1,3-Butanediol

1,3-Butanediol
Ball and stick 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
CAS Number	107-88-0 ; 6290-03-5 (R) ; 24621-61-2 (S) ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1731276; 1718944 (R); 1718943 (S)
ChEBI	CHEBI:52683 ;
ChEMBL	ChEMBL1231503 ;
ChemSpider	7608 ; 553103 (R) ; 394191 (S) ;
DrugBank	DB02202 ;
ECHA InfoCard	100.003.209
EC Number	203-529-7;
E number	E1502 (additional chemicals)
Gmelin Reference	2409; 2493173 (R); 1994384 (S)
KEGG	D10695 ;
MeSH	1,3-Butylene+glycol
PubChem CID	7896; 637497 (R); 446973 (S);
RTECS number	EK0440000;
UNII	3XUS85K0RA ;
CompTox Dashboard (EPA)	DTXSID8026773 ;
	InChI InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3 Key: PUPZLCDOIYMWBV-UHFFFAOYSA-N ;
	SMILES CC(O)CCO;
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
Solubility in water	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:
Pictograms
Signal word	Warning
Hazard statements	H319, H413
Precautionary statements	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; 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). verify (what is ?) 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] and as a precursor to some antibiotics.^[4]

Production and uses

Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol:^[5]

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.^[6]^[7] Fatty acid esters of 1,3-butanediol such as the acetoacetate or hexanoate have been researched for inducing ketogenesis.^[8]^[9]^[10]^[11]^[12]^[13]

Occurrence

1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper (Capsicum annuum), red bell peppers, and yellow bell peppers.^[14] 1,3 Butanediol, | quote = Also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule.^[15]

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.
^ 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.

[Ullmann-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] 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.

[Ullmann2-5] 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.

[6] 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.

[7] 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.

[8] 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.

[9] 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.

[10] 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.

[11] 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.

[12] 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

[13] 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.

[14] "Metabocard for 1,3-Butanediol". Human Metabolome Database. HMDB0031320. Retrieved 2022-05-12.

[15] "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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