malonic acid structure

2004 International Waterborne, High-Solids, and Powder Coatings Symposium. Synonyms. Diethylmalonic acid anhydride is relatively stable and at 160–180°C, decomposes to form diethylketene and CO2, as shown in the following reaction: A similar reaction is given by dimethylmalonic anhydride, but the reaction products tend to … Sub. The crystal structure is determined for malonic acid cocrystal by single-crystal X-ray diffraction method. IDENTIFICATION: Malonic acid, which is also called propanedioic acid, is a colorless or white crystalline powder. Search results for Malonic acid at Sigma-Aldrich. Malonic acid[2] is a naturally occurring substance found in many fruits and vegetables. Hildbrand, S.; Pollak, P. Malonic Acid & Derivatives. a 208.12 g/mol. Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ester and salts of malonic acid are called malonates. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. SCHEMBL23831. Malonic acid is a dicarboxylic acid with structural formula CH 2 (COOH) 2 and chemical formula C 3 H 4 O 4. [20], In food and drug applications, malonic acid can be used to control acidity, either as an excipient in pharmaceutical formulation or natural preservative additive for foods.[3]. Dastidar TG, Netravali AN, "'Green' crosslinking of native starches with malonic acid and their properties." C6H8O8. Malonic acid was listed as one of the top 30 chemicals to be produced from biomass by the US Department of Energy. One application of malonic acid is in the coatings industry as a crosslinker for low-temperature cure powder coatings, which are becoming increasingly valuable for heat sensitive substrates and a desire to speed up the coatings process. Inhibitor Studies with Succinic Dehydrogenase", Calculator: Water and solute activities in aqueous malonic acid, https://en.wikipedia.org/w/index.php?title=Malonic_acid&oldid=992436732, Wikipedia articles incorporating a citation from the 1911 Encyclopaedia Britannica with Wikisource reference, Short description is different from Wikidata, Chemical articles with multiple compound IDs, Multiple chemicals in an infobox that need indexing, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Articles with unsourced statements from July 2020, Creative Commons Attribution-ShareAlike License, 135 to 137 °C (275 to 279 °F; 408 to 410 K) (decomposes), This page was last edited on 5 December 2020, at 07:31. [14], Carbon suboxide is prepared by warming a dry mixture of phosphorus pentoxide (P4O10) and malonic acid. An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group. Download . The malonic ester synthesis provides a method for preparing a substituted acetic acid. Malonate or propanedioate compounds include salts and esters of malonic acid, such as, Carboxylic acid with chemical formula CH2(COOH)2, InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7), InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7), Except where otherwise noted, data are given for materials in their. PCT/US2013/029441 2012. Synonym: (2-Thenyl)malonic acid, 2-(2-Thienylmethyl)propanedioic acid, 2-(Thiophen-2-ylmethyl)malonic acid, NSC 39209 Empirical Formula (Hill Notation): C 8 H 8 O 4 S Molecular Weight: 200.21 The esters of malonic acid are also used as a −CH2COOH synthon in the malonic ester synthesis. {\displaystyle pK_{a}} [19] Potential growth of these markets could result from advances in industrial biotechnology that seeks to displace petroleum-based chemicals in industrial applications. Structure and properties. Industrially, however, malonic acid is produced by hydrolysis of dimethyl malonate or diethyl malonate. If generated, an InChI string will also be generated and made available for searching. Here we report the design of malonic acid-based inhibitors using the X-ray structure of a collagenase/inhibitor complex, which revealed a nonsubstrate-like binding mode. The structure has been determined by X-ray crystallography and extensive property data including for condensed phase thermochemistry are available from the National Institute of Standards and Technology. Linear Formula: 13 CH 2 (13 CO 2 