Triptolide palmitate , CAS No.2126920-51-0

CAS: 2126920-51-0 Cat. No.: T1455066 Formule: C₃₆H₅₄O₇ Poids moléculaire: 598.81

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Vue d’ensemble

Triptolide palmitate is the derivative of Triptolide. Triptolide palmitate exhibits cytotoxicity against cancer cell MCF-7 and A549, with IC 50 of 7.5 and 6.4 μM. Triptolide palmitate exhibits a half-time T 1/2 of 50.4 min in Sprague Dawley rats. Triptolide palmitate can be utilizd as drug carrier.

Specifications

Conditions de stockage de stockage

Store at 2-8°C,Protected from light

Expédié en

Wet ice

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Noms et identifiants

Poids moléculaire

598.81

Application Protocols

No item-specific tested application protocols have been provided for this product. As general, literature-based guidance for small-molecule bioactives:

• Stock preparation: Dissolve in anhydrous DMSO to prepare 10–50 mM stocks; vortex and, if needed, sonicate briefly. Filter through 0.22 µm PTFE for sterile applications.
• Working solutions: Dilute stocks into assay media with final DMSO typically ≤0.1–0.5% v/v. For aqueous delivery, consider co-solvent systems (e.g., DMSO/PEG400/saline) or surfactants (Tween 80) to improve dispersion.
• Controls: Include vehicle-only controls. Because of high lipophilicity, pre-equilibrate dosing solutions to minimize adsorption to plastics; use low-bind tips and plates.
• Stability: Prepare fresh on the day of use when possible. Avoid prolonged incubation in basic media; protect from light.

For any biological application, tailor conditions (concentration ranges, exposure times) to the specific model system and consult the primary literature. This product is for research use only.

Biological Roles

Triptolide palmitate is a lipophilic ester derivative of the natural product triptolide. It is commonly used in research as a tool compound to study how fatty-acid esterification modulates physicochemical properties and biological handling (literature/general guidance). No clinical/medical claims are made for this catalog item.

• Pro-moiety concept: The palmitate group increases hydrophobicity, which can influence membrane permeability, plasma protein binding, and depot behavior. In biological matrices containing esterases, the ester can be hydrolyzed to regenerate triptolide (literature).
• Biotransformation: Expected primary pathway is esterase-mediated cleavage; secondary transformations may include epoxide ring opening by nucleophiles or metabolic enzymes. Rates are matrix- and species-dependent (literature reports vary).
• Systems pharmacology research: Used to probe distribution into lipid-rich compartments, interactions with carrier lipoproteins, and the impact of lipidation on cellular uptake mechanisms (e.g., passive diffusion vs. endocytosis of lipid carriers; literature/general concepts).
• Assay considerations: Given high lipophilicity, nonspecific binding to plastics and serum proteins can be significant. Employ low-bind consumables and incorporate serum controls. Vehicle composition (e.g., %DMSO, PEG400, surfactants) can strongly affect apparent potency in cell-based assays (general guidance).

All uses are restricted to research and laboratory investigations.

Buffer Applications

This compound is a neutral, highly lipophilic small molecule and is not used as a buffering agent. It does not possess acid–base functionality suitable for maintaining pH. For experimental work, focus on:

• Using biologically compatible buffers (e.g., PBS, HEPES) for your system while delivering the compound via co-solvent vehicles (DMSO, PEG400) or surfactant-assisted dispersions.
• Verifying that buffer components (particularly high pH or nucleophilic additives) do not promote ester hydrolysis or epoxide ring opening.

No buffer recipes are applicable for this item.

Green Alternatives

Although this product is a bioactive compound rather than a process solvent, greener choices pertain to how you handle, dissolve, and purify it (literature/general guidance).

• Greener solvent options for handling/purification:

  • Prefer ethyl acetate and ethanol (where solubility allows) over chlorinated solvents. Heptane/ethyl acetate systems can replace hexane/DCM in flash chromatography.
  • For stock solutions, consider bio-based 2-methyltetrahydrofuran (2-MeTHF) or Cyrene when compatible with stability; verify ester/epoxide stability first.

• Process considerations:

  • Minimize DCM and chloroform use; substitute with dimethyl carbonate or anisole for certain extractions or recrystallizations if solubility permits.
  • Use aqueous surfactant systems (e.g., polysorbates) to disperse the compound and reduce organic solvent volumes in bioassays.

• Trade-offs:

  • Chlorinated solvents offer strong solvency for lipophilic esters but have higher environmental and safety burdens.
  • 2-MeTHF and ethyl acetate are greener but may provide slower dissolution or lower solubility; assess concentration limits and stability.

