Cas no 168037-13-6 (Undecyl a-D-Maltopyranoside)

Undecyl α-D-Maltopyranoside is a non-ionic detergent commonly used in membrane protein solubilization and stabilization. Its alkyl maltoside structure, featuring an 11-carbon hydrophobic tail and a hydrophilic maltose headgroup, provides balanced amphiphilic properties, making it effective for disrupting lipid bilayers while preserving protein functionality. This detergent is particularly advantageous for crystallography and biochemical studies due to its mild denaturing effects and high critical micelle concentration (CMC), facilitating easy removal via dialysis. Its chemical stability and compatibility with a wide pH range further enhance its utility in structural biology and protein purification workflows.
Undecyl a-D-Maltopyranoside structure
Undecyl a-D-Maltopyranoside structure
Product Name:Undecyl a-D-Maltopyranoside
CAS No:168037-13-6
MF:C23H44O11
MW:496.588869094849
CID:65792
PubChem ID:44462510
Update Time:2025-06-11

Undecyl a-D-Maltopyranoside Chemical and Physical Properties

Names and Identifiers

    • Undecyl alpha-D-maltopyranoside
    • UNDECYL A-D-MALTOPYRANOSIDE
    • Undecyl α-D-maltoside
    • n-Undecyl α-D-maltopyranoside
    • UNDECYL MALTOSIDE (HIGH ALPHA)
    • 168037-13-6
    • Undecyl 4-O-alpha-D-glucopyranosyl-alpha-D-glucopyranoside
    • (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-undecoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
    • DTXSID80659191
    • Undecyl alpha-D-maltoside, >=90% (GC)
    • UNDECYLALPHA-D-MALTOPYRANOSIDE
    • alpha-D-Glucopyranoside, undecyl 4-O-alpha-D-glucopyranosyl-
    • (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-4,5-DIHYDROXY-2-(HYDROXYMETHYL)-6-(UNDECYLOXY)OXAN-3-YL]OXY}-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL
    • Undecyl a-D-Maltopyranoside
    • MDL: MFCD09750649
    • Inchi: 1S/C23H44O11/c1-2-3-4-5-6-7-8-9-10-11-31-22-20(30)18(28)21(15(13-25)33-22)34-23-19(29)17(27)16(26)14(12-24)32-23/h14-30H,2-13H2,1H3/t14-,15-,16-,17+,18-,19-,20-,21-,22+,23-/m1/s1
    • InChI Key: UYEMNFYVTFDKRG-BFNKVOCASA-N
    • SMILES: O([C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@@H]1[C@@H](CO)O[C@@H]([C@@H]([C@H]1O)O)OCCCCCCCCCCC

Computed Properties

  • Exact Mass: 496.288
  • Monoisotopic Mass: 496.288
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 7
  • Hydrogen Bond Acceptor Count: 11
  • Heavy Atom Count: 34
  • Rotatable Bond Count: 15
  • Complexity: 539
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 10
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 179A^2
  • XLogP3: 0.8

Experimental Properties

  • Density: 1.3±0.1 g/cm3
  • Melting Point: Not available
  • Boiling Point: 696.4±55.0 °C at 760 mmHg
  • Flash Point: 374.9±31.5 °C
  • PH: 7.5-8.5 (1% in H2O)
  • Solubility: H2O: soluble20%, clear to very faintly turbid, colorless
  • PSA: 178.53000
  • LogP: -0.84210
  • Vapor Pressure: 0.0±5.0 mmHg at 25°C

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Additional information on Undecyl a-D-Maltopyranoside

Comprehensive Guide to Undecyl a-D-Maltopyranoside (CAS No. 168037-13-6): Properties, Applications, and Innovations

Undecyl a-D-Maltopyranoside (CAS No. 168037-13-6) is a specialized non-ionic surfactant widely recognized for its unique biochemical properties and applications in membrane protein research, drug delivery systems, and biotechnological processes. As a derivative of maltose, this compound features an undecyl (C11) alkyl chain linked to the a-D-maltopyranoside headgroup, offering balanced hydrophilicity and lipophilicity. Its structural versatility makes it a preferred choice for solubilizing membrane proteins while maintaining their native conformation—a critical factor in structural biology and pharmaceutical development.

In recent years, the demand for high-purity glycosides like Undecyl a-D-Maltopyranoside has surged due to advancements in cryo-EM (cryogenic electron microscopy) and GPCR (G-protein-coupled receptor) studies. Researchers frequently search for "best surfactants for membrane protein stabilization" or "alternatives to DDM (n-Dodecyl β-D-maltoside)," highlighting the compound's relevance. Compared to traditional detergents, this maltoside derivative exhibits lower critical micelle concentration (CMC), enhancing its efficiency in protein extraction and crystallization workflows.

The compound's eco-friendly profile aligns with the growing emphasis on green chemistry in life sciences. Unlike harsh ionic detergents, Undecyl a-D-Maltopyranoside is biodegradable and compatible with sensitive biological systems, addressing queries like "sustainable surfactants for lab use." Its applications extend to liposome formulation and nanoparticle coating, where stability and low cytotoxicity are paramount—topics trending in mRNA vaccine and cancer therapeutics research.

From a technical perspective, CAS No. 168037-13-6 is characterized by a molecular weight of 408.5 g/mol and a hydrophilic-lipophilic balance (HLB) of ~14, ideal for micelle formation. Analytical techniques such as HPLC and mass spectrometry confirm its >98% purity, a key metric for reproducibility in peer-reviewed studies. Storage recommendations (-20°C under inert gas) and solubility data (water, methanol) are frequently searched by lab technicians optimizing experimental protocols.

Innovations in Undecyl a-D-Maltopyranoside formulations now target high-throughput screening platforms. A 2023 study demonstrated its synergy with lipid cubic phases to improve membrane protein crystallography success rates—addressing the persistent challenge of "protein aggregation prevention." Such developments resonate with pharmaceutical companies investing in rational drug design, where 3D protein structures are indispensable.

Market trends indicate rising adoption in biosensor development and diagnostic assays, leveraging the compound's ability to preserve protein functionality. FAQs like "how to choose maltoside chain length" underscore the importance of the C11 alkyl tail in balancing detergent strength and biocompatibility. Suppliers now offer custom glycosylation services to tailor properties for niche applications, from neurobiology to industrial enzymology.

In summary, Undecyl a-D-Maltopyranoside (CAS No. 168037-13-6) represents a convergence of academic research and industrial innovation. Its optimized structure addresses contemporary needs in structural biology, therapeutic development, and sustainable lab practices, making it a staple reagent in 21st-century life sciences. Ongoing studies exploring its role in membrane mimetics and artificial cell systems promise to further expand its scientific footprint.

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