FComEx: 2-Hydroxybutyric acid (PC000512)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:06 UTC

Update date

2017-01-19 02:36:26 UTC

FoodComEx ID

PC000512

FoodDB Record

FDB021867

Chemical Information

Name

2-Hydroxybutyric acid

Description

2-Hydroxybutyric acid is an organic acid that is involved in propanoate metabolism. It is produced in mammalian tissues (principaly 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 by-product when cystathionine is cleaved to cysteine that is incorporated into glutathione. 2-Hydroxybutyric acid is often found in the urine of patients suffering from lactic acidosis and ketoacidosis. 2-Hydroxybutyric acid generally appears at high concentrations in situations related to deficient energy metabolism (e.g., birth asphyxia) and also in inherited metabolic diseases affecting the central nervous system during neonatal development, such as "cerebral" lactic acidosis, glutaric aciduria type II, dihydrolipoyl dehydrogenase (E3) deficiency, and propionic acidemia. More recently it has been noted that elevated levels of alpha-hydroxybutyrate in the plasma is a good marker for early stage type II diabetes (PMID: 19166731). It was concluded from studies done in the mid 1970's that an increased NADH2/NAD ratio was the most important factor for the production of 2-hydorxybutyric acid (PMID: 168632) [HMDB]

CAS Number

600-15-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(RS)-2-Hydroxybutyrate	hmdb
(RS)-2-Hydroxybutyric acid	hmdb
2-hydroxy-Butanoate	hmdb
2-hydroxy-Butanoic acid	hmdb
2-hydroxy-DL-Butyrate	hmdb
2-hydroxy-DL-Butyric acid	hmdb
2-Hydroxy-n-butyrate	hmdb
2-Hydroxy-n-butyric acid	hmdb
2-Hydroxybutanoate	hmdb
2-Hydroxybutanoic acid	hmdb
2-Hydroxybutyrate	hmdb
a-Hydroxy-n-butyrate	hmdb
a-Hydroxy-n-butyric acid	hmdb
a-Hydroxybutanoate	hmdb
a-Hydroxybutanoic acid	hmdb
a-Hydroxybutyrate	hmdb
a-Hydroxybutyric acid	hmdb
alpha-hydroxy-n-butyrate	hmdb
alpha-hydroxy-n-butyric acid	hmdb
alpha-Hydroxybutanoate	hmdb
alpha-Hydroxybutanoic acid	hmdb
alpha-Hydroxybutyrate	hmdb
alpha-Hydroxybutyric acid	hmdb
DL-2-Hydroxybutanoate	hmdb
DL-2-Hydroxybutanoic acid	hmdb
DL-a-Hydroxybutyrate	hmdb
DL-a-Hydroxybutyric acid	hmdb
DL-alpha-Hydroxybutyrate	hmdb
DL-alpha-Hydroxybutyric acid	hmdb
α-hydroxybutanoate	Generator
α-hydroxybutanoic acid	Generator
α-hydroxybutyrate	Generator
α-hydroxybutyric acid	Generator

Chemical Formula

C4H8O3

IUPAC name

2-hydroxybutanoic acid

InChI Identifier

InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)

InChI Key

AFENDNXGAFYKQO-UHFFFAOYSA-N

Isomeric SMILES

CCC(O)C(O)=O

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents