This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
External Descriptors
Not available
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
302.500 g/mol
XLogP3
5.200
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
302.225 Da
Monoisotopic Mass
302.225 Da
Topological Polar Surface Area
40.500 Ų
Heavy Atom Count
22
Formal Charge
0
Complexity
416.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
3
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
Lösungsrechner
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Bewertungen
Kundenbewertungen
Application Protocols
Scope note
This section is typically for tested applications of antibodies/assay kits (e.g., WB, IHC, IF, FC). It does not directly apply to a small-molecule compound.
General small-molecule handling protocols (research context)
Stock preparation:
Dissolve in dry DMSO to 10–50 mM. Vortex and, if needed, sonicate briefly. Filter through 0.22 µm PTFE for particle removal when required by the assay.
Working solutions:
Dilute into aqueous buffers/media with vigorous mixing to a final DMSO content typically ≤0.5–1% v/v. Inspect for precipitation; if observed, adjust vehicle or concentration.
Light/air protection:
Prepare small single-use aliquots; flush headspace with inert gas. Store aliquots protected from light to minimize oxidation.
Analytical confirmation:
Verify concentration by UV–vis (if a distinct λmax is established) or quantitative NMR with an internal standard. Check purity by HPLC prior to critical assays.
Recording and controls:
Document solvent lot, co-solvent %, time from stock preparation, and storage conditions. Include vehicle-only controls in all experiments.
Note
No validated, item-specific application protocols are provided. For specialized uses (e.g., crystallography ligands, surface immobilization), develop and validate custom protocols.
Biological Roles
Item-specific facts (from Product Data)
No biological/biochemical data are specified for this item. For research use only.
Literature/general context (non-clinical)
Provenance: “Totara-” diterpenoids are commonly reported from coniferous species (e.g., Podocarpaceae). Such secondary metabolites are studied for their roles in plant chemical ecology and defense (literature).
Chemical biology interest: Phenolic diterpenoids are often evaluated in vitro as redox-active scaffolds, membrane-interacting hydrophobes, or as ligands in target-agnostic phenotypic screens (literature). These studies inform SAR and mechanism hypotheses in chemical biology; they are not medical claims.
Assay considerations:
Solubility/aggregation: Hydrophobic natural products can form colloids at micromolar concentrations; include nonionic detergents (e.g., 0.01–0.05% Tween-20) or BSA, and verify activity with detergent controls to rule out nonspecific effects (literature best practice).
Redox/photostability: Phenolic moieties may undergo air/light-induced changes; use fresh DMSO stocks, protect from light, and limit freeze–thaw to maintain consistency across replicates.
Nonspecific binding: High lipophilicity can lead to protein/plastic binding; use low-bind labware and confirm free concentration via equilibrium dialysis or ultrafiltration if quantitative potency data are needed.
Documentation
For any biological role claims in publications, cross-verify the structure and purity of the exact lot used (qNMR/HPLC/HRMS) and report vehicle controls, stock stability, and light/air protection measures.
Buffer Applications
Scope note
Totaradiol is a hydrophobic small molecule and is not a buffering agent. No buffer pKa or capacity is applicable.
Practical guidance (when working in aqueous systems)
Solubilization: Prepare concentrated stocks in DMSO or ethanol and dilute into buffered media with vigorous mixing. Keep final organic co-solvent ≤0.5–1% v/v when possible to avoid perturbing biological assays.
Vehicles: If precipitation occurs upon dilution, consider co-solvents (up to assay-compatible limits), cyclodextrin complexation, or micellar systems (e.g., TPGS-750-M, Kolliphor EL) validated for your assay.
pH effects: While totaradiol itself is not a buffer, phenolic OH (if present) can exhibit weak acidity; however, at typical assay concentrations, the compound will not provide meaningful buffering capacity. Maintain pH with a standard buffer system appropriate to your biology (PBS, HEPES, MOPS, etc.).
Documentation
Because no aqueous formulation properties are specified for this item, establish empirical solubility, stability, and precipitation thresholds in your intended buffer. Record vehicle composition and pH for reproducibility.
