Acitretin sodium , CAS No.925701-88-8

CAS: 925701-88-8 Cat. No.: A1421149 Formula: C₂₁H₂₅NaO₃ Peso molecolare: 348.41

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Acitretin (Ro 10-1670) sodium is a second-generation, systemic retinoid that has been used in the treatment of psoriasis. Acitretin sodium also can be used for the research of Alzheimer’s disease.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

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

Nomi e identificatori

• Peso molecolare: 348.41

Application Protocols

No tested application protocols, assay conditions, or recommended dilutions are provided for this SKU. General suggestions for handling bioactive retinoids in vitro:

• Prepare light-protected DMSO stocks at an appropriate concentration (e.g., 10–50 mM), aliquot, and store at -20°C.
• Dilute into assay buffer or media with controlled final DMSO ≤0.1–0.5% v/v as tolerated; include matching vehicle controls.
• Use amber plates/vials and minimize light exposure during incubations.
• Confirm concentration and integrity by HPLC–UV where data quality is critical.

For detailed, validated protocols, please refer to peer-reviewed literature or develop in-house SOPs tuned to your assay system.

Biological Roles

General literature background (non-clinical):

• Acitretin is a synthetic retinoid structurally related to vitamin A derivatives. Retinoids modulate gene expression by binding to nuclear receptors—retinoic acid receptors (RARα/β/γ) and retinoid X receptors (RXRα/β/γ). Ligand-bound receptors act as transcription factors regulating differentiation, proliferation, and keratinization pathways in various cell types.
• The sodium salt form does not alter the pharmacophore at the receptor-binding site (the retinoid scaffold), but it can influence solubility, ionization state, and formulation behavior.
• Retinoids exhibit photoisomerization (e.g., all-trans to cis isomers) and are susceptible to oxidative degradation; these processes can change receptor affinity profiles and should be controlled during biological experiments.
• In vitro, acitretin is commonly used as a tool compound to interrogate retinoid-responsive promoters, RA signaling crosstalk, and to benchmark retinoid pathway modulators in reporter assays.
• Protein interactions beyond RAR/RXR are reported for retinoids in literature (binding/transport via cellular retinoic acid-binding proteins, CRABP), which can influence intracellular distribution and effective concentrations.

Important notes for researchers:

• Maintain rigorous vehicle controls due to the sensitivity of cells to co-solvents.
• Verify isomeric composition before and after experiments where receptor subtype selectivity is under study.
• Avoid any inference of therapeutic performance; this product is supplied strictly for research use only.

Buffer Applications

This compound is not a classical buffering agent and is not used to set or maintain pH. However, buffer composition significantly impacts its behavior in bioassays.

Practical guidance (general):

• Use physiologically relevant buffers (e.g., PBS, HBSS, or HEPES-buffered media) and keep co-solvent content low (DMSO/ethanol typically ≤0.1–0.5% v/v for sensitive systems).
• Consider serum proteins (e.g., albumin) that can bind retinoids; this may improve apparent solubility but will also alter free (unbound) concentrations—account for this in experimental design.
• Maintain neutral to slightly basic pH to preserve the carboxylate form, recognizing that ionic strength and buffer species can affect aggregation/solubility.
• Prepare concentrated DMSO stocks and dilute into buffer with vigorous mixing; add solvent last to a rapidly stirred buffer to minimize local supersaturation.
• Filter or centrifuge to remove any precipitate before dosing.

If you require true buffer capacity from 6–8 pH, pair with standard buffers (e.g., HEPES, Tris, phosphate). The compound itself does not impart buffering capacity.

Green Alternatives

For this bioactive retinoid salt, “green alternatives” primarily pertain to solvent and handling choices that reduce hazard and waste, since the active itself is fixed.

Strategies (general):

• Prefer DMSO over DMF/NMP when feasible—DMSO has a more favorable environmental and toxicological profile for lab-scale use.
• Use aqueous buffer with minimal co-solvent for working solutions; keep DMSO or ethanol fractions as low as assay tolerance allows.
• Implement micro-scale assays and aliquoting to minimize waste from degraded solutions.
• Employ amber vials and inert gas headspace to extend solution life, reducing the need for repeated preparations.

