| Revision as of 17:24, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473858507 of page 2-Methyl-2,4-pentanediol for the Chem/Drugbox validation project (updated: ''). |
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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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| verifiedrevid = 400006890 |
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|ImageFile=2-Methyl-2,4-pentanediol.png |
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| verifiedrevid = 477214070 |
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|ImageSize=200px |
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|IUPACName=2-Methyl-2,4-pentanediol |
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| ImageFile =2-Methyl-2,4-pentanediol.png |
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|OtherNames=Hexylene glycol; Diolane; 1,1,3-Trimethyltrimethylenediol; 2,4-Dihydroxy-2-methylpentane |
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| PIN = 2-Methylpentane-2,4-diol |
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| OtherNames = 2-Methyl-2,4-pentanediol<br>Hexylene glycol<br>Diolane<br>1,1,3-Trimethyltrimethylenediol<br>2,4-Dihydroxy-2-methylpentane<br>Isol |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Abbreviations = MPD |
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| CASNo =107-41-5 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo1_Ref = {{cascite|changed|??}} |
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| CASNo1 = 99210-90-9 |
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| CASNo1_Comment= (R) |
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| CASNo2_Ref = {{cascite|changed|??}} |
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| CASNo2 = 99210-91-0 |
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| CASNo2_Comment= (S) |
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| Abbreviations = MPD |
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| Beilstein = 1098298 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 62995 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 2104293 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7582 |
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| ChemSpiderID = 7582 |
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| EC_number = 203-489-0 |
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| PubChem =7870 |
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| RTECS = SA0810000 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = KEH0A3F75J |
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| UNII = KEH0A3F75J |
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| UNNumber = 1993 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| SMILES =CC(CC(C)(C)O)O |
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| CASNo=107-41-5 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| PubChem=7870 |
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| StdInChI = 1S/C6H14O2/c1-5(7)4-6(2,3)8/h5,7-8H,4H2,1-3H3 |
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| SMILES=CC(CC(C)(C)O)O |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = SVTBMSDMJJWYQN-UHFFFAOYSA-N |
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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 = colourless liquid |
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| Density= |
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| Density =0.92 g/mL |
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| MeltingPtC = -40 |
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| BoilingPtC = 197 |
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| Solubility = miscible<ref name=PGCH/> |
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| Odor = mild, sweetish<ref name=PGCH/> |
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| VaporPressure = 0.05 mmHg (20°C)<ref name=PGCH/> |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPtC = 98.3 |
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| FlashPt_ref = <ref></ref> |
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| PEL = none<ref name=PGCH>{{PGCH|0328}}</ref> |
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| ExploLimits = 1.3%-7.4%<ref name=PGCH/> |
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| IDLH = N.D.<ref name=PGCH/> |
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| REL = C 25 ppm (125 mg/m<sup>3</sup>)<ref name=PGCH/> |
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| GHS_ref=<ref>{{cite web |title=Hexylene Glycol |url=https://pubchem.ncbi.nlm.nih.gov/compound/7870#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319}} |
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| PPhrases = {{P-phrases|264|264+265|280|302+352|305+351+338|321|332+317|337+317|362+364}} |
