(S)-Trolox - Moligand™, 10 mM in DMSO , CAS No.53174-06-4

CAS: 53174-06-4 Cat. No.: S1493375 Fórmula: C₁₄H₁₈O₄ Peso molecular: 250.29 Número CE: 625-557-2

GRAU & PUREZA Moligand™, 10 mM in DMSO

Storage

Argon charged,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Visão geral

(S)-Trolox is an analogue of vitamin E, in which the phytyl chain is replaced with a carboxyl group. (S)-Trolox is frequently used as a model compound for studies of structural features, as well as a standard for evaluation of antioxidant activity. (S)-Trolox has potent and specific neuroprotective and antioxidant effects .

Especificações

Especificações e pureza

Moligand™, 10 mM in DMSO

Condições de armazenamento de armazenamento

Argon charged,Store at -80°C

Enviado em

Dry ice packs + Cold packs

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Grau

Moligand™

Nomes e identificadores

SMILES isoméricas

CC1=C(C2=C(CC[C@@](O2)(C)C(=O)O)C(=C1O)C)C

WGK Alemanha

3

Peso molecular

250.29

Reaxy-Rn

5052542

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5052542&ln=

Propriedades químicas e físicas

• Rotação específica [α]: [α]26/D −65°, c = 1.2 in ethanol
• Ponto de fusão (°C): 160 °C (dec.) (lit.)

Application Protocols

The catalog entry does not list validated application protocols. Below are general, literature-based procedures commonly used with Trolox. Adjust to your system and consult primary references.

1. Preparation of stock solutions

• Dissolve (S)-Trolox in anhydrous DMSO or ethanol to 10–100 mM. Vortex and warm gently if needed. Aliquot and store protected from light.

2. ABTS•+ radical cation decolorization assay (TEAC)

• Generate ABTS•+ by oxidizing ABTS with a suitable oxidant (e.g., persulfate) overnight; dilute to an absorbance of ~0.7 at 734 nm.
• Add Trolox working solutions (serial dilutions) to ABTS•+ solution; incubate at room temperature (e.g., 6 min).
• Measure ΔA734 and construct a calibration curve to express sample antioxidant capacity as Trolox equivalents.

3. DPPH free radical scavenging assay

• Prepare DPPH methanolic solution with A517 ~0.9.
• Mix with Trolox standards and test samples; incubate in the dark for 20–30 min at room temperature.
• Record A517 and calculate % inhibition; express results vs Trolox standard curve.

4. Single-molecule fluorescence anti-blinking additive

• Add Trolox from a DMSO stock to imaging buffer to a low-µM to sub-mM range, together with oxygen-scavenging system (e.g., glucose oxidase/catalase). Optimize concentration empirically to balance photostability and background.

Note: Maintain consistent solvent percentages across standards and samples.

Biological Roles

General/literature perspective (no medical claims):

• Mechanistic analog of vitamin E (tocopherols): (S)-Trolox features a hindered phenolic OH that donates a hydrogen atom to reactive radicals, forming a resonance-stabilized chromanoxyl radical. This interrupts radical chain propagation in lipid and biomembrane models.
• Redox cycling: the chromanoxyl radical can undergo termination (dimerization/disproportionation) or be reduced back in the presence of appropriate reductants, allowing study of antioxidant regeneration pathways.
• Kinetics: steric shielding by methyl groups (2,5,7,8) enhances selectivity for peroxyl radicals and reduces side reactions typical of simple phenols.
• Solubility advantage: compared to tocopherol, the carboxylate handle enhances aqueous compatibility, enabling assays in buffered systems, protein solutions, and live-cell surrogates without the need for detergents at high levels.
• Stereochemical considerations: while radical quenching at the phenolic site is not stereocenter-dependent, the (S) configuration may influence binding or orientation in chiral microenvironments (proteins, membranes), which can be relevant in precision biophysics experiments.

Note: Use is limited to research settings for probing antioxidant mechanisms and calibrations; it is not intended for nutritional or therapeutic use.

Buffer Applications

(S)-Trolox is not a buffering agent. However, it is frequently used in buffered media for antioxidant assays and photostability additives.

Practical guidance (general, non-spec):

• Dissolution: prepare a concentrated stock in DMSO or ethanol, then dilute into buffer (e.g., PBS, phosphate, HEPES) with vigorous mixing to avoid precipitation. Alternatively, dissolve directly by adjusting buffer to mildly basic pH to form the carboxylate salt.
• pH considerations: keep working pH near neutral to limit phenoxide formation; excessively basic conditions accelerate oxidation and can alter assay outcomes.
• Additive compatibility: Trolox is compatible with common oxygen-scavenging systems (e.g., glucose oxidase/catalase) used in single-molecule fluorescence; verify final organic cosolvent content for biological samples.
• Filtration: 0.22 µm filtration can clarify solutions for spectrophotometric assays.

