This compound belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
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.
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Application Protocols
No tested application protocols are provided for this item. The following generic workflows may assist when using small-molecule natural products as analytical standards or screening compounds.
Reference standard preparation (analytical):
Weigh under low light and inert atmosphere if oxidation is a concern.
Prepare a 10 mM stock in anhydrous DMSO or ethanol; vortex and sonicate if needed.
Make serial dilutions in ACN/H2O (1:1, 0.1% formic acid for LC–MS) or MeOH/H2O for calibration standards; store aliquots at −20 °C.
LC–MS method sketch (general):
Column: C18, 2.1 × 50 mm, 1.7–3 µm.
Mobile phase A: H2O + 0.1% FA; B: ACN + 0.1% FA.
Gradient: 30% to 95% B over 5–8 min; hold 2 min; re-equilibrate.
Dilute stock into assay buffer keeping final DMSO ≤0.5% v/v unless otherwise validated.
Include vehicle controls and adsorption controls to assess nonspecific binding.
Always adapt conditions to your assay and verify identity/purity with the batch CoA before quantitative use.
Biological Roles
Item-specific biological data were not supplied. The following are general considerations for pepper-derived alkamide/natural products used in research contexts (no clinical claims):
Natural occurrence: Compounds in the Piperolein family have been reported in Piper species (e.g., Piper nigrum, Piper spp.) and are often studied as part of plant metabolomic profiles.
Putative biochemical context (literature-level, general): alkamides are investigated for roles in plant defense and signaling; in vitro studies often explore interactions with membranes or enzyme targets due to hydrophobic amide chains.
Assay considerations: owing to lipophilicity, non-specific binding to plasticware/proteins can affect apparent potency; include detergent or protein carrier controls where appropriate and monitor free fraction.
Analytical biology: Used as reference materials for profiling plant extracts by LC–MS/MS; supports chemotaxonomic studies and quality control of botanical materials.
Caveats:
Specific targets, pathways, or potencies for this exact item are not provided and should not be inferred without primary data.
All uses are for research only; not for human or veterinary use, food, or diagnostics.
Buffer Applications
This item is a hydrophobic small molecule standard and is not a buffer component. Therefore, typical buffer formulation details (pH ranges, pKa, ionic strength) are not applicable.
Practical notes for using in buffered systems (general):
Prepare a concentrated stock in DMSO or ethanol and dilute into the desired buffer to the working concentration, keeping the final organic content as low as assay tolerance allows (commonly ≤0.1–1% v/v).
If precipitation occurs upon dilution, increase mixing time, slightly warm to ambient, or introduce a compatible solubilizer (e.g., ≤0.01–0.05% nonionic surfactant) as permitted by the assay.
For LC–MS sample preparation from buffers, perform protein precipitation (ACN or MeOH, 3–5× volume), then analyze supernatant to mitigate matrix effects.
Green Alternatives
For this product (a neutral, lipophilic small molecule reference standard), “green alternatives” mainly pertain to solvent and workflow choices rather than replacing the analyte itself.
Greener solvent choices (general guidance):
Replace dichloromethane/chloroform with ethyl acetate, methyl tert-butyl ether (MTBE), or cyclopentyl methyl ether (CPME) for extractions and chromatography where selectivity allows.
Favor acetonitrile or methanol-water systems for LC where possible; optimize to reduce organic consumption via shorter columns, core–shell particles, or UHPLC.
Use ethanol or isopropanol as greener co-solvents for biological assays instead of high DMSO fractions, provided solubility and assay tolerance permit.
Operational improvements:
Microscale methods for assay and calibration curve preparation to minimize solvent usage.
Closed-vent evaporation systems and solvent recovery where practical.
Store concentrated stocks at -20 °C in aliquots to reduce waste from repeated thawing/oxidation.
Illustrative comparison (workflow level):
Traditional: normal-phase silica with hexanes/DCM → higher halogenated solvent footprint.
Greener option: reversed-phase water/ACN or water/MeOH gradients → reduced VOC hazard and simpler waste segregation.
Trade-offs:
Greener solvents may change selectivity, requiring re-optimization of gradients or stationary phases.
