dextran sulfates - 500 kDa LS , CAS No.9011-18-1

CAS: 9011-18-1 Cat. No.: D397468 EC Number: 618-471-1 PubChem CID: 2337

GRADE & PURITY 500 kDa LS

Synonyms

4-aminobenzoic acid-ethyl ester | Anaesthesinum | Benzoak | ETHYL4-AMINOBENZOATE | Norcaine | Norcainum | Aethoform | Anaesthin | Bensokain | HSDB 7225 | BENZOCAINE [USP MONOGRAPH] | CAS-94-09-7 | Benzoic acid, 4-amino-, ethyl ester | Chiggerex | Ethoform

Storage

Store at 2-8°C,Argon charged,Desiccated

Shipped In

Wet ice

Overview

Product Description：

Dextran sulfates are produced by sulfation of selected dextran fractions.

The dextran sulfate is supplied as the sodium salt and is stabilised by a small addition of phosphate salts. A certificate of analysis is supplied with each batch. The molecular weight range, sulfur content, moisture etc. are carefully controlled.

Structure

Dextran is a polysaccharide derived from the bacterium Leuconostoc mesenteroides B512F and consists of an α-D-(1 – 6) linear glucan with a low content (ca. 5%) of sidechains linked to the 3-carbon of glucose. Dextran sulfate is a sulfated derivative of selected dextran fraction. The sulfate content of our low sulfated dextran sulfates lies between 8 to 13 %.

Applications

Dextran sulfate have a wide range of applications areas and properties. Some examples are:

Anti-coagulation agent in cell media

Selective precipitation of lipoproteins

Acceleration of DNA hybridisation.

Releasing DNA from DNA-histones complexes

Inhibition tRNA-binding to ribosomes

Inhibition of ribonucleases

Anti-viral properties

Used in cosmetics for anti-inflammation properties and osmotic retention of water

Separation of microorganisms and macromolecules

Adjuvant in vaccines

Studies of perm selectivity of membranes

Specifications

Synonyms

4-aminobenzoic acid-ethyl ester | Anaesthesinum | Benzoak | ETHYL4-AMINOBENZOATE | Norcaine | Norcainum | Aethoform | Anaesthin | Bensokain | HSDB 7225 | BENZOCAINE [USP MONOGRAPH] | CAS-94-09-7 | Benzoic acid, 4-amino-, ethyl ester | Chiggerex | Ethoform

Specifications & Purity

500 kDa LS

Storage

Store at 2-8°C,Argon charged,Desiccated

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Product Properties

ALogP

1.9

Names and Identifiers

IUPAC Name

ethyl 4-aminobenzoate

InChIKey

BLFLLBZGZJTVJG-UHFFFAOYSA-N

INCHI

1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3

Isomeric SMILES

CCOC(=O)C1=CC=C(C=C1)N

WGK Germany

2

RTECS

HH9290000

PubChem CID

2337

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoic acid esters
• Alternative Parents: Aminobenzoic acids and derivatives Benzoyl derivatives Aniline and substituted anilines Carboxylic acid esters Amino acids and derivatives Monocarboxylic acids and derivatives Primary amines Organopnictogen compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aminobenzoic acid or derivatives - Benzoate ester - Benzoyl - Aniline or substituted anilines - Amino acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Amine - Organonitrogen compound - Organooxygen compound - Primary amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
• External Descriptors: substituted aniline - benzoate ester

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: readily soluble in water
• Specific Rotation[α]: 93° (C=6,H2O)
• Molecular Weight: 165.190 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 165.079 Da
• Monoisotopic Mass: 165.079 Da
• Topological Polar Surface Area: 52.300 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 151.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No manufacturer-validated protocols are specified for this item. The following are generalized literature-style procedures for research use. Adjust to your system and consult primary references.

1. Preparing a 1% w/v stock solution

• Add 1.0 g dextran sulfate slowly to ~80 mL water or PBS under vigorous stirring.
• Rinse vessel walls to avoid dry clumps; warm to 30–40°C if needed.
• After dissolution, bring to 100 mL total volume; mix thoroughly.
• Filter sterilize (0.22–0.45 μm) if required. Store 2–8°C.

2. Polyelectrolyte complex nanoparticles with chitosan

• Prepare 0.5–1.0 mg/mL dextran sulfate in water (pH ~7) and chitosan in 0.1 M acetate buffer (pH 5.5).
• While stirring chitosan, add dextran sulfate dropwise to achieve N+/S− ≈ 1:1 (adjust using DS from CoA).
• Optionally include 50–150 mM NaCl to tune size/ζ-potential. Age 15–30 min before characterization.

