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Recensioni
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Application Protocols
No vendor-tested bioassay protocols are provided for this item. It is supplied for research use as a chemical standard or tool compound.
General usage examples (literature/practice; verify and optimize in your lab):
LC–MS/MS calibration: Prepare serial dilutions in ACN:water (1:1) with 0.1% formic acid from a DMSO primary stock; include an isotopically labeled internal standard where available. Store working solutions at ≤4 °C (short term) or −20 °C (long term) in amber vials.
Receptor assays: Dilute DMSO stocks into assay buffer to achieve 0.1–10 μM test concentrations; keep final DMSO ≤0.1–0.5% v/v. Include vehicle controls and adsorptive loss controls.
GC–MS: Derivatize aliquots with MSTFA (60 °C, 30 min), then inject under appropriate temperature program; confirm identity by ion ratios/retention index. Validate matrix effects and recovery.
Biological Roles
Context (literature/general; not a medical claim and not specific to this catalog lot):
Chemical class: Classical phytocannabinoid analog with an extended n‑heptyl side chain relative to Δ9‑THC.
Molecular targets: Acts as a ligand at cannabinoid receptors (CB1 and CB2), G protein‑coupled receptors that modulate neuronal and immune signaling. Side‑chain length can markedly influence affinity and efficacy in cannabinoid receptor pharmacology (literature observations across homologous series).
Physicochemical considerations: Extreme lipophilicity drives strong membrane partitioning, potentially leading to slow on/off kinetics and prolonged apparent effects in biological systems (qualitative, literature for lipophilic cannabinoids).
Metabolism (general cannabinoid pathways): Phase I oxidations (allylic/benzylic oxidation, side‑chain ω‑ and ω‑1‑hydroxylation) primarily via hepatic CYP450 isozymes; Phase II conjugation (glucuronidation of the phenolic OH). Metabolites can be more polar and amenable to LC–MS detection.
Transport/distribution: High affinity for lipid compartments and serum proteins; low aqueous solubility necessitates co‑solvents, cyclodextrins, or surfactants for in vitro exposure studies.
Use in research:
Probe for structure–activity relationships in cannabinoid signaling.
Internal standard candidate (with isotopologues) for quantitative bioanalysis of complex matrices.
Note: All studies should be designed in accordance with institutional approvals and regulations; this product is for research use only.
Buffer Applications
THCP is a highly hydrophobic small molecule and is not used as a buffering agent. It does not participate in classical buffer systems.
Practical note for assay buffers (general):
To introduce THCP into aqueous buffers for biochemical assays, dissolve as a concentrated stock in DMSO or ethanol and dilute into buffer with a co‑solvent/surfactant (e.g., 0.1–1% DMSO final, optional 0.01–0.1% nonionic surfactant). Verify that the vehicle does not affect assay readouts.
Green Alternatives
This product is a target analyte/standard rather than a process solvent or reagent. As such, “green alternative” substitution is generally not applicable to the compound itself.
Practical greening of workflows involving THCP (general guidance):
Prefer ethyl acetate or 2‑MeTHF instead of chlorinated solvents for extraction/workup when analytically suitable; confirm recovery and stability.
Use ethanol/water or ethanol/PEG co‑solvent systems where possible in bioassays to reduce DMSO reliance, while maintaining analyte solubility.
Minimize solvent volumes by using micro‑scale SPE and microvials for calibration standards.
Consolidate analytical runs and employ column/gradient conditions that shorten runtime without compromising resolution to reduce solvent consumption.
Tradeoffs to consider:
Non-chlorinated alternatives may alter extraction selectivity and matrix effects; method re‑validation is required.
Highly lipophilic cannabinoids can exhibit reduced solubility in greener solvents; ensure adequate solubility to prevent precipitation and adsorption losses.
Pharmaceutical Uses
This product is supplied strictly for research use only. No therapeutic, diagnostic, or clinical uses are claimed or supported.
Analytical reference material: Can serve as a calibrant/control in quality control laboratories developing methods to detect and quantify cannabinoid profiles in plant extracts, concentrates, or research formulations.
Preformulation studies: Useful for investigating solubilization strategies for highly lipophilic small molecules (e.g., cosolvent systems, lipid vehicles, cyclodextrin inclusion) in a research setting.
