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β-Hydroxybutyric acid, also known as 3-hydroxybutyric acid or BHB, is an organic compound and a beta hydroxy acid with the chemical formula CH 3 CH(OH)CH 2 CO 2 H; its conjugate base is β-hydroxybutyrate, also known as 3-hydroxybutyrate. β-Hydroxybutyric acid is a chiral compound with two enantiomers: D-β-hydroxybutyric acid and L-β-hydroxybutyric acid.
Skeletal formula of 3-hydroxyisobutyric acid Hydroxybutyric acid is a group of four-carbon organic compounds that have both hydroxyl and carboxylic acid functional groups . [ 1 ] They can be viewed as derivatives of butyric acid .
Ketogenesis pathway. The three ketone bodies (acetoacetate, acetone, and beta-hydroxy-butyrate) are marked within orange boxes. Ketogenesis is the biochemical process through which organisms produce ketone bodies by breaking down fatty acids and ketogenic amino acids.
Ketone bodies are transported from the liver to other tissues, where acetoacetate and β-hydroxybutyrate can be reconverted to acetyl-CoA to produce reducing equivalents (NADH and FADH 2), via the citric acid cycle. Though it is the source of ketone bodies, the liver cannot use them for energy because it lacks the enzyme thiophorase (β ...
[4] [3] Although, β-hydroxybutyrate is technically not a ketone due to the structure of the molecule (OH- attached to carbonyl group makes this an acid),BHB acts like a ketone, providing the body with energy in the absence of glucose. [1] In fact, β-Hydroxybutyrate is the most abundant ketone-like molecule in the blood during ketosis. [5] Acetone
The enzyme 3-hydroxybutyryl-CoA dehydratase (EC 4.2.1.55) catalyzes the chemical reaction (3 R )-3-hydroxybutanoyl-CoA ⇌ {\displaystyle \rightleftharpoons } crotonoyl-CoA + H 2 O This enzyme belongs to the family of lyases , specifically the hydro-lyases, which cleave carbon-oxygen bonds.
In enzymology, 3-hydroxybutyrate dehydrogenase (EC 1.1.1.30) is an enzyme that catalyzes the chemical reaction: ()-3-hydroxybutanoate + NAD + acetoacetate + NADH + HThus, the two substrates of this enzyme are ()-3-hydroxybutanoate and NAD +, whereas its three products are acetoacetate, NADH, and H +.
β-Hydroxybutyryl-CoA (or 3-hydroxybutyryl-coenzyme A) is an intermediate in the fermentation of butyric acid, and in the metabolism of lysine and tryptophan. [1] [2] The L-3-hydroxybutyl-CoA (or (S)-3-hydroxybutanoyl-CoA) enantiomer is also the second to last intermediate in beta oxidation of even-numbered, straight chain, and saturated fatty acids.