Green Alternatives
Context
No item-specific green credentials are provided. The following considerations are general, literature-based guidance for handling hydrophobic phenolic diterpenoids and designing greener workflows.
Opportunities for greener practice
Solvent substitution:
Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-MeTHF, CPME, or toluene where reaction and solubility permit.
Favor alcohols (EtOH, iPrOH) or water/biobased co-solvents for extractions if the compound’s partitioning allows.
Energy efficiency:
Use room-temperature catalysis (DMAP-catalyzed acylations, enzymatic acylations) to reduce heating requirements.
Explore flow setups for improved heat/mass transfer and reduced solvent hold-up.
Benign auxiliaries:
Employ catalytic rather than stoichiometric additives (e.g., catalytic DMAP, Sc(OTf)3) when compatible.
Consider solid-supported reagents for cleaner workups and less aqueous waste.
Oxidation control:
To minimize use of excess antioxidants or oxygen scavengers, handle under inert gas and protect from light; this reduces byproduct formation and rework.
Illustrative comparison (general; not item-specific)
Conventional vs greener options for common steps:
O-acylation: DCM/pyridine → EtOAc or 2-MeTHF with catalytic DMAP and an organic base (DIPEA), or enzymatic acylation in iPrOH.
O-alkylation: DMF with NaH → Me-THF or CPME with carbonate bases and phase-transfer catalysts; or micellar catalysis (aqueous TPGS-750-M) if substrate solubility permits.
Validation note
Always validate greener substitutions at small scale, confirming conversion, selectivity, and product stability for this specific compound/lot.
Pharmaceutical Uses
Item-specific facts (from Product Data)
No pharmacopeial status, excipient role, or GMP attributes are specified. This product is labeled For research use only.
General, non-clinical context
Natural-product diterpenoids like totaradiol are used in discovery-stage medicinal chemistry as reference substances, screening hits, or semi-synthetic scaffolds for structure–activity relationship (SAR) exploration. Such use occurs strictly in preclinical research environments.
Formulation screening for in vitro/in vivo research (non-clinical):
Vehicles for hydrophobes: Captisol, PEG400/saline mixtures, lipid emulsions, or nanosuspensions; selection depends on route and model, and must comply with institutional guidelines.
Solid-state characterization: If scaling for repeated studies, evaluate crystallinity, amorphous content, and polymorphism to ensure consistent exposure.
Analytics for research formulations:
Stability-indicating HPLC/LC–MS to monitor degradation (oxidation of phenolic groups, hydrolysis of esters if derivatized).
Quantitation in matrices via LC–MS/MS using stable-isotope-labeled internal standards where available or appropriate surrogate standards.
Compliance note
Absent explicit GMP/compendial statements, this material should not be used for manufacturing or as an excipient. For any regulated application, request detailed quality documentation or source a compendial-grade alternative.
Physical Properties
Item-specific facts (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Melting/boiling point: 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.
Literature/general information (context; not item specifications)
Physical state: Many diterpenoid phenolic diols occur as off-white to pale solids or resins at ambient temperature; they are typically hydrophobic and exhibit very low water solubility (literature).
Solubility profile: Frequently soluble in DMSO and moderately soluble in alcohols (MeOH, EtOH) and nonpolar/medium-polar organic solvents (EtOAc, CHCl3, toluene). Actual solubility should be established experimentally for this specific lot (literature guidance).
Thermal behavior: Natural-product diterpenoids can exhibit broad or multiple melting events due to polymorphism or resinous character; some are prone to gradual oxidation/discoloration on prolonged air/light exposure (literature).
Spectroscopic handles: Phenolic OH typically displays broad O–H stretches in IR (~3200–3600 cm⁻¹, literature). Aromatic/terpenoid frameworks show characteristic 1H/13C NMR resonances; exact chemical shifts depend on substitution and stereochemistry.
Practical notes
Establish a working solubility screen (DMSO, EtOH, MeCN, THF, EtOAc) before planning assays or derivatizations.
If UV methods are intended, determine an experimental UV–vis profile for this lot; phenolic diterpenoids often absorb in the near-UV due to aromatic character (literature).