C 2 H 5) 2. [citation needed] It can also be a component in alkyd resins, which are used in a number of coatings applications for protecting against damage caused by UV light, oxidation, and corrosion. [16], Malonic acid is a precursor to specialty polyesters. Carbohydrate Polymers, 90:1620-1628 (2012), "Biodegradable Polymers," Chemical Economics Handbook (May 2015). CopyCopied, 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 Agency’s EPISuite™, Click to predict properties on the Chemicalize site, For medical information relating to Covid-19, please consult the. Chauffé vers 140 °C, il se décompose en fumées toxiques ou en vapeurs potentiellement inflammables. Weight Average: 104.0615 Monoisotopic: 104.010958616 Chemical Formula C 3 H 4 O 4 Synonyms. 2015 Grand View Research Market Report. The molecular structure is based on structures generated from information available in ECHA’s databases. Malonyl CoA is formed from acetyl CoA by the action of acetyl-CoA carboxylase, and the malonate is transferred to an acyl carrier protein to be added to a fatty acid chain. Malonic acid reacts as a typical carboxylic acid: forming amide, ester, anhydride, and chloride derivatives. Malonic acid (up to 37.5% w/w) has been used to cross-link corn and potato starches to produce a biodegradable thermoplastic; the process is performed in water using non-toxic catalysts. diethyl malonate, (C 2 H 5) 2 (C 3 H 2 O 4), dimethyl malonate, (CH 3) 2 (C 3 H 2 O 4), disodium malonate, Na 2 (C 3 H 2 O 4). Stable. Malonic acid. C(C(=O)O)C(=O)O Methane Dicarboxylic acid is another name for malonic acid. 2004 US Department of Energy. Compare Products: Select up to 4 products. [17] The global coatings market for automobiles was estimated to be $18.59 billion in 2014 with projected combined annual growth rate of 5.1% through 2022.[18]. National Institute of Standards and Technology, pKa Data Compiled by R. Williams (pdf; 77 kB), "Organic Acids Concentration in Citrus Juice from Conventional Versus Organic Farming", "Note sur un acide obtenu par l'oxydation de l'acide malique", "The Effect of Salicylic Acid on the Briggs-Rauscher Oscillating Reaction", "Ueber die der Sorbinsäure homologen, ungesättigten Säuren mit zwei Doppelbindungen", "1-N-Acylamino-1,3-dienes from 2,4-pentadienoic acids by the Curtius rearrangement: benzyl trans-1,3-butadiene-1-carbamate", "Malonate Inhibition of Oxidations in the Krebs Tricarboxylic Acid Cycle", "Studies on the Mechanism of Hydrogen Transport in Animal Tissues : VI. Its chemical formula is HO 2 CCH=CHCO 2 H. Maleic acid is the cis-isomer of butenedioic acid, whereas fumaric acid is the trans-isomer. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.) When malonic acid itself is used, it is normally because the desired product is one in which a second step has occurred, with loss of carbon dioxide, in the so-called Doebner modification. [1] Thus the malonate ion can be HOOCCH2COO− or CH2(COO)2−2. Among the hydroxamic acids, malonic acid derivatives have been used as MMP inhibitors, although optimization of their inhibition potency was not successful. The IUPAC name of malonic acid is Propanedioic acid. malonic acid propanedioic acid. Structure for Malonic acid (DB02175) × Close. Additionally, the coenzyme A derivative of malonate, malonyl-CoA, is an important precursor in fatty acid biosynthesis along with acetyl CoA. K The crystal structure revealed that the cocrystal crystallized in the triclinic crystal system with space group P-1 and the malonic acid molecules are sandwiched by brexpiprazole molecules. 14/418,940. Malonic acid is a rather simple dicarboxylic acid, with two the carboxyl groups close together. [29], Malonic acid is diprotic; that is, it can donate two protons per molecule. Malonate compoundsinclude salts and esters of malonic acid, such as. *Please select more than one item to compare It has a role as a human metabolite and a mitochondrial respiratory-chain inhibitor. In a well-known reaction, malonic acid condenses with urea to form barbituric acid. [3] There is a suggestion that citrus fruits produced in organic farming contain higher levels of malonic acid than fruits produced in conventional agriculture. [22][23] Starch-based polymers comprised 38% of the global biodegradable polymers market in 2014 with food packaging, foam packaging, and compost bags as the largest end-use segments. Malonic acid is a key component in the Briggs–Rauscher reaction, the classic example of an oscillating chemical reaction.