If a true buffer system is required, select standard buffers (phosphate, HEPES, TRIS) based on assay pH; Trolox does not define buffer capacity.

Green Alternatives

The environmental profile of (S)-Trolox use is dominated by solvent choice and solution handling rather than the molecule itself.

Greener practice recommendations (literature/general):

• Prefer bio-derived ethanol or water (adjusted pH) for working solutions when compatible with the assay, instead of high-boiling dipolar aprotic solvents.
• Use minimal DMSO volumes and prepare concentrated stock solutions to reduce solvent waste.
• Employ amber glassware and oxygen-limited handling to maximize solution lifetime, thereby reducing repeated preparations.

Comparison of solvent choices for Trolox work (qualitative):

• Ethanol (green): renewable, low toxicity, easy to remove; moderate solvency; suitable for spectroscopic assays.
• Water at pH 7–8 (greener): no VOCs; requires neutralization/base; limited stability against oxidation—prepare fresh.
• DMSO/DMF (less green): excellent solvency and stability; higher environmental/health burden; reserve for stock solutions.

Trade-offs:

• Ethanol/water improve EHS profile but may constrain maximum achievable concentration and long-term stability.
• DMSO provides reliable solubilization and dosing precision but should be minimized and properly disposed of.

Waste minimization: aliquot concentrated stocks to avoid freeze–thaw cycles and discard fewer partially used solutions.

Pharmaceutical Uses

(S)-Trolox is offered strictly for research use. It is not an approved API or excipient.

Formulation research context (general):

• Antioxidant excipient screening: used as a model hindered phenolic antioxidant to study stabilization of oxidation-prone drug substances in pre-formulation or forced-degradation studies.
• Mechanistic probes: aids in distinguishing radical versus non-radical oxidation pathways by selective quenching of peroxyl radicals.
• Conjugation handle: the carboxylic acid enables synthesis of Trolox–drug conjugates or Troloxylated polymers for research on antioxidant delivery or stabilization.

Compliance notes:

• No pharmacopeial monograph applies to this stereodefined research-grade material.
• Any use in manufacturing development is exploratory; suitability, impurity profiles, and leachables must be established independently.

Do not use in humans or clinical applications.

Physical Properties

The following reflect general characteristics of Trolox-type chroman carboxylic acids and literature descriptions, not Aladdin item specifications.

Item-specific properties (specification values):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable/Not typically determined for this solid; refer to CoA/Spec Sheet if needed.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance (non-spec):

• Physical state: typically a crystalline solid; phenolic carboxylic acid.
• Solubility profile: sparingly soluble in water as free acid; readily soluble in polar organic solvents (DMSO, DMF, ethanol) and in aqueous buffers at elevated pH where the carboxyl group is deprotonated.
• Acid–base behavior: contains a carboxylic acid (deprotonates first) and a phenolic OH (less acidic), enabling pH-tunable solubility. Formation of sodium/potassium salts markedly enhances aqueous solubility.
• Stability: phenolic antioxidants are air/light sensitive over time due to radical oxidation; steric protection from the 2,5,7,8-methyl pattern confers enhanced stability relative to simple phenols.

Always verify lot-specific physical properties on the CoA before method development.

Quality and Grades

Grade for this product: Moligand™.

What Moligand™ implies (general description):

• Intended for research applications where ligand-like small molecules are used in chemical biology, biophysics, and mechanistic enzymology.
• Emphasis on identity confirmation and stereochemical integrity for chiral compounds. Typical release testing includes NMR/LC-MS identity and enantiomeric enrichment determination by chiral HPLC or derivatization (details are lot-specific).
• Low-level impurities, residual solvents, or inorganic residues are controlled within internal specifications suitable for discovery research. Exact impurity thresholds are not disclosed here.

What is specific to this item:

• Stereochemically defined (S)-Trolox under inert packaging (argon charged) and cold chain to preserve antioxidant integrity and minimize oxidative aging.
• Item-specific attributes such as assay purity, water content, and enantiopurity: Not specified for this item; refer to CoA/Spec Sheet.

How to use grade information in method development:

• For quantitative antioxidant assays or SAR work, consult the CoA for exact purity and enantiopurity to set dosing on a pure-compound basis.
• If low-UV background is critical (e.g., HPLC detection near phenolic absorbance bands), review the UV/trace impurity profile on the CoA.

Regulatory note: For research use only; not for human or veterinary use.

