|
|
| Line 1: |
Line 1: |
| {{chembox
| | The author's title is Christy. To perform domino is some thing I truly appreciate performing. North Carolina is the location he enjoys most but now [http://cpacs.org/index.php?document_srl=90091&mid=board_zTGg26 tarot readings] he is contemplating other choices. Distributing manufacturing is exactly where my primary income arrives from and it's something I really appreciate.<br><br>Feel free [http://www.zavodpm.ru/blogs/glennmusserrvji/14565-great-hobby-advice-assist-allow-you-get-going free psychic readings] to surf to my web blog: clairvoyant psychic ([http://myfusionprofits.com/groups/find-out-about-self-improvement-tips-here/ http://myfusionprofits.com]) |
| | verifiedrevid = 443847685
| |
| | Name = Glyoxylic acid
| |
| | ImageFile_Ref = {{chemboximage|correct|??}}
| |
| | ImageFile = Glyoxylic acid.png
| |
| | ImageSize = 150px
| |
| | ImageName = Structure of glyoxylic acid
| |
| | ImageFile1 = Glyoxylic-acid-3D-balls.png
| |
| | ImageSize1 = 160px
| |
| | ImageName1 = Ball-and-stick model of glyoxylic acid
| |
| | IUPACName = oxoethanoic acid
| |
| | OtherNames = formylformic acid; oxoethanoic acid
| |
| | Section1 = {{Chembox Identifiers
| |
| | PubChem = 760
| |
| | KEGG_Ref = {{keggcite|correct|kegg}}
| |
| | KEGG = C00048
| |
| | InChI = 1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
| |
| | InChIKey = HHLFWLYXYJOTON-UHFFFAOYAU
| |
| | ChEMBL_Ref = {{ebicite|correct|EBI}}
| |
| | ChEMBL = 1162545
| |
| | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| |
| | StdInChI = 1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
| |
| | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| |
| | StdInChIKey = HHLFWLYXYJOTON-UHFFFAOYSA-N
| |
| | CASNo_Ref = {{cascite|correct|CAS}}
| |
| | CASNo = 298-12-4
| |
| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| |
| | ChemSpiderID = 740
| |
| | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| |
| | DrugBank = DB04343
| |
| | ChEBI_Ref = {{ebicite|correct|EBI}}
| |
| | ChEBI = 16891
| |
| | SMILES = C(=O)C(=O)O
| |
| }}
| |
| | Section2 = {{Chembox Properties
| |
| | C=2|H=2|O=3
| |
| | MeltingPt = 80 °C<ref name=Merck>''[[Merck Index]], 11th Edition, '''4394'''</ref>
| |
| | BoilingPt = 111 °C
| |
| | Density = 1.384 g/mL
| |
| | pKa = 3.18,<ref>Dissociation Constants Of Organic Acids and Bases (600 compounds), http://zirchrom.com/organic.htm.</ref> 3.32 <ref>pKa Data Compiled by R. Williams, http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf.</ref>
| |
| }}
| |
| | Section4 = {{Chembox Related
| |
| | OtherAnions = [[glyoxylate]]
| |
| | Function = [[carboxylic acid]]s
| |
| | OtherFunctn = [[formic acid]]<br />[[acetic acid]]<br />[[glycolic acid]]<br />[[oxalic acid]]<br />[[propionic acid]]<br />[[pyruvic acid]]
| |
| | OtherCpds = [[acetaldehyde]]<br />[[glyoxal]]<br />[[glycolaldehyde]]
| |
| }}
| |
| }}
| |
| | |
| '''Glyoxylic acid''' or '''oxoacetic acid''' is an [[organic compound]]. Together with [[acetic acid]], [[glycolic acid]], and [[oxalic acid]], glyoxylic acid is one of the C<sub>2</sub> [[carboxylic acid]]s. It is a colourless solid that occurs naturally and is useful industrially.
