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1,2,4-Butanetriol

Topic: Chemistry

 From HandWiki - Reading time: 2 min

1,2,4-Butanetriol is an organic compound with the formula HOCH
2CH(OH)CH
2CH
2OH. 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.[1]

Uses

1,2,4-Butanetriol is used in production of alkyd resins. It is also a precursor to 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.[2]

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[3][4] 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.[5] The oxidation of butynediol with mercuric oxide followed by reduction of the resulting ketone.[6]

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.[7][8]

References

  1. ↑ Lichtenthaler, Frieder W. (2010). "Carbohydrates as Organic Raw Materials". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.n05_n07. ISBN 978-3-527-30673-2. 
  2. ↑ Industry Study Final Report - Weapons Industry (Report). 2014. p. 10. https://es.ndu.edu/Portals/75/Documents/industry-study/reports/2014/es-is-report-weapons-2014.pdf. Retrieved December 7, 2025. 
  3. ↑ 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. Bibcode: 2003JAChS.12512998N. 
  4. ↑ "Biosynthetic Pathways". http://www.frostchemlab.com/biosynthetic-pathways.htm. Retrieved 24 November 2010. 
  5. ↑ Ritter, Stephen K. (May 31, 2004). "Biomass or Bust". Chemical & Engineering News. pp. 31–34. http://pubsapp.acs.org/email/cen/html/060804150713.html. 
  6. ↑ Gergel, Max G.. The Ageless Gergel. pp. 121. https://library.sciencemadness.org/library/books/the_ageless_gergel.pdf. 
  7. ↑ 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. 
  8. ↑ 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 (1). doi:10.1186/s13068-020-01744-6. PMID 32670405. Bibcode: 2020BB.....13..118F. 



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