This compound belongs to the class of organic compounds known as n-acyl amines. These are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
289.400 g/mol
XLogP3
3.500
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
9
Exact Mass
289.204 Da
Monoisotopic Mass
289.204 Da
Topological Polar Surface Area
49.300 Ų
Heavy Atom Count
21
Formal Charge
0
Complexity
426.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
5
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
5
Covalently-Bonded Unit Count
1
Calculadoras de soluciones
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Application Protocols
No vendor-validated protocols are provided for this item. The following are general starting points to assist experimental planning; they are not product specifications.
Preparation of stock solutions:
Dissolve Hydroxy-γ-isosanshool in DMSO or ethanol to 10–100 mM. Vortex and sonicate briefly if needed. Filter through 0.22 µm PTFE for analytical work.
Cell-based assays:
Dilute stock into prewarmed assay buffer or media to the desired final concentration, keeping solvent ≤0.5–1% v/v. Mix thoroughly to prevent local precipitation. Include vehicle controls.
LC–MS quantitative analysis:
Use a C18 column with a water (0.1% formic acid)/acetonitrile or methanol gradient. Monitor multiple isomers; consider using an internal standard (stable-isotope labeled analog if available). Protect autosampler vials from light.
Stability checks:
Assess solution stability at room temperature and 4 °C over 24–72 h by LC–UV or LC–MS. Store long-term stocks at low temperature (see Storage tab) and minimize freeze–thaw.
Users should adapt conditions to their system and consult the CoA/SDS for any lot-specific constraints.
Biological Roles
Literature context (not product claims):
Hydroxy-sanshools, including γ-isoforms, are alkamides associated with the characteristic tingling/pungent sensation of Zanthoxylum species. They serve as chemical stimuli in somatosensory systems.
Reported molecular pharmacology: members of the sanshool family modulate transient receptor potential (TRP) channels (e.g., TRPV1/TRPA1) and can inhibit certain two-pore domain potassium (K2P/TREK/TASK) channels, thereby altering neuronal excitability. Potency and selectivity depend on isomerism and substitution; hydroxy substitution can influence activity and membrane partitioning.
Membrane interactions: the long hydrophobic chain facilitates partitioning into lipid bilayers; the amide and hydroxy functionalities support interfacial localization, affecting local channel environment (literature biophysics perspective).
Metabolic fate (general): oxidative metabolism (allylic oxidation, epoxidation of double bonds), conjugation (glucuronidation/sulfation of the hydroxy), and amide hydrolysis are common biotransformations in vitro.
Use cases in research:
Model compound for chemosensory signal transduction, desensitization, and cross-adaptation studies.
Reference standard for metabolomics/food chemistry to track processing stability and bioavailability proxies.
Note: The above describes general scientific knowledge about hydroxy-sanshools. It does not imply any validated biological activity, potency, or application for this specific catalog lot. For research use only.
Buffer Applications
This compound is a hydrophobic alkamide and is not typically used as a buffering agent or buffer component.
Practical guidance:
If introducing into aqueous buffers for bioassays, dissolve first in a suitable organic cosolvent (e.g., DMSO or ethanol) and then dilute into the buffer with strong mixing to keep final organic content at ≤0.5–1% v/v.
Consider using surfactants (e.g., 0.01–0.1% Tween 80) or cyclodextrins for improved dispersion if compatible with your assay.
Filter-sterilize diluted solutions where sterility is required; use low-binding plastics or silanized glass to minimize adsorption losses.
For conventional buffer recipes (phosphate, HEPES, Tris), this compound does not play an acid/base role and has no defined buffering range.
Green Alternatives
While Hydroxy-γ-isosanshool itself is the analyte/active of interest rather than a process solvent, greener choices can be made for its handling, purification, and analysis.
Greener handling solvents (general guidance):
Prefer ethanol or isopropanol for stock solutions and cleaning when compatible with your assay, rather than chlorinated solvents.
Use ethyl acetate or MTBE for extractions instead of dichloromethane/chloroform when selectivity permits.
For chromatography, consider water–acetonitrile gradients instead of water–methanol when energy use/solvent recycling policies favor MeCN in your facility; alternatively, MeOH is less toxic and may be preferable depending on EHS priorities.
Stability vs sustainability trade-offs:
Chlorinated solvents offer excellent solvating power and low peroxide risk but pose higher environmental/health burdens; non-halogenated esters and alcohols reduce EHS impact but may require light/oxygen control to prevent analyte oxidation.
