exo-Tetrahydrocannabivarin methyl ether , CAS No.132213-92-4

CAS: 132213-92-4 Cat. No.: E1445175 Fórmula: C₂₀H₂₈O₂ Peso molecular: 300.44

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

exo-Tetrahydrocannabivarin methyl ether (Δ9,11-Tetrahydrocannabivarin methyl ether) is structurally similar to known phytocannabinoids.

Specifications

Condições de armazenamento de armazenamento

Store at -20°C

Enviado em

Ice chest + Ice pads

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

Nomes e identificadores

Peso molecular

300.44

Application Protocols

No validated, product-specific application protocols are provided for this SKU. The following general procedures are commonly used for lipophilic small molecules in research:

• Preparation of stock solutions:

  • Dissolve in anhydrous DMSO to 10–50 mM. Sonicate gently if needed. Record exact concentration by mass and volume; consider purity correction from CoA for analytical work.
  • Aliquot into amber, low-bind or silanized glass vials to minimize adsorption. Flush with inert gas (N2/Ar) and store at −20 °C.

• LC–MS reference standard (general):

  • Prepare a primary stock in MeOH or ACN (with 0.1% formic acid if needed for ionization). Serially dilute to calibration levels in 50:50 water/organic with 0.1% additive.
  • Use ESI+ or APCI+; monitor characteristic [M+H]+ and common fragments of benzochromene ethers (optimize on instrument).

• In vitro assay dosing (general):

  • Dilute DMSO stocks into assay buffer or media under vigorous mixing to final DMSO ≤0.1–0.5% v/v (as permitted). Include carrier protein/surfactant to mitigate adsorption.
  • Prepare vehicle controls matched to the highest DMSO content used.

• Solid-phase handling:

  • If received as a solid, allow vial to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation. If oil, warm gently and vortex before aliquoting.

These steps are generic guidance; validate and adapt to your laboratory SOPs.

Biological Roles

Item-specific biological data/claims are not provided and are not made. This product is for research use only.

Literature/general context for the chemical class:

• Cannabinoid frameworks (including varin analogues) are lipophilic ligands often studied in the context of the endocannabinoid system (e.g., CB1/CB2 receptors) and related lipid-signaling pathways in nonclinical research. Masking phenolic OH groups as methyl ethers typically reduces hydrogen-bond donor capacity and can modulate receptor affinity, selectivity, and metabolic stability relative to the phenolic parent (general SAR trends; no claims for this specific item).
• The varin (C3) side chain is known to influence physicochemical properties (slightly reduced hydrophobicity vs. C5 analogues) and can alter target interactions in vitro (literature, analogous compounds).
• Exo isomerism (exocyclic double bond) changes the 3D shape of the benzochromene ring system; such geometric differences are a common variable studied in structure–activity relationships (literature phenomenon).

Practical implications for lab research:

• For biochemical assays, high lipophilicity often necessitates DMSO stock solutions and careful dilution into assay buffers with surfactants (e.g., Tween-20) or carrier proteins (e.g., 0.1–1% BSA) to avoid nonspecific adsorption and precipitation.
• When comparing activity to other analogues, ensure identical solvent/vehicle composition due to strong vehicle effects on apparent potency for hydrophobic ligands.

No medical, diagnostic, or therapeutic uses are implied or supported for this product.

Buffer Applications

This item is a hydrophobic small molecule and is not a buffering reagent. Direct use as a buffer component is not applicable.

Practical notes for incorporating into aqueous assay buffers (general guidance):

• Prepare concentrated stocks in dry DMSO (e.g., 10–50 mM). Vortex thoroughly to ensure complete dissolution.
• Dilute into pre-warmed buffer (e.g., PBS, HEPES, or assay-specific media) under vigorous mixing to a final DMSO content typically ≤0.1–1% v/v, depending on assay tolerance.
• To improve apparent solubility and reduce adsorption losses, include 0.01–0.1% nonionic surfactant (e.g., Tween-20) and/or 0.1–1% fatty-acid-free BSA as carrier protein, as compatible with your assay.
• Use glass vials or silanized tubes to minimize surface binding. Rinse delivery syringes/tips with small aliquots of vehicle to recover quantitative amounts.
• Filter sterilization is generally not recommended for hydrophobic compounds due to retention on membranes; instead, prepare sterile stocks by dissolving in sterile-filtered solvents under aseptic conditions if required.

