1,2,4-Butanetriol
![]() | |
![]() | |
Names | |
---|---|
Preferred IUPAC name Butane-1,2,4-triol | |
Other names 1,2,4-Butanetriol 1,2,4-Trihydroxybutane Triol 124 2-Deoxyerthritol | |
Identifiers | |
CAS Number |
|
3D model (JSmol) |
|
ChEBI |
|
ChEMBL |
|
ChemSpider |
|
ECHA InfoCard | 100.019.385 ![]() |
EC Number |
|
PubChem CID |
|
RTECS number |
|
UNII |
|
CompTox Dashboard (EPA) |
|
InChI
| |
| |
Properties | |
Chemical formula | C4H10O3 |
Molar mass | 106.121 g·mol−1 |
Density | 1.19 |
Boiling point | 190 to 191 °C (374 to 376 °F; 463 to 464 K) 18 torr |
Hazards | |
GHS labelling: | |
Pictograms | ![]() |
Warning | |
Hazard statements | H315, H319, H335 |
Precautionary statements | P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 |
NFPA 704 (fire diamond) | ![]() 2 1 0 |
Flash point | 112 °C (234 °F; 385 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
1,2,4-Butanetriol is a clear or slightly yellow, odorless, hygroscopic, flammable, viscous liquid. It is an alcohol with three hydrophilic alcoholic hydroxyl groups. It is similar to glycerol and erythritol. It is chiral, with two possible enantiomers.
1,2,4-Butanetriol is used in the manufacture of butanetriol trinitrate (BTTN), an important military propellant.
1,2,4-Butanetriol is also used as a precursor for two cholesterol-lowering drugs, Crestor and Zetia, which are derived from D-3,4-dihydroxybutanoic acid, by using 3-hydroxy-gamma-butyrolactone as a chiral synthon[1][2] It is used as one of the monomers for manufacture of some polyesters and as a solvent.
1,2,4-Butanetriol can be prepared synthetically by several different methods such as hydroformylation of glycidol and subsequent reduction of the product, sodium borohydride reduction of esterified malic acid, or catalytic hydrogenation of malic acid.[3] However, of an increasing importance is the biotechnological synthesis using genetically engineered Escherichia coli and Pseudomonas fragi bacteria.[4]
References
- ^ Niu, Wei; Molefe, Mapitso N.; Frost, J. W. (2003). "Microbial Synthesis of the Energetic Material Precursor 1,2,4-Butanetriol". Journal of the American Chemical Society. 125 (43): 12998–12999. doi:10.1021/ja036391+. ISSN 0002-7863. PMID 14570452.
- ^ "Biosynthetic Pathways". Archived from the original on 2011-06-26. Retrieved 24 November 2010.
- ^ Ritter, Stephen K. (May 31, 2004). "Biomass or Bust". Chemical & Engineering News. pp. 31–34.
- ^ Gilbert, Meghan (February 12, 2004). "Propelling Research". The State News. Archived from the original on 2004-08-22.