Small comparison (general, not item specification):
Ethanol: low toxicity, renewable sources available; good solubility; may interact with bioassays at >1% v/v.
DMSO: excellent solvency, low volatility; generally acceptable in assays at ≤0.5–1% v/v; less green but often necessary.
Ethyl acetate: biodegradable, low toxicity; suitable for workups; limited miscibility with water.
Operational tips:
Minimize solvent volumes by preparing concentrated stocks and using microvials.
Employ amber glassware and inert headspace to extend solution lifetime, reducing waste from frequent remakes.
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this item.
Context (general, non-clinical):
Hydroxy-sanshools are studied as natural-product reference compounds in pre-formulation and delivery research due to their lipophilicity and sensory bioactivity. Typical roles are as research actives in in vitro models rather than as formulation excipients.
In dosage-form research, they may be incorporated into lipid-based formulations, microemulsions, or polymeric carriers to explore solubilization and release kinetics. These activities remain within research and development settings.
Regulatory note:
Not specified for this item; refer to CoA/Spec Sheet for any available compliance statements. This product is supplied strictly for research use only and is not intended for human or animal administration, diagnostic, or therapeutic applications.
Operational guidance:
For formulation screening, prepare concentrated stocks in ethanol or DMSO and evaluate compatibility with your vehicle (e.g., PEG 400, polysorbates, propylene glycol). Monitor for precipitation upon dilution and for isomerization under processing conditions (heat, light).
Physical Properties
Item-specific specifications (this listing):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties of hydroxy-sanshool alkamides (for planning only; not item specifications):
Physical state: typically a low-melting solid, wax, or viscous oil depending on isomer ratio and purity; strongly lipophilic.
Solubility profile: sparingly soluble in water; readily soluble in organic solvents such as ethanol, methanol, isopropanol, acetone, ethyl acetate, dichloromethane, chloroform, and DMSO; soluble in edible oils and nonpolar lipids.
Partitioning: high logP expected for long-chain alkamides (literature class behavior); favors hydrophobic phases.
UV/Vis: conjugated double bonds provide π→π* absorption in the near-UV; exact λmax depends on E/Z composition and conjugation length.
Volatility: low; long-chain amide with minimal vapor pressure at ambient temperature.
Thermal behavior: conjugated polyenes can isomerize under heat or light; amide linkage is thermally robust but hydroxy-bearing allylic positions may undergo slow oxidation if exposed to air/UV.
Do not use the above as acceptance criteria. For precise numerical values (bp, mp, density, refractive index, UV cutoff, water/peroxide/metal limits), consult the product’s CoA/SDS or request a specification sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
In the absence of a stated grade, researchers should rely on the Certificate of Analysis (CoA) for identity confirmation (e.g., NMR/HRMS/LC–MS/HPLC purity) and any residual solvent or byproduct limits.
Sanshool-type alkamides often exist as E/Z isomer mixtures. If your application is stereochemistry-sensitive (analytical standards, receptor pharmacology, or materials), verify the reported isomer ratio and purity methodology (e.g., chiral or cis/trans-resolved HPLC).
Stabilizers: none are declared in this listing. If antioxidants (e.g., BHT) or acid scavengers are included in a specific lot, they will appear on the CoA. Presence/absence of stabilizers can materially affect chromatographic baselines and bioassay backgrounds.
UV/LC suitability: If using for HPLC/UPLC calibration or quantitative assays, request UV absorbance profile and impurity map to ensure compatibility with your detection wavelength and matrix.
Trace analyses (water, metals, peroxides, residual solvents): Not specified for this item; refer to CoA/Spec Sheet.
Recommendations:
For bioassays or sensory-receptor studies, consider performing a brief pre-use QC: 1H NMR for E/Z content, LC–MS for identity, and HPLC for purity at your analysis wavelength. Store and handle under inert conditions where feasible to maintain isomer composition.
Reaction and Applications
This compound is primarily used as a reference alkamide standard and as a probe for chemosensory and ion-channel biology. While not a common reagent in synthesis, its functional groups open several application avenues.
Research/application themes (literature/general):
Sensory chemistry and neurochemistry: hydroxy-sanshools are studied for activating/ modulating somatosensory channels; Hydroxy-γ-isosanshool is used in receptor screening, structure–activity relationships, and desensitization kinetics research.
Natural products/foodomics: marker compound for Zanthoxylum species; used in targeted LC–MS quantitation, authenticity testing, and processing stability studies (E/Z isomerization, oxidation).
Formulation science: evaluation in lipid carriers, emulsions, and encapsulation systems due to lipophilicity and conjugation-sensitive stability.