Always validate vehicle effects on your system. No buffer recipes are provided because the compound does not serve as a buffering agent.

Green Alternatives

While exo-Tetrahydrocannabivarin methyl ether itself is a target molecule rather than a solvent, greener choices can be made in its handling and synthesis (literature/practice):

Greener solvent substitutions (general guidance):

• Replace dichloromethane/chloroform with:
  • 2-Methyltetrahydrofuran (2-MeTHF): biomass-derived, good solvating power for lipophilic cannabinoids; compatible with many reductions and organometallics.
  • Cyclopentyl methyl ether (CPME): hydrophobic ether, low peroxide formation rate, high bp; useful for extractions and hydrogenations.
  • Ethyl acetate or propyl acetate: greener ester alternatives for chromatography and workup.
  • Toluene over benzene/chloroform where feasible.

Workup and purification:

• Use heptane/EtOAc gradients instead of hexane/DCM when column chromatography is needed.
• Consider reverse-phase flash/prep using aqueous ACN or MeOH to minimize halogenated solvent waste.

Process considerations:

• For demethylation (if performed), explore greener demethylation approaches (e.g., AlCl3/thiols or catalytic transfer demethylation) as alternatives to BBr3, balancing efficacy with EHS outcomes (literature-dependent, may be substrate-specific).
• Minimize protecting group manipulations by convergent synthesis planning, thereby reducing solvent and reagent usage.

Trade-offs:

• 2-MeTHF and CPME can alter selectivity and rates relative to DCM/THF; solubility of highly lipophilic substrates may still necessitate aromatic solvents.
• Reverse-phase methods generate aqueous-organic waste; ensure appropriate treatment.

Note: Selection should be confirmed by small-scale trials to ensure performance with this scaffold.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item; it is supplied strictly for research use only.

Nonclinical and manufacturing-relevant contexts (general):

• Analytical reference: May serve as a noncompendial reference standard for method development, impurity profiling, and stability-indicating assays of varin-series cannabinoids in R&D or QC environments (where legally permitted). Suitability should be established by the user.
• Formulation research: Hydrophobic cannabinoids are often formulated using lipid-based systems (e.g., ethanol/PEG, polysorbate micelles, lipid nanoparticles) in preclinical studies. The methyl ether can be used to explore how phenolic masking affects solubility and stability in model formulations. No therapeutic claims are made.
• Stability studies: The exo double bond and benzylic positions can be oxidation- or isomerization-prone; formulation screening (antioxidants, amber primary packaging, headspace control) may inform handling in research settings.

Important limitations:

• This product is not a drug, API, or GMP material, and is not intended for human or veterinary use.
• Any use as a system suitability or in-house standard must be justified and validated by the user’s quality system. Consult applicable regulations before use in regulated workflows.

Physical Properties

Item-specific physico-chemical data:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Purity/Grade: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (mp): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point (bp): Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• UV cut-off/λmax: Not specified for this item; refer to CoA/Spec Sheet.
• Water content/peroxides/metals: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations for analogous cannabinoid methyl ethers (for planning only):

• Physical state: typically viscous oils or low-melting solids; highly lipophilic with very low aqueous solubility.
• Solubility: readily soluble in nonpolar and moderately polar organic solvents (e.g., dichloromethane, toluene, ethyl acetate, THF). DMSO and ethanol commonly used for bioassay stocks.
• Partitioning: high logP/logD expected for cannabinoid frameworks (literature, analogous compounds), implying strong adsorption to plastics and surfaces.
• Spectroscopy: aromatic benzochromene chromophore shows UV absorption in the near-UV (ca. 210–230 nm strong, and 270–280 nm weaker bands in analogous cannabinoids; literature), and distinctive 1H NMR aromatic, benzylic/allylic, and O–CH3 resonances in the 3.7–3.9 ppm range (literature, general trend).

Important: The above generalized properties are not specifications for this SKU. Always confirm exact physico-chemical values for your lot using the CoA or by in-house characterization as required by your method.