Quality and Grades
Item-specific facts (from Product Data)
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpretation (general)
Natural-product small molecules such as diterpenoid diols are often offered as research grade with HPLC purity metrics (e.g., area % by UV at a specified wavelength). In the absence of a stated grade, confirm the analytical method (HPLC/UPLC, GC, qNMR) and detection wavelengths used to determine purity on the CoA.
Identity confirmation: For structurally complex terpenoids, orthogonal methods (1H/13C NMR, HRMS/ESI, IR, and, where applicable, optical rotation and chiral HPLC) provide stronger assurance than a single assay. Request or review these data when your application is structure-sensitive (e.g., SAR, stereochemical studies).
Residual solvents and elemental impurities: If you require compliance to ICH Q3C/Q3D or similar, request specific testing. In the absence of declared limits on metals or solvents, treat them as Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: Phenolic compounds can auto-oxidize; if no stabilizer is listed for this item, you may add an antioxidant scavenger in your own workflow (e.g., ascorbate or minimal BHT) only if compatible with downstream assays. Validate that any additive does not interfere with analytics.
Lot-to-lot comparability: For natural-product items, minor differences in impurity profiles may occur. For critical work, reserve sufficient quantity of a single lot to complete a study and document analytical comparability if a lot change is required.
Reaction and Applications
Item-specific facts (from Product Data)
Manufacturer applications: Not specified.
Research use note: For research use only.
General applications (literature; context for diterpenoid phenolic diols)
Screening libraries: Totaradiol is categorized under small-molecule/natural-product libraries for target discovery, phenotypic screening, and mechanism-of-action studies in chemistry and chemical biology (non-clinical).
Derivatization chemistry: The presence of two hydroxyl groups (implied by “-diol”) enables a range of O-functionalizations:
O-acylation (acyl chlorides/anhydrides with base or DMAP catalysis) to prepare esters for prodrugs or SAR analogs (non-clinical research context).
O-alkylation (Williamson ether synthesis) under phase-transfer or polar aprotic conditions.
Silyl protection (TBS/TIPS) to manage site-selectivity in multi-step synthesis.
Carbonate/urethane formation for linker installation.
Phenolic reactivity (if one OH is phenolic): Electrophilic substitution on an activated aromatic ring (nitration/sulfonylation) should be planned cautiously to preserve terpenoid integrity. Mitsunobu inversion is possible on aliphatic secondary alcohol centers, if present.
Analytical applications: Reference standard for chromatographic method development in natural-product workflows; QC marker in botanical authentication (chemistry-focused use).
Practical tips
Dry, oxygen-minimized conditions help limit phenolic oxidation during multi-step synthesis.
Monitor reactions by LC-MS and 2D NMR to confirm site-selectivity on diol substrates.
If chiral centers are present, track enantiomeric/diastereomeric integrity via chiral HPLC or Mosher’s ester analysis.
Reaction Conditions
Item-specific facts (from Product Data)
No reaction condition specifications are provided for this item.
General conditions (literature guidance for common transformations of diols/phenols; adjust empirically)
O-acylation (selective):
Solvent: CH2Cl2, EtOAc, or 2-MeTHF (dry).
Reagents: Acyl chloride or anhydride (1.1–1.5 eq), base (Et3N or DIPEA, 2–3 eq), catalytic DMAP (5–10 mol%).
Temp/time: 0 °C to rt, 0.5–4 h. Monitor by TLC/LC–MS. Protect from moisture.
O-alkylation (Williamson):
Solvent: Acetone, MeCN, or CPME; phase-transfer (toluene/H2O + TBAB) for heterogenous setups.
Base: K2CO3 or Cs2CO3 (2–3 eq) for phenols; NaH for aliphatic OH if needed (use caution).
Electrophile: Alkyl halide or sulfate (1.2–2 eq). 25–60 °C, 2–16 h.
Silylation (protection):
Solvent: DMF, CH2Cl2, or toluene (dry).
Reagents: TBSCl (1.2–2 eq per OH), imidazole or Et3N; 0 °C to rt, 1–3 h. Fluoride-mediated deprotection (TBAF) later.
Mild oxidations of allylic/benzylic sites (if present):
DMP in CH2Cl2 at 0 °C→rt; 0.5–2 h; quench with bicarbonate. Alternatively, TEMPO/bleach systems in biphasic media for greener options.
