1,3-Butanediol

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 a colorless, bittersweet, water-soluble liquid. It is one of four common structural isomers of butanediol.[1][2]

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
3D model (JSmol)
Beilstein Reference
 1731276

1718944 (R)
1718943 (S)

ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.209
EC Number
  • 203-529-7
E number E1502 (additional chemicals)
Gmelin Reference
 2409

2493173 (R)
1994384 (S)

KEGG
MeSH 1,3-Butylene+glycol
PubChem CID
RTECS number
  • EK0440000
UNII
InChI
  • InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3 N
    Key: PUPZLCDOIYMWBV-UHFFFAOYSA-N 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).
N verify (what is YN ?)
Infobox references

Production and uses

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

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

Occurrence

In biology, 1,3-butanediol is used as a hypoglycaemic agent. 1,3-Butanediol can be converted into β-hydroxybutyrate and serve as a substrate for brain metabolism.[4]

1,3-Butanediol has been detected, but not quantified, in several different foods, such as green bell peppers, orange bell peppers, pepper (c. annuum), red bell peppers, and yellow bell peppers. [5] 1,3 Butanediol, also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule.[6]

References
  1. Gräfje, Heinz; Körnig, Wolfgang; Weitz, Hans-Martin; Reiß, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka (2000). "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_455.
  2. Parchem, fine & specialty chemicals. "1,3 Butylene Glycol".
  3. 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.
  4. Marie, Christine; Bralet, Anne-Marie; Bralet, Jean (1987). "Protective Action of 1,3-Butanediol in Cerebral Ischemia. A Neurologic, Histologic, and Metabolic Study". Journal of Cerebral Blood Flow & Metabolism. 7 (6): 794–800. doi:10.1038/jcbfm.1987.136. PMID 3693436.
  5. "Human Metabolome Database: Showing metabocard for 1,3-Butanediol (HMDB0031320)". hmdb.ca. Retrieved 2022-05-12.
  6. "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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