Reaction and Applications

(S)-Trolox is widely used as a soluble vitamin E surrogate and radical-scavenging standard in chemical biology and analytical chemistry.

Common research applications (literature/general):

• Antioxidant benchmarking: reference compound in DPPH and ABTS•+ radical quenching assays; results are often expressed as Trolox equivalents (TEAC). The defined stereochemistry enables stereochemical controls where relevant.
• Lipid peroxidation models: quenches AAPH-generated peroxyl radicals (ROO•) in micelles/liposomes; used to calibrate chain-breaking antioxidant efficiency.
• Photophysics/biophysics: additive in single-molecule fluorescence to mitigate triplet-state blinking (oxygen scavenging cocktails often include Trolox). Enantiopurity facilitates reproducibility in high-precision studies.
• Redox mechanism studies: hydrogen atom transfer (HAT) from the phenolic OH to peroxyl/aryl radicals; subsequent chromanoxyl radical resonance stabilization allows kinetic and EPR investigations.

Practical notes:

• Work freshly and oxygen-reduced for kinetic assays; even stabilized phenols slowly oxidize.
• For accurate TEAC calibration, standardize concentration spectrophotometrically and maintain consistent solvent composition and temperature.
• Avoid strong bases and metal contaminants that catalyze oxidation; pre-chelate buffers where necessary.

Manufacturer Applications: Not specified in the catalog entry beyond general research use; the above expands typical utilization of Trolox in research contexts.

Reaction Conditions

General, literature-based conditions for transforming (S)-Trolox; these are guidance, not product specifications.

• Amide coupling at the carboxyl group:

  • Typical reagents: EDCI (1.1–1.5 eq) with HOBt/HOAt or Oxyma; or HATU/TBTU with DIPEA.
  • Solvents: DMF, DCM, or MeCN; greener alternatives include 2-MeTHF or EtOAc when substrates allow.
  • Temperature/time: 0–25°C, 1–16 h. Monitor for O- vs N-acylation; employ phenol protection if needed.
  • Stereochemical integrity: minimal risk of epimerization at C-2 under mild conditions; verify by chiral HPLC.

• Esterification:

  • Fischer esterification in alcohol solvent with catalytic acid (e.g., H2SO4) can lead to phenolic side reactions; Steglich conditions (DCC/DMAP) are milder and more selective.

• Phenolic protection:

  • Silyl ethers (TBS/TBDPS) using imidazole and TBS-Cl in DMF; or benzyl ethers via NaH/benzyl halide. Deprotect under standard conditions (TBAF or hydrogenolysis).

• Oxidation sensitivity:

  • Avoid strong oxidants and prolonged base; perform transformations under inert atmosphere and protect from light to prevent chroman oxidation.

Expected yields: substrate-dependent; typical couplings furnish 60–90% after purification in literature reports. Always optimize for your substrate set.

Safety and Handling

Safety details specific to this catalog entry:

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

General laboratory guidance for phenolic carboxylic acids (literature-based, not a substitute for the SDS):

• Likely hazards: may cause skin/eye irritation and respiratory tract irritation as dust. Phenolic compounds can be harmful if ingested in quantity.
• PPE: wear lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust exposure.
• Incompatibilities: strong oxidizers (can accelerate degradation), strong bases (can promote phenoxide formation and potential air oxidation), and strong electrophiles that can acylate/alkylate the phenolic oxygen.
• Handling: minimize exposure to air and light to preserve antioxidant integrity. Use clean, dry tools; quickly recap vials. When preparing solutions, use oxygen-reduced solvents if long-term stability is required.
• First aid (overview): in case of eye/skin contact, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always follow the SDS.
• Waste: collect solutions/solids as organic chemical waste; do not discharge to drains.

Note: This item is shipped cold and should be stored inerted at -80°C (see Storage tab) to maintain quality.

Solvent Selection

(S)-Trolox contains both a carboxylic acid and a hindered phenolic OH, providing tunable solubility.

Practical guidance:

• Primary solvents for stocks: DMSO and DMF provide rapid dissolution and stability; ethanol or methanol can also be used for near-term work.
• Aqueous systems: dissolve as a salt (e.g., Na⁺/K⁺) or adjust pH above the carboxyl pKa to improve solubility; avoid very high pH that forms phenoxide, which can accelerate oxidation.
• Nonpolar media: limited solubility; consider co-solvent strategies (e.g., DMSO 1–5% v/v) or surfactants for biological model systems.
• Light/oxygen: prepare solutions freshly or under reduced oxygen; protect from light (amber vials) to slow autoxidation.