• Waste reduction:

  • Prepare small, single-use DMSO aliquots to avoid repeated thawing and disposal of expired solutions.
  • Adopt microscale assay formats to cut solvent consumption and waste generation.

Pharmaceutical Uses

This catalog item is supplied strictly for research use only. The following information provides non-clinical, formulation-oriented context from the literature; it does not imply suitability for human or veterinary use.

• Excipient/vehicle compatibility (literature/general): The palmitate ester’s lipophilicity supports exploration of lipid-based delivery systems (self-emulsifying formulations, nanoemulsions, liposomes) and co-solvent systems (PEG400, propylene glycol, ethanol) for preformulation studies.
• Pro-moiety rationale: Fatty-acid esterification is a common research strategy to alter solubility, permeability, and metabolic activation through esterase cleavage, enabling controlled release of the parent molecule in biological matrices.
• Solid-state handling: Lipidated esters may show semisolid behavior or low-melting transitions depending on purity and polymorph; characterize by DSC/TGA as part of preformulation (general guidance). Item-specific appearance is not provided here.
• Analytical control: Develop stability-indicating methods (LC–MS or HPLC–UV) capable of resolving the ester from triptolide and potential degradants; monitor under ICH-like stress conditions (light, heat, humidity, pH) to inform storage and handling in research settings.

No pharmacopeial monograph or medicinal product claims are made for this item.

Physical Properties

Item-specific specifications have not been provided for this catalog entry. Where useful, literature or general expectations are noted and clearly labeled.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: ~598.8 g/mol (literature/computed for C36H54O7). Not a product specification.
• Molecular formula: C36H54O7 (literature/computed). Not a product specification.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not applicable; decomposition expected before boiling (literature expectation for complex diterpenoids).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility:
  • Likely soluble in polar aprotic organic solvents such as DMSO and DMF; improved solubility in nonpolar/medium polarity solvents (e.g., dichloromethane, ethyl acetate) relative to triptolide due to the palmitate chain (literature/general guidance).
  • Aqueous solubility expected to be very low without co-solvents or surfactants (literature/general guidance).
• Partitioning: High lipophilicity anticipated (cLogP likely >5 due to C16 chain; literature expectation). No item-specific logP provided.
• pKa: Not applicable (no ionizable centers expected in the palmitate ester under neutral conditions; literature/general chemistry).
• Stability notes (literature/general): Esters are susceptible to hydrolysis under strong acidic/basic conditions and to enzymatic cleavage; the epoxide rings may undergo nucleophilic ring-opening under strongly nucleophilic or acidic conditions.

Quality and Grades

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

Interpretation and context for this product class (general guidance):

• For small-molecule bioactives such as triptolide esters, catalog offerings are typically supplied at research grade with purity established by HPLC/LC–MS and identity confirmed by NMR/HRMS. In the absence of an item-specific purity declaration, consult the product’s CoA for assay, chromatographic purity, and residual solvent profile.
• UV/fluorescence behavior: Triptolide scaffolds typically exhibit modest UV absorbance in the 200–280 nm region; if HPLC methods are used, ensure appropriate wavelength selection and assess potential co-eluting lipophilic impurities (literature/general guidance). No item-specific UV cutoffs are provided here.
• Stabilizers: None stated for this item. If stabilizers or antioxidants are required for certain workflows (e.g., to mitigate slow hydrolysis or epoxide reactivity), this will be listed on the CoA/Spec Sheet.
• Documentation: For regulated or traceable research, request batch-specific CoA including identity (NMR/HRMS), purity (HPLC area%), water/volatile content (KF/TGA), and any residual inorganic profile as needed. Where applicable, a Spec Sheet will also note lot-specific storage and shelf-life guidance.

Reaction and Applications

This material is primarily used as a bioactive small-molecule research tool and pro-moiety, not as a general-purpose reagent. Nevertheless, several chemistry-facing use cases are relevant (literature/general guidance):

• Prodrug/pro-moiety studies: Triptolide palmitate serves as a model for evaluating lipophilic esterification to modulate permeability, plasma protein binding, and enzymatic activation (esterase-mediated cleavage to release triptolide).
• Metabolic stability assays: Suitable for in vitro microsomal/S9 fraction or plasma stability tests to quantify ester hydrolysis kinetics and to profile potential epoxide reactivity.
• Formulation research: The C16 ester is valuable for nanoemulsion, lipid nanoparticle, or liposomal loading studies designed to enhance encapsulation efficiency of highly lipophilic payloads.
• Analytical development: Provides a standard for LC–MS method development differentiating parent ester vs. hydrolysis product (triptolide), including MRM transitions after establishing ionization pathways (ESI/APCI, literature-driven).
• Synthetic reference: Can be used as a reference compound in SAR sets comparing chain length (e.g., laurate, myristate, palmitate, stearate) vs. physicochemical and bioperformance metrics.

