| Revision as of 15:32, 19 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit |
Latest revision as of 11:37, 26 November 2024 edit undo5.178.188.143 (talk) →History and synthesisTag: Visual edit |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 433546399 |
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| verifiedrevid = 456366461 |
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| ImageFile = 1,6-Hexanediol.svg |
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| ImageFile = 1,6-Hexanediol.svg |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| IUPACName = hexane-1,6-diol |
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| PIN = Hexane-1,6-diol |
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| OtherNames = Hexamethylene glycol; 1,6-Dihydroxyhexane; 1,6-Hexylene glycol; Hexamethylenediol; HDO |
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| OtherNames = Hexamethylene glycol; 1,6-Dihydroxyhexane; 1,6-Hexylene glycol; Hexamethylenediol; HDO |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 629-11-8 |
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| CASNo = 629-11-8 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = |
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| PubChem = 12374 |
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| EC_number = 211-074-0 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| RTECS = MO2100000 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13839416 |
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| ChemSpiderID = 13839416 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 458616 --> |
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| ChEMBL = 458616 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 43078 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = ZIA319275I |
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| UNII = ZIA319275I |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB02210 |
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| DrugBank = DB02210 |
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| SMILES = OCCCCCCO |
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| SMILES = OCCCCCCO |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI=1S/C6H14O2/c7-5-3-1-2-4-6-8/h7-8H,1-6H2 |
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| StdInChI=1S/C6H14O2/c7-5-3-1-2-4-6-8/h7-8H,1-6H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = XXMIOPMDWAUFGU-UHFFFAOYSA-N |
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| StdInChIKey = XXMIOPMDWAUFGU-UHFFFAOYSA-N |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6|H=14|O=2 |
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| C=6 | H=14 | O=2 |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = 0.967 |
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| MeltingPtC = 42 |
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| MeltingPtC = 42 |
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| BoilingPtC = 250 |
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| BoilingPtC = 250 |
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| Solubility = 500g/L <ref name="Merck">''Chemicals and reagents'' 2008-2010, Merck</ref> |
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| Solubility = |
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| SolubleOther = soluble in ] and ], slightly soluble in ], insoluble in ].<ref name="CRC">CRC Handbook of Chemistry and Physics, 87th Edition</ref> |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPtC = 102 |
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| Autoignition = |
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| AutoignitionPt = |
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}} |
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}} |
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}} |
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}} |
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'''1,6-Hexanediol''' (HOCH<sub>2</sub>(CH<sub>2</sub>)<sub>4</sub>CH<sub>2</sub>OH) is a colorless crystalline solid that melts at 42 °C and boils at 250 °C. It is well soluble in water. |
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'''1,6-Hexanediol''' is an ] with the formula (CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH)<sub>2</sub>. It is a colorless water-soluble solid.<ref name=Ull>{{Ullmann|author1=Peter Werle|author2=Marcus Morawietz|author3=Stefan Lundmark|author4=Kent Sörensen|author5=Esko Karvinen|author6=Juha Lehtonen|title=Alcohols, Polyhydric|year=2008|doi=10.1002/14356007.a01_305.pub2}}</ref> |
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== Production == |
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== History and synthesis == |
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] and his graduate student Edward Haworth first prepared the compound in 1894 during their research on ]. They boiled 1,6-dibromohexane (which they were also the first to synthesize) with dilute ] solution and named the product '''hexamethylene glycol'''.<ref>{{Cite journal |last=Haworth |first=E. |last2=Perkin |first2=W. H. |date=1894 |title=Hexamethylene dibromide and its action on sodium and on ethylic sodio-malonate |url=https://books.google.com/books?id=Deo2AAAAYAAJ&pg=PA598 |journal=Journal of the Chemical Society, Transactions |language=en |volume=65 |issue=0 |pages=591–602 |doi=10.1039/CT8946500591 |issn=0368-1645}}</ref> |