Transformations and derivatization (synthetic utility aspects):
Hydrogenation of the conjugated chain to modulate geometry and lipophilicity; selective partial hydrogenation to probe SAR.
Protection of the hydroxy group (e.g., silyl ethers) to stabilize during photochemical or oxidative studies; deprotection under mild conditions.
Amide modifications: N-acylation or transamidation under activating conditions to generate analogs; careful to avoid conjugated chain isomerization.
Practical notes:
Work under subdued light and inert atmosphere when running reactions or long assays; conjugated polyenes can isomerize.
For analytical applications, develop LC methods that resolve E/Z isomers (e.g., C18 with temperature control and shallow gradients). Use freshly prepared standards for quantitative accuracy.
Reaction Conditions
There are no item-specific reaction condition recommendations for this product. The following general conditions reflect literature practices for alkamide/polyene manipulations and should be adapted to your system.
Representative conditions (literature/general):
Selective hydrogenation: H2 (1–3 atm), Pd/C (1–10 wt%), EtOAc or EtOH, 0–25 °C, minutes to hours; monitor to avoid over-reduction of the polyene.
Epoxidation of conjugated C=C: mCPBA (1.0–1.2 equiv per C=C), CH2Cl2 or EtOAc, 0 °C to rt; quench and promptly purify to limit rearrangements.
Hydroboration–oxidation: 9-BBN (1.0–1.5 equiv), THF, 0–25 °C; oxidation with H2O2/NaOH; regioselectivity depends on substitution and conjugation.
Allylic alcohol protection: TBDMS-Cl, imidazole, DMF, rt; or TIPS-Cl, pyridine, rt; deprotection with TBAF (THF) at 0–25 °C.
Amide reduction: BH3·THF complex, 0 °C to reflux; caution with polyenes—prefer low temperature and slow addition; work up under inert conditions.
Analytical/control:
Use low-light chromatography (amber columns or foil wrapping) and cool stacks to preserve E/Z ratios.
LC–MS with APCI or ESI (positive) is commonly used; adduct formation can be prominent due to the amide.
Yields and times vary with isomer composition and substituent patterns; consult primary literature for closely related hydroxy-sanshools when planning scale-up.
Safety and Handling
Item-specific hazard data provided in this listing:
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General laboratory safety guidance for lipophilic alkamides (literature/Best Practice; not product-specific):
Likely hazards: may cause skin/eye irritation; avoid inhalation of aerosols and ingestion. Conjugated polyenes can auto-oxidize to irritant byproducts.
PPE: lab coat, safety glasses, and chemical-resistant gloves (e.g., nitrile). Handle in a fume hood when weighing or preparing solutions.
First aid overview: rinse affected skin/eyes with water for at least 15 minutes; remove contaminated clothing; seek medical attention per local procedures and SDS instructions if irritation persists.
Incompatibilities: strong oxidizers (risk of exothermic reaction); strong acids/bases may hydrolyze the amide or dehydrate/transform the allylic alcohol. Avoid prolonged exposure to light, heat, and air to limit E/Z isomerization and oxidation.
Spill response: absorb on inert material (vermiculite, diatomite), collect for disposal. Wash area with ethanol or detergent solution. Prevent entry into drains.
Waste: dispose in accordance with institutional and local regulations for organic chemical waste.
Always consult the product’s SDS for authoritative hazard classification, exposure limits, and emergency procedures. This product is supplied for research use only.
Solvent Selection
Solubility/miscibility guidance (literature/general for alkamides; verify with your lot):
Preferred stock solvents: DMSO and ethanol provide reliable dissolution at millimolar concentrations for plating and bioassays. Prepare concentrated stocks (e.g., 10–100 mM) and dilute into assay media with vigorous mixing to minimize precipitation.
Secondary solvents: methanol, isopropanol, acetone, ethyl acetate, acetonitrile (moderate); nonpolar media (MCT oil, PEG-containing vehicles) for formulation studies.
Aqueous systems: poor intrinsic water solubility. Use cosolvent systems (EtOH or DMSO ≤1–2% v/v final), cyclodextrins, or lipid carriers to achieve dispersion.
Polarity/handling:
Polarity class: nonpolar to weakly polar amphiphile (amide + hydroxy provide limited H-bonding; long chain dominates lipophilicity).
Dielectric behavior: not typically used as a solvent; behaves as a hydrophobic solute with strong partitioning into organic phases and lipid bilayers.
