N-Octyl β-D-thioglucopyranoside

n-Octyl β-D-thioglucopyranoside
Names
	IUPAC name (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-octylsulfanyl-oxane-3,4,5-triol
	Other names (1S)-Octyl-β-D-thioglucoside
Identifiers
CAS Number	85618-21-9;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.115.951
PubChem CID	363418;
CompTox Dashboard (EPA)	DTXSID50893686 ;
	SMILES CCCCCCCCS[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O;
Properties
Chemical formula	C14H28O5S
Molar mass	308.434 g/mol
Appearance	Colourless Waxy Semi-Solid
Melting point	125 to 131 °C (257 to 268 °F; 398 to 404 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

n-Octyl β-D-thioglucopyranoside (octylthioglucoside, OTG) is a detergent that is used for cell lysis or to solubilise membrane proteins without denaturing them. This is particularly of use in order to crystallise them or to reconstitute them into lipid bilayers. It has a critical micelle concentration of 9 mM.^[1]

It is an analog of the commonly used detergent octyl glucoside, the presence of the thioether linkage making it resistant to degradation by beta-glucosidase enzymes.

References

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