3. Lipoprotein precipitation (analytical fractionation)

• To a defined volume of proteinaceous sample, add MgCl2 solution and dextran sulfate solution to reach empirically established final concentrations.
• Mix gently and incubate on ice or at room temperature for 10–20 min.
• Centrifuge; collect supernatant and/or pellet as needed. Validate recovery by appropriate analytical assays.

Note: Optimize polymer MW, DS, ionic strength, and temperature for each application.

Biological Roles

Dextran sulfate is not a natural metabolite; it is a chemically sulfated derivative of microbial dextran. Its high charge density makes it a functional mimic of sulfated glycosaminoglycans (GAGs) in vitro (literature).

Literature/general interactions:

• Electrostatic binding to cationic proteins, peptides, and domains (e.g., lysine/arginine-rich regions). This can modulate aggregation, solubility, and adsorption to surfaces.
• Mimicry of heparan sulfate binding: can sequester basic growth factors and modulate their availability in model systems.
• Influences colloidal stability of lipoproteins and other complexes via charge neutralization and bridging.
• As a strongly anionic crowding agent, can affect enzyme kinetics and nucleic acid–protein interactions through excluded volume and electrostatics.

Notes for research use:

• Effects are highly dependent on molecular weight, degree of sulfation, ionic strength, and pH. Lot-specific parameters (CoA) should guide experimental design.
• Can interfere with certain enzymatic assays (e.g., polymerases, proteases) by nonspecific binding; include appropriate controls.
• In cell-free or cell-based models, polyanions may alter uptake or adhesion through surface charge effects; titrate carefully and monitor cytocompatibility in your specific system.

All statements are for research context only; no clinical or therapeutic claims are implied.

Buffer Applications

Dextran sulfate is not a buffer in the acid–base sense, but it is commonly formulated in aqueous buffers for research workflows.

General preparation (literature):

• Stock solutions: 1–10% w/v in water, PBS, or Tris buffer. Add powder slowly to vigorously stirred solvent to avoid clumping; warm (≤40°C) if needed.
• pH: use neutral to slightly alkaline buffers (pH 6.5–8.0) for stability and full ionization. Avoid strong acids/bases which can hydrolyze sulfate esters and glycosidic bonds.
• Ionic strength: adjust NaCl (0–500 mM) to tune viscosity and complexation behavior; higher salt screens electrostatics and can reduce solution viscosity.
• Sterilization: filter through 0.22–0.45 μm; autoclaving can cause degradation and desulfation—validate if heat-sterilization is required.

Compatibility:

• Compatible with common biological buffers (PBS, HEPES, MES, Tris). Divalent cations (e.g., Mg2+, Ca2+) can promote precipitation with cationic macromolecules; leverage or avoid accordingly.

Storage of solutions (general):

• Short term at 2–8°C; add antimicrobial preservatives if compatible with downstream use. For long-term storage, aliquot and freeze to minimize microbial growth and degradation. Check solution clarity and pH before use.

Item-specific buffer specs are not provided for this product; consult CoA for any declared parameters.

Green Alternatives

Dextran sulfate is itself a water-processable, nonvolatile polymer derived from a renewable carbohydrate (dextran from microbial sucrose fermentation). From a green chemistry perspective, it often replaces petroleum-derived polyanions in water-based processes.

Comparison (literature/general):

• Attribute | Dextran sulfate | Poly(styrene sulfonate) (PSS)
• Origin | Biobased (microbial dextran, then sulfation) | Petrochemical
• Solvent | Water | Water/DMF/DMSO (synthesis); aqueous use
• Volatility | Nonvolatile solid | Nonvolatile solid
• Biodegradability | Potentially biodegradable (carbohydrate backbone) | Lower biodegradability
• Toxicity profile | Widely used in research with low volatility; assess per SDS | Varies by MW/counterion; assess per SDS

Trade-offs:

• Sulfation chemistry can involve strong sulfonating agents; sourcing from responsible suppliers and proper waste treatment is essential.
• For highly specific biomolecular interactions, natural glycosaminoglycans (e.g., heparin, chondroitin sulfate) may offer higher affinity but raise sourcing and variability concerns.

Greener practice tips:

• Use aqueous media exclusively; avoid unnecessary organic co-solvents.
• Optimize ionic strength and pH to minimize reagent excess in polyelectrolyte assembly.
• Recover and recycle polyelectrolyte complexes where feasible; dispose of sulfate-containing aqueous waste per local regulations.

