147025-06-7

Basic information

• Product Name: DODECYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• Synonyms: DODECYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;Dodecyl2-acetamido-2-deoxy-b-D-glucopyranoside;DODECYL 2-ACETAMIDO-2-DEOXY-SS-D-GLUCOPYRANOSIDE;Dodecyl 2-acetamido-2-deoxy-β-D-glucopyranoside;Dodecyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside
• CAS NO: 147025-06-7
• Molecular Formula: C₂₀H₃₉NO₆
• Molecular Weight: 389.52676
• EINECS: 1533716-785-6
• Mol File: 147025-06-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 165-167℃
• Appearance: /
• CAS DataBase Reference: DODECYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DODECYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(147025-06-7)
• EPA Substance Registry System: DODECYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(147025-06-7)

Safety Data

• Hazardous Substances Data: 147025-06-7(Hazardous Substances Data)

Usage

General Description

Dodecyl 2-acetamido-2-deoxy-beta-D-glucopyranoside is a chemical compound used primarily as a surfactant and detergent in various commercial and industrial applications. It is a derivative of glucose and consists of a dodecyl hydrophobic tail and a hydrophilic glucoside head group. This structure allows it to effectively lower the surface tension of water, making it useful in cleaning products and as a dispersing agent in pharmaceuticals. Additionally, it has been investigated for its potential as a drug delivery system due to its ability to solubilize and stabilize hydrophobic drugs. Overall, dodecyl 2-acetamido-2-deoxy-beta-D-glucopyranoside has versatile applications in various fields, making it a valuable chemical in the market.

Upstream product

• 112-53-8 1-dodecyl alcohol 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 173725-26-3 n-dodecyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranoside 
• 112929-24-5 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 211567-22-5 dodecyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 159302-84-8 n-dodecyl 2-amino-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 211567-29-2 1-dodecyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside 
• 211567-35-0 Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-dodecyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine 
• 211567-26-9 Methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-7-acetylamino-6-dodecyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 195006-97-4 dodecyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside 
• 824396-58-9 N-[8-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-6-dodecyloxy-2-styryl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 824396-63-6 1-dodecyl 2-acetamido-3-O-benzyloxycarbonyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 824396-53-4 1-dodecyl 2-acetamido-3-O-benzyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 824396-65-8 1-dodecyl 2-acetamido-2-deoxy-3-O-methanesulfonyl-(R)-4,6-O-(E-2-methyl-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 824396-64-7 1-dodecyl 2-acetamido-2-deoxy-3-O-methanesulfonyl-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside 

Relevant articles and documents

Effect of Aglycon Structure on Saccharide Elongation by Cells

Alkyl N-acetyl-β-D-glucosaminide (GlcNAc primers) with different aglycon moieties were synthesized and used to determine the effect of the aglycon structure on cellular saccharide elongation. Dodecyl N-acetyl-β-D-glucosaminide (GlcNAc-C12), tridecan-7-yl N-acetyl-β-D-glucosaminide (GlcNAc-2C6), and pentacosan-13-yl N-acetyl-β-D-glucosaminide (GlcNAc-2C12) primers were synthesized by glycosylation of dodecan-1-ol, tridecan-7-ol, and pentacosan-13-ol, respectively, with peracetylglucosamine. These primers were introduced to mouse B16 melanoma cells to prepare glycolipids. After 48 h incubation, results showed that GlcNAc-C12 was elongated to give NeuAc-Gal-GlcNAc-C12. GlcNAc-2C6 was also elongated to afford Gal-GlcNAc-2C6 and NeuAc-Gal-GlcNAc-2C6. On the other hand, GlcNAc-2C12 primer was not elongated. Significantly, the results demonstrated that the amount of glycosylated product increased 1.5-times by modifying the aglycon structure of GlcNAc from C12 to 2 C6 despite having almost the same number of C-units.

Synthesis and protective anti-infective action of anomeric lipophilic glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine

Anomeric pairs of α-and β-dodecyl, α-and β-(1-pentylhexyl), and α-and β-cyclododecyl glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) were synthesized. The starting β-D-glucosaminides were obtained by the oxazoline method, and the corresponding α-isomers, by the mercuric iodide-catalyzed glycosylation of alcohols with α-glucosaminyl chloride peracetate in nitromethane at ～90°C. No reliable differences between the stimulation of mouse resistance to the infection with Staphylococcus aureus (doses of 2, 20, and 200 μg/mouse) and Escherichia coli (doses of 0.05, 1, and 20 μg/mouse) with the MDP α-and β-glycosides were found. Pleiades Publishing, Inc., 2006.

Alkylating agents from sugars. Cyclophosphamides derived from 2-amino- 2-deoxy-D-allose

Cyclophosphamides derived from alkyl 2-amino-4,6-O-benzylidene-2-deoxy- β-D-allopyranosides have been synthesized with good yield by treatment of the corresponding 2-amino-2-deoxy-D-allose derivatives with bis(2- chloroethyl)phosphoramide dichloride. The ring-forming reaction took place with very high diastereoselectivity. Subsequent hydrogenolysis gave excellent yields of cyclophosphamides derived from alkyl 2-amino-2-deoxy-β-D- allopyranosides, with hydrophilicity greater than that of the precursors. The starting material was easily available from 2-acetamido-2-deoxy-D-glucose.