1,2,4-Butanetriol

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	3068-00-6 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:88063 ;
ChEMBL	ChEMBL1356759;
ChemSpider	17287 ;
ECHA InfoCard	100.019.385
EC Number	221-323-5;
PubChem CID	18302;
RTECS number	EK7176000;
UNII	NK798C370H ;
CompTox Dashboard (EPA)	DTXSID8044416 ;
	InChI InChI=1S/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2 Key: ARXKVVRQIIOZGF-UHFFFAOYSA-N ; InChI=1/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2 Key: ARXKVVRQIIOZGF-UHFFFAOYAQ;
	SMILES OCC(O)CCO; OCCC(O)CO;
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
Signal word	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). verify (what is ?) Infobox references

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.

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]

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

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.^[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

^ 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.

[1] ttps://es.ndu.edu/Portals/75/Documents/industry-study/reports/2014/es-is-report-weapons-2014.pdf

[NiuMolefe2003-2] 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.

[3] "Biosynthetic Pathways". Archived from the original on 2011-06-26. Retrieved 24 November 2010.

[4] Ritter, Stephen K. (May 31, 2004). "Biomass or Bust". Chemical & Engineering News. pp. 31–34.

[5] Gergel, Max G. The Ageless Gergel (PDF). p. 121.

[6] 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.

[7] 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.

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