Octyl β-D-thioglucopyranoside is a nonionic detergent with applications in membrane biochemistry. Octyl β-D-thioglucopyranoside has solubilizing ability for E. coli membrane proteins.

Physicochemical Properties

Molecular Formula	C14H28O5S
Molecular Weight	308.43
Exact Mass	308.165
CAS #	85618-21-9
PubChem CID	656909
Appearance	White to off-white solid powder
Density	1.2±0.1 g/cm3
Boiling Point	489.7±45.0 °C at 760 mmHg
Melting Point	125-131 °C
Flash Point	250.0±28.7 °C
Vapour Pressure	0.0±2.8 mmHg at 25°C
Index of Refraction	1.548
LogP	1.83
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	9
Heavy Atom Count	20
Complexity	254
Defined Atom Stereocenter Count	5
SMILES	S([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)CCCCCCCC
InChi Key	CGVLVOOFCGWBCS-RGDJUOJXSA-N
InChi Code	InChI=1S/C14H28O5S/c1-2-3-4-5-6-7-8-20-14-13(18)12(17)11(16)10(9-15)19-14/h10-18H,2-9H2,1H3/t10-,11-,12+,13-,14+/m1/s1
Chemical Name	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-octylsulfanyloxane-3,4,5-triol
Synonyms	2-HYDROXYMETHYL-6-OCTYLSULFANYL-TETRAHYDRO-PYRAN-3,4,5-TRIOL; (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(octylsulfanyl)oxane-3,4,5-triol; octyl beta-d-thioglucopyranoside; 85618-21-9; n-octyl-beta-D-thioglucopyranoside; Octyl thioglucoside; b-D-Glucopyranoside, octyl 1-thio-; octyl b-d-thioglucopyranoside;
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Non-ionic detergent
ln Vitro	n-Octyl beta-D-thioglucopyranoside, a new non-ionic detergent, was synthesized. Properties, and applicability to membrane proteins, of this detergent were investigated. The detergent was easily removed by dialysis. The solubilizing power of this detergent for Escherichia coli membrane proteins was similar to that of n-octyl beta-D-glucopyranoside, which has been widely used in membrane biochemistry. No inactivation of proteins was observed after the solubilization. n-Octyl beta-D-thioglucopyranoside was superior to n-octyl beta-D-glucopyranoside in that it was much more stable and could be synthesized at much lower cost [1].
Enzyme Assay	Determination of glucosides [1] Octyl thioglucoside was determined either by g.l.c. after trimethylsilylation or by the anthrone method (Roe, 1955). Octyl glucoside and glucose were determined by the anthrone and glucose oxidase methods (Okada et al., 1981) respectively. Solubilization of membrane proteins [1] Membrane vesicles of E. coli were prepared as described previously (Tsuchiya et al., 1982b). Extractability of the proteins from the membrane vesicles was determined as described by Hanatani et al. (1984). ATPase assay [1] ATPase activity was measured as described by Tsuchiya et al. (1982a). One unit of ATPase activity is defined as lymol of ATP hydrolysed/ min.
References	[1]. Characteristics of n-octyl beta-D-thioglucopyranoside, a new non-ionic detergent useful for membrane biochemistry. Biochem J. 1984 Sep 15;222(3):829-32.
Additional Infomation	N-Octyl-beta-D-thioglucopyranoside is a S-glycosyl compound. The effect of octyl thioglucoside on the solubilization of E. coli membrane proteins was tested at concentrations of the detergent higher than the CMC. With increasing concentrations of octyl thioglucoside, an increasing amount of protein was solubilized (Fig. 3). The solubilizing power of octyl thioglucoside for the membrane proteins was similar to that of octyl glucoside and nonanoyl and decanoyl N-methylglucamides (Hanatani et al., 1984). We measured the H+ -translocating ATPase activity in the solubilized fractions. The H+- E 30 a) = 20 co 0 translocating ATPase is a membrane enzyme composed of two portions, F1 (extrinsic membrane component) and Fo (intrinsic membrane component). The ATPase was solubilized with octyl thioglucoside (Fig. 3). The activity was sensitive to dicyclohexylcarbodi-imide (results not shown), which means that the ATPase was solubilized as F1-Fo complex. The specific activity of the ATPase was 2.5 units/mg of protein, which was comparable with the value shown by the F1-Fo complex when it is solubilized with other detergents (about 3 units/mg of protein; T. Tsuchiya, unpublished work). Solubilization and reconstitution of the melibiose carrier of E. coli membrane were also successfully performed with octyl thioglucoside (T. Tsuchiya & S. Saito, unpublished work). The specific activity of melibiose transport in the'reconstituted proteoliposomes was similar to that of proteoliposomes reconstituted with octyl glucoside. Thus the solubilizing power and nondenaturing property of octyl thioglucoside on E. coli membrane proteins are similar to those of octyl glucoside[1]

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.2422 mL	16.2111 mL	32.4223 mL
	5 mM	0.6484 mL	3.2422 mL	6.4845 mL
	10 mM	0.3242 mL	1.6211 mL	3.2422 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.