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{{chembox
| 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]]sGlyoxylate 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&nbsp;&times;&nbsp;10<sup>&minus;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>&minus;</sup>  +  H<sup>+</sup>
With base, glyoxylic acid [[disproportionation|disproportionates]]:
:2 OCHCOOH  +  H<sub>2</sub>O  →  HOCHCOOH  +  HOOC&ndash;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&nbsp;mg/kg.
 
==References==
<references/>
 
[[Category:Carboxylic acids]]
[[Category:Aldehydes]]

Revision as of 04:53, 13 December 2013

Template:Chembox

Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially.

Structure and nomenclature

Glyoxylic acid is usually described with the chemical formula OCHCO2H, 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)2CHCO2H, described as the "monohydrate." This diol exists in equilibrium with the dimeric hemiacetal in solution:[1] Henry's law constant of glyoxylic acid is KH = 1.09 × 104 × exp[(40.0 × 103/R) × (1/T − 1/298)].[2]

2 (HO)2CHCO2H O[(HO)CHCO2H]2 + H2O

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.[1]

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 organisms, such as bacteria,[3] fungi, and plants [4] to convert fatty acids into carbohydrates. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.

Historically glyoxylic acid was prepared from oxalic acid electrosynthetically.[5][6]

Reactions and uses

Glyoxylic acid is about 10x stronger acid than acetic acid, with an acid dissociation constant of 4.7 × 10−4 (pKa = 3.32):

(HO)2CHCOOH (HO)2CHCO2 + H+

With base, glyoxylic acid disproportionates:

2 OCHCOOH + H2O → 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 with urea and 1,2-diaminobenzene.

Phenol derivatives

Its condensation with phenols is versatile. The immediate product is 4-hydroxymandelic 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.[1][7][8]

Safety

The compound is not very toxic with an Template:LD50 for rats of 2500 mg/kg.

References

  1. 1.0 1.1 1.2 Georges Mattioda and Yani Christidis “Glyoxylic Acid” Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. Electronic Instrument Positions Staff (Standard ) Cameron from Clarence Creek, usually spends time with hobbies and interests which include knotting, property developers in singapore apartment For sale and boomerangs. Has enrolled in a world contiki journey. Is extremely thrilled specifically about visiting .
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    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

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    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

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    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

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    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

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    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

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    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

    Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.

    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

    There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
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  7. One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting

    In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang

    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

    Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.

    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

    There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
  8. 20 year-old Real Estate Agent Rusty from Saint-Paul, has hobbies and interests which includes monopoly, property developers in singapore and poker. Will soon undertake a contiki trip that may include going to the Lower Valley of the Omo.

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