Hematein - Moligand™, 10 mM in DMSO , CAS No.475-25-2

CAS: 475-25-2 Cat. No.: H1495226 Formula: C₁₆H₁₂O₆ Peso molecolare: 300.26 Beilstein Registry Number: 93039 Numero EC: 207-492-8

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Panoramica

Hematein is a oxidation product of hematoxylin acted as a dye. Hematein is an allosteric casein kinase II inhibitor with an IC 50 of 0.74 μM. Hematein inhibits Akt/PKB Ser129 phosphorylation, the Wnt/TCF pathway and increases apoptosis in lung cancer cells.

Specifications

Specifiche e purezza

Moligand™, 10 mM in DMSO

Condizioni di conservazione di stoccaggio

Store at -80°C

Spedito in

Dry ice packs + Cold packs

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Grado

Moligand™

Proprietà del prodotto

• pKa: pKa: 8.02 (Predicted)

Nomi e identificatori

• Isomeri SMILES: C1C2=CC(=C(C=C2C3=C4C=CC(=O)C(=C4OCC31O)O)O)O
• WGK Germania: 3
• Peso molecolare: 300.26
• Beilstein: 93039
• Reaxy-Rn: 6069698
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6069698&ln=

Proprietà chimiche e fisiche

• Indice di rifrazione: n20D1.82 (Predicted)
• Punto di ebollizione (°C): ~753.1° C at 760 mmHg (Predicted)
• Punto di fusione (°C): 140° C

Application Protocols

No item-specific, validated protocols are provided for this SKU. The following are literature-style examples intended as starting points for research optimization only.

Example A: Concentrated stock for screening

• Dissolve hematein at 10–50 mM in DMSO (amber vial). Filter 0.2 µm. Store aliquots at ≤−20°C. For assays, dilute into buffer to ≤1–2% DMSO final.

Example B: Aluminum–hematein complex (acidic, alum-based)

• Prepare 0.5–1.0% (w/v) hematein in 95% ethanol. Separately prepare alum solution (e.g., aluminum potassium sulfate dodecahydrate) in water, acidify lightly (acetate or trace HCl) to pH ~2–3. Combine with vigorous stirring; allow to mature 12–48 h until color stabilizes. Optimize dye:alum ratio and pH for your substrate.

Example C: Iron–hematein complex

• Prepare hematein in ethanol/water. Add ferric chloride (or ferric ammonium sulfate) under acidic conditions with stirring. Adjust concentration and acidity to tune tone/intensity. Use immediately or after brief aging.

Good practices

• Record pH, solvent composition, metal ion source, concentrations, and timing. Test on small samples first. Protect solutions from light and air to reduce drift.

Note: Always adapt to your substrate/system and confirm compatibility. These examples are not validated for this item lot.

Biological Roles

Literature perspective (no clinical/diagnostic claims)

• Origin and relationship: Hematein is the oxidized form of hematoxylin, a natural product obtained from Haematoxylum campechianum (logwood). Oxidation generates a quinonoid system that enhances metal-chelation and color stability.
• Binding/interaction mode: As a polyphenolic ligand, hematein forms coordination complexes with hard cations (especially Al3+ and Fe3+). These complexes exhibit strong affinity for anionic, phosphate-rich matrices. In research staining systems, aluminum-hematein (“hemalum”) preferentially localizes to nucleic-acid–dense regions via mordant-mediated interactions with phosphate groups.
• pH/ionic effects: Ionization state and metal speciation govern hue and binding strength. Acidic conditions favor stable Al3+–hematein complexes with distinct spectral signatures; basic conditions increase phenolate formation and shift spectra/binding.
• Use in bioassays/materials: Hematein–metal complexes serve as chromogenic probes for mapping polyanionic sites on biomaterials, testing decalcification/metal exchange in tissues and scaffolds, and developing educational demonstrations of ligand–biopolymer interactions.

Notes

• Interactions are primarily coordination and electrostatic in nature; there is no sequence specificity. For quantitative biophysical studies, control ionic strength, competing ligands, and metal:ligand ratios.

Buffer Applications

Not a classical buffering reagent.

Literature guidance for related use

• While hematein itself is not used to set or maintain pH, it is commonly formulated in buffered or mildly acidic solutions (e.g., acetate- or citrate-buffered alum solutions) to control complexation state and hue.
• Practical tip: Select a buffer that maintains the desired acidity (often pH ~2–4 for aluminum complexes) without strongly chelating the mordant metal ion. Avoid phosphate buffers for aluminum complex systems, as phosphate can sequester Al3+ and diminish dye performance.

For buffer preparation details (pH range, ionic strength), consult your staining or complexation protocol and validate empirically for your substrate/system.

