1,3-Butanediol
Skeletal formula of 1,3-butanediol
Ball and stick model of 1,3-butanediol (S)
Ball and stick model of 1,3-butanediol (S)
Spacefill 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
3D model (JSmol)
1731276

1718944 (R)
1718943 (S)

ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.209 Edit this at Wikidata
EC Number
  • 203-529-7
E number E1502 (additional chemicals)
2409

2493173 (R)
1994384 (S)

KEGG
MeSH 1,3-Butylene+glycol
RTECS number
  • EK0440000
UNII
  • InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3 ☒N
    Key: PUPZLCDOIYMWBV-UHFFFAOYSA-N ☒N
  • CC(O)CCO
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)
1.44
Thermochemistry
227.2 J K−1 mol−1
−501 kJ mol−1
−2.5022 MJ mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H319, H413
P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 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).
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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.

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

1,3-Butanediol is used as a hypoglycaemic agent.

1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper (Capsicum annuum), red bell peppers, and yellow bell peppers.[4] 1,3 Butanediol, also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule.[5]

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. ISBN 978-3527306732.
  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. ISBN 978-3527306732.
  4. ^ "Human Metabolome Database: Showing metabocard for 1,3-Butanediol (HMDB0031320)". hmdb.ca. Retrieved 2022-05-12.
  5. ^ "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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