29836-26-8Relevant articles and documents
Enzymatic synthesis of octyl glucoside catalyzed by almond β-glucosidase in organic media
Ducret, Amelie,Carriere, Jean-Francois,Trani, Michael,Lortie, Robert
, p. 653 - 656 (2002)
The synthesis of n-octyl-β-D-glucopyranoside can be performed by direct condensation of 1-octanol and glucose, catalyzed by immobilized almond β-glucosidase, using solid glucose suspended in 1-octanol as a reaction media. Both the rate of reaction and the conversion could be enhanced by using acetonitrile and N,N-dimethylformamide (DMF) as co-solvents, the latter giving the best results. The rate of reaction was dependent on the concentration of DMF and on the initial water activity (aw), with higher water activity fostering faster reactions. The rate increased with DMF concentration, up to 20% DMF, but diminished rapidly at higher concentrations. Product concentration could be increased from 40 to 100 mM by going from 0 to 20% DMF; however, it was not sensitive to the initial water activity.
Synthesis of octyl glucopyranoside by almond β-glucosidase adsorbed onto Celite R-640
Basso, Alessandra,Ducret, Amélie,Gardossi, Lucia,Lortie, Robert
, p. 2005 - 2008 (2002)
The synthesis of octyl glucoside from p-nitrophenyl glucopyranoside (p-NPG) and 1-octanol was carried out with almond β-glucosidase adsorbed onto Celite R-640. The influence of the amount of water added to the system as well as the addition of co-solvents
Development of novel inhibitors specific for human heparanase-1
Ohmae, Masashi,Fujita, Yuki,Takada, Junko,Kimura, Shunsaku
, p. 797 - 798 (2013)
The octylglycosides 1-3 having heparan sulfate fragments were designed as inhibitors specific for human heparanase-1. Inhibition experiments for the heparanase revealed the inhibitory effects of 1 and 3 (IC50 = 6 and 1.4mM, respectively). It was difficult for compound 2 to inhibit the heparanase activity. Furthermore, the inhibitory action of 3 was specific for the heparanase, whereas 1 and 2 also inhibited the hydrolysis activity of exoenzyme β-glucuronidase from bovine liver.
Sweet surfactants: Packing parameter-invariant amphiphiles as emulsifiers and capping agents for morphology control of inorganic particles
Voggel, Michael,Meinusch, Rebecca M.,Siewert, Vanessa,Kunkel, Marius,Wittmann, Valentin,Polarz, Sebastian
, p. 7214 - 7227 (2018/09/26)
Surfactants are not only pivotal constituents in any biological organism in the form of phospholipids, they are also essential for numerous applications benefiting from a large, internal surface, such as in detergents, for emulsification purposes, phase transfer catalysis or even nanoparticle stabilization. A particularly interesting, green class of surfactants contains glycoside head groups. Considering the variability of glycosides, a large number of surfactant isomers become accessible. According to established models in surfactant science such as the packing parameter or the hydrophilic lipophilic balance (HLB), they do not differ from each other and should, thus, have similar properties. Here, we present the preparation of a systematic set of glycoside surfactants and in particular isomers. We investigate to which extent they differ in several key features such as critical aggregation concentration, thermodynamic parameters, etc. Analytical methods like isothermal titration calorimetry (ITC), tensiometry, dynamic light scattering (DLS), small angle-X-ray scattering (SAXS), transmission electron microscopy (TEM) and others were applied. It was found that glycosurfactant isomers vary in their emulsification properties by up to two orders of magnitude. Finally, we have investigated the role of the surfactants in a microemulsion-based technique for the generation of zinc oxide (ZnO) nanoparticles. We found that the choice of the carbohydrate head has a marked effect on the shape of the formed inorganic nanocrystals.
Estrogenicity of octyl glucoside synthesized by direct glucosidation as non-endocrine disruptive surfactant
Chung, Kyong-Hwan,Kim, Hangun,Park, Young-Kwon,Kim, Byung-Hoon,Kim, Jung-Sik,Jung, Sang-Chul
, p. 1478 - 1481 (2017/12/12)
The estrogenicity of octyl glucoside was studied with its preparation method using microporous zeolites. Its estrogenicity was estimated using E-assay method to confirm the possibility as nonendocrine disruptive surfactant. The octyl glucoside was synthesized from D-glucose with 1-octanol by direct glucosidation. The high conversion of D-glucose was obtained on H-FAU zeolite which has a mild acid strength. The conversion and yield were improved with increasing of acid site amount of the zeolite catalysts. The octyl glucopyranoside is more hydrophilic than nonylphenol and has a high wettability. The octyl glucosides represented extremely lower estrogenic cell proliferation compared with nonylphenol.