Green Alternatives

Greener practice focuses on solvent/mordant choice and waste minimization rather than replacing the chromophore itself.

Solvent and formulation choices (literature guidance)

• Prefer ethanol/water mixtures over methanol or high-boiling aprotics when feasible. Ethanol–water can achieve sufficient solubility for many staining and complexation tasks with lower toxicity and easier recovery.
• Avoid chlorinated solvents; hematein does not require them.
• Use minimal DMSO/DMF for stock preparation; dilute into aqueous buffers promptly to reduce aprotic solvent waste.

Mordants and additives

• Choose aluminum salts (e.g., alum) in place of heavier/less benign metals when color performance allows. Avoid chromium-containing mordants.
• Buffer with citrate/acetate systems instead of strong mineral acids when compatible with performance.

Comparison (literature; qualitative)

• Ethanol–water vs DMSO stocks: Ethanol–water offers safer handling and easier scaling; DMSO affords higher concentration but increases solvent hazard classification.
• Aluminum vs iron mordants: Aluminum complexes generally use milder acidity and yield purple-blue tones; iron mordants may require stronger acidity and can increase metal-related waste challenges.

Operational green tips

• Prepare only the quantity needed; many dye baths have limited shelf life.
• Implement micro-scale staining/assay formats to reduce consumption.
• Segregate metal-containing waste for appropriate recycling/disposal.

Pharmaceutical Uses

Not typically used as a pharmaceutical excipient or processing aid.

Literature context (formulation science)

• Hematein is a research dye/ligand. In pharmaceutical development settings, its role would be limited to analytical visualization or material studies (e.g., surface functionalization assays), not as an API or compendial excipient.
• Pharmacopeia status: No monograph known for hematein as an excipient (literature). Do not assume compliance with USP/EP/JP; consult regulatory resources if considering any non-clinical manufacturing application.

Operational note

• Any use should remain within research and development labs. For regulated environments, verify impurity profiles and extractables/leachables of the full formulation independently.

Physical Properties

Item-specific specs

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

Literature/typical properties (for reference; not item specifications)

• Physical state: Solid, colored organic dye (polyphenolic/quinonoid)
• Melting behavior: Often reported to darken/decompose on heating; sharp mp not reliably observed (literature).
• Solubility: Sparingly soluble in water; soluble in ethanol and methanol; readily soluble in polar aprotic solvents (e.g., DMSO, DMF); enhanced solubility in alkaline aqueous media due to phenolate formation (literature).
• Acid–base: Multiple phenolic pKa values typically in the ~7–11 range; quinone/phenol tautomerism influences apparent acidity and color (literature, qualitative).
• UV–Vis: Strong absorption in the visible when metal-complexed (aluminum/iron lakes); free dye exhibits characteristic bands in near-UV/visible depending on pH/tautomer state (literature qualitative).
• LogP/refractive index/density/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Practical notes

• Color and spectral properties are highly sensitive to pH, oxidation state, and metal complexation; record conditions (pH, solvent, metal salt) alongside spectral data.
• For quantitative solubility or extinction coefficients in your specific system, determine empirically as values vary with formulation.

Quality and Grades

Item-specific grade

• Grade/Purity: Moligand™ (Aladdin Scientific small-molecule/ligand library quality)

What Moligand™ generally implies (program-level, not a specification)

• Designed for discovery: Supplied as a research-grade small molecule suitable for screening, coordination studies, and method development.
• Informatics-ready: Items are typically provisioned with structure/cas metadata to support library registration; verify exact identifiers on the item’s CoA/Spec Sheet before ELN/LIMS upload.
• Purity/impurity profile: Not specified for this item; refer to CoA/Spec Sheet for exact purity, residual solvents, water, and elemental analysis if provided.

Relevance to hematein

• Hematein’s utility as a chelating chromophore depends on oxidation state and trace-metal background. For reproducible complexation (e.g., Al3+/Fe3+ lakes), consider controlling/recording trace metal content of solvents and salts used in your protocol.
• Stabilizers: None specified for this item. If you formulate long-lived solutions, protect from air/alkali or add stabilizers per your method; validate in-house as stabilizers may alter color/complexation equilibria.

Documentation

• For lot-specific specifications, analytical methods (HPLC/LC–MS, NMR), and acceptance criteria, consult the CoA/Spec Sheet. These documents supersede general statements here.