Practical tips:

• Use rigorously anhydrous solvents and neutral conditions if isolating or storing in solution to minimize hydrolysis.
• For biological assays, prepare fresh DMSO stocks and limit freeze–thaw. Include appropriate vehicle controls given the lipophilicity of the palmitate ester.

Reaction Conditions

The compound is not commonly used as a reagent in classical organic reactions; however, literature/general conditions relevant to its functional groups are provided for method development and stability studies:

• Ester hydrolysis (to parent triptolide):

  • Basic: Aqueous Na2CO3/NaHCO3 in MeOH/H2O at 0–25°C can effect partial to complete cleavage; stronger bases (NaOH) accelerate but risk epoxide opening and degradation. Time: minutes to hours depending on conditions.
  • Acidic: Dilute HCl or H2SO4 in MeOH/H2O at 0–25°C; proceed cautiously to limit side reactions. Monitor by LC–MS/HPLC.
  • Enzymatic: Porcine liver esterase or human carboxylesterases in phosphate buffer (pH ~7.4) at 37°C; hydrolysis half-lives vary widely; establish empirically for your system.

• Epoxide stability: Avoid nucleophiles (thiols, amines) and strong Lewis/Brønsted acids which can open epoxides. If studying adduct formation, mild nucleophiles in aprotic solvents at 0–25°C can promote controlled ring opening (literature/general chemistry).

• Solvent and temperature: Conduct manipulations at ambient or lower temperatures in anhydrous, neutral solvents (DCM, EtOAc, toluene, or dry DMSO/DMF). Protect from light.

• Analytical monitoring: Use stability-indicating HPLC (e.g., C18, water/acetonitrile with 0.1% formic acid) or LC–MS. Establish calibration for both ester and triptolide; verify mass transitions before quantitation.

All values above are general literature guidance; optimize for your specific setup.

Safety and Handling

• GHS/CLP information: Not specified for this item; refer to SDS for authoritative hazard classification, pictograms, and H-statements.
• Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance (not a substitute for SDS):

• PPE: Wear lab coat, nitrile gloves (change frequently), and safety glasses or face shield when handling powders/solutions. Use a certified chemical fume hood to avoid inhalation exposure.
• Toxicity caution: Triptolide derivatives are potent bioactives; avoid skin contact, inhalation, or ingestion. Handle microgram-to-milligram quantities with care, minimizing aerosol and dust formation (general literature caution).
• Incompatibilities: Avoid strong acids/bases that can hydrolyze the ester; avoid strong nucleophiles that may open epoxide rings. Keep away from oxidizing agents and reducing agents that could modify sensitive functionalities (general chemistry guidance).
• First aid (general): In case of skin contact, wash with soap and water; for eye exposure, rinse with water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air; if ingested, do not induce vomiting; seek medical attention. Always follow institutional protocols.
• Special risks: Epoxide-bearing molecules can be alkylating; avoid prolonged contact and ensure proper containment. Use amber glassware or foil wrap to limit light exposure, consistent with product storage note.
• Waste: Collect organic solutions and contaminated materials as hazardous chemical waste according to local regulations.

Solvent Selection

Triptolide palmitate is a highly lipophilic, neutral ester. Solvent choice is driven by its hydrophobicity and the need to preserve ester and epoxide integrity.

• Primary dissolution (literature/general guidance):

  • DMSO: Excellent for preparing concentrated stock solutions (e.g., 10–50 mM) for bioassays; mix thoroughly and protect from light.
  • DMF or NMP: Alternative polar aprotic co-solvents when DMSO is unsuitable. Assess potential reactivity over time.
  • Chlorinated/ethyl acetate solvents (DCM, CHCl3, EtOAc): Good solubility for preparative workup and chromatography; avoid prolonged exposure to acidic stabilizers in some solvent grades.
  • Alcohols (MeOH/EtOH): Limited solubility expected; may promote transesterification under basic conditions—use cautiously.
  • Aqueous systems: Very poor solubility; employ co-solvents (DMSO <1–2% v/v in final assay where feasible) or vehicles (PEG400, Tween 80, cyclodextrins) for dispersion (general formulation practice).

