6801-91-8

Basic information

• Product Name: n-decanyl β-D-galactopyranoside
• CAS NO: 6801-91-8
• Molecular Weight: 320.426
• Mol File: 6801-91-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: n-decanyl β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: n-decanyl β-D-galactopyranoside(6801-91-8)
• EPA Substance Registry System: n-decanyl β-D-galactopyranoside(6801-91-8)

Safety Data

• Hazardous Substances Data: 6801-91-8(Hazardous Substances Data)

Upstream product

• 112-30-1 1-Decanol 
• 25878-60-8 D-galactose pentaacetate 
• 440652-81-3 isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 2816-24-2 o-nitrophenyl D-galactopyranoside 
• 103168-14-5 Decyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 

Relevant articles and documents

Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics

A series of 19 synthetic alkyl and thioalkyl glycosides derived from D-mannose, D-glucose and D-galactose and having C10–C16 aglycone were investigated for cytotoxic activity against 7 human cancer and 2 non-tumor cell lines as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-D-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-D-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides (18, 19) were inactive against all tested bacteria and yeast strains, they could be a target-specific for eukaryotic cells. On the other hand, β-D-glucopyranosides with tetradecyl (11) and hexadecyl (12) aglycone inhibited only Gram-positive bacterial strain Enterococcus faecalis. The studied glycosides induce changes in the lipid bilayer thickness and lateral phase separation at high concentration, as derived from SAXS experiments on POPC model membranes. In general, glucosides and galactosides exhibit more specific properties. Those with longer aglycone show high cytotoxicity and therefore, they are more promising candidates for cancer cell line targeted inhibition.

Synthesis and Properties of Alkyl β-d-Galactopyranoside

A series of alkyl β-d-galactopyranosides were prepared by the trichloroacetimidate method with d-galactose and alcohols with different chain lengths as raw materials. Their solubility, surface tension, emulsification, foaming, wettability, thermotropic liquid crystalline properties, and thermal stability were investigated. Alkyl β-d-galactopyranosides are soluble in water and ethanol, and the solubility decreases with increasing alkyl chain length. Decyl β-d-galactopyranoside was insoluble in water, but soluble in ethanol. Dissolution of alkyl β-d-galactopyranoside in water is an endothermic process with dissolution enthalpies greater than zero. Nonyl β-d-galactopyranoside had an excellent emulsifying?property, better foaming ability and the best foam stability. The CMC values of alkyl β-d-galactopyranosides decrease with increasing of alkyl chain length. Alkyl β-d-galactopyranosides are thermally stable up to 270?°C. Alkyl β-d-galactopyranosides show the distinctive optical texture of a thermotropic liquid crystal smectic A type phase. Decyl β-d-galactopyranoside showed the strongest wettability.

Synthesis of C7-C16-alkyl glycosides: Part III - Synthesis of alkyl D-galactopyranosides in the presence of tin(IV) chloride as a Lewis acid catalyst

The Lewis acid catalyzed glycosylation reaction of β-peracetylated sugar derivative (galactose) with fatty alkanols is used in a synthesis of C7-C16-alkyl galactopyranosides. The process occurs under the influence of tin(IV) chloride as a Lewis acid catalyst.