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
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Identifiers | |||
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3D model (JSmol)
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1731276 1718944 (R) | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.003.209 | ||
EC Number |
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E number | E1502 (additional chemicals) | ||
2409 2493173 (R) | |||
KEGG | |||
MeSH | 1,3-Butylene+glycol | ||
PubChem CID
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RTECS number |
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UNII | |||
CompTox Dashboard (EPA)
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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) | ||
Refractive index (nD)
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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: | |||
Warning | |||
H319, H413 | |||
P305+P351+P338 | |||
NFPA 704 (fire diamond) | |||
Flash point | 108 °C (226 °F; 381 K) | ||
394 °C (741 °F; 667 K) | |||
Related compounds | |||
Related butanediol
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1,2-Butanediol | ||
Related compounds
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2-Methylpentane | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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:[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] Fatty acid esters of 1,3-butanediol such as the acetoacetate or hexanoate have been researched for inducing ketogenesis.[7][8][9][10][11]
Occurrence
1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper (Capsicum annuum), red bell peppers, and yellow bell peppers.[12] 1,3 Butanediol, also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule.[13]
References
- ^ Gräfje, Heinz; Körnig, Wolfgang; Weitz, Hans-Martin; Reiß, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka, Heinz (2000). "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_455. ISBN 9783527306732.
- ^ Parchem, fine & specialty chemicals. "1,3 Butylene Glycol".
- ^ 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, Wu S. A short-chain carbonyl reductase mutant is an efficient catalyst in the production of (R)-1,3-butanediol. Microb Biotechnol. 2023 Jun;16(6):1333-1343. doi:10.1111/1751-7915.14249 PMID 36946330
- ^ Kohlpaintner, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen (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, Breese GR. Effects of acute and chronic 1,3-butanediol treatment on central nervous system function: a comparison with ethanol. J Pharmacol Exp Ther. 1981 Feb;216(2):306-14. PMID 7193248
- ^ Hashim SA, VanItallie TB. Ketone body therapy: from the ketogenic diet to the oral administration of ketone ester. J Lipid Res. 2014 Sep;55(9):1818-26. doi:10.1194/jlr.R046599 PMID 24598140
- ^ Place DE, Kanneganti TD. Fueling Ketone Metabolism Quenches Salt-Induced Hypertension. Trends Endocrinol Metab. 2019 Mar;30(3):145-147. doi:10.1016/j.tem.2019.01.004 PMID 30670332
- ^ Evans M, McClure TS, Koutnik AP, Egan B. Exogenous Ketone Supplements in Athletic Contexts: Past, Present, and Future. Sports Med. 2022 Dec;52(Suppl 1):25-67. doi:10.1007/s40279-022-01756-2 PMID 36214993
- ^ 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. Front Physiol. 2023 Jun 22;14:1196535. doi:10.3389/fphys.2023.1196535 PMID 37427402
- ^ Deemer SE, Roberts BM, Smith DL, Plaisance EP, Philp A. Exogenous ketone esters as a potential therapeutic for treatment of sarcopenic obesity. Am J Physiol Cell Physiol. 2024 Jul 1;327(1):C140-C150. doi:10.1152/ajpcell.00471.2023 PMID 38766768
- ^ "Human Metabolome Database: Showing metabocard for 1,3-Butanediol (HMDB0031320)". hmdb.ca. 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.