1,3-Butanediol
Verifiedfieldschanged
Watchedfieldschanged
Verifiedrevid477205091
PinButane-1,3-diol
Othernames1,3-butylene glycol, butane-1,3-diol, or 1,3-dihydroxybutane

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:

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

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 studied for inducing ketogenesis.[9][10][11][12][13][14][15]

Occurrence

1,3-Butanediol has been detected in bell peppers (Capsicum annuum).[16] 1,3 Butanediol maintains FDA GRAS status as a flavor molecule.[17]

References

  1. ^
  2. ^ "1,3 Butylene Glycol". Parchem Fine & Specialty Chemicals
  3. ^ Dymsza HA (November 1975). "Nutritional application and implication of 1,3-butanediol". Federation Proceedings. 34 (12): 2167–2170. PMID 1102338
  4. ^ Dymsza HA (Nov 1975). "Nutritional application and implication of 1,3-butanediol". Fed Proc. 34 (12): 2167–70. PMID 1102338
  5. ^ Guo X, Gao Y, Liu F, Tao Y, Jin H, Wang J, Wu S (June 2023). "A short-chain carbonyl reductase mutant is an efficient catalyst in the production of (R)-1,3-butanediol". Microbial Biotechnology. 16 (6): 1333–1343. doi:10.1111/1751-7915.14249. PMC 10221522. PMID 36946330
  6. ^
  7. ^ Frye GD, Chapin RE, Vogel RA, Mailman RB, Kilts CD, Mueller RA, Breese GR (February 1981). "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. doi:10.1016/S0022-3565(25)32419-5. PMID 7193248
  8. ^ Lowder J, Fallah S, Venditti C, Musa-Veloso K, Kotlov V (2023). "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. 14. doi:10.3389/fphys.2023.1195702. PMC 10338333. PMID 37457035
  9. ^ Hashim SA, VanItallie TB (September 2014). "Ketone body therapy: from the ketogenic diet to the oral administration of ketone ester". Journal of Lipid Research. 55 (9): 1818–1826. doi:10.1194/jlr.R046599. PMC 4617348. PMID 24598140
  10. ^ Place DE, Kanneganti TD (March 2019). "Fueling Ketone Metabolism Quenches Salt-Induced Hypertension". Trends in Endocrinology and Metabolism. 30 (3): 145–147. doi:10.1016/j.tem.2019.01.004. PMID 30670332
  11. ^ Evans M, McClure TS, Koutnik AP, Egan B (December 2022). "Exogenous Ketone Supplements in Athletic Contexts: Past, Present, and Future". Sports Medicine. 52 (Suppl 1): 25–67. doi:10.1007/s40279-022-01756-2. PMC 9734240. PMID 36214993
  12. ^ Mah E, Blonquist TM, Kaden VN, Beckman D, Boileau AC, Anthony JC, Stubbs BJ (2023). "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. 14. doi:10.3389/fphys.2023.1196535. PMC 10324611. PMID 37427402
  13. ^ Stubbs BJ (2023). "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. doi:10.1177/23978473231197835
  14. ^ Deemer SE, Roberts BM, Smith DL, Plaisance EP, Philp A (July 2024). "Exogenous ketone esters as a potential therapeutic for treatment of sarcopenic obesity". American Journal of Physiology. Cell Physiology. 327 (1): C140–C150. doi:10.1152/ajpcell.00471.2023. PMID 38766768
  15. ^ Ottosen RN (2024). "Preparation and Preclinical Characterization of a Simple Ester for Dual Exogenous Supply of Lactate and Beta-hydroxybutyrate". Journal of Agricultural and Food Chemistry. 72 (36): 19883–19890. doi:10.1021/acs.jafc.4c04849. PMC 11403612
  16. ^ "Metabocard for 1,3-Butanediol". Human Metabolome Database. HMDB0031320. Retrieved 2022-05-12.
  17. ^ "FDA GRAS for 1,3 Butanediol for flavoring CFR - Code of Federal Regulations Title 21". www.accessdata.fda.gov. Archived September 15, 2003 at the Wayback Machine. Retrieved 2022-05-12.