1,3-Butanediol Explained

1,3-Butanediol is an organic compound with the formula CH3CH(OH)CH2CH2OH. With two alcohol functional groups, the molecule is classified as a diol. The compound is also chiral, but most studies do not distinguish the enantiomers. The compound is a colorless, bittersweet, water-soluble liquid. It is one of four common structural isomers of butanediol.[1] [2] It is used in flavoring,[3] and as a precursor to some antibiotics.[4]

Production and uses

Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol:

CH3CH(OH)CH2CHO + H2 → CH3CH(OH)CH2CH2OHDehydration of 1,3-butanediol gives 1,3-butadiene:

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

Pharmacology

1,3-Butanediol has sedative, hypotensive and hypoglycaemic action comparable to ethanol, with the (R) enantiomer being more active.[5] [6] Fatty acid esters of 1,3-butanediol such as the acetoacetate or hexanoate have been researched for inducing ketogenesis.[7] [8] [9] [10] [11] [12]

Occurrence

1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper (Capsicum annuum), red bell peppers, and yellow bell peppers.[13] 1,3 Butanediol, | quote = Also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule.[14]

Notes and References

  1. Web site: 1,3 Butylene Glycol. Parchem Fine & Specialty Chemicals .
  2. Dymsza HA . Nutritional application and implication of 1,3-butanediol . Federation Proceedings . 34 . 12 . 2167–2170 . November 1975 . 1102338 .
  3. Dymsza HA. Nutritional application and implication of 1,3-butanediol. Fed Proc. 1975 Nov;34(12):2167-70
  4. Guo X, Gao Y, Liu F, Tao Y, Jin H, Wang J, Wu S . A short-chain carbonyl reductase mutant is an efficient catalyst in the production of (R)-1,3-butanediol . Microbial Biotechnology . 16 . 6 . 1333–1343 . June 2023 . 36946330 . 10.1111/1751-7915.14249 . 10221522 .
  5. Frye GD, Chapin RE, Vogel RA, Mailman RB, Kilts CD, Mueller RA, Breese GR . Effects of acute and chronic 1,3-butanediol treatment on central nervous system function: a comparison with ethanol . The Journal of Pharmacology and Experimental Therapeutics . 216 . 2 . 306–314 . February 1981 . 7193248 .
  6. Lowder J, Fallah S, Venditti C, Musa-Veloso K, Kotlov V . An open-label, acute clinical trial in adults to assess ketone levels, gastrointestinal tolerability, and sleepiness following consumption of (R)-1,3-butanediol (Avela™) . Frontiers in Physiology . 2023 . 14 . 1195702 . 37457035 . 10.3389/fphys.2023.1195702 . free . 10338333 .
  7. Hashim SA, VanItallie TB . Ketone body therapy: from the ketogenic diet to the oral administration of ketone ester . Journal of Lipid Research . 55 . 9 . 1818–1826 . September 2014 . 24598140 . 10.1194/jlr.R046599 . free . 4617348 .
  8. Place DE, Kanneganti TD . Fueling Ketone Metabolism Quenches Salt-Induced Hypertension . Trends in Endocrinology and Metabolism . 30 . 3 . 145–147 . March 2019 . 30670332 . 10.1016/j.tem.2019.01.004 .
  9. Evans M, McClure TS, Koutnik AP, Egan B . Exogenous Ketone Supplements in Athletic Contexts: Past, Present, and Future . Sports Medicine . 52 . Suppl 1 . 25–67 . December 2022 . 36214993 . 10.1007/s40279-022-01756-2 . 9734240 .
  10. Mah E, Blonquist TM, Kaden VN, Beckman D, Boileau AC, Anthony JC, Stubbs BJ . A randomized, open-label, parallel pilot study investigating metabolic product kinetics of the novel ketone ester, bis-hexanoyl (R)-1,3-butanediol, over one week of ingestion in healthy adults . Frontiers in Physiology . 2023 . 14 . 1196535 . 37427402 . 10.3389/fphys.2023.1196535 . free . 10324611 .
  11. 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;
  12. Deemer SE, Roberts BM, Smith DL, Plaisance EP, Philp A . Exogenous ketone esters as a potential therapeutic for treatment of sarcopenic obesity . American Journal of Physiology. Cell Physiology . 327 . 1 . C140–C150 . July 2024 . 38766768 . 10.1152/ajpcell.00471.2023 .
  13. Web site: Human Metabolome Database . Metabocard for 1,3-Butanediol . HMDB0031320 . 2022-05-12 .
  14. Web site: FDA GRAS for 1,3 Butanediol for flavoring CFR - Code of Federal Regulations Title 21 . 2022-05-12 . www.accessdata.fda.gov.

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