Comparison of common co-solvents (general considerations):

• DMSO: relatively benign, high solvency; biodegradable; strong solvating power for retinoids; can affect cells above ~0.5%.
• Ethanol: renewable feedstock options; acceptable at low percentages biologically; flammable/volatile.
• DMF/NMP: powerful but with reproductive toxicity flags; avoid for bioassays if alternatives suffice.

Operational green tips:

• Use low-adsorption plastics or glass to reduce compound loss to surfaces and avoid re-preparations.
• Validate room-temperature stability windows to avoid unnecessary cold-chain energy use during short operations, while still returning materials to -20°C promptly after use.

Note: No change to the active ingredient is implied; solvent selection and process optimization are the primary levers for greener practice with this SKU.

Pharmaceutical Uses

No clinical or therapeutic claims are made for this product. The information below pertains to laboratory and formulation research contexts only.

Potential roles in research and development (general):

• Reference material for analytical method development (e.g., LC–UV/LC–MS) evaluating retinoid stability, isomerization, and impurity profiling.
• Pre-formulation studies exploring solubilization strategies for lipophilic, anionic actives (co-solvents, cyclodextrins, micelles, protein carriers).
• Compatibility screens with excipients under accelerated conditions (light, heat, oxidative stress) to map degradation pathways typical for polyene retinoids.
• Permeation/partitioning experiments in model membranes or liposomes to understand distribution behavior of retinoid carboxylates.

Regulatory/compendial status:

• Pharmacopeial listings, if any, are not provided for this SKU. Verify any compendial status independently if relevant to your program.

Item-specific note:

• Grade/Purity and pharmacopeial compliance are not specified for this item; refer to CoA/Spec Sheet if required for regulated applications.

Physical Properties

Item-specific physicochemical specifications are not provided in this listing. The following guidance distinguishes catalog facts from general literature expectations.

Item-specific (from Product Data):

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

General/literature expectations for acitretin salts (non-authoritative, for planning only):

• State: typically a solid at ambient conditions.
• Solubility profile: retinoids are strongly lipophilic; the sodium carboxylate increases polarity. Researchers often dissolve in DMSO to make concentrated stocks; limited aqueous solubility may be observed, especially in basic or buffered media with co-solvent. Actual solubility is lot/formulation dependent—verify experimentally.
• Light/air sensitivity: conjugated polyenes can undergo photoisomerization and oxidative degradation. Amber light and inert-atmosphere handling can improve stability.
• Partitioning: high hydrophobicity is typical for retinoids; the anionic form is more polar than the free acid but still may partition into nonpolar phases or bind to plastic surfaces.

Do not treat the above as specifications. For exact values (mp, bp, density, solubility limits, logP, pKa, refractive index, UV/Vis maxima), consult the Certificate of Analysis (CoA) or request the Specification Sheet for this SKU.

Quality and Grades

Grade and purity are not listed for this SKU. The following explains how to interpret common grades if provided on the CoA/Spec Sheet.

Item-specific (from Product Data):

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

General guidance for small-molecule bioactives:

• Research grade: suitable for discovery biology/chemistry; purity typically ≥95% by HPLC unless stated otherwise. Confirm residual solvents, water content, and assay method on the CoA.
• HPLC grade (solids): indicates elevated purity and often documented low-UV impurities, useful for spectroscopic/analytical workflows.
• Reference standard grade: tight identity/purity documentation with certified values; used for method development and calibration.

Stabilizers and form considerations:

• Retinoids are often stabilized by inert gas blanketing and light-protective packaging. If an antioxidant or stabilizer is present, it will be declared on the CoA.
• If provided as a hydrate/solvate or trituration with an excipient, potency corrections may be necessary when preparing stock solutions.

What to check on receipt:

• Assay method and purity (HPLC/UPLC, NMR).
• Counter-ion content (Na+ assay) and any residual organic solvents.
• Isomeric composition (all-trans vs. isomers) where relevant to your application.
• Any special light/oxygen protections recommended by the manufacturer.

For specification-controlled applications (e.g., regulated bioanalysis), request and retain the batch CoA for this item.

Reaction and Applications

This SKU is primarily positioned as a bioactive small molecule for research rather than a synthetic reagent. Accordingly, classical synthetic reaction applications (e.g., cross-couplings, Grignards) are not the main use-case.

