54549-25-6

Basic information

• Product Name: decyl D-glucoside
• Synonyms: decyl D-glucoside;D-Glucopyranoside, decyl;Einecs 259-218-1;APG10
• CAS NO: 54549-25-6
• Molecular Formula: C₁₆H₃₂O₆
• Molecular Weight: 320.42168
• EINECS: 259-218-1
• Mol File: 54549-25-6.mol

Chemical Properties

• Boiling Point: 476.5 °C at 760 mmHg
• Flash Point: 242 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 4.4E-11mmHg at 25°C
• Refractive Index: 1.511
• PKA: 12.95±0.70(Predicted)
• CAS DataBase Reference: decyl D-glucoside(CAS DataBase Reference)
• NIST Chemistry Reference: decyl D-glucoside(54549-25-6)
• EPA Substance Registry System: decyl D-glucoside(54549-25-6)

Safety Data

• Hazardous Substances Data: 54549-25-6(Hazardous Substances Data)

Usage

Contact allergens

Decyl glucoside or decyl d-glucoside, also named decylbeta- d-glucopyranoside, belongs to the alkyl glucosides family and is obtained by condensation of the fatty alcohol decyl alcohol and a d-glucose polymer. This nonionic surfactant and cleansing agent has been widely used for several years, due to its foaming power and good tolerance in rinse-off products such as shampoos, hair dyes and colors, and soaps. Decyl glucoside is also employed in leave-on products such as no-rinsing cleansing milks, lotions, and several sunscreen agents and is contained as a stabilizing surfactant of organic microparticles in sunscreen agent Tinosorb? M.

InChI:InChI=1/C16H32O6/c1-2-3-4-5-6-7-8-9-10-21-16-15(20)14(19)13(18)12(11-17)22-16/h12-20H,2-11H2,1H3/t12-,13-,14+,15-,16?/m1/s1

Synthetic route

D-Glucose (2280-44-6) + 1-Decanol (112-30-1) → Decyl α/β-D-glucopyranoside (54549-25-6)

Conditions	Yield
With succinic acid; choline chloride at 80 - 95℃; Reagent/catalyst; Inert atmosphere; Green chemistry;	74%
With amyloglucosidase of Rhizopus mold In di-isopropyl ether; acetate buffer at 68℃; for 72h; pH=4.0;	29 % Turnov.
With toluene-4-sulfonic acid at 100℃; for 8h;
With 1-butyl-3-methylimidazolium hydrogen sulfate; sulfuric acid at 70 - 110℃; for 5h; Reagent/catalyst; Temperature; Inert atmosphere;

D-Glucose (2280-44-6) + didecyl sulfate (66186-16-1) → Decyl α/β-D-glucopyranoside (54549-25-6)

Conditions	Yield
With sodium hydride In various solvent(s) Ambient temperature;	57%

D-glucose (50-99-7) + 1-Decanol (112-30-1) → 1-decyl-D-glucofuranoside + Decyl α/β-D-glucopyranoside (54549-25-6)

Conditions	Yield
With H-FAU at 130℃; Reagent/catalyst;	A 20.2% B 55.1%
With H-MOR at 130℃; Reagent/catalyst;	A 40% B 15.4%

D-glucose (50-99-7) + 1-Decanol (112-30-1) → decyl glucofuranoside + Decyl α/β-D-glucopyranoside (54549-25-6)

Conditions	Yield
With H-FAU(3) catalyst for 4h; Reagent/catalyst;	A 15.6% B 50.4%

1-Decanol (112-30-1) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → Decyl α/β-D-glucopyranoside (54549-25-6)

Conditions	Yield
With sodium methylate; silver carbonate; silver(l) oxide 2) MeOH; Multistep reaction;

1-Decanol (112-30-1) + oat spelt xylan → n-decyl L-arabinoside (1309041-48-2) + Decyl α/β-D-glucopyranoside (54549-25-6) + Decyl α/β-D-Xylopyranoside

Conditions	Yield
With sulfuric acid; water at 90℃; for 3h;

Upstream product

• 2280-44-6 D-Glucose 
• 66186-16-1 didecyl sulfate 
• 112-30-1 1-Decanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 9004-34-6 cellulose 
• 50-99-7 D-glucose 

Relevant articles and documents

Decyl glucoside synthesized by direct glucosidation of d-glucose over zeolite catalysts and its estrogenicity as non-endocrine disruptive surfactant

The estrogenicity of decyl glucoside was asserted as a non-endocrine disruptive surfactant with its preparation method using zeolite catalysts. Its estrogenicity was estimated using E-Assay method. The decyl glucoside was synthesized by direct glucosidation from D-glucose with 1-decanol. The conversion and yield were improved with increasing of amount of acid sites of the zeolite catalysts. The decyl glucopyranoside is more hydrophilic than nonylphenol and has a high wettability. The decyl glucopyranosides exhibited extremely lower proliferation of estrogenic cell compared with nonylphenol.

