1,3-Butanediol is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula CH₃CH(OH)CH₂CH₂OH, not to be confused with 1,4 Butanediol. With two alcohol functional groups, the molecule is classified as a

diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...

. The compound without the R (or D) designation is racemic, which is what has been used in most studies before 2023. The compound is a colorless, bittersweet, water-soluble liquid. It is one of four common

structural isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

s of

butanediol Butanediol, also called butylene glycol, may refer to any one of four stable structural isomers: * 1,2-Butanediol * 1,3-Butanediol * 1,4-Butanediol *2,3-Butanediol Geminal diols There are also two geminal diols (gem-diols), which are less stable: ...

. It is used in grape flavoring, and as a precursor to some

antibiotic An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting pathogenic bacteria, bacterial infections, and antibiotic medications are widely used in the therapy ...

Production and uses

Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol: :CH₃CH(OH)CH₂CHO + H₂ → CH₃CH(OH)CH₂CH₂OH Dehydration of 1,3-butanediol gives 1,3-

butadiene 1,3-Butadiene () is the organic compound with the formula CH2=CH-CH=CH2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two ...

: :CH₃CH(OH)CH₂CH₂OH → CH₂=CH-CH=CH₂ + 2H₂O

Pharmacology

1,3-Butanediol has

sedative A sedative or tranquilliser is a substance that induces sedation by reducing irritability or Psychomotor agitation, excitement. They are central nervous system (CNS) Depressant, depressants and interact with brain activity, causing its decelera ...

hypotensive Hypotension, also known as low blood pressure, is a cardiovascular condition characterized by abnormally reduced blood pressure. Blood pressure is the force of blood pushing against the walls of the arteries as the heart pumps out blood and is ...

and hypoglycaemic action comparable to ethanol, with the (R), also known as (D), enantiomer being more active. Fatty acid esters of 1,3-butanediol such as the acetoacetate, lactate or hexanoate have been researched for inducing

ketogenesis Ketogenesis is the biochemical process through which organisms produce ketone bodies by breaking down fatty acids and ketogenic amino acids. The process supplies energy to certain organs, particularly the brain, heart and skeletal muscle, unde ...

. Recent research highlights the stereospecific metabolism of (R)-1,3-butanediol, emphasizing its efficient conversion to β-hydroxybutyrate via alcohol dehydrogenase. This process involves zinc coordination and maintains cellular redox balance. Notably, (R)-1,3-butanediol induces mild euphoric effects through ketone body signaling pathways, distinct from the GABAergic mechanisms associated with ethanol.

Occurrence

1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper (''

Capsicum annuum ''Capsicum annuum'' is a fruiting plant from the family Solanaceae (nightshades), within the genus Capsicum which is native to the northern regions of South America and to southwestern North America. The plant produces Berry, berries of many color ...

''), red bell peppers, and yellow bell peppers. 1,3 Butanediol, , quote = Also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule.

Biochemistry

The metabolism of (R)-1,3-butanediol is compartmentalized within hepatic cells, occurring in both cytosolic and mitochondrial domains. Enzymatic studies have quantified the distribution of alcohol dehydrogenase isoforms involved in its conversion to β-hydroxybutyrate, underscoring the molecule's potential in therapeutic ketone body production.

References

{{DEFAULTSORT:Butanediol, 1,3- Alkanediols