54549-27-8

Basic information

• Product Name: hexadecyl D-glucoside
• Synonyms: hexadecyl D-glucoside;D-Glucopyranoside, hexadecyl;Hexadecyl D-glucopyranoside
• CAS NO: 54549-27-8
• Molecular Formula: C₂₂H₄₄O₆
• Molecular Weight: 404.58116
• EINECS: 259-220-2
• Mol File: 54549-27-8.mol

Chemical Properties

• Boiling Point: 543.6°C at 760 mmHg
• Flash Point: 282.6°C
• Appearance: /
• Density: 1.07g/cm³
• Vapor Pressure: 4.38E-14mmHg at 25°C
• Refractive Index: 1.504
• PKA: 12.95±0.70(Predicted)
• CAS DataBase Reference: hexadecyl D-glucoside(CAS DataBase Reference)
• NIST Chemistry Reference: hexadecyl D-glucoside(54549-27-8)
• EPA Substance Registry System: hexadecyl D-glucoside(54549-27-8)

Safety Data

• Hazardous Substances Data: 54549-27-8(Hazardous Substances Data)

Usage

Uses

Used in Personal Care and Cosmetic Industry:
Hexadecyl D-glucoside is used as a non-ionic surfactant for its excellent foaming properties and mildness, making it suitable for incorporation into shampoos, body washes, and skincare formulations.
Used in Environmentally-Friendly Cleaning Products:
Hexadecyl D-glucoside is used as a key component in environmentally-friendly cleaning products due to its low toxicity, contributing to the development of safer and more sustainable cleaning solutions.

InChI:InChI=1/C22H44O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-27-22-21(26)20(25)19(24)18(17-23)28-22/h18-26H,2-17H2,1H3/t18-,19-,20+,21-,22?/m1/s1

Upstream product

• 2280-44-6 D-Glucose 
• 36653-82-4 1-Hexadecanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 685841-27-4 peracetylated 1-O-palmityl-D-glucose 

Downstream Products

• 75319-63-0 hexadecyl β-D-glucopyranoside 

Relevant articles and documents

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.

Preparation and surface activity of phosphated alkyl oligoglucosides

A family of phosphated alkyl oligoglucoside surfactants was prepared by reacting alkyl oligoglucosides with phosphorus oxychloride. The alkyl oligoglucosides were obtained by an usual method in which the glucose is reacted with a fatty alcohol containing 10-18 carbon atoms. These novel phosphated surfactants have been found to exhibit good surface tension, foaming and wetting power. The critical micelle concentration was found to increase with the length of hydrocarbon chain of the surfactant. The surface excess concentration and the interfacial area per surfactant molecule are reported. These phosphated surfactants also exhibit a good performance to improve the whiteness and wetting of cotton fabrics in a hydrogen oxide bleaching system, and they are also found to be more biodegradable than conventional surfactants. AOCS 2010.

Medicament comprising a reducing alkyl-sugar monomer for the treatment of inflammatory disorders

The invention relates to a medicament comprising at least one reducing alkyl-sugar monomer having a hydroxyl function which is substituted by an alkoxy radical at C2-C40, said medicament being preferably intended to regulate inflammatory mechanisms. The reducing sugar is preferably selected from the group containing rhamnose, fucose and glucose. The invention also relates to a cosmetic treatment method involving the topical application of a composition comprising at least one reducing alkyl-sugar monomer having a hydroxyl function which is substituted by an alkoxy radical at C2-C40.

Synthesis of n-alkyl glucosides by amyloglucosidase

Amyloglucosidase from Rhizopus mold (3.2.1.3) has been employed for the synthesis of n-alkyl glucosides from alcohols of carbon chain lengths Cl to C18 by both shake flask and reflux methods. Glucoside yields obtained from the reflux method (5-44%) are better than those from the shake flask method (3-28%). While the shake flask method favoured glucosylation of medium chain length alcohols, the reflux method at pH 5.0, favoured glucosylation of all the chain lengths. n-Octyl-D-glucoside, n-octyl-maltoside and n-octyl-sucroside are also synthesized and optimum conditions for the synthesis of n-octyl-D-glucoside at both shake flask and reflux methods have been worked out.

1-O-Palmityl-D-glucuronate Endows Liposomes with Long Half-Life In Vivo

More liposomes containing 1-O-palmityl-D-glucuronic acid (PGA), a synthetic glycolipid, bound to macrophages than those containing phosphatidylglycerol did in vitro; however, PGA-liposomes circulated longer in vivo.PGA-liposomes did not aggregate in the presence of serum, but liposomes containing 1-O-palmityl-D-glucose or myristic acid aggregated rapidly, suggesting that both carbohydrate and carboxyl group of PGA are important for preventing liposomal aggregation in serum.This low agglutinative character may be one of the factors for long circulation of PGA-liposomes in vivo.