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
• Article Data: 10

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

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

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.

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)

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.