Comparison (general):
Hydroxy-γ-isosanshool vs non-hydroxylated sanshools: the hydroxy group slightly increases polarity and H-bonding, improving solubility in polar organics (MeOH/EtOH) relative to the parent isosanshool while retaining poor water solubility.
Practical tips:
Filter stock solutions (0.22 µm PTFE) to remove particulates before quantitative work.
Use amber vials, minimize headspace oxygen, and consider inert gas blanket for multi-week storage to mitigate oxidation/isomerization.
Storage and Reconstitution
Item-specific instruction:
Storage Conditions: Room temperature (as listed). Protect from light and moisture.
General best practices for this chemotype (supplementary guidance; not to override item-specific instruction):
Solid/neat material: store in amber, airtight containers under dry conditions. If feasible, blanket headspace with inert gas (N2/Ar) to limit oxidation and E/Z isomerization of the polyene chain.
Short-term solution storage: prepare concentrated stocks in DMSO or ethanol. For working solutions used within days, store at 2–8 °C, protected from light.
Long-term solution storage: aliquot and store at −20 °C or below to minimize degradation; avoid repeated freeze–thaw by using single-use aliquots.
Reconstitution: warm to ambient temperature before opening to prevent moisture condensation. Dissolve in a small volume of dry solvent with gentle vortexing/sonication. Verify concentration by UV or quantitative NMR if required for analytical work.
Shipping:
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Always follow your institution’s chemical hygiene plan. For any discrepancies, defer to the lot-specific CoA and SDS. Research use only.
Structure and Identity
Hydroxy-γ-isosanshool is a polyunsaturated alkamide related to the pungent/tingling constituents of Zanthoxylum (Sichuan pepper). It features a long-chain, conjugated diene/ triene system attached to an amide bearing a hydroxy substituent.
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 chemistry/literature):
Core motif: an aliphatic amide (–C(O)–NH–) linked to a polyunsaturated alkyl chain.
Unsaturation: multiple conjugated C=C bonds (E/Z geometry may occur in the natural isomer series); a γ-isomer denotes the position of the double-bond pattern relative to the amide carbonyl (literature convention for sanshools).
Substituents: one hydroxy group on the chain (allylic/benzylic-type alcohol environment in many reported structures; literature).
2D description in words: a terminal or near-terminal hydroxy-bearing alkenyl fragment, joined via a trans-rich conjugated diene/triene to an amide nitrogen, typically N-monosubstituted with a small alkyl/alkenyl group in the sanshool family (literature archetype).
Notes:
Exact stereochemistry (E/Z per double bond) and hydroxy position can vary across reported hydroxy-isoforms; confirm with the Certificate of Analysis (CoA) for this catalog item.
Synthetic Utility
Although Hydroxy-γ-isosanshool is primarily a target/analyte rather than a reagent, its functional groups permit useful transformations and it serves as a scaffold for SAR studies.
Functional group reactivity (general):
Conjugated polyene: susceptible to E/Z isomerization, epoxidation (e.g., mCPBA, Shi), hydroboration–oxidation, and selective hydrogenation. Photochemical reactions can rearrange the double-bond topology; control light exposure.
Allylic alcohol: can be protected (TBDMS/TIPS) to prevent side reactions; oxidized (Dess–Martin, Swern) to the corresponding enone/enal fragment depending on position; used as a handle for carbonate/ester formation.
Amide: relatively stable but can be N-acylated or engaged in coupling after activation (e.g., via conversion to imidazolides) to generate analog libraries. Direct reduction (e.g., BH3·THF) yields amines for further diversification.
Applications enabled:
Synthesis of labeled standards: incorporation of stable isotopes (13C/2H) at the carbonyl or allylic positions for quantitative LC–MS.
SAR libraries: systematic variation of chain length, degree of unsaturation, and hydroxy protection state to probe receptor/channel interactions.
Materials interfaces: covalent attachment through the alcohol or amide nitrogen to surfaces/polymers for membrane-mimetic studies.
Best practices:
Conduct oxygen- and light-sensitive steps under inert gas with amber glassware. Include radical inhibitors (e.g., BHT) during extended reactions when compatible with downstream assays.
Target Specificity
Target/antigen details are not applicable to this small-molecule product, and no item-specific biological target validation data are provided.
General literature note (for context only, not a claim for this lot): hydroxy-sanshools have been studied as modulators of somatosensory ion channels (e.g., TRPV1, TRPA1, and certain K2P channels). However, potency, selectivity, and efficacy are highly dependent on isomerism, assay conditions, and membrane composition. Users should generate in-house validation data for their specific experimental setup.
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