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1,2,4 Butanetriol

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Formula  C4H10O3
Density  1.19 g/cm³
1,2,4-Butanetriol wwwsigmaaldrichcomcontentdamsigmaaldrichstr

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 Niu, W (2003). "Microbial synthesis of the energetic material precursor 1,2,4-butanetriol". Am. Chem. Soc. 125 (43): 12998–12999. doi:10.1021/ja036391+.  "Biosynthetic Pathways". Retrieved 24 November 2010. . It is 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. However, of an increasing importance is the biotechnological synthesis using genetically engineered Escherichia coli and Pseudomonas fragi bacteria.

References

1,2,4-Butanetriol Wikipedia


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