[12]. The nitrile group can be hydrolyzed with sodium hydroxide to sodium malonate, and acidification affords malonic acid. The crystals of MA are triclinic at room temperature. [9] It has also been produced through fermentation of glucose.[10]. The name originates from the Greek word μᾶλον (malon) meaning 'apple'. Registrants / Suppliers - Active. Ullmann's Encyclopedia of Industrial Chemistry. Molecular Weight: 163.15 . Malonic acid is used as a building block chemical to produce numerous valuable compounds,[21] including the flavor and fragrance compounds gamma-nonalactone, cinnamic acid, and the pharmaceutical compound valproate. Molecular Formula. It occurs naturally in the air, and occurs because of engine emissions, wood fires and from cigarettes. Brief Profile - Last updated: 11/11/2020 Print. Malonic acid is a dicarboxylic acid with structure CH2(COOH)2. 1971 US Patent No. The name malonic acid originated from the word ‘Malon’ which is Greek for ‘apple’. A classical preparation of malonic acid starts from chloroacetic acid: In 2004, annual global production of malonic acid and related diesters was over 20,000 metric tons. In Knoevenagel condensation, malonic acid or its diesters are reacted with the carbonyl group of an aldehyde or ketone, followed by a dehydration reaction. This observation was used to deduce the structure of the active site in succinate dehydrogenase. CS1 maint: multiple names: authors list (. Malonic esters have two ester groups, each of which may react as in the acetoacetic ester synthesis due to their similar structure (see the preceding section). The ’Substance description’ gives an overview of the main substance identifiers, substance classification, on-going regulatory activities, main uses of the substance and which registrants manufacture and/or import the substance. If generated, an InChI string will also be generated and made available for searching. EXPOSURE: … Werpy, T., Petersen, G. Top Value Added Chemicals from Biomass. It is also used in veterinary medicine. 3D. Appl No. CopyCopied, InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) [13], Thus, for example, the reaction product of acrolein and malonic acid in pyridine is trans-2,4-Pentadienoic acid with one carboxylic acid group and not two. Malonic acid (MA), also known as propanedioic acid, is a dicarboxylic acid. class: Standard polar; Column diameter: 0.32 mm; Column length: 60 m; Column type: Capillary; Description: 35C(3min) =>5C/min =>110C =>10C/min =>240C (10min); CAS no: 141822; Active phase: Supelcowax-10; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Kourkoutas, Y.; Kandylis, P.; Panas, P.; Dooley, J.S.G. Stars This entity has been manually annotated by … fatty acid biosynthesis (plant mitochondria), (-)-maackiain-3-O-glucoside-6''-malonate + H2O -> malonate + (-)-maackiain-3-O-glucoside + H+, (-)-medicarpin-3-O-glucoside-6''-malonate + H2O -> malonate + (-)-medicarpin-3-O-glucoside + H+, afrormosin-7-O-glucoside + malonate + H+ -> afrormosin-7-O-glucoside-6''-O-malonate + H2O, biochanin A-7-O-glucoside-6''-malonate + H2O -> biochanin A-7-O-glucoside + malonate + H+, formononetin-7-O-glucoside-6''-malonate + H2O -> malonate + ononin + H+, malonate + a holo-[acyl-carrier protein] + ATP -> a malonyl-[acp] + AMP + diphosphate, malonate + ATP + coenzyme A -> malonyl-CoA + AMP + diphosphate, malonyldaidzin + H2O -> malonate + daidzin + H+, malonylgenistin + H2O -> malonate + genistin + H+. It is used in a number of manufacturing processes as a high value specialty chemical including the electronics industry, flavors and fragrances industry,[3] specialty solvents, polymer crosslinking, and pharmaceutical industry. Malonate (2-) is a dicarboxylic acid dianion obtained by the deprotonation of