Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Glutaric acid: Difference between pages

{{distinguish|Glutamic acid}}

| Watchedfields = changed

| verifiedrevid = 476994743

| Name = Glutaric acid

| ImageFile = kwas_glutarowy.svg

| ImageSize = 220

| ImageAlt = Skeletal formula of glutaric acid

| ImageFile1 = Glutaric acid molecule ball from xtal.png

| ImageSize1 = 220

| ImageAlt1 = Ball-and-stick model of the glutaric acid molecule

| PIN = Pentanedioic acid <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->

| OtherNames = Glutaric acid<br />Propane-1,3-dicarboxylic acid<br />1,3-Propanedicarboxylic acid<br />Pentanedioic acid<br />n-Pyrotartaric acid

|Section1={{Chembox Identifiers

| PubChem = 743

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = H849F7N00B

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 203-817-2

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

|Section2={{Chembox Properties

| Formula = C₅H₈O₄

| MolarMass = 132.12 g/mol

| MeltingPtC = 95 to 98

| BoilingPtC = 200

| BoilingPt_notes = /20 mmHg

'''Glutaric acid''' is the [[organic compound]] with the [[chemical formula|formula]] C₃H₆(COOH)₂. Although the related "linear" [[dicarboxylic acid]]s [[adipic acid|adipic]] and [[succinic acid]]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}}

==Biochemistry==

Glutaric acid is naturally produced in the body during the [[metabolism]] of some [[amino acids]], including [[lysine]] and [[tryptophan]]. [[Inborn error of metabolism|Defects]] in this metabolic pathway can lead to a disorder called [[Glutaric aciduria type 1|glutaric aciduria]], where toxic byproducts build up and can cause severe [[encephalopathy]].

==Production==

Glutaric acid can be prepared by the ring-opening of [[Gamma-Butyrolactone|butyrolactone]] with [[potassium cyanide]] to give the potassium salt of the carboxylate-[[nitrile]] 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 [[3,4-Dihydropyran|dihydropyran]] gives glutaric acid. It can also be prepared from reacting [[1,3-Dibromopropane|1,3-dibromopropane]] with [[sodium cyanide|sodium]] or [[potassium cyanide]] to obtain the dinitrile, followed by hydrolysis. Using [[periodate]], it is obtained from oxidation of [[1,3-Cyclohexanedione|1,3-cyclohexanedione]], which proceeds with decarboxylation.<ref>{{March6th|page=1736}}</ref>

==Uses==

* [[1,5-Pentanediol]], a common [[plasticizer]] and precursor to [[polyester]]s is manufactured by [[hydrogenation]] 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>

* Glutaric acid itself has been used in the production of polymers such as polyester [[polyols]], [[polyamides]]. 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>

* [[Pyrogallol]] can be produced from glutaric diester.<ref>{{Cite patent|title=Method of synthesis of pyrogallol|pubdate=1977-09-06|country=US|number=4046817|assign=[[IMC_Global|IMC Chemical Group]]|inventor1-last=Shipchandler|inventor1-first=Mohammed T.}}</ref>

==Safety==

Glutaric acid may cause irritation to the skin and eyes.<ref name=cameochemicals>[http://cameochemicals.noaa.gov/chemical/20436 Glutaric acid], cameochemicals.com</ref> Acute hazards include the fact that this compound may be harmful by ingestion, inhalation or skin absorption.<ref name=cameochemicals/>

==References==

<references/>

==External links==

* [http://www.aim.env.uea.ac.uk/aim/accent2/inputpage.php Calculator: Water and solute activities in aqueous glutaric acid]

{{Navbox linear saturated dicarboxylic acids}}

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[[Category:Dicarboxylic acids]]