Reaction and Applications

Application landscapes (literature; for research use only)

• Metal–ligand complexation: Hematein forms intensely colored lakes with hard trivalent metal ions (e.g., Al3+, Fe3+). These chelates are useful models for coordination chemistry, colorant science, and as chromogenic indicators.
• Acid–base/tautomeric equilibria: The phenol/quinone system supports reversible redox and keto–enol equilibria, enabling pH-dependent color changes and redox labeling studies.
• Dye–substrate interactions: Through metal bridges (mordants), hematein complexes bind strongly to anionic substrates (e.g., phosphate-rich biomaterials), serving as probes for surface functionalization and adsorption studies.
• Analytical staining systems: Alum/iron-hematein formulations (“hemalum/iron-hematein”) are classic nuclear stains; in research labs these systems provide robust contrast for microscopy method development and material visualization.

Practical tips

• Control oxidation state: Stock solutions age; maintain consistency by preparing fresh or storing frozen, minimizing air exposure.
• Metal source and pH: Aluminum potassium sulfate (alum) or ferric salts are common metal sources. Complexation typically proceeds in mildly acidic aqueous–alcoholic media; optimize pH for hue and contrast.
• Background reduction: Trace metal contamination and buffer composition affect bath stability and tone; use high-purity salts and deionized water.
• Documentation: Record exact reagent lots, metal:dye ratios, pH, solvent composition, and time/temperature—small deviations can yield visible differences.

Reaction Conditions

General conditions from literature (guidance only; optimize per system)

• Metal complexation (aluminum-hematein): Dissolve hematein in ethanol/water, combine with aluminum potassium sulfate (“alum”) in mildly acidic medium (often acetate-adjusted to pH ~2–4). Typical dye:metal ratios range from 1:1 to 1:3 (mol). Gentle warming (25–40°C) can hasten complexation; allow maturation time for bath stabilization.
• Iron complexation: Use ferric chloride or ferric ammonium sulfate in acidic aqueous–alcoholic media. Complexes are typically darker/black–blue; excess iron can over-oxidize or shift hue—titrate carefully.
• O-alkylation/esterification of phenols: K2CO3 or Cs2CO3 in DMF/acetone, 20–60°C, with alkyl halides/acid chlorides. Protect from air and light; monitor by TLC/LC–MS as color masks UV visualization.
• Redox interconversion: Reduction to hematoxylin achievable with mild reducing agents under controlled pH; re-oxidation by air or mild oxidants (literature qualitative). Track by UV–Vis/NMR rather than color alone.

Expected outcomes

• Complexation is typically rapid (minutes to hours) but color intensifies with aging due to equilibrium and oxidation drift. Yields for derivatizations vary (40–80% typical for O-alkylation under optimized, small-scale conditions—literature ranges).

Notes

• Report solvent grade, metal salt identity, pH, temperature, and time. Small changes markedly affect hue and binding properties.

Safety and Handling

Item-specific safety from Product Data

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

General laboratory safety guidance (literature/practice; not a substitute for SDS)

• Hazards: Phenolic/quinonoid dyes may cause skin/eye staining and irritation. Dust may be irritating to the respiratory tract. Avoid inhalation, ingestion, and skin/eye contact.
• PPE: Use lab coat, nitrile gloves, and splash goggles. When handling powders or preparing solutions, work in a fume hood; consider a dust mask/respirator per institutional policy.
• Incompatibilities: Strong oxidizers or reducers can alter dye oxidation state and color; strong bases/acids shift ionization and complexation behavior. Avoid contact with reactive metals in strongly basic solutions.
• First aid (overview): In case of skin contact, wash with soap and water. For eye contact, rinse cautiously with water for several minutes; remove contact lenses if present and easy to do. If inhaled, move to fresh air. If swallowed, rinse mouth and seek medical advice. Always consult the SDS for authoritative instructions.
• Special risks: Solutions in alcoholic or aprotic solvents are flammable as dictated by the solvent. Metal-complexing solutions (e.g., with Al3+ or Fe3+) are typically acidic—handle as corrosive per formulation.
• Waste: Collect dye-containing and metal-mordant solutions as hazardous waste according to local regulations; avoid discharge to drains.

Solvent Selection

Solubility/miscibility profile (literature; general guidance)

• Water: Sparingly soluble at neutral pH; significantly more soluble in basic aqueous media (phenolate formation). Color/hue is pH dependent.
• Alcohols (EtOH, MeOH, i-PrOH): Good solubility; commonly used for stock solutions and dye formulation.
• Polar aprotics (DMSO, DMF, NMP): Very good solubility—useful for high-concentration stocks for screening; dilute into buffered systems as needed.
• Nonpolar solvents (hexanes, toluene): Poor solubility; generally unsuitable.

Selection tips

• Screening/assays: Prepare a concentrated DMSO stock (e.g., 10–50 mM) and dilute into aqueous buffers with ≤1–2% DMSO final to minimize solvent effects.
• Histochemical/mordant studies: Alcohol–water mixtures facilitate wetting and ensure uniform deposition prior to metal complexation.
• Spectroscopy: Use ethanol or DMSO for baseline-stable spectra; report pH and metal content when applicable, as spectra shift markedly with complexation and ionization.