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1,6-Hexanediol is prepared industrially by the ] of ]. |
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1,6-Hexanediol is industrially made by the ] of ] or its esters.<ref name="Ull" /><ref>{{cite journal|title=Hexamethylene glycol|first1=W. A. |last1=Lazier|first2=J. W.|last2=Hill|first3=W. J.|last3=Amend|journal=Org. Synth.|year=1939|volume=19|page=48|doi=10.15227/orgsyn.019.0048}}</ref> Laboratory preparation could be achieved by reduction of ] with ], although this method is impractical on a commercial scale. |
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==Properties== |
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As 1,6-hexanediol contains ] groups, it undergoes the typical chemical reactions of ]s such as ], ], and ]. Oxidation with ] gives ].<ref>{{cite journal |doi=10.1016/s0040-4039(00)75204-x |title=Pyridinium Chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds |date=1975 |last1=Corey |first1=E.J. |last2=Suggs |first2=J.William |journal=Tetrahedron Letters |volume=16 |issue=31 |pages=2647–2650 }}</ref> |
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Dehydration of 1,6-hexanediol gives ], 2-methyltetrahydropyran and 2-ethyltetrahydrofuran. Corresponding thiophene and pyrrolidone can be made by reacting 1,6-hexanediol with ] and ] respectively.<ref name="BASF">BASF intermediates, BASF</ref> |
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== Uses == |
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== Uses == |
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1,6-Hexanediol is widely used for industrial ] and ] production. |
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1,6-Hexanediol is widely used for industrial ] and ] production..<ref name=Ull/> |
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1,6-Hexanediol can improve the hardness and flexibility of polyesters as it contains a fairly long hydrocarbon chain. In polyurethanes, it is used as a ], and the resulting modified polyurethane has high resistance to hydrolysis as well as mechanical strength, but with a low glass transition temperature. |
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It is also an intermediate to acrylics as a crosslinking agent, e.g. ].<ref name=Ull/> ]s have also been made from 1,6-hexanediol, along with ], ] and ].<ref name="BASF" /> |
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== Uses to study biomolecular condensates == |
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1,6-Hexanediol has been used to characterize ]. The material properties of condensates can be examined to determine if they are solid or liquid condensates. 1,6-Hexanediol has been reported to interfere with weak hydrophobic protein-protein or protein-RNA interactions that comprise liquid condensates. 1,6-Hexanediol has been reported to dissolve liquid but not solid condensates.<ref>{{cite journal |last1=Kroschwald |first1=Sonja |last2=Maharana |first2=Shovamayee |last3=Simon |first3=Alberti |date=2017-05-22 |title=Hexanediol: a chemical probe to investigate the material properties of membrane-less compartments |journal=Matters |language=en |doi=10.19185/matters.201702000010 |issn=2297-8240|doi-access=free }}</ref> ] and ] have been observed to have minimal effect on behavior of disorderd proteins as compared to 1,6-hexanediol.<ref>{{cite journal |last1=Kato |first1=Masato |last2=McKnight |first2=Steven L. |date=2018-06-20 |title=A Solid-State Conceptualization of Information Transfer from Gene to Message to Protein |url=https://pubmed.ncbi.nlm.nih.gov/29195049/?dopt=Abstract |journal=Annual Review of Biochemistry |volume=87 |pages=351–390 |doi=10.1146/annurev-biochem-061516-044700 |issn=1545-4509 |pmid=29195049|s2cid=28314614 }}</ref><ref>{{cite journal |last1=Franco |first1=Hector L. |last2=Nagari |first2=Anusha |last3=Kraus |first3=W. Lee |date=2015-04-02 |title=TNFα signaling exposes latent estrogen receptor binding sites to alter the breast cancer cell transcriptome |journal=Molecular Cell |volume=58 |issue=1 |pages=21–34 |doi=10.1016/j.molcel.2015.02.001 |issn=1097-4164 |pmc=4385449 |pmid=25752574}}</ref> |
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==Safety== |
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1,6-Hexanediol<ref>{{Cite web |last=Solutions |first=Navux Commerce |title=1,6 Hexanediol (Cas 629-11-8) - Bulk Specialty Chemical Supplier & distributor |url=https://www.parchem.com/chemical-supplier-distributor/1-6-hexanediol-008442 |access-date=2024-06-27 |website=www.parchem.com}}</ref> has low toxicity and low flammability, and is generally considered as safe. It is not irritating to skin, but may irritate the respiratory tract or mucous membranes. Dust or vapor of the compound can irritate or damage the eyes.<ref name="Merck" /> |
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==References== |
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==References== |
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{{Unreferenced|date=June 2011}} |
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{{reflist}} |
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{{reflist}} |
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{{DEFAULTSORT:Hexanediol, 1,6-}} |
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{{DEFAULTSORT:Hexanediol, 1, 6-}} |
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