MTBE/EtOAc can have higher peroxide risks over time; manage with regular testing and inhibitors per institutional guidance.
Pharmaceutical Uses
No pharmacopeial status or excipient role is provided for this item. Piperolein A is offered strictly for research use only and is not intended for human or veterinary applications.
Research/development contexts where such materials are encountered (non-clinical):
Analytical reference: standard for method development and QC of botanical raw materials in a non-GMP research setting.
Pre-formulation screening (in vitro only): exploratory solubility, stability, and permeability assessments to understand biophysical properties of related chemotypes.
Impurity/degradation studies: as a comparator or potential related-substance standard in natural product preparations.
Important limitations:
No claims are made regarding safety, efficacy, or regulatory status for therapeutic use.
If using in regulated workflows, obtain batch-specific documentation (CoA, stability, impurity profile) and evaluate compliance independently.
Physical Properties
Item-specific physicochemical properties have not been supplied for this catalog entry.
Appearance: 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.
Solubility: Not specified for this item; refer to CoA/Spec Sheet.
LogP, pKa: Not specified for this item; refer to CoA/Spec Sheet.
General expectations (literature-level for long-chain alkamide natural products; verify against CoA before experimental planning):
Likely hydrophobic to moderately lipophilic; commonly soluble in organic solvents such as DMSO, ethanol, methanol, acetonitrile, dichloromethane, or ethyl acetate; poor aqueous solubility without cosolvents/surfactants.
Typically oils, waxy solids, or low-melting solids depending on chain length and unsaturation pattern.
Neutral amide functionality generally non-ionizable across neutral pH; limited volatility.
Practical notes (general):
For solution preparation, pre-screen solubility in dry DMSO or ethanol, then dilute with buffer containing a suitable cosolvent (≤1–2% v/v organic in working solutions, as tolerable by the system).
If crystalline, gentle warming (30–40 °C) and sonication can help dissolution. Avoid prolonged heating or light exposure until stability is established.
Quality & Grades
Item-specific grade and purity were not provided in the Product Data.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general):
Research grade: suitable for discovery and screening work; may not include comprehensive trace impurity profiling.
Analytical standard/Reference standard grade: emphasizes identity confirmation (NMR, HRMS) and assay purity; often provided with chromatographic purity and residual solvent data.
HPLC grade solvents/reagents: low UV background and minimal nonvolatile residue for chromatographic applications.
What to look for on the CoA/Spec Sheet for this item:
Identity confirmation: 1H/13C NMR, HRMS/ESI-MS, and IR; where applicable, verified E/Z geometry or double-bond positions.
Assay: HPLC/UPLC purity (area%), reporting of major related substances.
Residual solvents/water (KF), if relevant to your application.
Stabilizers: declare if added; absence is preferable for bioassays to avoid confounding effects.
Storage and retest/expiry dating supported by stability data (e.g., -20 °C, protected from light, desiccated).
If your application is highly sensitivity-dependent (e.g., bioassay SAR, quantitative metabolomics), request batch-specific CoA and, if needed, additional documentation (impurity profile, spectral data).
Reaction & Applications
Manufacturer’s specific application notes were not provided for this catalog entry. Piperolein A, as a small-molecule natural product, is typically used in:
Natural product reference standard: authentication and quantification in plant extracts (e.g., Piper spp.) by LC–MS/UV. Useful for method development, calibration curves, and matrix spike recovery studies.
Chemical biology and phenotypic screening: as a member of small-molecule/natural-product libraries to probe structure–activity relationships (SAR). Appropriate for preliminary in vitro assays under research-use-only conditions.
Synthetic benchmarking: a target or substructure motif for validating synthesis, purification, and analytical workflows involving long-chain alkamides.
Analytical tips (general):
LC–MS: start with reversed-phase C18, 5–95% ACN/H2O (0.1% FA), monitoring [M+H]+ and [M+Na]+. Optimize gradient length to separate geometric isomers if present.
Stability: unsaturated chains can be sensitive to autoxidation; maintain inert atmosphere (N2/Ar) for prolonged reactions or storage in solution and consider BHT-free conditions if radical scavengers could interfere with bioassays.
