1,2,4-Butanetriol

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1,2,4-Butanetriol

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1,2,4-Butanetriol is an organic compound with the formula Template:Chem2. It is an colorless, odorless, hygroscopic, oily liquid. Containing three alcohol groups, it is classified as a polyol, similar to glycerol and erythritol. It is chiral.

Uses

1,2,4-Butanetriol is used in the manufacture of butanetriol trinitrate (BTTN), an important component of US military rocket motor solid fuel. As of 2014, it was commercially produced by a single Chinese company.

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 It is used as one of the monomers for manufacture of some polyesters and as a solvent.

Preparation

1,2,4-Butanetriol can be prepared synthetically by several methods, such as hydroformylation of glycidol and subsequent reduction of the product. It can also be prepared by reduction of malic acid esters with sodium borohydride. The oxidation of butynediol with mercuric oxide followed by reduction of the resulting ketone.

Genetically engineered bacteria produce these triols in enantiopure form. Pseudomonas fragi converts D-xylose to D-xylonic acid, which is decarboxylated by a strain of Escherichia coli to D-triol. Similarly, D-arabinose is converted to D-arabinonic acid, which is converted to the L-triol.