Excipient interactions (research): Screening of surfactants (polysorbates), co‑solvents (ethanol, PEG400, propylene glycol), and lipids (MCT oil) to achieve stable dispersions suitable for in vitro work; any such use must remain within non-clinical research.
Physical Properties
Item-specific specifications (this lot):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed general properties for Δ9‑THCP (for context; not item specifications):
Molecular formula (literature): C23H34O2
Molecular weight (literature): ~346.52 g/mol
Physical state: typically a viscous oil or low-melting glassy solid; highly lipophilic.
Solubility: insoluble in water; soluble in nonpolar and moderately polar organics (chloroform, dichloromethane, ethyl acetate, hexanes); soluble in alcohols; readily soluble in DMSO.
Acid/base: weakly acidic phenol (pKa of phenolic OH in classical cannabinoids typically ~10; literature).
Partitioning: very high hydrophobicity (logP expected higher than Δ9‑THC; literature values for Δ9‑THC ~7.2 suggest THCP is greater; literature/estimates).
UV/Vis: aromatic chromophore with absorption in the near‑UV; exact λmax depends on solvent and ionization state (literature).
Volatility: nonvolatile under ambient pressure; distillable only under high vacuum if at all; prone to thermal/oxidative degradation when heated (literature).
Note: Do not treat literature values as specifications for this item. Consult the product’s CoA/Spec Sheet for tested values relevant to your lot.
Quality and Grades
Item-specific quality data:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on quality considerations for THCP reference materials (general):
Reference standard suitability: For analytical and bioanalytical applications (e.g., LC–MS/MS quantitation, receptor binding assays), impurity profile and isomeric purity are critical. Cannabinoids can exist as Δ8/Δ9 positional isomers and as various oxidation products; chromatographic resolution of these is desirable.
Stereochemical integrity: Classical cannabinoids possess two stereocenters. Specify and control absolute configuration ((6aR,10aR) vs other diastereomers) when stereochemistry matters for activity or chromatographic behavior.
Residual solvents and volatile impurities: For high-sensitivity LC–MS applications, low residual solvent background and low non-volatile residue are preferred. Typical acceptance criteria are method-dependent; consult the CoA.
Water content: Excess moisture can impact weighability and solution stability; Karl Fischer water is often monitored for oils, but this item’s water specification is not provided. For exact values, see the CoA/Spec Sheet.
UV background: For HPLC/UV detection, low background absorbance and absence of UV‑active impurities near the analyte’s λmax are advantageous.
Stabilizers: None stated for this item. If present in other lots/products, stabilizers (e.g., antioxidants) can alter analytical baselines and must be disclosed on the CoA.
Documentation: Each lot’s CoA should report identity (NMR, MS), purity (HPLC/UPLC area %), and if applicable enantiomeric/diast. ratios. Absent explicit specs in this listing, rely on the lot‑specific CoA for quantitative details.
Reaction and Applications
As a research chemical, THCP is primarily used as:
Analytical reference standard: For developing and validating LC–MS/MS and GC–MS methods in forensic/toxicology or cannabis chemistry labs. Includes calibration curves, retention time/ion ratio confirmation, and matrix effect studies. Derivatization (e.g., silylation) may be used for GC‑MS (literature practice).
Molecular pharmacology tool: A hydrophobic ligand for cannabinoid receptor research (CB1/CB2) in binding and signaling assays (radioligand displacement, β‑arrestin, cAMP). Prepare concentrated DMSO stocks and dilute into assay buffer with low final organic content.
Metabolism studies: In vitro microsomal/S9 incubations to map phase I/II metabolites (oxidation at the side chain and allylic positions; conjugation of the phenolic OH), followed by HRMS structural elucidation (literature/general cannabinoid metabolism).
Stability/isomerization investigations: Δ9 → Δ8 isomerization under acid/heat and oxidative degradations can be profiled to establish handling constraints.
Practical tips:
Dry, oxygen‑reduced conditions and amberware mitigate oxidative loss. If performing long incubations, include antioxidants (e.g., BHT) only if compatible with detection.
For quantitative transfers at low μg/mL, add carrier (e.g., 0.1 mg/mL BSA or 0.01% Triton X‑100) where compatible to reduce adsorption; validate absence of assay interference.
For GC‑MS, silylate phenolic and alicyclic OH groups using BSTFA or MSTFA + 1% TMCS in anhydrous acetonitrile or pyridine (literature) to improve volatility and peak shape.