Research application themes (general, non-clinical):

• Ligand studies with retinoid receptors and downstream transcriptional readouts in cell-based assays.
• Probe/standard in analytical workflows (e.g., LC–MS/UV) to characterize retinoid stability, isomerization, and metabolism in vitro.
• Formulation research examining solubilization strategies for highly lipophilic anionic molecules (co-solvents, cyclodextrins, proteins).

Assay setup tips (general good practice for retinoids):

• Prepare fresh, light-protected DMSO stocks; minimize freeze–thaw and exposure to air. Consider aliquoting under inert gas.
• Control final co-solvent content (e.g., keep DMSO ≤0.1–0.5% v/v in sensitive cell assays) and include vehicle controls.
• Monitor for photoisomerization; where critical, analyze pre- and post-assay samples by HPLC to verify isomeric integrity.
• Employ amberware and maintain reduced light conditions during handling and incubation.

If you seek a synthetic reagent role (e.g., derivatization of the carboxylate), note that the sodium salt can be neutralized to the free acid for esterification or amide coupling studies, though this is typically outside the scope of bioassay use. For detailed protocols and stoichiometries, refer to primary literature or standard organic synthesis texts.

Reaction Conditions

No item-specific reaction condition data are provided for this SKU. The compound is generally used as a bioactive standard rather than as a reagent. If conducting derivatization, consider the following literature-level guidance (non-binding):

• Solvents: dry DCM, THF, or DMF for coupling steps; DMSO for stock solutions in analytical contexts. Maintain low light exposure.
• Atmosphere: inert gas (N2/Ar) to limit oxidation of the polyene.
• Temperature: keep reactions cold to ambient when possible; elevated temperatures can accelerate isomerization/degradation.
• Reagents: for amide couplings, mild agents (e.g., EDC/HOBt, HATU) at low temperatures; for esterification, DCC/DMAP or acid chloride routes under anhydrous conditions.
• Workup: quench under subdued light; rapidly separate phases; use antioxidants where appropriate; purify with protected chromatography (amber glassware, low-light) to retain the all-trans configuration.

Expected yields and times are highly substrate- and condition-dependent; consult primary literature for retinoid-specific transformations. Always verify structure and isomeric purity by HPLC/UPLC and NMR.

Safety and Handling

Hazard classification is not provided in this listing. Handle as a bioactive, lipophilic small molecule with potential toxicity; consult the SDS for authoritative guidance.

From Product Data (item-specific):

• Storage: Store at -20°C.
• Shipping: Ice chest + ice pads.
• Research Use: For research use only.

GHS information for this item:

• Signal word: Not specified for this item; refer to SDS.
• H-statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General laboratory precautions (good practice for retinoid-like compounds; not item-specific):

• Wear appropriate PPE: lab coat, nitrile gloves, safety glasses.
• Work in a chemical fume hood; avoid inhalation and skin contact.
• Light and oxygen precautions: protect from light (use amber glass/aluminum foil) and minimize air exposure to reduce photo/oxidative degradation.
• Avoid contact with strong oxidizers and strong acids/bases unless intended; salts may undergo acid-base reactions.
• Clean spills with inert absorbent; dispose per institutional and local regulations.

First aid (overview; defer to SDS):

• Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing.
• Inhalation: move to fresh air; seek medical attention if symptoms persist.
• Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

Always consult the specific SDS for SKU A1421149 before use.

Solvent Selection

Choosing a solvent system for acitretin sodium requires balancing lipophilicity of the retinoid scaffold with the ionic carboxylate.

• Polarity class (general): retinoid salts are overall amphiphilic, with strong hydrophobic character; most researchers prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into assay buffer with careful control of final DMSO percentage.
• Water compatibility: true aqueous solubility can be limited; modest solubility may improve at basic pH or with co-solvents/surfactants (e.g., DMSO, ethanol) or carriers such as serum albumin in biochemical assays. Verify empirically.
• Alternative polar aprotics: DMF or NMP can dissolve many retinoids but may be less desirable biologically; DMSO is generally preferred for bioassays due to lower toxicity at small percentages.
• Alcohols: ethanol may dissolve the free acid efficiently; for the sodium salt, mixed EtOH/water or EtOH/DMSO systems can help.
• Nonpolar solvents (e.g., hexanes, toluene) are typically not suited for the salt form but may dissolve the neutral acid after acidification; not recommended unless part of a synthetic workflow.