Hydrogenation of unsaturation (if present):
Pd/C (5–10 wt%), EtOH or EtOAc, 1–3 bar H2, rt–40 °C, 2–12 h; monitor to avoid over-reduction.
Notes
The above are literature-style starting points, not specifications. Confirm compatibility with this specific structure/lot and optimize for selectivity and stability.
Safety and Handling
Item-specific facts (from Product Data)
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
Storage conditions: Room temperature (per Product Data).
General safety guidance (literature/best practice; defer to SDS as authoritative)
Potential hazards: Phenolic/terpenoid small molecules may cause skin/eye irritation and respiratory irritation if dust/aerosol is generated. Avoid inhalation, ingestion, and contact with skin/eyes.
PPE: Laboratory coat, safety glasses or face shield, and suitable chemical-resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure.
Handling: Avoid dust formation. Use clean, dry tools; cap promptly after use. For weighing, antistatic measures can help if material is resinous or powdery.
Incompatibilities: Strong oxidizers, strong bases or acids that can induce undesired oxidation, hydrolysis, or polymerization of phenolic/allylic sites (literature). Separate from peroxides and radical initiators.
Stability considerations: Phenolic diterpenoids may slowly oxidize or darken upon extended exposure to air, heat, or light. Protect from direct light and moisture; consider storing under inert atmosphere for long-term stability (best practice).
First aid (overview; follow SDS): In case of skin contact, wash with soap and water. For eye exposure, rinse cautiously with water for several minutes and remove contact lenses if present and easy to do. If inhaled, move to fresh air. If ingested, rinse mouth—do not induce vomiting; seek medical attention in all cases of significant exposure.
Waste: Dispose according to institutional and local regulations for organic laboratory chemicals.
Solvent Selection
Item-specific facts (from Product Data)
No solvent recommendations are specified for this item; refer to CoA/Spec Sheet.
Literature-based guidance (general for hydrophobic phenolic diterpenoids)
Polarity class: Low to medium polarity, largely hydrophobic; often displays good affinity for aprotic organic solvents.
Moderate: Methanol, ethanol, isopropanol (warming/sonication may help).
Poor: Water and aqueous buffers without co-solvent.
Typical use scenarios:
Bioassays: Prepare concentrated DMSO stock (e.g., 10–50 mM) and dilute into assay buffer to ≤0.5–1% DMSO final. Verify absence of precipitation.
Synthesis/derivatization: Choose dry, oxygen-free solvents (Et2O, THF, toluene, CH2Cl2) for sensitive transformations (acylations, silylations, Mitsunobu-type reactions), as phenolic/allylic OH can be base/acid sensitive.
Practical tips:
Determine an empirical solubility curve at intended temperatures.
Filter sterilization of DMSO stocks (0.22 µm PTFE) may be used for cell-free assays; avoid prolonged plastic contact if adsorption is observed.
If UV detection is used, test solvent/background absorbance and choose LC-MS grade when applicable.
Comparison note (literature)
For greener workflows, consider 2-MeTHF or CPME instead of THF/Et2O, and EtOAc or Me-THF instead of CH2Cl2 where feasible; validate solubility and reaction performance.
Storage and Reconstitution
Item-specific facts (from Product Data)
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Keep container tightly closed in a dry, well-ventilated place at room temperature as specified. To mitigate gradual oxidation of phenolic/allylic functionalities, protect from light and consider storing under inert gas, especially for long-term holding.
Avoid prolonged exposure to heat and humidity. If the material is resinous, minimize headspace and use amber vials.
Reconstitution/stock preparation:
For analytical or bioassay use, dissolve in anhydrous DMSO (typical 10–50 mM). If using alcohols (EtOH, iPrOH), confirm stability and absence of transesterification/solvolysis under your conditions.
Warm gently (≤40 °C) and sonicate briefly to aid dissolution if needed. Do not overheat.
Filter sterilize (0.22 µm PTFE) only if required by your workflow and compatible with the solvent.
Stability of solutions:
DMSO stocks are generally stable for days to weeks at 2–8 °C if protected from light and moisture. For longer storage, prepare single-use aliquots and freeze at −20 °C to −80 °C; avoid repeated freeze–thaw.