Pharmaceutical Uses

No pharmacopeial grade or excipient designation is specified for this catalog item; refer to the CoA/Spec Sheet for any compliance statements.

Research/formulation context (literature/general, non-clinical):

• Process aid for fractionation: used to precipitate cationic lipoproteins and basic proteins from complex biological matrices in analytical workflows.
• Component in in vitro delivery systems: as a polyanionic partner in polyelectrolyte complexes (e.g., with chitosan) for encapsulating biomolecules during research-scale formulation studies.
• Surface modification: contributes negative charge and hydrophilicity to coatings on medical research devices and analytical supports (strictly for research use in this context).

Considerations:

• Molecular weight and degree of sulfation strongly influence viscosity, binding, and precipitation thresholds—select lots accordingly.
• Endotoxin/bioburden, heavy metals, and residual solvent/reagent controls are critical for sensitive biological applications; these are lot- and grade-specific and are Not specified for this item.

Compliance note: For research use only. Not for use in diagnostic procedures, foods, drugs, or medical devices unless explicitly qualified by additional regulatory documentation.

Physical Properties

Item-specific numerical specifications are not provided for this catalog entry; consult the CoA/Spec Sheet for lot-defined data.

Literature/general properties (non-spec):

• Physical state/appearance: typically a white to off‑white, hygroscopic, amorphous powder or flakes (literature).
• Solubility: readily soluble in water and many aqueous buffers across wide ionic strength; insoluble in most organic solvents (alcohols, ethers, hydrocarbons). High concentrations yield viscous solutions (literature).
• pKa: not applicable (strong sulfate esters; fully ionized in water over typical pH ranges; literature).
• Decomposition: polymers lack a true boiling point; thermal decomposition/char occurs upon heating; sulfate esters may hydrolyze slowly under strong acidic or basic conditions (literature).
• Optical rotation: dextran parent is dextrorotatory; the magnitude for dextran sulfate depends on MW and substitution (literature; not item-specific).
• Density, refractive index, intrinsic viscosity, moisture/ash/sulfur content: Not specified for this item; refer to CoA/Spec Sheet.

Practical solution guidance (general):

• Typical working concentrations: 0.01–5% w/v in aqueous media, depending on application (e.g., polyelectrolyte complexes vs. precipitation; literature).
• Filtration: 0.22–0.45 μm membranes; viscosity may require lower vacuum and larger pore size (literature).

Quality & Grades

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

How dextran sulfate quality is commonly defined (literature/general):

• Molecular weight distribution: supplied by nominal ranges (e.g., 5–500 kDa). Methods include GPC/SEC with appropriate standards. Broader dispersity increases viscosity variability and can impact performance in polyelectrolyte complexation and precipitation workflows.
• Degree of sulfation (DS) / sulfur content: reported as %S or mol sulfate per glucose unit. DS influences charge density, binding to cationic biomolecules, and precipitation efficiency.
• Inorganic content (ash), moisture, and residual reagents: typically controlled; moisture drives hygroscopic mass gains; ash indicates inorganic salts (e.g., Na+). Endotoxin/bioburden may be specified for cell culture applications in some grades.
• Clarity/color of solution: qualitative indicator of particulates or degradation.
• UV absorbance: occasionally reported to ensure low background in spectroscopic assays.

Stabilizers/additives: Not typically required; product is inherently stable when dry and protected from moisture/heat. Any stabilizers, if present, would be listed on the CoA (Not specified for this item).

Recommendation: Match MW range and DS to your application (e.g., LDL precipitation vs. polyelectrolyte multilayers). Verify lot-specific CoA parameters before critical work.

Reaction & Applications

Although not a small-molecule reagent for classical organic reactions, dextran sulfate is widely used as a functional polyanion in laboratory workflows (literature):

• Polyelectrolyte complexation: forms complexes and coacervates with polycations (e.g., chitosan, poly(allylamine), poly-L-lysine). Applications include nanoparticle assembly, layer-by-layer (LbL) films, and cargo encapsulation. Control parameters: charge ratio (N+/S−), ionic strength, pH, and mixing sequence.
• Precipitation and fractionation: selectively precipitates cationic lipoproteins (e.g., LDL/VLDL) and basic proteins in the presence of divalent cations (e.g., MgCl2). Useful for research sample cleanup and enrichment prior to analytical assays.
• Chromatographic/affinity media precursor: sulfated dextran motifs underlie certain strong cation-exchange surfaces; electrostatic capture of basic proteins and peptides.
• Enzyme and virus work (in vitro): polyanionic crowding/partitioning effects can modulate adsorption and aggregation; often included to suppress nonspecific binding to positively charged surfaces.
• Materials chemistry: template/stabilizer for inorganic nanoparticle dispersions; imparts colloidal stability via electrostatic repulsion.

