| Revision as of 12:32, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 473709703 of page Glutaric_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 16:54, 6 August 2024 edit AriBoaz (talk | contribs)36 editsm Added new name |
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{{distinguish|Glutamic acid}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443837853 |
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| verifiedrevid = 476994743 |
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| Name = Glutaric acid |
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| ImageFile = kwas_glutarowy.svg |
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| Name = Glutaric acid |
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| ImageFile = kwas_glutarowy.svg |
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<!-- | ImageSize = 200px --> |
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| ImageSize = 220 |
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| ImageName = Glutaric acid |
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| ImageAlt = Skeletal formula of glutaric acid |
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| ImageFile1 = Glutaric-acid-3D-balls.png |
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| ImageFile1 = Glutaric acid molecule ball from xtal.png |
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| ImageSize1 = 220px |
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| ImageSize1 = 220 |
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| ImageAlt1 = Ball-and-stick model of the glutaric acid molecule |
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| IUPACName = pentanedioic acid |
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| PIN = Pentanedioic acid <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
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| OtherNames = Propane-1,3-dicarboxylic acid; 1,3-propanedicarboxylic acid; pentanedioic acid; n-Pyrotartaric acid |
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| OtherNames = Glutaric acid<br />Propane-1,3-dicarboxylic acid<br />1,3-Propanedicarboxylic acid<br />Pentanedioic acid<br />n-Pyrotartaric acid<br />1,5-Pentanedioic acid |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| PubChem = 743 |
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| PubChem = 743 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C00489 |
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| KEGG = C00489 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 110-94-1 |
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| CASNo = 110-94-1 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = H849F7N00B |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 723 |
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| ChemSpiderID = 723 |
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| EINECS = 203-817-2 |
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| EINECS = 203-817-2 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB03553 |
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| DrugBank = DB03553 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = C(CC(=O)O)CC(=O)O |
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| SMILES = C(CC(=O)O)CC(=O)O |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>5</sub>H<sub>8</sub>O<sub>4</sub> |
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| Formula = C<sub>5</sub>H<sub>8</sub>O<sub>4</sub> |
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| MolarMass = 132.12 g/mol |
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| MolarMass = 132.12 g/mol |
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| MeltingPt = 95 to 98 °C |
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| MeltingPtC = 95 to 98 |
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| BoilingPt = 200 °C/20 mmHg |
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| BoilingPtC = 200 |
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| BoilingPt_notes = /20 mmHg |
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}} |
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'''Glutaric acid''' is the ] with the ] C<sub>3</sub>H<sub>6</sub>(COOH)<sub>2</sub>. Although the related "linear" ]s ] and ]s are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50% (w/w). {{Citation needed|date=October 2023}} |
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==Biochemistry== |
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Glutaric acid is naturally produced in the body during the ] of some ], including ] and ]. ] in this metabolic pathway can lead to a disorder called ], where toxic byproducts build up and can cause severe ]. |
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==Production== |
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Glutaric acid can be prepared by the ring-opening of ] with ] to give the potassium salt of the carboxylate-] that is hydrolyzed to the diacid.<ref>{{OrgSynth | author = G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan | title = Glutaric Acid and Glutaramide | volumw = 37 | page = 47 | year = 1957 | doi = 10.15227/orgsyn.037.0047}}</ref> Alternatively hydrolysis, followed by oxidation of ] gives glutaric acid. It can also be prepared from reacting ] with ] or ] to obtain the dinitrile, followed by hydrolysis. Using ], it is obtained from oxidation of ], which proceeds with decarboxylation.<ref>{{March6th|page=1736}}</ref> |
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==Uses== |
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* ], a common ] and precursor to ]s is manufactured by ] of glutaric acid and its derivatives.<ref>Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305</ref> |
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* Glutaric acid itself has been used in the production of polymers such as polyester ], ]. The odd number of carbon atoms (i.e. 5) is useful in decreasing polymer elasticity.<ref>{{Cite web|title=Glutaric acid, Pentanedioic acid, 99%|url=http://www.chemkits.eu/carboxylic-acids/232-glutaric-acid-pentanedioic-acid-110-94-1.html|access-date=2020-09-29|website=Chemkits.eu|language=en-us}}</ref> |
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* ] can be produced from glutaric diester.<ref>{{Cite patent|title=Method of synthesis of pyrogallol|pubdate=1977-09-06|country=US|number=4046817|assign=]|inventor1-last=Shipchandler|inventor1-first=Mohammed T.}}</ref> |
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==Safety== |
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Glutaric acid may cause irritation to the skin and eyes.<ref name=cameochemicals>, cameochemicals.com</ref> Acute hazards include the fact that this compound may be harmful by ingestion, inhalation or skin absorption.<ref name=cameochemicals/> |
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==References== |
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<references/> |
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==External links== |
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* |
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{{Navbox linear saturated dicarboxylic acids}} |
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{{Authority control}} |
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] |