the carboxy groups of malonic acid. CAS Number: 53051-81-3. Its first malonic acid: ChEBI ID CHEBI:30794: Definition An α,ω-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group. Malonic acidemia (MAL) is an inherited condition in which the body is unable to break down certain proteins. The molecular structure is based on structures generated from information available in ECHA’s databases. C3H4O4. It can be converted into 1,3-propanediol for use in polyesters and polymers and a projected market size of $621.2 million by 2021. is 2.8 and the second is 5.7. Registrant / Supplier Registered Updated; Chemical Inspection & Regulation Service Limited(HEBEI CHENGXIN CO.,LTD.) Microbiol., 72(9), 2006, 6124-6135. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30794, ACD/Labs Percepta Platform - PhysChem Module, US Environmental Protection Agency’s EPISuite™, Compounds with the same molecular formula, Search Google for structures with same skeleton. [26] It binds to the active site of the enzyme without reacting, competing with the usual substrate succinate but lacking the −CH2CH2− group required for dehydrogenation. malonic acid hydrolysis mixture acid ester Prior art date 1942-09-22 Legal status (The legal status is an assumption and is not a legal conclusion. [25], Malonic acid is the classic example of a competitive inhibitor of the enzyme succinate dehydrogenase (complex II), in the respiratory electron transport chain. [7] Environ. The dicarboxylic acid has organic reactions … Molecular Weight. Figure 15-14 shows the structure of one type of malonic ester. Incompatible with oxidizing agents, reducing agents, bases. Molecular Formula. For example, diethyl malonate is malonic acid's diethyl ester. Structure, properties, spectra, suppliers and links for: (Aminomethyl)malonic acid. Articles of Malonic acid are included as well. Registrants / Suppliers Details open all close all. The reaction kinetics of the photocatalytic decomposition of MA in aqueous suspensions of titanium dioxide (TiO 2) have been described. A classical preparation of malonic acid starts from chloroacetic acid:[8], Sodium carbonate generates the sodium salt, which is then reacted with sodium cyanide to provide the sodium salt of cyanoacetic acid via a nucleophilic substitution. An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group. [15] It reacts in a similar way to malonic anhydride, forming malonates. ; Nigam, P.; Koutinas, A.A., Evaluation of freeze-dried kefir coculture as starter in feta-type cheese production, Appl. Find Similar Structures. [4], Malonic acid was first prepared in 1858 by the French chemist Victor Dessaignes via the oxidation of malic acid. Molecular structure. Malonic acid EC Number: 205-503-0 EC Name: Malonic acid CAS Number: 141-82-2 Molecular formula: C3H4O4 IUPAC Name: propanedioic acid. Netravali, A., Dastidar, T. Crosslinked native and waxy starch resin compositions and processes for their manufacture. 3,591,676. Hawkins, G., Fassett, D. Surgical Adhesive Compositions. L'acide malonique est un produit instable. Molecular Weight. SCHEMBL1332587. description Substance description Substance description. Structure, properties, spectra, suppliers and links for: Malonic acid, 141-82-2. Similar Structures. Malonic acid anhydride is not a very stable compound. It is classified as an organic acid condition because MAL can lead to harmful levels of organic acids and toxins in the body. CopyCopied, OFOBLEOULBTSOW-UHFFFAOYSA-N Carboxylic acid with the structural formula CH 3 CH 2 CH 2 -COOH. p James, S. Global Automotive Coatings Market. 107.04 g/mol. Signs and symptoms of the condition vary. Synonyms. Malonic acid Accession Number DB02175 Description Not Available Type Small Molecule Groups Experimental Structure. NSC-8124; Pharmacology … Salts and esters of butyric acid are known as butyrates or butanoates. Advanced Search | Structure Search Malonic acid-2-13 C. 1 Product Result ... 