| Revision as of 04:41, 10 December 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit |
Latest revision as of 16:42, 9 October 2024 edit undoJCW-CleanerBot (talk | contribs)Bots130,145 editsm →Applications: task, replaced: Colloids and Surfaces. B, Biointerfaces → Colloids and Surfaces B: BiointerfacesTag: AWB |
| (35 intermediate revisions by 26 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 373416226 |
|
|
|
| Watchedfields = changed |
| ⚫ |
|Name = β-<small>D</small>-Octyl glucoside |
|
|
⚫ |
| verifiedrevid = 401570012 |
| ⚫ |
|ImageFile=octyl glucoside.png |
|
|
⚫ |
| Name = β-{{small|D}}-Octyl glucoside |
| ⚫ |
|ImageSize=200px |
|
|
⚫ |
| ImageFile = octyl glucoside.png |
| ⚫ |
|IUPACName=(2''R'',3''S'',4''S'',5''R'',6''R'')-2-(hydroxymethyl)-6-octoxyoxane-3,4,5-triol |
|
|
⚫ |
| ImageSize = 200px |
| ⚫ |
|OtherNames=''n''-octyl-β-<small>D</small>-glucoside |
|
|
|
| IUPACName = Octyl β-{{small|D}}-glucopyranoside |
|
⚫ |
| SystematicName = (2''R'',3''S'',4''S'',5''R'',6''R'')-2-(Hydroxymethyl)-6-(octyloxy)oxane-3,4,5-triol |
|
⚫ |
| OtherNames = ''n''-Octyl-β-{{small|D}}-glucoside |
|
|Section1={{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| CASNo_Ref = {{cascite}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo=29836-26-8 |
|
| CASNo = 29836-26-8 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| PubChem=62852 |
|
|
|
| UNII = V109WUT6RL |
| ⚫ |
| SMILES=CCCCCCCCO1((((O1)CO)O)O)O |
|
|
⚫ |
| PubChem = 62852 |
|
⚫ |
| SMILES = CCCCCCCCO1((((O1)CO)O)O)O |
|
|
| EINECS = 249-887-8 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = 56585 |
|
|
| InChI = 1/C14H28O6/c1-2-3-4-5-6-7-8-19-14-13(18)12(17)11(16)10(9-15)20-14/h10-18H,2-9H2,1H3/t10-,11-,12+,13-,14-/m1/s1 |
|
|
| InChIKey = HEGSGKPQLMEBJL-RKQHYHRCBI |
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChI = 1S/C14H28O6/c1-2-3-4-5-6-7-8-19-14-13(18)12(17)11(16)10(9-15)20-14/h10-18H,2-9H2,1H3/t10-,11-,12+,13-,14-/m1/s1 |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = HEGSGKPQLMEBJL-RKQHYHRCSA-N |
|
|
| RTECS = |
|
|
| MeSHName = C018619 |
|
}} |
|
}} |
|
|Section2={{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| Formula=C<sub>14</sub>H<sub>28</sub>O<sub>6</sub> |
|
| Formula=C<sub>14</sub>H<sub>28</sub>O<sub>6</sub> |
|
| MolarMass=292.37 g/mol |
|
| MolarMass=292.37 g/mol |
|
| Appearance= |
|
| Appearance= |
|
| Density= |
|
| Density= |
|
| MeltingPt= |
|
| MeltingPt= |
|
| BoilingPt= |
|
| BoilingPt= |
|
| Solubility= |
|
| Solubility= |
|
|
| CMC =0.025 ]<ref name=cmc>{{cite journal|last1=Shinoda|first1=Kozo|last2=Yamaguchi|first2=Tokio|last3=Hori|first3=Ryohei|title=The Surface Tension and the Critical Micelle Concentration in Aqueous Solution of β-D-Alkyl Glucosides and their Mixtures|journal=Bulletin of the Chemical Society of Japan|date=1961|volume=34|issue=2|pages=237–241|doi=10.1246/bcsj.34.237|doi-access=free}}</ref> |
|
|
| HLB = |
|
}} |
|
}} |
|
|Section3={{Chembox Hazards |
|
|Section3={{Chembox Hazards |
|
| MainHazards= |
|
| MainHazards= |
|
| FlashPt= |
|
| FlashPt= |
|
|
| AutoignitionPt = |
|
| Autoignition= |
|
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Octyl glucoside''' ('''''n''-octyl-β-<small>D</small>-glucoside''') is a ] frequently used to dissolve ]s for studies in ]. Like ] and ], it is a nonphysiological ] that makes ]s less "stiff".<ref>{{cite journal | pmid = 15111647 | year = 2004 | month = May | author = Lundbaek, Ja; Birn, P; Hansen, Aj; Søgaard, R; Nielsen, C; Girshman, J; Bruno, Mj; Tape, Se; Egebjerg, J; Greathouse, Dv; Mattice, Gl; Koeppe, Re, 2Nd; Andersen, Os | title = Regulation of sodium channel function by bilayer elasticity: the importance of hydrophobic coupling. Effects of Micelle-forming amphiphiles and cholesterol | volume = 123 | issue = 5 | pages = 599–621 | issn = 0022-1295 | pmc = 2234500 | doi = 10.1085/jgp.200308996 | journal = The Journal of general physiology | url = http://www.jgp.org/cgi/pmidlookup?view=long&pmid=15111647 | format = Free full text}}</ref> |
