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1,3-Butanediol

(Redirected from Butane-1, 3-diol)

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][3] It is used in flavoring,[4] and as a precursor to some antibiotics.[5]

1,3-Butanediol
Skeletal formula of 1,3-butanediol
Ball and stick model of 1,3-butanediol (S)
Ball and stick model of 1,3-butanediol (S)
Spacefill model of 1,3-butanediol (S)
Spacefill model of 1,3-butanediol (S)
Names
Preferred IUPAC name
Butane-1,3-diol
Other names
1,3-butylene glycol, butane-1,3-diol, or 1,3-dihydroxybutane
Identifiers
3D model (JSmol)
1731276

1718944 (R)
1718943 (S)

ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.209 Edit this at Wikidata
EC Number
  • 203-529-7
E number E1502 (additional chemicals)
2409

2493173 (R)
1994384 (S)

KEGG
MeSH 1,3-Butylene+glycol
RTECS number
  • EK0440000
UNII
  • InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3 ☒N
    Key: PUPZLCDOIYMWBV-UHFFFAOYSA-N ☒N
  • CC(O)CCO
Properties
C4H10O2
Molar mass 90.122 g·mol−1
Appearance Colourless liquid
Density 1.0053 g cm−3
Melting point −50 °C (−58 °F; 223 K)
Boiling point 204 to 210 °C; 399 to 410 °F; 477 to 483 K
1 kg dm−3
log P −0.74
Vapor pressure 8 Pa (at 20 °C)
1.44
Thermochemistry
227.2 J K−1 mol−1
−501 kJ mol−1
−2.5022 MJ mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H319, H413
P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 108 °C (226 °F; 381 K)
394 °C (741 °F; 667 K)
Related compounds
Related butanediol
 1,2-Butanediol

1,4-Butanediol
2,3-Butanediol

Related compounds
 2-Methylpentane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Production and uses

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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

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1,3-Butanediol has sedative, hypotensive and hypoglycaemic action comparable to ethanol, with the (R) 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]

Occurrence

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1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper (Capsicum annuum), red bell peppers, and yellow bell peppers.[16] 1,3 Butanediol, | quote = Also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule.[17]

References

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  1. ^ Gräfje H, Körnig W, Weitz HM, Reiß W, Steffan G, Diehl, et al. (2000). "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_455. ISBN 9783527306732.
  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. Nutritional application and implication of 1,3-butanediol. Fed Proc. 1975 Nov;34(12):2167-70 PMID 1102338
  5. ^ Guo X, Gao Y, Liu F, Tao Y, Jin H, Wang J, et al. (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. ^ Kohlpaintner C, Schulte M, Falbe J, Lappe P, Weber J (2008). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_321.pub2. ISBN 978-3527306732.
  7. ^ Frye GD, Chapin RE, Vogel RA, Mailman RB, Kilts CD, Mueller RA, et al. (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. 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: 1195702. 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, et al. (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: 1196535. doi:10.3389/fphys.2023.1196535. PMC 10324611. PMID 37427402.
  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; 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, 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. doi:10.1021/acs.jafc.4c04849
  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. Retrieved 2022-05-12.
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