n-DODECYL-beta-D-MALTOSIDE CAS No. 69227-93-6

Product Description

n-Dodecyl-β-D-maltoside (DDM) is a high-purity, non-ionic detergent formed by linking a 12-carbon dodecyl chain to a maltose headgroup through a stable β-glycosidic bond, creating an amphiphile that dissolves freely in aqueous buffers yet is insoluble in non-polar solvents. Its low critical micelle concentration (~0.17 mM) and mild, non-denaturing micelles (~4–6 nm, ~50–60 kDa) make it the work-horse of membrane-protein research, enabling gentle extraction, solubilization and long-term stabilization of targets such as GPCRs, ion channels and transporters while preserving native structure and activity. Consequently, DDM is routinely used in X-ray crystallography and cryo-EM to obtain high-quality protein crystals or samples, and in affinity chromatography to purify intact membrane complexes. Compared with harsher or cheaper alternatives like Triton X-100 or SDS, DDM minimizes protein unfolding, but its relatively high cost and potential interference with mass spectrometry must be weighed; newer agents such as LMNG offer even greater stability when extended solubilization is required.

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Product Use & Characteristics

Identity & Nomenclature

• Abbreviation: DDM

• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-dodecoxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

• Molecular Formula / MW: C₂₄H₄₆O₁₁ / 510.6 g mol⁻¹

Structure & Composition

• Amphiphile: 12-carbon alkyl chain (dodecyl) β-linked to a disaccharide maltose head-group (two glucose units)

• β-glycosidic bond → resistant to many glycosidases

Physical Appearance

• White to off-white powder or waxy solid

Solubility & Compatibility

• Soluble: water, ethanol, aqueous buffers

• Insoluble: non-polar solvents

• HLB ≈ 14.2

• Compatible with: trypsin, Lys-C, Glu-C, PNGase F, LC-MS/MS (no detergent-removal required)

Micelle Parameters

• Critical Micelle Concentration (CMC): ~0.17 mM (25 °C) ≈ 0.0087 % w/v

• Aggregation Number: ~98

• Micelle Size: 4–6 nm

• Micelle Molecular Weight: ~50–60 kDa

Safety & Metabolism

• Non-ionic, non-toxic, non-mutagenic, non-irritating

• Metabolites: CO₂ + H₂O (via sugar & fatty-acid degradation)

Uses

• Membrane-protein extraction, solubilization, stabilization (GPCRs, ion channels, transporters)

• Structural biology: crystallography, cryo-EM, X-ray studies

• Chromatography: affinity purification of membrane proteins

• Cell lysis: non-denaturing membrane disruption

• Biopharmaceutical formulation: anti-aggregation excipient (e.g., rhIFN-β-1b) – outperforms polysorbate 20 under light stress

• Glycoproteomics: extraction of minute hydrophobic samples (e.g., 50 µg mouse brain) without detergent removal; 110 % more N-glycosylation sites identified vs. SDS/Triton methods

Advantages

• Mild, preserves native protein structure/activity

• Low CMC → effective at low concentrations

• High purity (≥ 98 %) for structural studies

• No detergent-removal step needed for MS or enzymatic workflows

Limitations

• Higher cost than Triton X-100 or SDS

• Possible interference with some analytical techniques (e.g., certain MS ionization modes)

Storage & Handling

• Store tightly closed, protected from light, at room temperature or 4 °C

• Avoid prolonged heating to prevent glycosidic hydrolysis

Why us!

Qingdao Sigma Chemical Co., Ltd., established in January 2017 and headquartered in Qingdao, China, is a reliable chemical supplier. Specializing in pharmaceuticals, biochemical intermediates, and research chemicals, the company offers a diverse product portfolio, including peptides (e.g., Tirzepatide, Semaglutide), nootropics, veterinary products, and APIs, often marketed with ≥99% purity and COA certification. We provides R&D, custom synthesis, and contract manufacturing services at various scales, while claiming a global export presence across 100+ countries. With international warehouses in the USA, Europe, Australia, and Canada, Qingdao Sigma Chemical also facilitates drop-shipping and reshipments, positioning itself as a key supplier for laboratory and research applications.