1,3-Butanediol

Last updated
1,3-Butanediol
1,3-Butanediol.png
Ball and stick model of 1,3-butanediol (S) 1,3-Butanediol-3D-balls.png
Ball and stick model of 1,3-butanediol (S)
Spacefill model of 1,3-butanediol (S) 1,3-Butanediol-3D-spacefill.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-529-7
E number E1502 (additional chemicals)
2409

2493173 (R)
1994384 (S)

KEGG
MeSH 1,3-Butylene+glycol
PubChem CID
RTECS number
  • EK0440000
UNII
  • InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3 X mark.svgN
    Key: PUPZLCDOIYMWBV-UHFFFAOYSA-N X mark.svgN
  • CC(O)CCO
Properties
C4H10O2
Molar mass 90.122 g·mol−1
AppearanceColourless 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
Std molar
entropy
(S298)
227.2 J K−1 mol−1
−501 kJ mol−1
−2.5022 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H319, H413
P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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]

Related Research Articles

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<span class="mw-page-title-main">Dicarbonyl</span> Molecule containing two adjacent C=O groups

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β-Hydroxybutyric acid Chemical compound

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References

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  2. "1,3 Butylene Glycol". Parchem Fine & Specialty Chemicals.
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  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.
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  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.
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  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.
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  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
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  15. "FDA GRAS for 1,3 Butanediol for flavoring CFR - Code of Federal Regulations Title 21". www.accessdata.fda.gov. Retrieved 2022-05-12.