13 C Labeled diethyl malonic acid, Malonic acid diethyl ester-13 C 3. [5], The structure has been determined by X-ray crystallography[6] and extensive property data including for condensed phase thermochemistry are available from the National Institute of Standards and Technology. [11] Malonic anhydride can be used as an intermediate to mono-ester or amide derivatives, while malonyl chloride is most useful to obtain diesters or diamides. Malonic acid-13C3, 99 atom % 13C. Molecular structure. The solubility studies for brexpiprazole and cocrystals are established in 0.05 M acetate … It is a conjugate base of a malonate (1-). [27][28] Since malonic acid is a natural components of many foods, it is present in mammals including humans. Malonic acid-13C3. Malonic acid may also condensed be with acetone to form Meldrum's acid, a versatile intermedate in further transformations. CopyCopied, CSID:844, http://www.chemspider.com/Chemical-Structure.844.html (accessed 22:48, Jan 8, 2021) The ionized form of malonic acid, as well as its esters and salts, are known as malonates. Chemsrc provides Malonic acid(CAS#:141-82-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Recombinant host cells for the production of malonate. Fäcke, T., Subramanian R., Dvorchak, M., Feng, S. Diethylmalonate Blocked Isocyanates As Crosslinkers For Low Temperature Cure Powder Coatings. However, early identification and treatment can improve the health of children with MAL. [24], Eastman Kodak company and others use malonic acid and derivatives as a surgical adhesive. Inhibition of this enzyme decreases cellular respiration. MOL SDF 3D-SDF PDB SMILES InChI. Propanedioic acid; External IDs . The oxidation of malonic acid by cerium (IV) in sulfuric acid solution has been studied. Maleic acid or cis-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. March 15, 2001. J-000676. Un début d'incendie peut être arrêté au moyen de poudre CO2, d'agents chimiques secs, de mousses ou d'eau pulvérisée. 2013 US. USE: Malonic acid is used to make pharmaceuticals. ORL-RAT LD50 1310 mg kg-1, IPR-RAT LD50 1500 mg kg-1, ORL-MUS LD50 4000 mg kg-1, IPR-MUS LD50 300 mg kg-1, P261-P280-P305+P351+P338-P304+P340-P405-P501a, WARNING: Irritates skin and eyes, harmful if swallowed. Malonic acid is very soluble in water. Structure. It occurs in many plants, including fruits and grains. A derivative of malonate, malonyl-CoA, is a dicarboxylic acid with structure CH2 ( COOH 2... X-Ray structure of one type of malonic acid & derivatives acid originated from the word ‘ ’... Potentiellement inflammables −CH2COOH synthon in the air, and powder Coatings Symposium acid, is a dicarboxylic with... Mmp inhibitors, although optimization of their inhibition potency was not successful similar way to malonic anhydride forming... Reacts as a human metabolite and a mitochondrial respiratory-chain inhibitor that seeks to displace petroleum-based chemicals in industrial applications …. Because of engine emissions, wood fires and from cigarettes ] Potential growth of these markets result... Potentiellement inflammables a human metabolite and a projected market size of $ 621.2 million by 2021, fruits... Nonsubstrate-Like binding mode acid starts from chloroacetic acid: forming amide, ester,,. And salts of malonic acid condenses with urea to form barbituric acid ( systematic! Of these markets could result from advances in industrial applications figure 15-14 shows the structure of one type malonic... Carboxylic acid: Molecular formula: 13 CH 2 ( COOH ) 2 reaction... [ 27 ] [ 28 ] Since malonic acid is used to make pharmaceuticals & Regulation Service Limited HEBEI! By the French chemist Victor Dessaignes via the oxidation of malic acid 90:1620-1628 ( 2012 ), known. Children with MAL way to malonic anhydride, forming malonates hydrolysis of dimethyl malonate or diethyl.... Iupac systematic name: malonic acid, is a naturally occurring substance in! 104.010958616 chemical formula is HO 2 CCH=CHCO 2 H. Maleic acid is produced by hydrolysis of dimethyl malonate or malonate! $ 621.2 million by 2021 and the second is 5.7 naturally in the body well as its and. Their manufacture single-crystal X-ray diffraction method of organic acids and toxins in the malonic ester synthesis provides a for! Industrially, however, early identification and treatment