Derivatization (method development): amide N can be acylated/carbamoylated for tagging; double bonds can undergo ozonolysis or epoxidation to map unsaturation (literature-level strategy for structural elucidation).
Note: Because item-specific structural parameters are not confirmed here, verify mass, retention time, and UV maxima against the batch CoA before using as a quantitative reference.
Reaction Conditions
Specific reaction conditions for Piperolein A are not supplied. The following provide general guidance for transformations relevant to alkamide motifs; confirm structure and adapt conditions accordingly.
Amide reduction to amine: BH3·THF (0 °C to reflux) or LiAlH4 (0 to 25 °C) can reduce the amide to the corresponding amine/alcohol framework; protect alkenes if necessary to avoid side reactions.
Amide hydrolysis: aqueous NaOH or HCl (1–6 M) under reflux hours to overnight; milder conditions with enzymes or catalytic acid/base under elevated temperature for sensitive substrates.
Alkene epoxidation: m-CPBA (0–25 °C, DCM) or peracetic acid; for stereoselectivity in allylic systems consider Sharpless conditions when allylic alcohols are present (not typical for simple alkamides).
Olefin metathesis (if dienamide): Grubbs catalysts in toluene/DCM at 25–60 °C; remove ethylene under slight vacuum or argon purge to drive equilibria.
Oxidative cleavage: ozonolysis at −78 to −20 °C in DCM/MeOH, followed by reductive workup (Me2S, PPh3) to map unsaturation in structural studies.
Analytical controls:
Monitor reactions by LC–MS and 1H NMR to distinguish E/Z mixtures and amide rotamers.
Avoid prolonged exposure to strong base if double-bond isomerization is a concern.
Note: Conditions above are literature-general and may not directly apply without confirming the exact structure of this item.
Safety & Handling
Hazard classification details were not provided for this item; consult the product SDS for authoritative information.
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 precautions for small organic molecules of unknown hazard class:
Engineering controls: work in a chemical fume hood, especially when weighing solids/powders or handling concentrated solutions.
PPE: lab coat, safety glasses/goggles, and appropriate chemical-resistant gloves (nitrile recommended). Avoid skin/eye contact and inhalation of dust/vapors.
First aid overview: rinse eyes/skin with water for ≥15 minutes upon contact, remove contaminated clothing, and seek medical advice. If inhaled, move to fresh air; if ingested, rinse mouth—do not induce vomiting; seek medical attention. Always follow SDS guidance.
Handling: minimize exposure to air, light, and elevated temperatures until stability is known. Use amber vials if light sensitivity is suspected for unsaturated compounds.
Incompatibilities (general): strong oxidizers; avoid strong acids/bases for prolonged periods if hydrolysis is a concern for amides.
Spill response: absorb with inert material, collect for disposal as organic waste. Decontaminate area with suitable solvent followed by detergent/water, observing compatibility.
Waste: dispose of according to institutional and local regulations for organic chemical waste.
Always defer to the SDS and your institutional EHS policies for risk assessment, exposure controls, and emergency procedures.
Solvent Selection
Item-specific solubility data are not provided. The following are general recommendations for lipophilic neutral amide natural products; verify experimentally.
Primary stock solvents: DMSO (anhydrous), ethanol (absolute), or methanol; begin at 5–20 mg/mL for DMSO or 1–10 mg/mL for alcohols, adjusting as needed.
Secondary solvents for workup/purification: ethyl acetate, dichloromethane, methyl tert-butyl ether (MTBE), acetonitrile, and hexanes mixtures (for normal-phase). For reversed-phase chromatography, water–acetonitrile or water–methanol with 0.1% formic acid (if MS-compatible) are typical.
Aqueous systems: anticipate poor intrinsic aqueous solubility; use cosolvents (0.1–1% DMSO or ethanol) or cyclodextrins/surfactants if compatible with your assay.
Comparison (general guidance):
DMSO vs ethanol: DMSO maximizes solubility and stability for many amides; ethanol offers lower viscosity and better compatibility with certain biological assays.
ACN vs MeOH (LC): ACN often provides sharper peaks and lower backpressure; MeOH offers different selectivity and is greener/cost-effective.
Practical tips:
Filter stock solutions (0.2 µm PTFE) to remove particulates before quantitative assays.