Practical tips:

• Dissolve with gentle stirring; pre-wet with small water aliquot to avoid clumping. Add slowly to vortex of solvent.
• Filter sterilize viscous solutions using 0.45 μm membranes if 0.22 μm fouls.
• Titrate charge equivalents: compute anion equivalents from sulfur content/DS (from CoA) to set N+/S− ratios precisely.
• Avoid strong acid/base and elevated temperatures to prevent desulfation/backbone hydrolysis.

Reaction Conditions

Dextran sulfate is used under mild, aqueous conditions. Representative research-use conditions from literature (general guidance; not item-specific):

• Polyelectrolyte complexation with chitosan:

  • Solvents: water, acetate buffer (pH 5–6) for chitosan solubility; mix with dextran sulfate in water/PBS.
  • Charge ratio: N+/S− from 0.5:1 to 2:1 adjusted via polymer concentrations and DS (from CoA).
  • Ionic strength: 0–150 mM NaCl tunes particle size and stability.
  • Temperature: ambient (20–25°C).

• LDL/lipoprotein precipitation (analytical sample prep):

  • Reagents: dextran sulfate in water and MgCl2 solution.
  • Conditions: combine defined volumes with serum/plasma or other proteinaceous matrices, incubate on ice or at 4–25°C for minutes to tens of minutes; centrifuge to separate precipitate. Optimize reagent stoichiometry empirically.

• Layer-by-layer film assembly:

  • Substrates: glass, silica, polymers.
  • Solutions: 0.1–1 mg/mL dextran sulfate and complementary polycation in 10–100 mM NaCl, pH 6–7.4.
  • Rinses: same buffer without polymer. Cycle deposition to target thickness.

• Sterilization/processing:

  • Filtration at 0.22–0.45 μm; avoid autoclaving when possible due to hydrolytic risk.

Always confirm compatibility with proteins/biomolecules in your exact buffer system; ionic strength and pH govern complexation and precipitation outcomes.

Safety & Handling

Hazard classification for this specific item is not provided. Always consult the product SDS for authoritative safety information.

• GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS.

General laboratory safety considerations (literature/practice):

• Low volatility solid; dust may cause mechanical irritation of eyes/respiratory tract. Avoid generating dust; use local exhaust when handling powders.
• PPE: lab coat, safety glasses, appropriate gloves (e.g., nitrile). Use a dust mask/respirator if airborne particles may form per risk assessment.
• Incompatibilities: strong acids or bases can promote hydrolysis/desulfation; strong oxidants may degrade polysaccharide backbone. Avoid prolonged exposure to elevated temperatures and moisture.
• Hygroscopic: keep containers tightly closed under dry inert atmosphere as provided. Reseal promptly after opening.
• First aid (overview; refer to SDS): rinse eyes/skin with water upon contact; move to fresh air if inhaled; rinse mouth if ingested and seek medical advice. No specific antidote known.
• Fire: combustible organic solid; use water spray, CO2, dry chemical, or foam. Thermal decomposition may produce SOx and carbonaceous fumes.
• Environmental: water-soluble polyelectrolyte; avoid uncontrolled release to drains without appropriate treatment.
• For research use only. Not for human or animal use.

Solvent Selection

Dextran sulfate is a strongly polyanionic, hydrophilic polymer. Solvent choice is almost exclusively aqueous.

• Primary solvents: water, physiological saline, phosphate-buffered saline (PBS), Tris, HEPES, and other common biological buffers (literature). It dissolves readily with gentle stirring; warming to 30–40°C can speed dissolution.
• Miscibility/polarity: insoluble in low- and medium-polarity organic solvents (alcohols, ketones, ethers, hydrocarbons). Limited compatibility with high-ionic-strength aqueous-organic mixtures depends on water content; precipitation often occurs beyond modest organic fractions.
• Ionic strength effects: higher salt can screen charge–charge repulsion, reducing viscosity and promoting complexation with cationic species (literature).
• pH window: stable and fully ionized under neutral to mildly alkaline conditions; avoid strong acid/base (hydrolysis/desulfation risk; literature).