Quality and Grades

Item-specific grade and purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting quality for this compound class:

• Research use only: This SKU is designated for laboratory research use, not for human or veterinary applications, food, or household use.
• Purity metrics: For cannabinoid scaffolds, typical CoAs report HPLC/GC purity, residual solvents, identity by NMR/HRMS, and, where relevant, stereochemical description. If stereochemistry is critical to your application (e.g., receptor binding studies), request/isolate a single isomer and review spectral data to confirm configuration.
• Stabilizers: Not specified for this item. Many phenolic cannabinoids are supplied neat or in amber vials without stabilizer; if present, stabilizers (e.g., small % ethanol) will be declared on the CoA.
• Impurities of interest: Potential isomeric cannabinoids (endo/exo isomers), oxidative byproducts (quinones or allylic oxidation products), and O-demethylated phenols may be relevant. Ensure method suitability to resolve these in your assay.
• Analytical grade vs. synthetic intermediate: If used as an analytical reference standard, low UV-background solvents and high chemical purity are preferred. If used as a building block, purity sufficient for the synthetic step may be acceptable, but confirm that trace acids/bases do not promote isomerization of the exo double bond.

Recommendation: Review the lot-specific CoA for purity, identity, and any stabilizer. For quantitative work (e.g., LC–MS calibration), perform independent confirmation (qNMR or purity-corrected weighing) as per your QA practices.

Reaction and Applications

Manufacturer Applications: Not specified in the Product Data.

General research and synthetic contexts for exo-cannabinoid methyl ethers (literature/practice):

• Reference/analytical standard: Employed in analytical method development and impurity profiling of varin-series cannabinoids; useful for retention time matching and MS/MS library building in nonclinical research.
• SAR and probe development: The methyl ether masks phenolic acidity, modulating lipophilicity and metabolic stability; valuable for in vitro receptor binding or transporter assays where phenolic hydrogen-bonding is intentionally attenuated (no clinical claims).
• Protecting group strategy: The O-methyl serves as a durable protecting group on the resorcinyl phenol. It survives many conditions used for terpene-like ring manipulations and can later be cleaved to regenerate the phenol (e.g., with BBr3).
• Scaffold transformations:
  • Hydrogenation of the exocyclic double bond (Pd/C, H2) to access saturated analogues.
  • Electrophilic epoxidation (mCPBA) of the exocyclic alkene to epoxides for further ring-opening elaboration.
  • Allylic/benzylic oxidation (SeO2 or Mn-based systems) to introduce ketones/alcohols on the terpene ring.
  • Halofunctionalization (NBS/NCS) at allylic positions for cross-coupling handles post-derivatization.
• Purification/handling: Due to high lipophilicity, compounds may adhere to plastics or silica; pre-condition glassware, use silanized vials when necessary, and add small % of polar modifier (EtOAc, isopropanol) to eluent to reduce tailing.

Note: The above applications are general for this chemical class and are not product-specific endorsements.

Reaction Conditions

No item-specific synthetic conditions are provided. The following are literature/general conditions commonly applied to benzochromene-type cannabinoid methyl ethers; optimize for your substrate.

• O-Demethylation (to regenerate phenol):

  • Reagent: BBr3 (1.5–3.0 equiv) in dry dichloromethane.
  • Conditions: −78 °C to 0 °C, 1–4 h; quench with MeOH or aqueous NaHCO3 at low temperature.
  • Notes: Sensitive to moisture; strictly anhydrous conditions. Alternative milder options (e.g., BCl3, AlCl3/thiols) may be explored depending on tolerance.

• Hydrogenation of exocyclic alkene:

  • Catalyst: 5–10% Pd/C (5–10 wt%).
  • Conditions: H2 (1–3 atm), RT to 40 °C, 1–12 h in EtOAc, EtOH, or toluene.
  • Notes: Monitor to avoid over-reduction of aromatic ring; filter carefully to remove catalyst.

• Epoxidation of exocyclic double bond:

  • Reagent: mCPBA (1.1–1.5 equiv) in DCM or toluene, 0 °C to RT, 0.5–4 h.
  • Notes: Buffer with NaHCO3 to control acidity; separate diastereomers as needed.

• Allylic bromination (for handles):

  • Reagent: NBS (1.1 equiv) with AIBN or light, in CCl4, DCM, or cyclohexane, reflux or photochemical conditions.
  • Notes: Consider greener solvents (e.g., EtOAc, MeCN) and radical initiators under flow/LED.

