82494-09-5

Basic information

• Product Name: N-DECYL-BETA-D-MALTOPYRANOSIDE
• Synonyms: 1-O-Decyl-beta-D-maltoside;Decyl beta-maltopyranoside;Decyl-β-D-maltoside solution;Detergent Screening Solution 24/Fluka kit no 66317;DECYL BETA-D-MALTOPYRANOSIDE;DECYL-BETA-D-MALTOSIDE;N-DECYL-4-O-ALPHA-D-GLUCOPYRANOSYL-BETA-D-GLUCOPYRANOSIDE;N-DECYL-BETA-D-MALTOPYRANOSIDE
• CAS NO: 82494-09-5
• Molecular Formula: C22H42O11
• Molecular Weight: 482.56
• EINECS: 231-791-2
• Mol File: 82494-09-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 689.4 °C at 760 mmHg
• Flash Point: 370.8 °C
• Appearance: White/Powder
• Density: 1.32 g/cm³
• Vapor Pressure: 5.36E-22mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL, clear
• BRN: 4923334
• CAS DataBase Reference: N-DECYL-BETA-D-MALTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-DECYL-BETA-D-MALTOPYRANOSIDE(82494-09-5)
• EPA Substance Registry System: N-DECYL-BETA-D-MALTOPYRANOSIDE(82494-09-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 82494-09-5(Hazardous Substances Data)

Usage

Description

N-DECYL-BETA-D-MALTOPYRANOSIDE, also known as n-Decyl-β-D-maltoside, is a nonionic surfactant that is commonly used to solubilize and stabilize membrane proteins. It is a glycoside resulting from the attachment of a decyl group to the reducing-end anomeric center of a beta-maltose molecule. It has a critical micelle concentration (CMC) value of 1.8 mM and is available as a white to off-white powder.

Uses

Used in Pharmaceutical Industry:
N-DECYL-BETA-D-MALTOPYRANOSIDE is used as a solubilizing agent for membrane proteins, which aids in their purification, characterization, and structural studies. It is particularly useful in the expression of functional recombinant GPCRs.
Used in Biochemistry Research:
N-DECYL-BETA-D-MALTOPYRANOSIDE is used as a tool in the study of α-helical membrane protein crystallization, which helps in understanding the structure and function of these proteins.
Used in Analytical Chemistry:
N-DECYL-BETA-D-MALTOPYRANOSIDE is used as a micelle agent in micellar electrokinetic chromatography for the investigation of enantiomer separation of drugs, enabling the analysis and separation of chiral compounds.
Used in Biochemistry Applications:
N-DECYL-BETA-D-MALTOPYRANOSIDE is used as a solubilizing agent to aid in the extraction and stabilization of active cytochrome oxidase from mitochondria, which is crucial for various biochemical and biophysical studies.

InChI:InChI=1/C22H42O11/c1-2-3-4-5-6-7-8-9-10-30-21-19(29)17(27)20(14(12-24)32-21)33-22-18(28)16(26)15(25)13(11-23)31-22/h13-29H,2-12H2,1H3/t13-,14-,15-,16+,17-,18-,19-,20-,21-,22-/m1/s1

Upstream product

• 22352-19-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate 
• 98808-72-1 1-decyl-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 112-30-1 1-Decanol 
• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 
• 20764-63-0 β-cellobioseoctaacetate 
• 14227-66-8 acetobromocellobiose 
• 120907-49-5 decyl-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside] 
• 5965-66-2 LACTOSE 
• 161259-75-2 Decyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosil)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 

Relevant articles and documents

Simple preparation method of alkyl maltoside surfactant

The invention belongs to the technical field of fine chemicals, and specifically discloses a preparation method of sugar-based nonionic surfactant alkyl-beta-D-maltoside. The preparation method includes the steps of performing an acylation reaction on maltose to obtain octa-O-acetyl-D-maltose, performing condensation on the octa-O-acetyl-D-maltose and fatty alcohol, and performing deprotection toobtain the alkyl-beta-D-maltoside. The preparation method provided by the invention is simple and easy to implement, has the advantages of mild and controllable conditions, low costs, and practicability.

Alkyl melibioside and alkyl cellobioside surfactants: Effect of sugar headgroup and alkyl chain length on performance

The potential of glycolipid surfactants, composed of a sugar headgroup and lipid tail, as highly biodegradable and less toxic alternatives to commonly used surfactants motivates the systematic study of structure-function relationships of various glycolipid surfactants. Advances in the efficient synthesis of high purity amphipathic glycolipid surfactants enable the analysis of a diverse set of glycolipids. The solution phase properties of two suites of glycolipid surfactants, n-alkyl-O-melibiosides and n-alkyl-O-cellobiosides, with varying straight-chain alkyl tails of 8, 10 and 12 carbons are investigated in this work. This study substantiates their efficient surfactant performance and reveals their aggregate structure and microenvironment as it relates to molecular structure. Surface tensiometry demonstrates critical micelle concentrations of 0.2-40 mM with minimum surface tension values of 36-40 mN m-1. Time resolved fluorescence quenching (TRFQ) spectroscopy is used to calculate micelle aggregation number (12-70 molecules per micelle) and assess relative micropolarity and microfluidity within the aggregates. The average aggregation numbers determined by TRFQ and apparent hydrodynamic radii determined by dynamic light scattering vary with alkyl chain length and headgroup size, but these properties are relatively insensitive to changes in concentration. The aggregates form nearly spherical, tightly-packed micelles with a small population of vesicles and polydispersity present at low concentrations or with short alkyl chain length.

Specific maltose derivatives modulate the swarming motility of nonswarming mutant and inhibit bacterial adhesion and biofilm formation by pseudomonas aeruginosa

We have demonstrated that specific synthetic maltose derivatives activate the swarming motility of a Pseudomonas aeruginosa nonswarming mutant (rhlA) at low concentration, but inhibit it at high concentration. Although these molecules are not microbicidal, active maltose derivatives with bulky hydrocarbon groups inhibited bacterial adhesion, and exhibited biofilm inhibition and dispersion (IC50 ～20 μM and DC50 ～30 μM, respectively). Because the swarming motility of the rhlA mutant is abolished by the lack natural rhamnolipids, the swarming activation suggests that maltose derivatives are analogues of rhamnolipids. Together, these results suggest a new approach of controlling multiple bacterial activities (bacterial adhesion, biofilm formation, and swarming motility) by a set of disaccharide-based molecules.