Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2-Hydroxybutyric acid: Difference between pages
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Saving copy of the {{chembox}} taken from revid 443315128 of page 2-Hydroxybutyric_acid for the Chem/Drugbox validation project (updated: 'CASNo'). |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:2-Hydroxybutyric_acid|oldid=443315128}} 443315128] of page [[2-Hydroxybutyric_acid]] with values updated to verified values.}} |
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{{chembox |
{{chembox |
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|ImageFile=2-hydroxybutyric acid.png |
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| ImageFile=(RS)-2-Hydroxybutanic Acid Structural Formula V1.svg |
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|OtherNames=''alpha''-hydroxybutyrate |
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| ImageFile1 = 2-Hydroxybutyric-acid-3D-balls.png |
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| ImageSize1 = 160 |
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| ImageAlt1 = 2-Hydroxybutyric acid molecule |
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| OtherNames=α-Hydroxybutyric acid |
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| ChemSpiderID = 10792 |
| ChemSpiderID = 10792 |
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| KEGG = C05984 |
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| InChI = 1/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7) |
| InChI = 1/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7) |
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| InChIKey = AFENDNXGAFYKQO-UHFFFAOYAH |
| InChIKey = AFENDNXGAFYKQO-UHFFFAOYAH |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = AFENDNXGAFYKQO-UHFFFAOYSA-N |
| StdInChIKey = AFENDNXGAFYKQO-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 565-70-8 --> |
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| CASNo=565-70-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = O0ADR0I4H5 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 1148 |
| ChEBI = 1148 |
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| SMILES=CCC(O)C(=O)O |
| SMILES=CCC(O)C(=O)O |
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| MeSHName=2-hydroxybutyric+acid |
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|Section2= |
|Section2={{Chembox Properties |
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| C=4 | H=8 | O=3 |
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|Section3= |
|Section3={{Chembox Hazards |
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|Section4={{Chembox Related |
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| OtherAnions = [[hydroxybutyrate]] |
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| OtherFunction_label = [[carboxylic acid]]s |
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| OtherFunction = [[propionic acid]]<br />[[lactic acid]]<br />[[3-Hydroxypropionic acid|3-hydroxypropionic acid]]<br />[[malonic acid]]<br />[[butyric acid]]<br />[[hydroxypentanoic acid]] |
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| OtherCompounds = [[erythrose]]<br />[[threose]]<br />[[1,2-butanediol]]<br />[[1,3-butanediol]]<br />[[2,3-butanediol]]<br />[[1,4-butanediol]] |
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'''2-Hydroxybutyric acid''', is a [[hydroxybutyric acid]] with the [[hydroxyl]] group on the carbon adjacent to the [[carboxyl]]. It is a [[Chirality (chemistry)|chiral]] compound having two [[enantiomers]], <small>D</small>-2-hydroxybutyric acid and <small>L</small>-2-hydroxybutyric acid. Its [[conjugate base]] is known as '''''alpha''-hydroxybutyrate''' and '''α-hydroxybutyrate'''. |
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<gallery> |
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(R)-2-Hydroxybutanic Acid Structural Formula V1.svg|{{smallcaps|d}}-2-hydroxybutyric acid|alt=Molecular diagram of 2-hydroxybutyric acid, with the central alcohol carbon labeled "(R)" |
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(S)-2-Hydroxybutanic Acid Structural Formula V1.svg|{{smallcaps|l}}-2-hydroxybutyric acid|alt=Molecular diagram of 2-hydroxybutyric acid, with the central alcohol carbon labeled "(S)" |
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</gallery> |
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2-Hydroxybutyrate, the [[conjugate base]] of 2-hydroxybutyric acid, is produced in mammalian tissues (principally hepatic) that catabolize [[threonine|<small>L</small>-threonine]] or synthesize [[glutathione]]. [[Oxidative stress]] or detoxification demands can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of [[cysteine|<small>L</small>-cysteine]] for glutathione synthesis become limiting, so [[homocysteine]] is diverted from the [[transmethylation]] pathway forming methionine into the [[transsulfuration]] pathway forming cystathionine. 2-Hydroxybutyrate is released as a byproduct when [[cystathionine]] is cleaved to cysteine that is incorporated into glutathione. Chronic shifts in the rate of glutathione synthesis may be reflected by urinary excretion of 2-hydroxybutyrate. |
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α-hydroxybutyrate may be useful as an early indicator of [[insulin resistance]] in [[Diabetes mellitus type 2|non-diabetic]] subjects.<ref name="pmid20526369">{{cite journal |vauthors=Gall WE, Beebe K, Lawton KA, Adam KP, Mitchell MW, Nakhle PJ, Ryals JA, Milburn MV, Nannipieri M, Camastra S, Natali A, Ferrannini E, ((RISC Study Group)) | title=alpha-hydroxybutyrate is an early biomarker of insulin resistance and glucose intolerance in a nondiabetic population | journal= [[PLOS ONE]] | volume=5 | issue=5 | year=2010 | pages=10883 | doi=10.1371/journal.pone.0010883 | pmc=2878333 | pmid=20526369| bibcode=2010PLoSO...510883G | doi-access=free }}</ref> Moreover, elevated serum α-hydroxybutyrate predicts worsening [[Impaired glucose tolerance|glucose tolerance]].<ref name="pmid23160532">{{cite journal |vauthors=Ferrannini E, Natali A, Camastra S, Nannipieri M, Mari A, Adam KP, Milburn MV, Kastenmüller G, Adamski J, Tuomi T, Lyssenko V, Groop L, Gall WE | title=Early metabolic markers of the development of dysglycemia and type 2 diabetes and their physiological significance | journal= [[Diabetes (journal)|Diabetes]] | volume=62 | issue=5 | year=2013 | pages=1730–1737 | doi=10.2337/db12-0707 | url=http://diabetes.diabetesjournals.org/content/62/5/1730.long | pmc=3636608 | pmid=23160532}}</ref> |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Hydroxybutyric acid, 2-}} |
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[[Category:Alpha hydroxy acids]] |
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