• Analytical QC (general):

  • HPLC: C18, gradient 60→95% ACN/H2O over 10–20 min with 0.1% formic acid; detect at 220 and 280 nm.
  • LC–MS: ESI+ often gives [M+H]+ for cannabinoid ethers; optimize cone voltage to minimize in-source fragmentation.

All conditions are general literature guidance and not specifications for this SKU.

Safety and Handling

Authoritative safety information should be taken from the product SDS.

Item-specific data (from Product Data):

• GHS Classification: Not specified for this item; refer to SDS.
• 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.
• Storage Conditions: Store at −20 °C.
• Shipped in: Ice chest + ice pads (maintain cold chain on receipt).

General handling guidance for lipophilic cannabinoid ethers (literature/practice):

• Hazards: Treat as a combustible organic and potential irritant. Avoid inhalation of dust/aerosols and skin/eye contact. Some cannabinoids can oxidize or isomerize under heat, light, or air.
• PPE: Lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood to prevent exposure and to control solvent vapors during dissolution.
• Incompatibilities: Strong oxidizers, strong acids/bases (may promote isomerization or ether cleavage under forcing conditions). Avoid prolonged exposure to light and elevated temperatures.
• First aid (overview; defer to SDS): After skin contact, wash with soap and water. After eye contact, rinse cautiously with water for several minutes and seek medical advice if irritation persists. If inhaled, move to fresh air. If swallowed, rinse mouth and seek medical attention as needed.
• Fire safety: Use CO2, dry chemical, or foam for small fires. Avoid water jets that can spread burning liquids.

Waste: Collect organic solutions and residues as halogenated or non-halogenated organic waste according to your solvent system and institutional regulations.

Solvent Selection

This compound is a highly lipophilic, neutral organic molecule. No item-specific solubility values are provided; guidance below is based on literature and practical experience with cannabinoid ethers.

• Polarity/miscibility profile (literature/general):

  • Readily soluble in nonpolar to moderately polar organic solvents: dichloromethane (DCM), chloroform, toluene, THF, ethyl acetate, MTBE, acetone.
  • Soluble in DMSO and ethanol for stock solutions; DMSO is preferred for preparing concentrated assay stocks (e.g., 10–50 mM), then dilute into aqueous buffers with vigorous mixing and surfactant/carrier protein if needed.
  • Practically insoluble in water; risk of precipitation upon aqueous dilution without co-solvent systems.

• Selection by application:

  • Analytical (HPLC/LC–MS): MeOH or ACN with water (0.1% formic acid or ammonium formate) are typical eluents. Stronger organic (e.g., 95% ACN) may be required to elute retained cannabinoids from C18.
  • Preparative/flash chromatography: Hexanes/ethyl acetate or heptane/DCM gradients are standard; include 0.1–1% triethylamine if tailing occurs on silica.
  • Synthesis: DCM or toluene for electrophilic steps; DCM at low temperature for demethylation (if intended), toluene/EtOAc for hydrogenation and peracid epoxidation.

• Comparison (general):

  • DCM vs toluene: DCM offers better solvating power and low-temperature control; toluene is less polar, higher bp, and greener profile.
  • DMSO vs ethanol for stocks: DMSO gives higher solubility and stability; ethanol may be preferable for biological compatibility but limits max concentration.

Storage and Reconstitution

Item-specific storage and shipping (from Product Data):

• Storage Conditions: Store at −20 °C.
• Shipped In: Ice chest + ice pads. Maintain cold chain upon receipt.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for this compound class:

• Light/air sensitivity: Cannabinoid frameworks can isomerize or oxidize under light, heat, and air. Store in amber vials with minimal headspace. Consider inert gas blanket (N2/Ar) after each use.
• Moisture: Although aryl methyl ethers are not highly hygroscopic, keeping the material dry improves stability and analytical reproducibility. Store with a desiccant.
• Aliquoting: To avoid freeze–thaw cycles and adsorption losses, prepare small aliquots (e.g., 1–10 mg or 50–200 µL solutions) in compatible containers. Use low-bind or silanized glass vials for solutions.