| |
| | |
| ==Structure and nomenclature==
| |
| Glyoxylic acid is usually described with the [[chemical formula]] OCHCO<sub>2</sub>H, i.e. containing an [[aldehyde]] [[functional group]] (see image in upper right). In fact the aldehyde is not observed in solution or as a solid. In general aldehydes with electron-withdrawing substituents often exist mainly as their hydrate. Thus, the formula for glyoxylic acid is really (HO)<sub>2</sub>CHCO<sub>2</sub>H, described as the "monohydrate." This [[diol]] exists in equilibrium with the dimeric hemiacetal in solution:<ref name=Ull>Georges Mattioda and Yani Christidis “Glyoxylic Acid” Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a12_495}}</ref> Henry's law constant of glyoxylic acid is K<sub>H</sub> = 1.09 × 10<sup>4</sup> × exp[(40.0 × 10<sup>3</sup>/R) × (1/T − 1/298)].<ref>{{cite journal|last=Ip|first=H. S. Simon|coauthors=Huang, X. H. Hilda, Yu, Jian Zhen|title=Effective Henry's law constants of glyoxal, glyoxylic acid, and glycolic acid|journal=Geophysical Research Letters|volume=36|issue=1|doi=10.1029/2008GL036212}}</ref>
| |
| :2 (HO)<sub>2</sub>CHCO<sub>2</sub>H <math>\overrightarrow{\leftarrow}</math> O[(HO)CHCO<sub>2</sub>H]<sub>2</sub> + H<sub>2</sub>O
| |
| | |
| ==Preparation==
| |
| The compound is formed by [[organic oxidation]] of [[glyoxal]] with hot [[nitric acid]], the main side product being oxalic acid. [[Ozonolysis]] of [[maleic acid]] is also effective.<ref name=Ull/>
| |
| | |
| The [[conjugate base]] of gloxylic acid is known as glyoxylate and is the form that the compound exists in solution at neutral pH. Glyoxylate is an intermediate of the [[glyoxylate cycle]], which enables [[organism]]s, such as bacteria,<ref name="Holms">{{cite journal|author=Holms WH|year=1987|title=Control of flux through the citric acid cycle and the glyoxylate bypass in Escherichia coli|journal=Biochem Soc Symp.|volume=54|pages=17–31|pmid=3332993}}</ref> fungi, and plants <ref name="Escher and Widmer F">{{cite journal|author=Escher CL, Widmer F|year=1997|title=Lipid mobilization and gluconeogenesis in plants: do glyoxylate cycle enzyme activities constitute a real cycle? A hypothesis|journal=Biol Chem.|volume=378|pages=803–813|pmid=9377475|issue=8}}</ref> to convert [[fatty acid]]s into [[carbohydrate]]s. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.
| |
| | |
| Historically glyoxylic acid was prepared from oxalic acid [[Electrosynthesis|electrosynthetically]].<ref>{{cite journal|last=Tafel, Julius; and Friedrichs, Gustav|title=Elektrolytische Reduction von Carbonsäuren und Carbonsäureestern in schwefelsaurer Lösung|journal=Berichte der deutschen chemischen Gesellschaft|year=1904|volume=37|issue=3|pages=3187-3191|doi=10.1002/cber.190403703116|url=http://onlinelibrary.wiley.com/doi/10.1002/cber.190403703116/abstract|accessdate=19 December 2013}}</ref><ref>{{cite book|last=Cohen|first=Julius|title=Practical Organic Chemistry 2nd Ed.|year=1920|publisher=Macmillan and Co. Limited|location=London|pages=102-104|url=http://www.sciencemadness.org/library/books/practical_organic_chemistry.pdf}}</ref>
| |
| | |
| ==Reactions and uses==
| |
| Glyoxylic acid is about 10x stronger acid than acetic acid, with an [[acid dissociation constant]] of 4.7 × 10<sup>−4</sup> (pK<sub>a</sub> = 3.32):
| |
| :(HO)<sub>2</sub>CHCOOH <math>\overrightarrow{\leftarrow}</math> (HO)<sub>2</sub>CHCO<sub>2</sub><sup>−</sup> + H<sup>+</sup>
| |
| With base, glyoxylic acid [[disproportionation|disproportionates]]:
| |
| :2 OCHCOOH + H<sub>2</sub>O → HOCHCOOH + HOOC–COOH
| |
| | |
| Even though the aldehyde is a very minor component of its solutions, glyoxylic acid behaves as an aldehyde in its reactions. For example, it gives heterocycles upon [[condensation reaction|condensation]] with [[urea]] and [[1,2-diaminobenzene]].
| |
| | |
| ===Phenol derivatives===
| |
| Its condensation with phenols is versatile. The immediate product is 4-hydroxy[[mandelic acid]]. This species reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug [[Amoxicillin]]. Reduction of the 4-hydroxymandelic acid gives [[4-hydroxyphenylacetic acid]], a precursor to the drug [[Atenolol]]. Condensations with [[guaiacol]] in place of phenol provides a route to [[vanillin]], a net [[formylation]].<ref name=Ull/><ref>{{cite journal|last=Fatiadi, Alexander; and Schaffer, Robert|title=An Improved Procedure for Synthesis of
| |
| DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)|journal=Journal of Research of the National Bureau of Standards - A. Physics and Chemistry|year=1974|volume=78A|issue=3|pages=411-412|doi=10.6028/jres.078A.024|url=http://nvlpubs.nist.gov/nistpubs/jres/78A/jresv78An3p411_A1b.pdf|accessdate=19 December 2013}}</ref><ref>{{cite book|last=Kamlet, Jonas; and Mathieson, Olin|title=Manufacture of vanillin and its homologues U.S. Patent 2,640,083|year=1953|publisher=U.S. Patent Office|url=https://docs.google.com/viewer?url=patentimages.storage.googleapis.com/pdfs/US2640083.pdf}}</ref>
| |
| | |
| ==Safety==
| |
| The compound is not very toxic with an {{LD50}} for rats of 2500 mg/kg.
| |
| | |
| ==References==
| |
| <references/>
| |
| | |
| [[Category:Carboxylic acids]]
| |
| [[Category:Aldehydes]]
| |
The author's title is Christy. To perform domino is some thing I truly appreciate performing. North Carolina is the location he enjoys most but now tarot readings he is contemplating other choices. Distributing manufacturing is exactly where my primary income arrives from and it's something I really appreciate.
Feel free free psychic readings to surf to my web blog: clairvoyant psychic (http://myfusionprofits.com)