Documentation
Because detailed stability data are not provided for this item, verify solution stability empirically (periodic HPLC/LC–MS) under your exact storage conditions.
Structure and Identity
Item-specific facts (from Product Data)
Product name: Totaradiol (SKU: T1009991)
CAS: 3772-56-3
CID: 9995105
InChIKey: 244026 (as provided)
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.
Literature/general information (for context; not item specifications)
Compound class: Commonly described as a plant-derived diterpenoid/phenolic-type small molecule isolated from coniferous species (literature). Exact substitution and stereochemistry should be verified against an authoritative structure database or the CoA.
Core features typically associated with “totara-” diterpenoids: a tricyclic or polycyclic terpenoid framework bearing one or more phenolic/aliphatic hydroxyl groups (literature). The term “-diol” suggests two hydroxyl functionalities, which may be phenolic, allylic, or secondary alcohols, depending on the isomer (literature).
2D structural description (generic, literature): a fused-ring hydrocarbon backbone (terpenoid) with one aromatic/phenolic ring or phenolic-like functionality and additional aliphatic substituents; two OH groups located on aromatic and/or aliphatic positions. The precise regiochemistry and absolute configuration vary by isomer and must be confirmed for this catalog entry.
Notes
Because no definitive structural string (SMILES/InChI) or empirical formula is provided for this specific item, users should consult the product CoA or an authenticated database entry keyed to CAS 3772-56-3 to confirm stereochemistry, regiochemistry, and exact functional group disposition prior to use in structure-sensitive experiments.
Synthetic Utility
Item-specific facts (from Product Data)
No synthetic-grade or reactivity specifications are provided for this item.
General synthetic insights (literature-based for phenolic/diterpenoid diols)
Functional handles: Two OH groups enable differential protection and selective transformations. Strategies include:
Chemoselective acylation of aliphatic vs phenolic OH using acyl chlorides/anhydrides with tailored bases and catalysts (e.g., DMAP, pyridine, imidazole).
Silyl protection (TBS, TES, TIPS) to control regioselectivity; removal under fluoride or mild acid.
Carbonate and carbamate linkers for conjugation or pro-moiety installation (research contexts).
Backbone modifications: Limited electrophilic aromatic substitution on activated rings (if phenolic). Allylic/benzylic positions on terpenoid frameworks can undergo oxidation (e.g., Dess–Martin, SeO2) or reduction (e.g., catalytic hydrogenation) with attention to chemoselectivity.
Stereochemical control: If secondary alcohols are present, Mitsunobu inversion or oxidation–reduction sequences can adjust stereochemistry. Use chiral auxiliaries or enzymatic resolutions for enantio/diastereoselective access when needed.
Late-stage diversification: Sulfonate ester formation (tosyl, nosyl) enables displacement to ethers, azides, or halides. Phenolic O-arylation via Chan–Lam (Cu) or Buchwald–Hartwig conditions can be explored if electronic/steric profiles permit.
Best practices
Employ multi-technique analytics (1D/2D NMR, HRMS) to verify regioselectivity on diol substrates.
Minimize air/light during steps prone to oxidation; add antioxidants or inert atmosphere where beneficial.
Pilot protecting-group schemes at small scale to establish orthogonality before scale-up.
Target Specificity
Scope note
This section pertains to biologics (antibodies, recombinant proteins), which is not applicable to a small-molecule natural product.
Item-specific facts
No antigen/epitope, clone, isotype, or species-reactivity data apply to this product.
Guidance
If using totaradiol in target-based studies, define target engagement with appropriate biophysical/biochemical assays (e.g., SPR, DSF, enzyme kinetics) and report assay conditions, controls, and compound purity. These are experimental design considerations, not intrinsic product attributes.
Wir verwenden Cookies, um die ordnungsgemäße Funktion der Website sicherzustellen und, soweit zulässig, Ihr Nutzererlebnis zu verbessern. Sie können Ihre Einstellungen jederzeit unter „Einstellungen“ verwalten. Weitere Informationen finden Sie in unserer Cookie-Richtlinie.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