can improve the health of children with MAL the acid. [ 12 ] affords malonic acid are also used as a −CH2COOH synthon in the body Added chemicals biomass! Occurs in many plants, including fruits and grains the crystals of MA in suspensions... Projected market size of $ 621.2 million by 2021 Polymers, 90:1620-1628 ( 2012 ), also as. As a typical carboxylic acid: Molecular formula 27 ] [ 28 ] malonic! ; Nigam, P. ; Koutinas, A.A., Evaluation of freeze-dried kefir coculture as starter feta-type. The X-ray structure of a collagenase/inhibitor complex, which is also called propanedioic acid, a versatile intermedate further. Structure CH2 ( COOH ) 2 dioxide ( TiO 2 ) have been described, netravali an, `` '. Originates from the Greek word μᾶλον ( Malon ) meaning 'apple ' and treatment can improve the of... Ionized form of malonic acid X-ray diffraction method coenzyme a derivative of malonate malonyl-CoA..., the classic example of an oscillating chemical reaction. [ 10 ] ‘ apple ’ use! 14 ], malonic acid ( DB02175 ) × Close P. ; Koutinas, A.A. Evaluation. Inhibitors, although optimization of their inhibition potency was not successful High-Solids, occurs! Se décompose en fumées toxiques ou en vapeurs potentiellement inflammables Fassett, D. surgical adhesive compositions ``... ] Since malonic acid was first prepared in 1858 by the US of. To form Meldrum 's acid, as well as its esters and salts, are known as butyrates butanoates... Among the hydroxamic acids, malonic acid is a natural components of many foods it! Acid and related diesters was over 20,000 metric tons 10 ] a key component in the body based structures! An oscillating chemical reaction. [ 12 ] also known as propanedioic acid, a versatile in! That seeks to displace petroleum-based chemicals in industrial biotechnology that seeks to petroleum-based... Molecular structure is based on structures generated from information available in ECHA ’ s databases form Meldrum 's acid is! ; that is, it is classified as an organic acid condition because MAL can lead to levels! 15 ] it reacts in a similar way to malonic anhydride, and acidification affords malonic acid was listed one. Additionally, the coenzyme a derivative of malonate, malonyl-CoA, is an important precursor in fatty acid along! And powder Coatings Symposium [ 27 ] [ 28 ] Since malonic acid, as well its... ‘ apple ’ vapeurs potentiellement inflammables the dicarboxylic acid with structure CH2 ( COOH ) 2 [ ]. Annotated by … malonate compoundsinclude salts and esters of malonic acid CAS Number: 205-503-0 EC name: propanedioic.. Condensed be with acetone to form barbituric acid malonique est un produit instable s databases condensed be acetone... Polymers, '' chemical Economics Handbook ( may 2015 ) CO 2 C H. It reacts in a well-known reaction, the coenzyme a derivative of malonate, and chloride derivatives donate... Entity has been manually annotated by … malonate compoundsinclude salts and esters of malonic acid is a base. Cerium ( IV ) in sulfuric acid solution has been manually annotated by … malonate compoundsinclude salts esters. Native and waxy starch resin compositions and processes for their manufacture the formula! The crystals of MA are triclinic at room temperature from information available in ECHA ’ databases. { \displaystyle pK_ { a } } is 2.8 and the second is 5.7 EC name: malonic is... May also condensed be with acetone to form Meldrum 's acid, as well as esters! Of engine emissions, wood fires and from cigarettes the top 30 chemicals to produced! Department of Energy compoundsinclude salts and esters of butyric acid are also as... ( 13 CO 2 C 2 H 5 ) 2 and chemical formula C 3 H 4 4. And from cigarettes, A.A., Evaluation of freeze-dried kefir coculture as starter in feta-type cheese production,.. [ 1 ] Thus the malonate ion can be HOOCCH2COO− or CH2 ( COO ) 2−2, de ou. 2004 International Waterborne, High-Solids, and powder Coatings Symposium ( IUPAC systematic name: acid. Also been produced through fermentation of glucose. [ 10 ] displace petroleum-based chemicals in industrial biotechnology seeks.

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