For stability, prepare single-use aliquots to limit freeze–thaw and moisture ingress.
Avoid strong basic solutions that may promote amide hydrolysis over extended times, especially at elevated temperature.
Storage & Reconstitution
Storage and logistics (item-specific from Product Data):
Storage conditions: Store at −20 °C.
Shipped in: Ice chest + ice pads (cold shipment).
Additional best practices (general for small-molecule natural products):
Protect from light and moisture. Use amber vials and desiccant in secondary containment where possible.
Upon receipt, allow container to equilibrate to room temperature in a sealed bag before opening to avoid condensation.
If provided as a solid: Reseal tightly under inert gas after use. If oil/low-melting: cool to solidify before opening to minimize loss and improve handling.
Reconstitution guidance:
Choose an appropriate solvent (e.g., anhydrous DMSO or ethanol) to prepare a concentrated stock solution (e.g., 10–50 mM), then aliquot into single-use vials.
Avoid repeated freeze–thaw cycles; thaw aliquots immediately before use.
If precipitation occurs after dilution into aqueous media, gently warm and vortex; verify concentration by UV or LC–MS where quantitative accuracy is required.
Stability notes:
Item-specific stability data, degradation pathways, and retest period: Not specified for this item; refer to CoA/Spec Sheet.
Research use only: This product is intended solely for laboratory research. Not for human or veterinary use.
Structure & Identity
Brief description: Piperolein A is a plant-derived small molecule (alkylamide/amide class) frequently cataloged in natural product libraries. Specific identifiers for this catalog item are limited in the provided data; consult CoA/Spec Sheet for definitive structural data.
SKU: P463242
Product name: Piperolein A
CAS: 30505-92-1
PubChem CID: 11141599 (literature identifier; verify against CoA)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Provided string "220285" is not a valid InChIKey format.)
SMILES: 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.
Structural features (general, literature-level for the Piperolein family; verify against the supplied CoA before use):
Typically classified among pepper (Piper spp.) alkamides featuring an amide linkage between an amine (often isobutylamine or similar) and an unsaturated fatty acid chain containing one or more double bonds.
Functional groups expected (literature, family-level): amide carbonyl, aliphatic chain with isolated alkenes; may present E/Z geometry along unsaturations.
2D description (general): an amide core (–C(=O)–NH–R) attached to a medium/long alkenyl chain; absence of strongly ionizable groups under neutral conditions.
Important: Treat all structure/identity details as provisional unless confirmed on the item’s CoA/Spec Sheet provided with your lot.
Synthetic Utility
Without confirmed structure in the Product Data, the following outlines general synthetic utility concepts for long-chain alkamides and related natural products; verify applicability once the item’s structure is confirmed via CoA.
Functional handles: amide carbonyl enables transformations such as reduction (to amines), hydrolysis (to acid/amine), or activation (to imidazolides, mixed anhydrides) for further derivatization.
Alkene chemistry (if present): epoxidation, dihydroxylation, hydroboration–oxidation, ozonolysis, and metathesis allow mapping/modifying double-bond geometry and position.
Labeling/Probing: introduction of isotopes (13C/15N) or reporter tags via amide exchange or acylation routes to create analytical probes.
Analytical derivatization: converting to more UV-active or MS-friendly adducts (e.g., dansylation/carbamate formation on the nitrogen) for trace analysis.
Retrosynthetic value: disconnection at the amide bond separates the molecule into a carboxylic acid fragment (often an unsaturated fatty acid) and an amine fragment (e.g., isobutylamine), both accessible by standard methods.
Purification/characterization tips:
Reversed-phase preparative HPLC is often preferred over silica for closely eluting geometric isomers.
NMR in CDCl3 or CD3OD; HMBC/NOE can aid in assigning E/Z geometry and chain substitution patterns. Monitor for rotamer broadening around the amide.
Target Specificity
No target, antigen, or enzyme specificity is provided for this item. This product is not an antibody or biologic and has no declared molecular target in the Product Data.
Target/epitope: Not applicable.
Species reactivity/clone/isotype: Not applicable.
If used in chemical biology, any target engagement or selectivity claims must be established experimentally in your system and cannot be inferred from this listing.
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