29980-16-3

Basic information

• Product Name: N-DODECYL A-D-GLUCOPYRANOSIDE
• Synonyms: N-DODECYL A-D-GLUCOPYRANOSIDE;dodecyl alpha-D-glucopyranoside;Dodecyla-D-glucopyranoside;1-O-Dodecyl-α-D-glucopyranose;Dodecyl α-D-gluco-hexopyranoside;Dodecyl alpha-D-glucoside;Lauryl alpha-D-glucopyranoside;n-Dodecyl alpha-D-glucopyranoside
• CAS NO: 29980-16-3
• Molecular Formula: C₁₈H₃₆O₆
• Molecular Weight: 348.47484
• EINECS: 249-988-7
• Mol File: 29980-16-3.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 499.1 °C at 760 mmHg
• Flash Point: 255.6 °C
• Appearance: /
• Density: 1.12 g/cm³
• Vapor Pressure: 4.72E-12mmHg at 25°C
• Refractive Index: 1.508
• Storage Temp.: −20°C
• CAS DataBase Reference: N-DODECYL A-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-DODECYL A-D-GLUCOPYRANOSIDE(29980-16-3)
• EPA Substance Registry System: N-DODECYL A-D-GLUCOPYRANOSIDE(29980-16-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 29980-16-3(Hazardous Substances Data)

Usage

General Description

N-dodecyl α-D-glucopyranoside is a chemical compound which functions as a non-ionic detergent. It is widely used in biochemical applications, especially when maintaining the native state of proteins is critical. It has a glucopyranose (a type of sugar molecule) core and a hydrophobic tail, a structure that makes it ideal for breaking down the lipid (fat) layers of cell membranes. It is also notable for having relatively low toxicity compared to other detergents. While it is a complex chemical, its main implication is in the realm of biochemistry, where it is employed for its detergent-like properties.

InChI:InChI=1/C18H36O6/c1-2-3-4-5-6-7-8-9-10-11-12-23-18-17(22)16(21)15(20)14(13-19)24-18/h14-22H,2-13H2,1H3/t14-,15-,16+,17-,18+/m1/s1

Upstream product

• 83-87-4 D-glucose pentaacetate 
• 75618-27-8 lauryl triflate 
• 112-53-8 1-dodecyl alcohol 
• 9004-34-6 cellulose 
• 71-36-3 butan-1-ol 
• 604-69-3 β-D-glucose pentaacetate 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 82305-29-1 n-dodecyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 117076-31-0 dodecyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 440652-81-3 isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 1427214-08-1 dodecyl 4,6-O-benzylidene-β-D-galactopyrnoside 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 25878-60-8 D-galactose pentaacetate 

Downstream Products

• 263247-09-2 dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside 
• 263247-10-5 dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside 
• 263247-08-1 dodecyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-β-D-galactopyranoside 
• 504422-56-4 dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-57-5 dodecyl 2,4,6-tri-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-51-9 dodecyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-54-2 dodecyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-50-8 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-52-0 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-53-1 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-58-6 dodecyl 2,3,4,6-tetra-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 258349-81-4 dodecyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-48-4 dodecyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 

Relevant articles and documents

Selective lipase-catalysed 6-O-acylation of alkyl α-D-glucopyranosides using functionalized ethyl esters

Alkyl α-D-glucopyranosides were selectively converted into their 6-O-acyl esters by lipase-catalysed transesterification with ethyl acrylate or ethyl 4-chlorobutanoate.Comparison of six lipase preparations showed large differences in activity and selectivity.The addition of zeolite CaA for selective adsorption of ethanol and water, exerted profound effects on conversion and regioselectivity of the transesterification.A quantitative conversion with high selectivity was achieved using lipases from C. antarctica in the presence of zeolite CaA.

Catalytic glycosylation of glucose with alkyl alcohols over sulfonated mesoporous carbons

Herein we investigated the catalytic performances of sulfonated mesoporous carbons in the glycosylation of carbohydrates with alkyl alcohols. Catalytic performances were compared to common solid acid catalysts previously reported for this reaction. Under optimized conditions, the targeted alkyl glycosides were obtained in 85% yield, together with a turn over frequency and a space time yield higher than those of the best heterogeneous catalysts reported so far in such reaction. Furthermore, the presence of mesoporous channels significantly lowered the deactivation rate of the catalyst in comparison to a non-porous sulfonated carbon.

Novel mixed-heteroatom macrocycles via templating: A new protocol

A series of novel thiadiaza and triaza crown ether attached galactose- and glucose-based glycolipids is synthesized, applying a new strategy. The key step is the formation of α-chloroacetamido precursors (14 and 21) from selectively protected bis(cyanomethyl)-glycolipids (13 and 19) in two steps. The cyclization reaction furnishes good yields in relatively short times in aqueous ethanol or acetonitrile. To generalize this method, macrocycles 3 and 25 are reported as well. Attempts to use the traditional synthetic approaches for cyclization failed to provide reasonable yields.