Method for preparing alkyl glycoside

The invention provides a method for preparing alkyl glycoside. The method comprises the following steps: providing a deep-eutectic solvent as a catalyst, wherein the deep-eutectic solvent consists ofcholine chloride and hydrogen-bond donors, and the structural formula of the choline chloride is shown as the formula (I) in the original specification; performing a reaction on the deep-eutectic solvent, glucose and fatty alcohol, so as to generate the alkyl glycoside, wherein the molar ratio of the choline chloride and the hydrogen-bond donors is 1: 1. Therefore, by utilizing the characteristicsof the deep-eutectic solvent of being uneasy in volatilization and combustion, good in heat stability and solubility, easy in recovery, repeatable in use and the like, the reaction is performed on the deep-eutectic solvent, the glucose and the fatty alcohol to generate the alkyl glycoside, the utilization rate of atoms in a synthesis process is as high as 100%, and the alkyl glycoside is low in toxicity and is biodegradable.

manufacturing method of decyl glucoside using zeolite catalyst

The invention relates to a zeolite catalyst using it will be burntcauchy writing base [tu[tu] manufacturing method is provided, more particularly zeolite catalyst to improve yield cauchy writing base [tu[tu]it will be burnt using specific and for improving product yields can be cauchy writing base [tu[tu]it will be burnt which selectively adjusts the method are disclosed. The present invention relates to glucose (glucose) 100 parts by weight of 200 to 3000 parts by weight of glass space this year (decanol) input and a reactor, reacting the glucose (decyl glucopyranoside) and it will be burntthe writing base nose ladle presbyopia [tu[tu]writing base nose bleed presbyopia [tu[tu]it will be burntspace this year zeolite catalyst under reaction to produce (decyl glucofuranoside) comprising the following steps. (by machine translation)

Method for preparing alkyl polyglycoside through concerted catalysis of ionic liquid compounding system

The invention belongs to a preparation method of alkyl polyglycoside, and particularly relates to a method for preparing the alkyl polyglycoside through concerted catalysis of an ionic liquid compounding system. According to the method disclosed by the invention, ionic liquid with catalytic activity is compounded with one or two of sulphuric acid, phosphoric acid, p-toluene sulfonic acid and dodecylbenzene sulfonic acid so that a novel catalysis system is formed, and the alkyl polyglycoside is prepared through the concerted catalysis of the novel catalysis system. The technology of the method disclosed by the invention has the advantages that the reaction efficiency of a unit catalyst is high and the reaction time is short.

Transformation of cellulose into biodegradable alkyl glycosides by following two different chemical routes

The transformation of cellulose into long-chain alkyl glycoside surfactants has been carried out following two different routes: (1) Direct transformation of cellulose to butyl-, hexyl-, octyl-, decyl- and dodecyl-α,β- glycosides in an ionic liquid media and Amberlyst-15Dry as catalysts, with mass yield of up to 82%; and (2) two steps reaction with transformation of cellulose into methyl glucosides, with a procedure described by Zhang et al., followed by transacetalation with 1-octanol and 1-decanol in the presence of Amberlyst-15Dry. A kinetic study for the direct transformation of cellulose using 1-octanol has shown that depolymerisation of cellulose continues during the Fischer glycosidation. Increasing the chain length of the alcohol decreases the global reaction rate owing to an increase in the lipophilicity of the alcohol that decreases its contact with the carbohydrates. Finally, several acid catalysts were tested and the best results were obtained with Amberlyst-15Dry.

Direct conversion of xylan into alkyl pentosides

Xylan has been used as a raw material in the synthesis of butyl, octyl and decyl glycosides. Mixtures of d-xylose-, l-arabinose- and d-glucose-based surfactants were obtained under smooth conditions with high yields in a one-pot process. The surface activities of octyl and decyl glycosides thus obtained have been studied and compared with that of pure alkyl d-xylosides. The results have confirmed that the new synthetic approach described in this paper is a potentially economical and efficient method for the preparation of environmentally friendly surfactants.

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.

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.

Anomeric O-Alkylation, 11. Anomeric O-Alkylation of O-Unprotected Hexoses and Pentoses - Convenient Synthesis of Decyl, Benzyl, and Allyl Glycosides

The base-promoted reaction of O-unprotected aldoses 1-6 with didecyl sulfate in DMPU affords decyl glycosides 1aα-6aα and 1aβ, 3aβ-6aβ in good overal yields.Similarly, the treatment of O-unprotected hexoses 1-4 and pentoses 5 and 6 with benzyl bromide and allyl bromide yields after subsequent O-acetylation monosaccharides 1cα-6cα, 1cβ, 3cβ-6cβ and 1dα-6dα, 1dβ, 3dβ-6dβ, respectively.The regio- and stereoselectivity in these reactions was determined by 1H-NMR spectroscopic data of the O-acetylated derivatives.Key Words: Aldoses, O-unprotected, glycoside formation / Anomeric oxides, alkylation / Alkylating agents, didecyl sulfate, benzyl bromide, allyl bromide / α-D-galacto-furanosides

Amphiphilic Carbohydrate-Based Mesogens, V. Mesogenic 1-O-Alkyl-D-glucitols from Alkyl D-Glucopyranosides

The endocyclic acetal bonds of alkyl D-glucopyranosides (hexyl to decyl, 1a-e) are regioselectively hydroborated with ethyldiboranes(6) in the presence of 9-methylsulfonyloxy-9-borabicyclononane (MSBBN) after conversion to their 2,3,4,6-tetra-O-diethylboryl derivatives 2a-e.Subsequent deboronations give the mesogenic 1-O-alkyl-D-glucitols 3a-e.