1,3-Butanediol

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1,3-Butanediol
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Template:Longitem Template:Unbulleted list
Template:Longitem 1731276

1718944 (R)
1718943 (S)

ChEBI Template:Unbulleted list
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EC Number Template:Unbulleted list
Template:Longitem 2409

2493173 (R)
1994384 (S)

KEGG Template:Unbulleted list
MeSH 1,3-Butylene+glycol
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Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance Colourless liquid
Density 1.0053 g cm−3
Melting point Template:Chembox CalcTemperatures
Boiling point Template:Chembox CalcTemperatures
log P −0.74
Vapor pressure 8 Pa (at 20 °C)
Template:Longitem 1.44
Template:Longitem 227.2 J K−1 mol−1
Template:Longitem −501 kJ mol−1
Template:Longitem −2.5022 MJ mol−1
Template:Longitem 1,2-Butanediol

1,4-Butanediol
2,3-Butanediol

Template:Longitem 2-Methylpentane

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1,3-Butanediol is an organic compound 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. 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 isomers of butanediol.[1][2][3] It is used in grape flavoring,[4] and as a precursor to some antibiotics.[5]

Production and uses

Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol:[6]

CH3CH(OH)CH2CHO + H2 → CH3CH(OH)CH2CH2OH

Dehydration of 1,3-butanediol gives 1,3-butadiene:

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Pharmacology

1,3-Butanediol has sedative, hypotensive and hypoglycaemic action comparable to ethanol, with the (R), also known as (D), enantiomer being more active.[7][8] Fatty acid esters of 1,3-butanediol such as the acetoacetate, lactate or hexanoate have been researched for inducing ketogenesis.[9][10][11][12][13][14][15] 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.[16]

Occurrence

1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper (Capsicum annuum), red bell peppers, and yellow bell peppers.[17] 1,3 Butanediol, | quote = Also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule.[18]

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.[16]

References

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  1. ↑ Template:Ullmann
  2. ↑ Script error: No such module "citation/CS1".
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  4. ↑ Dymsza HA. Nutritional application and implication of 1,3-butanediol. Fed Proc. 1975 Nov;34(12):2167-70 Template:Catalog lookup link
  5. ↑ Script error: No such module "Citation/CS1".
  6. ↑ Template:Ullmann
  7. ↑ Script error: No such module "Citation/CS1".
  8. ↑ Script error: No such module "Citation/CS1".
  9. ↑ Script error: No such module "Citation/CS1".
  10. ↑ Script error: No such module "Citation/CS1".
  11. ↑ Script error: No such module "Citation/CS1".
  12. ↑ Script error: No such module "Citation/CS1".
  13. ↑ Stubbs BJ, et al. A randomized, open-label, cross-over pilot study investigating metabolic product kinetics of the palatable novel ketone ester, bis-octanoyl (R)-1,3-butanediol, and bis-hexanoyl (R)-1,3-butanediol ingestion in healthy adults. Toxicology Research and Application 2023; Script error: No such module "CS1 identifiers".
  14. ↑ Script error: No such module "Citation/CS1".
  15. ↑ Ottosen RN, et al. Preparation and Preclinical Characterization of a Simple Ester for Dual Exogenous Supply of Lactate and Beta-hydroxybutyrate. Journal of Agricultural and Food Chemistry 2024; 72(36):19883–19890. Script error: No such module "CS1 identifiers".
  16. ↑ a b Script error: No such module "Citation/CS1".
  17. ↑ Script error: No such module "citation/CS1".
  18. ↑ Script error: No such module "citation/CS1".

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