Comparison (general):

• DMSO: highest solvating power; best for stock solutions in biology.
• DMF/NMP: strong solvents but with higher cytotoxicity concerns.
• Ethanol: acceptable co-solvent for some biochemical assays; volatility can aid removal in sample prep.

Always filter or clarify solutions if needed and confirm concentration by UV/Vis where appropriate; retinoids exhibit strong visible/UV absorbance that can be leveraged for quantitation after verifying extinction coefficients.

Storage and Reconstitution

Item-specific storage and shipping:

• Storage: Store at -20°C (per Product Data).
• Shipping: Ice chest + ice pads to maintain cold chain.

General reconstitution guidance (non-binding; verify with CoA/Spec Sheet):

• Stock solutions: dissolve the solid in anhydrous DMSO to make a concentrated stock (e.g., 10–50 mM). Mix gently until fully dissolved. If needed, use brief sonication under low-light conditions.
• Aliquoting: dispense into amber, airtight vials or low-adsorption tubes; flush with inert gas (N2/Ar) to minimize oxidation; store at -20°C.
• Stability: avoid repeated freeze–thaw cycles; use single-use aliquots. Monitor for discoloration or precipitation; discard if integrity is questionable.
• Working solutions: dilute stocks into buffer or media immediately before use, keeping final co-solvent low. Filter if necessary to remove particulates.
• Light protection: handle and store under reduced light; use amber glassware or foil wrap throughout preparation and storage.

Note: Exact solubility limits, extinction coefficients, and solution stability windows are not specified for this item; consult the CoA/Spec Sheet or perform a small-scale pilot to establish conditions for your application.

Structure and Identity

Acitretin sodium is the sodium salt form of the retinoid acitretin, a polyene carboxylate related to vitamin A derivatives, offered for research use.

• Product name: Acitretin sodium (SKU: A1421149)
• CAS: 925701-88-8 (product-specific)
• Category: Small molecules & compound libraries (catalog path: 全部 / 可售 / 小分子和化合物库)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general/literature description of the acitretin anion):

• Retinoid polyene backbone with multiple conjugated C=C bonds extending from a terminal carboxylate group.
• An aryl substituent (alkyl-/methoxy-substituted phenyl) appended to the polyene chain.
• In the sodium salt, the carboxylic acid is deprotonated and counterbalanced by Na+.
• 2D description: an extended, nearly linear conjugated chain (trans-alkenyl segments) terminating in a carboxylate, attached at the other end to a substituted phenyl ring; overall highly hydrophobic scaffold with one anionic site in the salt form.

Notes:

• This listing does not provide stereochemical or geometric isomer ratios; acitretin is typically handled as an all-trans configuration in research contexts, but confirm on the CoA for this specific lot.

Synthetic Utility

While this SKU is primarily intended for bioassay and analytical research, the underlying functional groups suggest possible synthetic manipulations if the free acid is accessed from the sodium salt.

General functional-group perspective:

• Conjugated polyene: sensitive to radical and electrophilic additions; prone to E/Z isomerization under light/acid. Typically preserved rather than elaborated in synthesis.
• Carboxylate/carboxylic acid: platform for esterification, amide coupling, or salt metathesis. The sodium salt can be neutralized (e.g., with dilute acid in biphasic systems) to furnish the free acid prior to coupling.
• Aryl substituent: generally inert under mild conditions; strong electrophiles/oxidants should be avoided to protect the polyene.

Representative synthetic operations (literature-general):

• Formation of prodrugs (e.g., esters) for permeability/solubility studies.
• Activated ester or acid chloride preparation under carefully controlled, anhydrous, low-light conditions, followed by coupling to amines/alcohols.
• Ion-pair extraction or phase-transfer strategies to manipulate the salt between organic and aqueous phases without degrading the polyene.

Cautions:

• Protect from light and oxygen during any transformation; consider antioxidants and inert atmospheres.
• Avoid strong acids/bases and elevated temperatures that could trigger polyene isomerization or decomposition.

For precise protocols, consult primary synthetic literature on retinoid derivatization; no item-specific reaction data are provided for this SKU.

Target Specificity

No target specificity data are provided for this item in the product listing. This tab is typically applicable to biological reagents with defined binding targets (e.g., antibodies). For small molecules such as acitretin sodium, consult primary literature for receptor profiling if relevant to your study. No item-specific target data are claimed here.