Reaction Conditions
Because THCP is most often a target/standard, detailed synthetic conditions are context‑dependent. The following literature‑style conditions relate to common manipulations of classical cannabinoids and are provided as general guidance only (not item specifications):
Silylation for GC–MS: MSTFA or BSTFA (with 1% TMCS) in anhydrous acetonitrile or pyridine, 50–70 °C, 15–30 min, affords bis‑TMS derivatives of phenolic and alicyclic OH groups, improving volatility and chromatographic behavior.
Hydrogenation of the ring double bond: H2 (1 atm) over 10% Pd/C in ethanol or ethyl acetate at rt to 40 °C, 1–6 h, yields the saturated analog; monitor by TLC/UPLC.
O‑Acylation of the phenol: Ac2O or acyl chloride (1.1–1.5 equiv) with a base (pyridine, triethylamine) in DCM at 0–25 °C, 0.5–2 h; protect from moisture and monitor to avoid over‑acylation.
Oxidation (allylic): MnO2 (excess) in DCM or toluene at rt to reflux may effect benzylic/allylic oxidation; cannabinoids are sensitive—optimize substrate loading and temperature.
Assay solution preparation (bioanalytical):
Prepare 10–50 mM stocks in anhydrous DMSO; dilute into buffer to 0.1–10 μM with ≤0.1–0.5% DMSO final. Use low‑bind consumables and protect from light/air. Validate vehicle controls.
Safety and Handling
Safety information specific to this item (from Product Data):
GHS classification / pictograms / H‑statements / signal word: Not specified for this item; refer to SDS.
Storage conditions: Store at −20 °C.
Shipping: Ice chest + ice pads.
General safety guidance for hydrophobic phenolic cannabinoids (literature/general; defer to SDS):
Likely hazards: May cause skin/eye irritation; harmful if swallowed; dust/vapors may cause respiratory irritation. Avoid generation of aerosols. Combustible organic solid/oil.
PPE: Use gloves (nitrile recommended), lab coat, and safety glasses or face shield. Handle in a chemical fume hood.
Incompatibilities: Strong oxidizers (risk of exotherm/oxidation), strong bases (phenolate formation; potential enhanced reactivity), strong acids (possible dehydration/rearrangements). Avoid prolonged exposure to air, heat, and light (oxidation/isomerization risk for Δ9 double bond).
Special handling notes: Highly lipophilic—may adsorb to plastics and glass; use low‑bind plastics or silanized glass when working at low μg/mL levels. Use amber vials to minimize photodegradation. Purge headspace with inert gas (N2/Ar) after opening.
First aid (overview; see SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present; seek medical attention if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical advice.
Waste: Dispose of as organic chemical waste according to institutional and local regulations.
Solvent Selection
THCP is extremely hydrophobic and phenolic; solvent choice is driven by solubility, stability, and downstream application.
DMSO: Excellent primary solvent; prepare 10–50 mM stocks; dilute into aqueous systems with co‑solvent to avoid precipitation.
Ethanol: Good solubility; compatible with many biochemical assays up to 0.1–1% v/v final. Combine with PEG400 or surfactants if higher concentrations are needed.
Nonpolar organics: Chloroform, dichloromethane, toluene, and ethyl acetate dissolve THCP well for synthetic/analytical workflows. For GC‑MS, derivatize in anhydrous solvents (e.g., ACN, pyridine) as appropriate.
Aqueous vehicles: Insoluble in water; use co‑solvent systems (e.g., 1–5% DMSO + 5–20% PEG400 or 1–2% ethanol + 0.5% Tween‑80) to achieve stable dispersions (literature practice for hydrophobics).
Adsorption and recovery:
Minimize loss to plastics by using low‑bind polypropylene or silanized glass. Pre‑wet pipette tips/vials with solvent containing analyte to improve recovery in low‑ng applications.
Stability considerations:
Protect from light and oxygen to limit oxidation/isomerization of the Δ9 double bond. Avoid strong bases in solution unless phenolate is intended.
When to choose alternatives:
For greener workflows, consider 2‑MeTHF or ethyl acetate in place of chlorinated solvents during workup/purification; ensure analyte recovery and stability are validated for your method.