|
'''Octyl glucoside''' ('''''n''-octyl-β-{{sm|d}}-glucoside''') is a ] frequently used to solubilise ]s for studies in ]. Structurally, it is a ] derived from ] and ]. Like ] and ], it is a nonphysiological ] that makes ]s less "stiff".<ref name="pmid15111647">{{cite journal | vauthors = Lundbaek JA, Birn P, Hansen AJ, Søgaard R, Nielsen C, Girshman J, Bruno MJ, Tape SE, Egebjerg J, Greathouse DV, Mattice GL, Koeppe RE, Andersen OS | title = Regulation of sodium channel function by bilayer elasticity: the importance of hydrophobic coupling. Effects of Micelle-forming amphiphiles and cholesterol | journal = The Journal of General Physiology | volume = 123 | issue = 5 | pages = 599–621 | date = May 2004 | pmid = 15111647 | pmc = 2234500 | doi = 10.1085/jgp.200308996 }}</ref> |
|
|
|
|
|
|
==Applications== |
|
It has become one of the most important detergents for purification of membrane proteins because it can readily be removed from final protein extracts.<ref>{{cite journal | pmid = 17207975 | year = 2007 | month = Apr | author = Morandat, S; El, Kirat, K | title = Solubilization of supported lipid membranes by octyl glucoside observed by time-lapse atomic force microscopy | volume = 55 | issue = 2 | pages = 179–84 | issn = 0927-7765 | doi = 10.1016/j.colsurfb.2006.11.039 | journal = Colloids and surfaces. B, Biointerfaces}}</ref> Above its critical micelle concentration of 0.7%, it was noted as the best detergent for improving selectivity of ] of ] modified proteins.<ref>{{cite journal | pmid = 16342243 | year = 2006 | month = Jan | author = Zhang, G; Neubert, Ta | title = Use of detergents to increase selectivity of immunoprecipitation of tyrosine phosphorylated peptides prior to identification by MALDI quadrupole-TOF MS | volume = 6 | issue = 2 | pages = 571–8 | issn = 1615-9853 | doi = 10.1002/pmic.200500267 | journal = Proteomics}}</ref> |
|
Octyl glucoside has become one of the most important detergents for purification of membrane proteins because it generally does not ] the protein and can readily be removed from final protein extracts.<ref name="pmid17207975">{{cite journal | vauthors = Morandat S, El Kirat K | title = Solubilization of supported lipid membranes by octyl glucoside observed by time-lapse atomic force microscopy | journal = Colloids and Surfaces B: Biointerfaces | volume = 55 | issue = 2 | pages = 179–84 | date = April 2007 | pmid = 17207975 | doi = 10.1016/j.colsurfb.2006.11.039 }}</ref> Above its ] of 0.025 M<ref name=cmc /> (~0.7% w/v), it was noted as the best detergent for improving selectivity of ] of ] modified proteins.<ref>{{cite journal | pmid = 16342243 |date=Jan 2006 |author1=Zhang, G |author2=Neubert, Ta | title = Use of detergents to increase selectivity of immunoprecipitation of tyrosine phosphorylated peptides prior to identification by MALDI quadrupole-TOF MS | volume = 6 | issue = 2 | pages = 571–8 | issn = 1615-9853 | doi = 10.1002/pmic.200500267 | journal = Proteomics|s2cid=26930507 }}</ref> This detergent has also been shown to rapidly inactivate infective HIV at concentrations above its CMC.<ref>{{cite journal | pmid = 21136887 |date=Jun 2008 | vauthors = Bosley A, Marshall HN, Badralmaa Y, Natarajan V | title = A method of HIV-1 inactivation compatible with antibody-based depletion of abundant proteins from plasma. | volume = 2 | issue = 6 | pages = 904–7 | doi = 10.1002/prca.200780086 | journal = Proteomics: Clinical Applications|s2cid=19247865 }}</ref> |
