Octyl glucoside

β-D-Octyl glucoside

Names
IUPAC name Octyl β-D-glucopyranoside
Systematic IUPAC name (2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-(octyloxy)oxane-3,4,5-triol
Other names n-Octyl-β-D-glucoside
Identifiers
CAS Number	29836-26-8 Y
3D model (JSmol)	Interactive image
ChemSpider	56585 Error creating thumbnail: N
ECHA InfoCard
EC Number	249-887-8
E number
MeSH	C018619
PubChem CID	62852
UNII	V109WUT6RL Y
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=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 Error creating thumbnail: N Key: HEGSGKPQLMEBJL-RKQHYHRCSA-N Error creating thumbnail: N 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 Key: HEGSGKPQLMEBJL-RKQHYHRCBI
SMILES CCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
Properties
Chemical formula	C14H28O6
Molar mass	292.37 g/mol
Surface tension:
CMC	0.025 M
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Error creating thumbnail: N verify (what is YError creating thumbnail: N ?) Infobox references

Octyl glucoside (n-octyl-β-d-glucoside) is a nonionic surfactant frequently used to solubilise integral membrane proteins for studies in biochemistry. Structurally, it is a glycoside derived from glucose and octanol. Like Genapol X-100 and Triton X-100, it is a nonphysiological amphiphile that makes lipid bilayers less "stiff".

Applications

Octyl glucoside has become one of the most important detergents for purification of membrane proteins because it generally does not denature the protein and can readily be removed from final protein extracts. Above its critical micelle concentration of 0.025 M (~0.7% w/v), it was noted as the best detergent for improving selectivity of immunoprecipitation of phosphotyrosine modified proteins. This detergent has also been shown to rapidly inactivate infective HIV at concentrations above its CMC.

The compound gained popularity with researchers following the publication of an improved synthesis in 1978. However, in 1990 the cost remained prohibitive for large-scale protein isolation.

Octyl glucoside has been proposed as a conditioning agent to prevent microbial colonization of contact lenses, due to its ability to lower the hydrophobicity of contact lenses and prevent adhesion of Staphylococcus epidermidis and Pseudomonas aeruginosa.

See also

• Decyl glucoside
• Lauryl glucoside
• Alkyl polyglycoside
• octyl thioglucoside

External links

• octyl glucoside bound to proteins in the PDB