General handling and reconstitution guidance for hydrophobic cannabinoid standards (not lot specifications):
Light/oxygen protection: Store in amber, airtight containers. After opening, purge headspace with nitrogen or argon to minimize oxidation/isomerization.
Aliquoting: Upon receipt, allow container to equilibrate to room temperature before opening to avoid moisture condensation. Immediately subdivide into single‑use aliquots to minimize freeze–thaw and headspace exposure.
Solid vs oil: If semi‑solid/oily, chill briefly to increase viscosity before accurate aliquoting, or weigh by difference. Use low‑bind tips/vials to reduce adsorption losses.
Reconstitution solvents: DMSO, ethanol, or ethyl acetate are recommended primary solvents. For bioassays, prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into buffer with co‑solvent/surfactant to prevent precipitation.
Solution stability: In dry, oxygen‑reduced DMSO at −20 °C and protected from light, many cannabinoids are stable for weeks to months (literature). Verify stability by LC–MS/HPLC before critical use; discard if discoloration or degradation peaks are observed.
Temperature excursions: Brief room‑temperature handling during weighing/aliquoting is acceptable; return to −20 °C promptly after use.
Research Use Note: For research use only.
Structure and Identity
Tetrahydrocannabiphorol (THCP) is a phytocannabinoid analog bearing an extended heptyl side chain relative to Δ9‑THC. It is a highly lipophilic small molecule intended for research use (reference standard, receptor/pharmacology studies, analytical development).
Item-specific identifiers (from Product Data):
SKU: T1445187
CAS: 54763-99-4
InChIKey: 259882 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature structural identity (for reference only; not item specifications):
Common name: Tetrahydrocannabiphorol (THCP; Δ9‑THCP)
Core scaffold: tricyclic dibenzopyran/benzopyran (classical cannabinoid) with a resorcinol-derived aromatic ring fused to a dihydropyran ring and a cyclohexene ring.
Side chain: linear n‑heptyl substituent at the C3 position of the resorcinol ring (vs pentyl in Δ9‑THC).
Functional groups: one phenolic hydroxyl; one alicyclic (benzylic/tertiary) alcohol; olefin (Δ9) within the cyclohexene ring; multiple aromatic carbons.
Stereochemistry (literature): two stereogenic centers typically assigned as (6aR,10aR) in the naturally occurring configuration of classical Δ9‑cannabinoids.
2D description in words: a phenolic ring para-alkylated with a heptyl chain, ortho-fused through an oxygen bridge to a partially saturated bicyclic ring system carrying a tertiary alcohol and an internal double bond; the overall framework is rigid and highly hydrophobic with one acidic phenolic proton.
Synthetic Utility
While THCP is typically the target molecule or an analytical standard rather than a reagent, its functional groups enable derivatization and probe synthesis (literature/general):
Phenolic OH transformations:
O‑alkylation or O‑acylation to modulate polarity and stability (e.g., acetate, carbonate, carbamate pro‑labels). These derivatives can aid in analytical separation or stability studies.
Ether/ester formation to create internal standards or handle‑tagged analogs (e.g., isotopically labeled derivatives).
Allylic/benzylic chemistry on the tricyclic core:
Selective hydrogenation of the Δ9 double bond (Pd/C, H2) to study saturation effects on chromatographic and receptor behavior.
Mild oxidation (e.g., MnO2 or SeO2 conditions) can yield allylic alcohol/ketone derivatives for mechanistic studies; care required to avoid over‑oxidation of the phenol.
Side‑chain modification (homologation or late‑stage editing):
Though THCP already bears a heptyl chain, cross‑coupling on appropriately functionalized precursors (e.g., via convergent resorcinol O‑alkylation followed by intramolecular cyclization) is typical in cannabinoid synthesis workflows (context for method development rather than THCP as a reagent).
Conjugation chemistry:
Carbamate/urethane linkages via the cyclic alcohol can attach reporter groups (fluorophores, affinity tags) for target engagement assays, provided steric/electronic effects are considered.
These transformations are commonly used to prepare analytical surrogates, internal standards, or SAR probes derived from the THCP scaffold.
Target Specificity
Not applicable. This product is a small‑molecule standard, not an antibody or biomolecular probe with clone/isotype/epitope specifications.
General note (literature): THCP is studied as a ligand for CB1/CB2 cannabinoid receptors; however, quantitative affinity/efficacy values are context‑ and assay‑dependent and are not provided as item specifications here.
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