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'''2-Methyl-2,4-pentanediol''' (MPD) is an ] with the formula (CH<sub>3</sub>)<sub>2</sub>C(OH)CH<sub>2</sub>CH(OH)CH<sub>3</sub>. This colourless liquid is a ] ]. It is produced industrially from ] by ].<ref name=Ullmann>Stylianos Sifniades, Alan B. Levy, "Acetone" in ''Ullmann’s Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2005. {{doi|10.1002/14356007.a01_079.pub3}}</ref> Total European and USA production was 15000 tonnes in 2000.<ref name=Siam13></ref> |
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2-Methyl-2,4-pentanediol exists as two enantiomers, (4''R'')-(−) and (4''S'')-(+). In the ], the 3-letter code "MPD" refers to the (''S'')-(−) enantiomer, while "MRD" is used to refer to the (''R'')-(+) version. Commercial products labeled "MPD" are usually the ],<ref name=Hampton>, MPD Product Page</ref> also sold as and referred to as "'''hexylene glycol'''".<ref name=Sigma>, Hexylene Glycol Product Page</ref><ref name="Bioscience">Hexylene Glycol at Jena Bioscience, Hexylene Glycol Product Page</ref> |
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==Uses== |
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2-Methyl-2,4-pentanediol exhibits both surfactant and emulsion-stabilizing properties. Its relatively high viscosity and low volatility are advantageous in coatings, cleansers, cosmetics, solvents, lubricants, and ]s.<ref name=Chemicalland21.com> Hexylene glycol</ref> Although it is an irritant at higher concentrations, it is sometimes used in skin care, hair care, soap, and eye cosmetic products at concentrations ranging from 0.1% - 25%.<ref>{{Cite journal|title = Antibacterial and antifungal properties of propylene glycol, and 1,3-butylene glycol in vitro|last = Kinnunen|first = T.|date = 1991|journal = Acta Dermato-Venereologica| doi=10.2340/0001555571148150 | s2cid=13239472 |doi-access = free}}</ref><ref>R. Rietschel; J. Fowler; A. Fisher Hexylene Glycol. In ''Fisher's Contact Dermatitis;'' Holmes, M., Ed.; BC Decker Inc.: Hamilton,Ontario, 2008; pp 290</ref> |
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It is biodegradable and unlikely to accumulate in the environment.<ref>Rhodia Hexylene glycol GPS Safety Summary. 2012.</ref> |
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==Laboratory uses== |
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In the laboratory it is a common ] and ] in ] ].<ref name=Stura>, Enrico Stura, University of Glasgow</ref> Since hexylene glycol is compatible with polar and nonpolar molecules, it competes with the solvent in a crystallography experiment causing the protein to precipitate.<ref>{{Cite journal|title = Comparative Effects of Salt, Organic and Polymer Precipitants on Protein Phase Behavior and Implications for Vapor Diffusion|last = Dumetz|first = A.|date = 2009|journal = J. Cryst. Growth| volume=9 | issue=2 | pages=682–691 | doi=10.1021/cg700956b }}</ref> Hexylene glycol is so effective in protein crystallography because its amphiphilic nature and small, flexible structure allows it to bind to many different locations on a protein secondary structure including alpha helices and beta sheets.<ref name=":0">{{Cite journal|title = An overview on 2-methyl-2,4-pentanediol in crystallization and in crystals of biological macromolecules|last = Anand|first = K|date = 2002|journal = Acta Crystallogr.| volume=58 | issue=10 | pages=1722–1728 |doi = 10.1107/s0907444902014610 | pmid=12351894 |pmc = 7161645| bibcode=2002AcCrD..58.1722A }}</ref> When hexylene glycol binds to these different locations, water is removed and the protein crystals anneal, which prevents ice formation during cryocrystallography techniques.<ref>{{Cite journal|title = Thornea Effects of cryoprotectant concentration and cooling rate on vitrification of aqueous solutions|last = Viatcheslav|first = Berejnov|date = 2006|journal = J. Appl. Crystallogr.}}</ref> Incorporation of hexylene glycol into solution has been known to improve the resolution of X-ray diffraction making protein structures easily identifiable.<ref>{{Cite journal|title = Strategies for Protein Crystallography|last = Vera|first = L|date = 2006|journal = Cryst. Growth Des.}}</ref> Additionally hexylene glycol is not a strong denaturing agent and thus does not significantly alter the structure of a protein during the crystallography procedure.<ref name=":0" /> |
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Hexylene glycol is also used as a lubricant for polishing specimens in ].<ref>{{cite web |url=https://consumables.alliedhightech.com/GreenLube-p/grnlub.htm |title=GreenLube |publisher=Allied High Tech |access-date=2023-09-23 |quote=GreenLube is a medium viscosity hexylene glycol based lubricant used for general metallographic preparation}}</ref> |
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Like related diols, it forms ]s. |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Methyl-2, 4-pentanediol, 2-}} |
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] |