1,3-Butanediol
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Names | |||
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Preferred IUPAC name Butane-1,3-diol | |||
Other names 1,3-butylene glycol, butane-1,3-diol, or 1,3-dihydroxybutane | |||
Identifiers | |||
CAS Number |
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3D model (JSmol) |
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Beilstein Reference | 1731276 1718944 (R) | ||
ChEBI |
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ChEMBL |
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ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.003.209 ![]() | ||
EC Number |
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E number | E1502 (additional chemicals) | ||
Gmelin Reference | 2409 2493173 (R) | ||
KEGG |
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MeSH | 1,3-Butylene+glycol | ||
PubChem CID |
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RTECS number |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |||
Chemical formula | 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) | ||
Refractive index (nD) | 1.44 | ||
Thermochemistry | |||
Std molar entropy (S⦵298) | 227.2 J K−1 mol−1 | ||
Std enthalpy of formation (ΔfH⦵298) | −501 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) | −2.5022 MJ mol−1 | ||
Hazards | |||
GHS labelling: | |||
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Warning | |||
H319, H413 | |||
P305+P351+P338 | |||
NFPA 704 (fire diamond) | ![]() 1 1 0 | ||
Flash point | 108 °C (226 °F; 381 K) | ||
Autoignition temperature | 394 °C (741 °F; 667 K) | ||
Related compounds | |||
Related butanediol | 1,2-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). ![]() ![]() ![]() Infobox references |
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]
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) enantiomer being more active.[7][8] Fatty acid esters of 1,3-butanediol such as the acetoacetate or hexanoate have been researched for inducing ketogenesis.[9][10][11][12][13][14]
Occurrence
1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper (Capsicum annuum), red bell peppers, and yellow bell peppers.[15] 1,3 Butanediol, | quote = Also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule.[16]
References
- ^ 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.
- ^ "1,3 Butylene Glycol". Parchem Fine & Specialty Chemicals.
- ^ Dymsza HA (November 1975). "Nutritional application and implication of 1,3-butanediol". Federation Proceedings. 34 (12): 2167–2170. PMID 1102338.
- ^ Dymsza HA. Nutritional application and implication of 1,3-butanediol. Fed Proc. 1975 Nov;34(12):2167-70 PMID 1102338
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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
- ^ 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.
- ^ "Metabocard for 1,3-Butanediol". Human Metabolome Database. HMDB0031320. Retrieved 2022-05-12.
- ^ "FDA GRAS for 1,3 Butanediol for flavoring CFR - Code of Federal Regulations Title 21". www.accessdata.fda.gov. Retrieved 2022-05-12.