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Chemical compound From Wikipedia, the free encyclopedia
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] It is used in flavoring,[4] and as a precursor to some antibiotics.[5]
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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 | |||
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) |
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: | |||
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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 |
1,2-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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Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol:[6]
Dehydration of 1,3-butanediol gives 1,3-butadiene:
1,3-Butanediol has sedative, hypotensive and hypoglycaemic action comparable to ethanol, with the (R) enantiomer being more active.[7][8] Fatty acid esters of 1,3-butanediol such as the acetoacetate or hexanoate have been researched for inducing ketogenesis.[9][10][11][12][13][14]
1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper (Capsicum annuum), red bell peppers, and yellow bell peppers.[15] 1,3 Butanediol, | quote = Also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule.[16]
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