1,2,4-Butanetriol is an organic compound with the formula HOCH2CH(OH)CH2CH2OH. 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.
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| Names | |
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| Preferred IUPAC name
Butane-1,2,4-triol | |
| Other names
1,2,4-Butanetriol
1,2,4-Trihydroxybutane Triol 124 2-Deoxyerthritol | |
| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.019.385 |
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CompTox Dashboard (EPA)
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| Properties | |
| 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 | |
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| Warning | |
| H315, H319, H335 | |
| 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) | |
| 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).
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Uses
edit1,2,4-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]
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[2][3] It is used as one of the monomers for manufacture of some polyesters and as a solvent.
Preparation
edit1,2,4-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.[4] The oxidation of butynediol with mercuric oxide followed by reduction of the resulting ketone.[5]
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.[6][7]
References
edit- ^ https://es.ndu.edu/Portals/75/Documents/industry-study/reports/2014/es-is-report-weapons-2014.pdf
- ^ 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.
- ^ Gergel, Max G. The Ageless Gergel (PDF). p. 121.
- ^ Niu, W.; Molefe, M. 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. PMID 14570452.
- ^ Francois, Jean Marie; Alkim, Ceren; Morin, Nicolas (2020). "Engineering Microbial Pathways for Production of Bio-based Chemicals from Lignocellulosic Sugars: Current Status and Perspectives". Biotechnology for Biofuels. 13: 118. doi:10.1186/s13068-020-01744-6. PMC 7341569. PMID 32670405.