• Polarity and miscibility (literature/general): Neutral, non-ionizable; favors nonpolar and medium-polar organic phases; immiscible with water.

• When to choose alternatives: If biological systems are sensitive to DMSO, consider PEG400 or Captisol-based vehicles. For purification, heptane/EtOAc gradients can improve resolution of fatty-acyl esters versus parent triptolide.

• Stability considerations: Avoid basic alcoholic solvents and strong acids that can cleave the ester or open epoxides; minimize heat and light during solvent handling.

Storage and Reconstitution

• Storage conditions (item-specific): Store at 2–8°C, protected from light. Ship on wet ice (as supplied). Keep container tightly closed to limit moisture ingress.
• Long-term handling (general guidance): For extended storage, consider keeping the solid desiccated and protected from light in amber glass. Avoid repeated warming/cooling cycles that may promote hydrolysis.
• Reconstitution (general research practice):
  • Prepare concentrated stock solutions in anhydrous DMSO (e.g., 10–50 mM). Mix thoroughly to ensure complete dissolution. Optionally, nitrogen or argon blanket can be used for long-term aliquots.
  • Filter sterilize through 0.22 µm PTFE if aseptic stocks are required.
  • Aliquot into single-use portions and store at −20°C to −80°C protected from light to minimize freeze–thaw. Note: Frozen storage guidance for solutions is general; follow any lot-specific directions on the CoA/Spec Sheet.
• Stability notes (general): Esters can hydrolyze in the presence of moisture, acids, or bases; epoxide functionalities may react with nucleophiles or under acidic conditions. Maintain neutral, anhydrous environments and avoid prolonged exposure to elevated temperatures or light.
• Spec-sheet deference: Appearance, purity, and any stabilizer content are not specified here. Refer to the CoA/Spec Sheet for lot-specific details and shelf-life.

Structure and Identity

Triptolide palmitate is a lipophilic ester derivative (pro-moiety) of the diterpene triepoxide triptolide, formed by acylation of a triptolide hydroxyl group with palmitic (hexadecanoic) acid.

• Item-specific identifiers:

  • CAS: 2126920-51-0
  • SKU: T1455066
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity (informational; not product specification):

  • Common name: Triptolide 14-O-palmitate (nomenclature may vary in literature)
  • Molecular formula (expected for the palmitate ester): C36H54O7 (literature/computed)
  • Molecular weight: ~598.8 g/mol (literature/computed)
  • Structural features: polycyclic abietane-like diterpenoid core bearing three epoxide rings (as in triptolide), with an esterified long-chain saturated fatty acyl group (C16) that increases hydrophobic surface area; multiple oxygen functionalities (epoxides and ester). No formal stereochemistry changes relative to triptolide are implied by simple esterification (all stereocenters retained; literature).

• 2D structural description (literature): polycyclic fused-ring skeleton with three strained epoxide rings and an exocyclic enone region on the triptolide core; one secondary/tertiary alcohol position is converted to a hexadecanoyl ester, depicted as a long linear alkyl chain terminating in the carbonyl linked to the oxygen of the triptolide core.

Synthetic Utility

While primarily a finished research compound, triptolide palmitate also serves as a useful synthetic and analytical benchmark in lipidation chemistry (literature/general guidance):

• Functional group map: Contains one long-chain fatty acyl ester and multiple epoxide rings on a rigid polycyclic diterpenoid core. The ester can be selectively hydrolyzed; epoxides can undergo nucleophilic opening under controlled conditions.
• Reference in SAR sets: Acts as a standard for evaluating chain-length effects (C12–C18) on physicochemical and bioassay outcomes. Useful for establishing structure–property relationships (solubility, logD, protein binding).
• Derivatization opportunities:
  • Transesterification or acyl exchange to access alternative fatty-acid esters under mild conditions (catalytic DMAP, vinyl esters; careful to avoid epoxide opening).
  • Selective protection strategies to modify the core without disturbing the palmitate (using neutral conditions and non-nucleophilic bases when required).
• Purification/analysis: Benchmark for chromatographic behavior of lipidated diterpenoids; often elutes later than the parent due to increased hydrophobicity. Aids in setting gradient windows and stationary phase selection (C18 vs. phenyl-hexyl) in LC method development.

Because the molecule contains strained epoxides, avoid strongly basic or acidic conditions during any synthetic manipulation to maintain integrity.

Target Specificity

Not applicable. This product is a small-molecule research compound, not an antibody or affinity reagent. No antigen, epitope, clone, isotype, or species reactivity information applies.