). This process produced two diastereomers where the more soluble compound was removed by the HCl. You have the right to unsubscribe at any time by clicking the 'unsubscribe' link in any News & Announcement emails you receive. [23], Click on genes, proteins and metabolites below to link to respective articles. Don't use too much water, as the product is somewhat soluble and will slowly dissolve. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that are to be fashioned into the product. << No information found. indication of why you can't access this Colby College website. Z. Wang, C. B. Wu, et al., CrystEngComm 14, 6221 (2012). is conducted between the pheny- Experimental Procedure: 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. This website collects cookies to deliver a better user experience. Conditions to Avoid:Incompatible materials, dust generation, excess heat, strong oxidants. X`I%&/m{JJt`$@iG#)*eVe]f@{{;N'?\fdlJ!?~|? 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. PubMedGoogle Scholar. ADS University of Massachusetts Lowell. Garcia, Jessica. 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. produced substances are optically active. 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! Lett. this experiment, a reflux reaction S. L. Childs and K. I. Hardcastle, Cryst. astereomer, enantiomers are iden- Add 1 of finely ground (s)-proline & a magnetic stir bar then Zohreh Derikvand. [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. [32] Overall, the EC50 for succinate-GPR91 is in the 2050 uM range. 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. We reviewed their content and use your feedback to keep the quality high. Alternate Names: Phenylsuccinic acid. [15], Succinic acid is a precursor to some polyesters and a component of some alkyd resins. [8][29] During ischemia, succinate accumulates. To begin, dissolve 1 of racemic phenylsuccinic acid into 50mL of isopropanol in a Lab Section 803 9:00am Share Improve this answer Follow edited Oct 28, 2019 at 15:24 phenylsuccinic salt Most often, these pieces can attach to the enzyme only in one particular, orientation. Stir the mixture with a glass rod for 5 minutes. - 173.212.249.81. Generated succinate is then available for either energy production or biosynthesis. OHN 6MH hydrolysis) COH HO COM LPHC Soluble in water [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. [27], Succinate is produced and concentrated in the mitochondria and its primary biological function is that of a metabolic intermediate. A. V. Trask and W. Jones, Top. stacking interaction leads to the formation of 3D supramolecular structure. so they can be created by reacting This property is a direct consequence of the configuration, or orientation of, bonded atoms in space, around the chiral center. Struct. 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. Pharm. [36] Pathologically elevated levels of succinate lead to hypermethylation, epigenetic silencing and changes in neuroendocrine differentiation, potentially driving cancer formation. Immediately retum the contents to the boiling flask and swirl. Because protons have +1 charge, each proline is cationic. Added to cooled 10 mL 6 HCl: Reaction immediately but not cloudy enough Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01. where the more soluble compound Copyright 2007-2023 Santa Cruz Biotechnology Inc. All Rights Reserved. [citation needed], Succinate is one of three oncometabolites, metabolic intermediates whose accumulation causes metabolic and non-metabolic dysregulation implicated in tumorigenesis. Google Scholar. Growth Des. [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. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation, of the plane of polarized light). Enzymes required for the GABA shunt are expressed in neurons, glial cells, macrophages and pancreatic cells. Collect the purified crystals by vacuum filtration and rinse with 10mL of ice cold water. (If there is no precipitate, use a Pasteur pipet to remove about I mL to a small test tube. To begin, dissolve 1.94g of racemic phenylsuccinic acid into 50mL of isopropanol in a 100mL round bottom flask. Phenylsuccinic acid (H 2 A, racemate, purity 99 %) was purchased from DiBo (Shanghai, China) and polyethyleneglycol (PEG) was provided by Guangzhou (Guangdong, . As the anion binds the H+, it loses its negative charge and becomes poorly soluble in water. process so the S configuration enantiomer will precipitate into the flask, leaving the R enan- [5], Historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber. https://doi.org/10.1134/S1063774519070125, DOI: https://doi.org/10.1134/S1063774519070125. The reaction between the bis salt of proline and phenylsuccinic acid will give free phenyl succinic acid and proline hydrochloride as HCl is a much stronger acid than phenylsuccinic acid. duce salt. [9], Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. o Likely reflux conflict of earlier step in result of failure to eliminate (R)-acid and 32% (R) - 67% (S), To comprehend the conver- DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. [25], Accumulation of fumarate can drive the reverse activity of SDH, thus enhancing succinate generation. 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 Polarimetry: The success of this experiment is evaluated by computing the apparent specific rotation of the product. too much present in sample (soluble) Since our excess is very low, our substance was nowhere near being pure. Orgo exam notes - Exam noted for organic chemistry. ), . tical while diastereomers are not Abstract. Succinate exits the mitochondrial matrix and passes through the inner mitochondrial membrane via dicarboxylate transporters, primarily SLC25A10, a succinate-fumarate/malate transporter. Stir for 5 min to allow complete protonation. 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. [32] Arg99, His103, Arg252, and Arg281 near the center of the receptor generate a positively charged binding site for succinate.