FComEx: (R)-3-Hydroxybutyric acid (PC000267)

Record Information

Version

1.0

Creation date

2015-10-09 22:29:35 UTC

Update date

2017-01-19 02:36:18 UTC

FoodComEx ID

PC000267

FoodDB Record

FDB021869

Chemical Information

Name

(R)-3-Hydroxybutyric acid

Description

(R)-3-Hydroxybutyric acid is a butyric acid substituted with a hydroxyl group in the beta or 3 position. It is involved in the synthesis and degradation of ketone bodies. Like the other ketone bodies (acetoacetate and acetone), levels of beta-hydroxybutyrate are raised in the blood and urine in ketosis. Beta-hydroxybutyrate is a typical partial-degradation product of branched-chain amino acids (primarily valine) released from muscle for hepatic and renal gluconeogenesis This acid is metabolized by 3-hydroxybutyrate dehydrogenase (catalyzes the oxidation of D-3-hydroxybutyrate to form acetoacetate, using NAD+ as an electron acceptor). The enzyme functions in nervous tissues and muscles, enabling the use of circulating hydroxybutyrate as a fuel. In the liver mitochondrial matrix, the enzyme can also catalyze the reverse reaction, a step in ketogenesis. 3-Hydroxybutyric acid is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid. In humans, beta-hydroxybutyrate is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low. It can also be used for the synthesis of biodegradable plastics . [HMDB]

CAS Number

625-72-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(R)-(-)-b-Hydroxybutyrate	hmdb
(R)-(-)-b-Hydroxybutyric acid	hmdb
(R)-(-)-beta-Hydroxybutyrate	hmdb
(R)-(-)-beta-Hydroxybutyric acid	hmdb
(R)-(-)-β-hydroxybutyrate	Generator
(R)-(-)-β-hydroxybutyric acid	Generator
(R)-3-Hydroxybutanoate	hmdb
(R)-3-Hydroxybutanoic acid	hmdb
(R)-3-Hydroxybutyrate	hmdb
3-D-hydroxybutyrate	hmdb
3-D-hydroxybutyric acid	hmdb
3-delta-hydroxybutyrate	hmdb
3-delta-hydroxybutyric acid	hmdb
BHIB	hmdb
D-(-)-3-hydroxybutyrate	hmdb
D-3-hydroxybutyrate	hmdb
D-3-hydroxybutyric acid	hmdb
D-beta-hydroxybutyrate	hmdb
delta-(-)-3-hydroxybutyrate	hmdb
delta-3-hydroxybutyrate	hmdb
delta-3-hydroxybutyric acid	hmdb
delta-beta-hydroxybutyrate	hmdb

Chemical Formula

C4H8O3

IUPAC name

(3R)-3-hydroxybutanoic acid

InChI Identifier

InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1

InChI Key

WHBMMWSBFZVSSR-GSVOUGTGSA-N

Isomeric SMILES

C[C@@H](O)CC(O)=O

Average Molecular Weight

104.1045

Monoisotopic Molecular Weight

104.047344122

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents