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词条 2-Hydroxybutyric acid
释义

  1. References

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| ImageFile=(RS)-2-Hydroxybutanic Acid Structural Formula V1.svg
| ImageSize=150px
| ImageFile1 = 2-Hydroxybutyric-acid-3D-balls.png
| ImageSize1 = 160
| ImageAlt1 = 2-Hydroxybutyric acid molecule
| IUPACName=2-Hydroxybutanoic acid
| OtherNames=alpha-hydroxybutyrate
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10792
| InChI = 1/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
| InChIKey = AFENDNXGAFYKQO-UHFFFAOYAH
| SMILES1 = O=C(O)C(O)CC
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 567588
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AFENDNXGAFYKQO-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo=565-70-8
| PubChem=11266
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 1148
| SMILES=CCC(O)C(=O)O
| MeSHName=2-hydroxybutyric+acid
|Section2={{Chembox Properties
| C=4 | H=8 | O=3
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| Solubility=
|Section3={{Chembox Hazards
| MainHazards=
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|Section4={{Chembox Related
| OtherAnions = hydroxybutyrate
| OtherFunction_label = carboxylic acids
| OtherFunction = propionic acid
lactic acid
3-hydroxypropionic acid
malonic acid
butyric acid
hydroxypentanoic acid
| OtherCompounds = erythrose
threose
1,2-butanediol
1,3-butanediol
2,3-butanediol
1,4-butanediol
}}

2-Hydroxybutyric acid, also known as alpha-hydroxybutyrate and α-hydroxybutyrate, is a hydroxybutyric acid with the hydroxyl group on the carbon adjacent to the carboxyl. It is a chiral compound having two enantiomers, D-2-hydroxybutyric acid and L-2-hydroxybutyric acid.

2-Hydroxybutyrate, the conjugate base of 2-hydroxybutyric acid, is produced in mammalian tissues (principally hepatic) that catabolize L-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 L-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.

α-hydroxybutyrate may be useful as an early indicator of insulin resistance in non-diabetic subjects.[1] Moreover, elevated serum α-hydroxybutyrate predicts worsening glucose tolerance.[2]

References

1. ^{{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}}
2. ^{{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 | 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}}
{{DEFAULTSORT:Hydroxybutyric acid, 2-}}

1 : Alpha hydroxy acids

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