87246-72-8

Basic information

• Product Name: 1-deoxy-1-[methyl(1-oxododecyl)amino]-D-glucitol
• Synonyms: 1-Deoxy-1-(methyl(1-oxododecyl)amino)-D-glucitol; N-Lauroyl meglumine; D-Glucitol, 1-deoxy-1-(methyl(1-oxododecyl)amino)-; 1-deoxy-1-[dodecanoyl(methyl)amino]-D-glucitol
• CAS NO: 87246-72-8
• Molecular Formula: C₁₉H₃₉NO₆
• Molecular Weight: 377.5161
• EINECS: 289-309-1
• Mol File: 87246-72-8.mol

Chemical Properties

• Boiling Point: 611.416°C at 760 mmHg
• Flash Point: 323.573°C
• Density: 1.125g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: 1-deoxy-1-[methyl(1-oxododecyl)amino]-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-deoxy-1-[methyl(1-oxododecyl)amino]-D-glucitol(87246-72-8)
• EPA Substance Registry System: 1-deoxy-1-[methyl(1-oxododecyl)amino]-D-glucitol(87246-72-8)

Safety Data

• Hazardous Substances Data: 87246-72-8(Hazardous Substances Data)

Usage

Uses

Used in Personal Care Industry:
1-deoxy-1-[methyl(1-oxododecyl)amino]-D-glucitol is used as a surfactant and emulsifying agent in personal care products such as shampoos and conditioners, providing foaming properties and enhancing the texture and performance of these products.
Used in Chemical Manufacturing:
1-deoxy-1-[methyl(1-oxododecyl)amino]-D-glucitol is used as a component in the production of pesticides, lubricants, and other chemical products, leveraging its surfactant properties to improve the performance and stability of these formulations.

Upstream product

• 106-33-2 ethyl laurate 
• 6284-40-8 1-deoxy-1-(methylamino)-D-glucitol 
• 143-07-7 lauric acid 
• 111-82-0 methyl n-dodecanoate 

Relevant articles and documents

Use Of N-Methyl-N-Acylglucamines As Solubilizers

The invention relates to the use of N-methyl-N-C8-C14-acylglucamines as solubilizers in cosmetic preparations. The invention further relates to clear lotions for the preparation of wet wipes, comprising a) 0.1 to 5.0 wt.-% of the N-methyl-N—C8-C14-acylglucamines, b) 0.05 to 5% of one or more water-insoluble or only partially water-soluble anti-microbial agents, c) 0 to 5 wt.-% of one or more oils, d) 85 to 99.85 wt.-% of water, e) 0 to 5 wt.-% of surfactants, and f) 0 to 5 wt.-% of additional auxiliaries and additives.

Mixed Sugar Compositions

Novel mixtures of sugar amides or sugar amines are disclosed that have improved thermal properties over the individual components. New feedstocks based on both the surfactant tail as well as the sugar head group allow for improved physical properties of sugar amide surfactant mixtures and thus improved formulatability. Furthermore, new sources of unique methyl esters from both bioengineering and or co-metathesis of fats and oils provide novel and improved sugar amide surfactant mixtures.

Enzymatic synthesis of N-alkanoyl-N-methylglucamide surfactants: Solvent-free production and environmental assessment

A biocatalysis based method for the solvent-free production of N-alkanoyl-N-methylglucamide (MEGA) surfactants was developed and used as a case study for the evaluation of different environmental assessment tools, such as the freeware package EATOS (Environmental Assessment Tool for Organic Synthesis). In order to also consider energy usage and process facilities, e.g. heating, stirring and vacuum, a complementary tool was needed; hence the EcoScale method and the use of an energy monitoring socket were also exploited. The solvent-free method followed by a simple hydrolysis step gave a final amide yield of 99% and a product essentially free of remaining substrate, N-methylglucamine (MEG). The latter is important since MEG can potentially be converted to carcinogenic nitrosamines. The absence of solvent in the reaction medium was also found to result in a significantly reduced potential environmental impact. The environmental tools used in this study were further scrutinized, and even if they represent some of the best freely available tools for evaluation of early stage process development, some points for further improvements are suggested.

Lipase-catalyzed chemoselective N-acylation of amino-sugar derivatives in hydrophobic solvent: Acid-amine ion-pair effects

Enzymatic N-acylation of N-methyl-glucamine (1-deoxy-1-methylamino-D-glucitol) in hexane using lipase from Rhizomucor miehei (Lipozyme) is described. N-methyl-glucamine was solubilized by oleic acid addition which resulted in the formation of an ion-pair between acid and amine function. This ion-pair, identified by Infra-Red spectroscopy, is essential for amide or ester synthesis. Its stability in hexane was also found to be the limiting factor of reaction yield which never exceeded 50% of acid conversion. The chemoselectivity of the reaction between oleic acid and N-methyl-glucamine towards amide or ester synthesis was under the control of acid/amine ratio. This is the first report showing the key role of substrate ionic state shen operating enzyme catalysis in non-conventional media.

Enzymatic synthesis of glycamide surfactants by amidification reaction

The condensation of a secondary amine (N-methyl-glucamine) with oleic acid was selected as a reaction model to study the production of glycamide surfactants by enzymatic amidification. Reactions catalyzed by immobilized lipase from Candida antarctica were carried out in 2-methyl-2-butanol. The acido-basic conditions (through the N-methyl glucamine / oleic acid ratio) control the chemoselectivity of the reaction allowing the synthesis of either amide, ester or amide-ester. At 90°C and with a N-methyl-glucamine I acid ratio of 1, a 100% conversion yield with 97% of amide synthesis was obtained in less than 50 hours. The process was applied to the preparation of a range of amides using various amines and acyl donors. This process is the first that describes successful amide bond synthesis from a hydroxylated secondary amine and fatty acid or fatty acid ester.