Selection guidance (literature):

• For complexing with polycations (e.g., chitosan, poly-L-lysine): use low- to moderate-ionic-strength buffers at pH 5–7 to balance complex formation and solubility.
• For precipitation of cationic lipoproteins/proteins: aqueous media with divalent cations (e.g., Mg2+) are commonly used to enhance complex formation (protocol-dependent).

Quick comparison (general):

• Dextran sulfate vs. heparin: both are polyanionic; dextran sulfate offers tunable MW/DS and is non-biological in origin, often preferred for physical separations; heparin has specific biological motifs and stronger protein-binding specificity.

Storage & Reconstitution

Item-specific storage conditions (from Product Data):

• Store at 2–8°C, Argon charged, Desiccated.
• Shipped on wet ice.

General guidance (literature; non-binding):

• Protect from moisture: dextran sulfate is hygroscopic. Keep container tightly closed; backfill with inert gas (as supplied) after each use.
• Light/heat: store away from direct light and heat sources. Avoid elevated temperatures that can accelerate hydrolysis/desulfation.
• Reconstitution: dissolve in water or compatible buffer with gentle stirring. Add powder slowly to avoid clumping; slight warming (≤40°C) can aid dissolution.
• Solution storage: for short-term use, store at 2–8°C. For longer-term storage, aliquot and freeze to minimize microbial growth and degradation. Avoid repeated freeze–thaw of concentrated solutions.
• Sterility: if required, filter sterilize through 0.22–0.45 μm. Avoid autoclaving unless validated for your application (risk of hydrolysis).
• Stability indicators: monitor for changes in color, unexpected turbidity/precipitation, or pH drift; discard if significant changes are observed.

For research use only. Always refer to the CoA/SDS for lot-specific stability and handling information.

Structure & Identity

Dextran sulfate (CAS 9011-18-1) is a polydisperse, sulfated polysaccharide derived from dextran. It is composed of repeating anhydroglucose units (primarily α-1→6 linked) bearing sulfate ester groups; variable branching (e.g., α-1→3) is typical (literature). As a polymer, exact composition (degree of polymerization and degree of sulfation) varies by lot.

• SKU: D397468
• Product name: dextran sulfates
• CAS: 9011-18-1
• CID: 2337 (dextran sulfate, polymer entry; literature cross-reference)
• InChIKey: 27766 (as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Polymeric, variable)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Polydisperse; often supplied by nominal Mn/Mw ranges in literature)

Structural features (literature):

• Backbone: α-D-glucopyranose units mainly connected via α-1→6 glycosidic bonds; occasional α-1→3 branches.
• Functional groups: multiple sulfate esters (–OSO3−), abundant hydroxyls (–OH) when not sulfated.
• Charge state: strongly polyanionic in neutral/alkaline aqueous media due to sulfate groups.
• 2D description: a linear/branched chain of chair-form glucopyranose rings, each with up to three sulfate substituents replacing hydroxyls at C2/C3/C4 (distribution depends on sulfation conditions; literature).

Synthetic Utility

Dextran sulfate is not a typical small-molecule building block, but it is a versatile macromolecular reagent and material component in synthetic and materials chemistry (literature):

• Polyelectrolyte assembly: serves as the anionic component for layer-by-layer films with cationic polymers (e.g., PAH, PEI, chitosan). Films can be used as catalytic supports, separation membranes, or responsive coatings.
• Nanomaterials templating: stabilizes metal and metal-oxide nanoparticles in water; provides electrostatic and steric repulsion, improving dispersion and preventing aggregation.
• Hydrogel formation: participates in ionically crosslinked networks with multivalent cations or polycations; covalent crosslinking of the dextran backbone (not sulfate) can be achieved with epoxide or radical chemistries after appropriate functionalization.
• Affinity/ion-exchange media: immobilization on solid supports yields strongly acidic cation-exchange surfaces that capture basic proteins and amines.

Reactivity considerations:

• Sulfate esters are poor nucleophiles; further derivatization typically targets remaining hydroxyls on under-sulfated positions or uses spacer chemistry on a dextran precursor prior to sulfation.
• Backbone stability: avoid conditions that cause desulfation (e.g., strong acid or strong base, high temperature) during processing.

Design tip: When precise functionality is required, define the charge density via DS (from CoA) and verify by elemental analysis before iterative materials synthesis.

Target Specificity

Not applicable. This product is a polymeric reagent, not an antibody or affinity ligand with defined antigen/epitope specificity. For selective interactions, dextran sulfate exhibits broad electrostatic binding to cationic proteins and domains (literature), but no item-specific target specificity is provided.