Small comparison (literature)

• Ethanol vs DMSO: Ethanol is volatile, protic, and compatible with aqueous systems; DMSO provides higher solubility but may coordinate weakly and affect equilibria.
• Aqueous base: Maximizes solubility but alters oxidation state/phenolate distribution; apply when the basic form is desired and control CO2 uptake.

Practical handling

• Filter dye solutions (0.2 µm) before use to remove particulates. Use amber glass to limit photodegradation. Record solvent grade (e.g., anhydrous vs denatured) as trace impurities can influence color/complexation.

Storage and Reconstitution

Item-specific instructions from Product Data

• Storage conditions: Store at −80°C.
• Shipped in: Dry ice packs + Cold packs.

General guidance

• Upon receipt: Minimize time at ambient temperature. Verify container integrity and allow the sealed vial to equilibrate to room temperature before opening to prevent moisture condensation.
• Aliquoting: If frequent use is expected, aliquot the solid under dry conditions to minimize freeze–thaw and headspace oxygen exposure.
• Light/air: Store in amber, airtight containers; limit exposure to air to maintain a defined oxidation state.

Reconstitution (general, literature-based suggestions)

• Solvents: DMSO, DMF, ethanol, or aqueous base can be used depending on application. Start with a small test dissolution to confirm clarity and color.
• Filtration: Filter reconstituted solutions (0.2 µm PTFE) to remove particulates before analytical or staining use.
• Working solution stability: Colored solutions may change over time with pH/air exposure. Prepare fresh when critical; otherwise, store chilled (≤4°C) for short periods or frozen (≤−20°C) for longer, protected from light. Exact shelf life is system-dependent and not specified for this item; refer to CoA/Spec Sheet.

Note

• For authoritative, lot-specific handling and reconstitution instructions, consult the CoA and SDS. Research use only.

Structure and Identity

Item-specific identifiers from Product Data

• SKU: H1495226
• Product name: Hematein
• CAS: 475-25-2
• Grade/Purity: Moligand™
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature identity (for reference; not item specification)

• Synonyms: Oxidized hematoxylin; hematein dye; hematein (aluminum lake forms “hemalum”)
• Molecular formula (literature): C16H12O6
• Molecular weight (literature): ~300.26 g/mol
• Structural class: Polyphenolic/quinonoid natural-dye derivative (oxidation product of hematoxylin)
• Functional groups: Multiple phenolic OH groups and an ortho-quinone motif capable of metal chelation (bidentate/hexadentate depending on tautomer/ionization state)

2D structural description (literature)

• Aromatic polycyclic core bearing adjacent phenolic and quinonoid oxygens; intramolecular hydrogen bonding and keto–enol tautomerism are common. The phenolic array supports chelation to hard metal ions (e.g., Al3+, Fe3+) to form intensely colored “lakes.” No defined stereocenters.

Notes

• The above literature details are provided to aid method development and ligand design. Always confirm structure-specific identifiers (SMILES, InChI/InChIKey) on the item’s CoA/Spec Sheet before reporting or informatics registration.

Synthetic Utility

Literature-based reactivity profile

• Chelating polyphenol/quinone: Hematein’s adjacent phenolic and quinonoid oxygens render it a versatile O-donor ligand. It forms stable complexes with hard Lewis acids (Al3+, Fe3+, Zr4+), useful in model coordination chemistry and as chromogenic indicators.
• Redox interconversion: Hematein and hematoxylin interconvert under redox conditions. This can be exploited in redox probes or to tune colorimetric responses.
• Functional group transformations: Phenolic OH groups permit etherification, esterification, and carbamate formation to modulate solubility and metal-binding strength. Protective group strategies (e.g., methylation/benzylation) allow stepwise derivatization for structure–color studies.
• Conjugation chemistry: Activation via carbonate or carbamate linkers enables immobilization on polymers/surfaces to create colorimetric sensors for metal ions/anions.
• Lake pigment formation: Precipitation of hematein with metal salts yields insoluble pigments (“lakes”), applicable for coatings, printing inks, or as solid-phase indicators in test devices.

Practical tips

• Control pH and oxygen during derivatization to maintain a defined oxidation state.
• Use non-chelating bases (e.g., K2CO3, Cs2CO3) in aprotic solvents for O-alkylation; avoid amine bases that may coordinate and discolor.
• Purify derivatives under inert/low-light conditions to prevent back-oxidation or photoisomerization.

Target Specificity

Not applicable to this product type.

• This item is a small-molecule dye/ligand, not an antibody or targeted biologic. No antigen, clone, isotype, or species reactivity information applies.