| Revision as of 16:04, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465357584 of page 1,2,4-Butanetriol for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 18:46, 14 November 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,495 edits a biotech review |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 424737780 |
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| verifiedrevid = 477202569 |
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| ImageFile = Butanetriol.png |
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| ImageFile = 1,2,4-Butanetriol.png |
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| ImageSize = |
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| ImageSize = |
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| IUPACName = Butane-1,2,4-triol |
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| ImageFile1 = 1,2,4-Butanetriol-3D-balls.png |
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| ImageName1 = C=black, H=white, O=red |
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| OtherNames = 1,2,4-Butanetriol<br />1,2,4-Trihydroxybutane<br />Triol 124<br />2-Deoxyerthritol |
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| ImageAlt1 = 1,2,4,-Butanetriol molecule |
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| Section1 = {{Chembox Identifiers |
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| PIN = Butane-1,2,4-triol |
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| Abbreviations = |
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| OtherNames = 1,2,4-Butanetriol<br />1,2,4-Trihydroxybutane<br />Triol 124<br />2-Deoxyerthritol |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 17287 |
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| ChemSpiderID = 17287 |
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| SMILES1 = OCCC(O)CO |
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| SMILES1 = OCCC(O)CO |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ARXKVVRQIIOZGF-UHFFFAOYSA-N |
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| StdInChIKey = ARXKVVRQIIOZGF-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 3068-00-6 --> |
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| CASNo = 3068-00-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 221-323-5 |
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| PubChem = |
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| UNII = NK798C370H |
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| EINECS = 221-323-5 |
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| SMILES = OCC(O)CCO |
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| PubChem = 18302 |
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| InChI = 1/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2 |
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| RTECS = EK7176000 |
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| SMILES = OCC(O)CCO |
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| InChI = 1/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2 |
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| RTECS = EK7176000 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| KEGG = |
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| ChEBI = 88063 |
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| ChEMBL = 1356759 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| Section2 = {{Chembox Properties |
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| C=4|H=10|O=3 |
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| C=4 | H=10 | O=3 |
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| Appearance = |
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| Appearance = |
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| Density = 1.19 |
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| Density = 1.19 |
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| BoilingPtC = 190 to 191 |
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| BoilingPt = 190–191 °C |
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| Boiling_notes = 18 torr |
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| BoilingPt_notes = 18 torr |
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| Section7 = {{Chembox Hazards |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| RPhrases = {{R36}} |
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| SPhrases = {{S24/25}} |
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| FlashPt = 112 °C |
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|Section7={{Chembox Hazards |
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| ExternalSDS = |
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| MainHazards = |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| NFPA-S = - |
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| GHSSignalWord = Warning |
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| GHSPictograms = {{GHS07}} |
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| HPhrases = {{H-phrases|315|319|335}} |
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| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |
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| FlashPtC = 112 |
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'''1,2,4-Butanetriol''' is an ] with the formula {{chem2|HOCH2CH(OH)CH2CH2OH}}. It is an colorless, odorless, ], ] liquid. Containing three ] groups, it is classified as a ], similar to ] and ]. It is ]. |
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==Uses== |
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1,2,4-Butanetriol is used in the manufacture of ] (BTTN), an important component of US military rocket motor solid fuel. As of 2014, it was commercially produced by a single Chinese company.<ref>https://es.ndu.edu/Portals/75/Documents/industry-study/reports/2014/es-is-report-weapons-2014.pdf</ref> |
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1,2,4-Butanetriol is also used as a precursor for two ]-lowering drugs, ] and ], which are derived from D-3,4-dihydroxybutanoic acid, by using 3-hydroxy-gamma-butyrolactone as a chiral synthon<ref name="NiuMolefe2003">{{cite journal|last1=Niu|first1=Wei|last2=Molefe|first2=Mapitso N.|last3=Frost|first3=J. W.|title=Microbial Synthesis of the Energetic Material Precursor 1,2,4-Butanetriol|journal=Journal of the American Chemical Society|volume=125|issue=43|year=2003|pages=12998–12999|issn=0002-7863|doi=10.1021/ja036391+|pmid=14570452 }}</ref><ref>{{cite web |url=http://www.frostchemlab.com/biosynthetic-pathways.htm |title=Biosynthetic Pathways |accessdate=24 November 2010 |archive-url=https://web.archive.org/web/20110626224831/http://www.frostchemlab.com/biosynthetic-pathways.htm |archive-date=2011-06-26 |url-status=dead }}</ref> |
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It is used as one of the monomers for manufacture of some ]s and as a ]. |
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==Preparation== |
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1,2,4-Butanetriol can be prepared synthetically by several methods, such as ] of ] and subsequent reduction of the product. It can also be prepared by reduction of ] esters with ].<ref>{{cite web |work=Chemical & Engineering News |date=May 31, 2004 |volume=82 |number=22 |pages=31–34 |first=Stephen K. |last=Ritter |title=Biomass or Bust |url=http://pubsapp.acs.org/email/cen/html/060804150713.html }}</ref> The oxidation of ] with ] followed by reduction of the resulting ketone.<ref>{{cite book|pages=121|title=The Ageless Gergel|first=Max G.|last=Gergel|url=https://library.sciencemadness.org/library/books/the_ageless_gergel.pdf}}</ref> |
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Genetically engineered bacteria produce these triols in enantiopure form. '']'' converts D-] to D-], which is decarboxylated by a strain of '']'' to D-triol. Similarly, D-] is converted to D-], which is converted to the L-triol.<ref>{{cite journal |doi=10.1021/ja036391|pmid=14570452 |date=2003 |last1=Niu |first1=W. |last2=Molefe |first2=M. N. |last3=Frost |first3=J. W. |title=Microbial synthesis of the energetic material precursor 1,2,4-butanetriol |journal=Journal of the American Chemical Society |volume=125 |issue=43 |pages=12998–12999 }}</ref><ref>{{cite journal |doi=10.1186/s13068-020-01744-6|doi-access=free |title=Engineering Microbial Pathways for Production of Bio-based Chemicals from Lignocellulosic Sugars: Current Status and Perspectives |date=2020 |last1=Francois |first1=Jean Marie |last2=Alkim |first2=Ceren |last3=Morin |first3=Nicolas |journal=Biotechnology for Biofuels |volume=13 |page=118 |pmid=32670405 |pmc=7341569 }}</ref> |
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==References== |
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<references/> |
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{{DEFAULTSORT:Butanetriol, 1, 2, 4-}} |
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] |
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] |
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] |