Reconstitution (general):

• Solvents: DMSO, ethanol, or dichloromethane/toluene depending on intended use. For biochemical assays, DMSO is preferred for concentrated stocks.
• Procedure: Allow the vial to warm to room temperature in a desiccator before opening. Add measured volume of dry solvent, vortex/sonicate until fully dissolved. If undissolved residue persists, verify identity and purity before heating; avoid prolonged heating.
• Solution stability: Not specified for this item; refer to CoA/Spec Sheet. As a precaution, prepare fresh working solutions daily; store master stocks at −20 °C protected from light for limited periods, and monitor by HPLC/LC–MS for degradation.

Labeling: Clearly mark concentration, solvent, date, and any stabilizer added. For regulated labs, retain chain-of-custody and storage logs.

Structure and Identity

Brief overview: exo-Tetrahydrocannabivarin methyl ether is a varin-side-chain cannabinoid analogue in which a phenolic hydroxyl is protected as a methyl ether. The "exo" descriptor refers to an exocyclic double bond in the benzochromene (dibenzopyran) core typical of exo-THC isomers (literature, structural interpretation based on nomenclature), and "varin" denotes a propyl (C3) side chain instead of the pentyl (C5) side chain of THC analogues (literature).

Item-specific identifiers (from Product Data):

• CAS: 132213-92-4
• 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.

Structural features (literature/general, inferred from name):

• Core: benzochromene/dibenzopyran cannabinoid scaffold bearing an exocyclic C=C ("exo" isomer family).
• Side chain: varin-type n-propyl chain at the resorcinyl ring position.
• Functional groups: aryl methyl ether (O–CH3) protecting one phenolic site; allylic/benzylic positions adjacent to the ring junction; multiple stereocenters typical of cannabinoid frameworks.
• 2D description in words: fused aromatic ring attached to a pyran ring generating a tricyclic benzochromene; one aromatic oxygen incorporated in the chromene ring; one phenolic oxygen methylated; a propyl substituent projects from the resorcinol ring; the terpene-derived ring junction defines the relative stereochemistry; the double bond is exocyclic to the ring junction (exo-configuration) (literature/analogy).

Notes:

• Exact stereochemical assignment, atom numbering, and tautomeric/positional details are not specified for this item; consult the CoA/SDS or primary literature for the specific isomer supplied.

Synthetic Utility

Functional elements that enable diverse transformations (literature/general to cannabinoid methyl ethers):

• Aryl methyl ether: robust protecting group for the phenol; compatible with many electrophilic and reductive conditions. Can be cleaved under Lewis acidic conditions (e.g., BBr3) to reveal the phenol for further coupling (e.g., carbonate/ether formation, metalation).
• Exocyclic alkene: handles for hydrogenation (saturation), epoxidation (mCPBA), hydroboration–oxidation (BH3·THF then H2O2/NaOH) to install tertiary/secondary alcohols, or halogenation (NBS) for allylic bromides.
• Benzylic/allylic C–H: amenable to selective oxidation (Mn, Cr-free greener alternatives like TEMPO/bleach may be explored with caution) to access ketones/alcohols, enabling diversification.
• Varin side chain (C3): lower steric demand relative to C5 chains may slightly alter reactivity in late-stage functionalization (LLSF) steps, including radical or photoredox-mediated C–H modifications.

Retrosynthetic value:

• Serves as a masked-phenol intermediate en route to phenolic THCV analogues after O-demethylation.
• Epoxide or halide derivatives derived from the exo alkene can be elaborated to diverse ring-opened or rearranged scaffolds, furnishing access to libraries for SAR.

Practical tips:

• Protect from acid/base during manipulations that could trigger chromene ring opening or isomerization.
• Use amber glassware and inert atmosphere for sensitive steps; include antioxidant (e.g., BHT, 0.01–0.1%) only if compatible and declared when purity is critical.
• Monitor reactions by LC–MS or HPLC with diode-array to track formation of isomeric/oxidized byproducts.

Target Specificity

Item-specific biological target data (e.g., receptor affinity, selectivity, or activity) are not provided in the Product Data for this SKU.

• Antigen/epitope/clone/isotype: Not applicable; this product is a small molecule, not an antibody or biological reagent.
• Literature context: Cannabinoid scaffolds are often investigated for interactions with CB1/CB2 and related lipid-binding proteins in nonclinical studies, but target specificity for exo-Tetrahydrocannabivarin methyl ether has not been established here.

If target information is required for your application, consult peer-reviewed literature for this exact CAS (132213-92-4) and confirm experimentally under your assay conditions.