Comparison (general use cases):

• DMSO: highest solvating power; preferred for concentrated stocks and precise dosing.
• Ethanol: greener, volatile; suitable for working solutions and spectrophotometric assays; ensure compatibility with assay biology.
• Aqueous buffer (pH 7–8 with base): good for immediate use in radical scavenging assays once fully dissolved; monitor for time-dependent oxidation.

Tip: Filter sterilize aqueous solutions through low-protein-binding membranes if using in biochemical assays to remove particulates; avoid prolonged storage in basic aqueous media.

Storage and Reconstitution

Item-specific conditions (from Product Data):

• Storage: Argon charged, Store at -80°C.
• Shipping: Dry ice packs + Cold packs.
• Research Use Note: For research use only.

General best practices for this compound class:

• Upon receipt: keep frozen at -80°C under inert atmosphere. Allow vial to warm to room temperature in a desiccator before opening to prevent condensation.
• Light/oxygen protection: store in amber, airtight containers. The phenolic antioxidant core is prone to slow oxidation; inerting and low temperature prolong shelf life.
• Reconstitution: prepare concentrated stocks in anhydrous DMSO or ethanol. For aqueous use, adjust pH or prepare a salt to enhance solubility. Filter if clarity is required for spectrophotometry.
• Aliquoting: divide into single-use portions to avoid repeated freeze–thaw and headspace oxygen exposure.
• Short-term storage of solutions: keep organic stocks at -20 to -80°C in amber vials. Avoid long storage in basic aqueous buffers; prepare fresh before critical assays.
• Stability monitoring: visually inspect for discoloration or precipitate; check UV–vis profile if quantitative work is intended.

Always refer to the product’s CoA and SDS for lot-specific stability and handling information.

Structure and Identity

High-purity (S)-Trolox supplied under Aladdin’s Moligand™ line. Trolox is a water-soluble chroman-2-carboxylic acid analog of vitamin E; the (S) designation refers to the absolute configuration at C-2 of the chroman ring.

Item-specific identifiers (as supplied on this catalog page):

• CAS: 53174-06-4
• Product name: (S)-Trolox
• Grade: Moligand™
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• PubChem CID (catalog reference): 688071

Structural description (general/literature):

• Core scaffold: substituted chroman (2,3-dihydro-1-benzopyran) fused aromatic–heterocyclic system.
• Functional groups: one phenolic hydroxyl (6-position), one carboxylic acid at the stereogenic C-2 of the chroman, and four methyl substituents (2,5,7,8-positions) typical of tocopherol analogs.
• Stereochemistry: single stereocenter at C-2; this product is the (S)-enantiomer.
• 2D depiction in words: a chroman ring bearing a para-phenolic OH on the benzene portion and a carboxyl substituent at the heterocyclic C-2, with geminal/neighboring methyl groups providing steric hindrance around the phenolic site.

Note: Exact identifiers (SMILES/InChIKey) and elemental analysis for this specific lot should be confirmed on the CoA.

Synthetic Utility

From a synthetic standpoint, (S)-Trolox is a chiral, bifunctional building block.

Transformations (general literature guidance):

• Amide/ester formation at the 2-carboxylic acid: standard peptide-coupling reagents (e.g., EDCI/HOBt, HATU, T3P) afford Trolox amides/esters. Phenolic OH may require protection (e.g., silyl or benzyl) to avoid O-acylation when chemoselectivity is critical.
• Phenolic derivatization: etherification (Mitsunobu, Williamson) or carbonate formation to tune redox potential and solubility; deprotection regenerates the active phenol.
• Radical probes: introduction of spin labels or redox-active tags at the carboxyl group yields mechanistic reporters for EPR/fluorescence studies.
• Polymer conjugation: carbodiimide-mediated coupling to poly(ethylene glycol) or other backbones generates antioxidant-functional materials.

Retrosynthetic value:

• The chroman core with an acid handle is a versatile fragment for constructing tocopherol mimetics with defined sterics/electronics.
• The (S) configuration can be preserved through mild coupling conditions; racemization is limited at C-2 under standard amide coupling but should be monitored by chiral HPLC.

Note: Exact protecting-group and coupling strategies should be optimized relative to the sensitivity of the phenolic moiety.

Target Specificity

(S)-Trolox is a small-molecule antioxidant standard and does not possess antigen/epitope specificity or biomolecular target selectivity in the sense of antibodies or inhibitors.

• No clone, isotype, or species reactivity applies.
• Any interactions studied are physicochemical (radical quenching, membrane interactions) rather than target-specific binding.

For binding/targeted reagents, refer to products explicitly designed as ligands, inhibitors, or antibodies.

Perguntas frequentes

What is Moligand??

Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.

How should this product be stored?

Store at ?80 °C under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 53174-06-4, the molecular formula is C14H18O4, and the molecular weight is 250.29 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.