|
|
|
|
|
The compound gained popularity with researchers following the publication of an improved synthesis in 1978.<ref>See search for "octyl AND glucoside" for a timeline of publications.</ref><ref>{{cite journal | pmid = 756493 | year = 1978 | month = | author = Keana, Jf; Roman, Rb | title = Improved synthesis of n-octyl-beta-D-glucoside: a nonionic detergent of considerable potential in membrane biochemistry | volume = 1 | issue = 3-4 | pages = 323–7 | issn = 0149-046X | journal = Membrane biochemistry}}</ref> However, in 1990 the cost remained prohibitive for large-scale protein isolation.<ref> {{cite journal | pmid = 2077942 | year = 1990 | month = Nov | author = Kobs, Sf | title = Recovery of octyl beta-glucoside from detergent/protein mixtures | volume = 191 | issue = 1 | pages = 47–9 | issn = 0003-2697 | journal = Analytical biochemistry | doi = 10.1016/0003-2697(90)90385-M}}</ref> |
|
The compound gained popularity with researchers following the publication of an improved synthesis in 1978.<ref>See search for "octyl AND glucoside" for a timeline of publications.</ref><ref>{{cite journal | pmid = 756493 | year = 1978 |author1=Keana, Jf |author2=Roman, Rb | title = Improved synthesis of n-octyl-beta-D-glucoside: a nonionic detergent of considerable potential in membrane biochemistry | volume = 1 | issue = 3–4 | pages = 323–7 | issn = 0149-046X | journal = Membrane Biochemistry | doi=10.3109/09687687809063854}}</ref> However, in 1990 the cost remained prohibitive for large-scale protein isolation.<ref>{{cite journal | pmid = 2077942 |date=Nov 1990 | author = Kobs, Sf | title = Recovery of octyl beta-glucoside from detergent/protein mixtures | volume = 191 | issue = 1 | pages = 47–9 | issn = 0003-2697 | journal = Analytical Biochemistry | doi = 10.1016/0003-2697(90)90385-M}}</ref> |
|
|
|
|
|
Octyl glucoside has been proposed as a conditioning agent to prevent microbial colonization of ]es, due to its ability to lower the ] of contact lenses and prevent adhesion of '']'' and '']''.<ref> {{cite journal | pmid = 17502827 | year = 2007 | month = May | author = Santos, L; Rodrigues, D; Lira, M; Oliveira, R; Real, Oliveira, Me; Vilar, Ey; Azeredo, J | title = The effect of octylglucoside and sodium cholate in Staphylococcus epidermidis and Pseudomonas aeruginosa adhesion to soft contact lenses | volume = 84 | issue = 5 | pages = 429–34 | issn = 1040-5488 | doi = 10.1097/OPX.0b013e318058a0cc | journal = Optometry and vision science : official publication of the American Academy of Optometry}}</ref> |
|
Octyl glucoside has been proposed as a conditioning agent to prevent microbial colonization of ]es, due to its ability to lower the ] of contact lenses and prevent adhesion of '']'' and '']''.<ref name="pmid17502827">{{cite journal | vauthors = Santos L, Rodrigues D, Lira M, Oliveira R, Real Oliveira ME, Vilar EY, Azeredo J | title = The effect of octylglucoside and sodium cholate in Staphylococcus epidermidis and Pseudomonas aeruginosa adhesion to soft contact lenses | journal = Optometry and Vision Science | volume = 84 | issue = 5 | pages = 429–34 | date = May 2007 | pmid = 17502827 | doi = 10.1097/OPX.0b013e318058a0cc | hdl = 1822/6663 | s2cid = 2509161 | hdl-access = free }}</ref> |
|
|
|
|
|
==See also== |
|
==See also== |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
|
* ] |
|
|
* ] |
|
|
|
|
|
==External links== |
|
|
* in the ] |
|
|
|
|
|
== References == |
|
== References == |
| Line 45: |
Line 69: |
|
] |
|
] |
|
] |
|
] |
|
|
] |