This compound belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
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
264.320 g/mol
XLogP3
1.300
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
0
Exact Mass
264.136 Da
Monoisotopic Mass
264.136 Da
Topological Polar Surface Area
70.700 Ų
Heavy Atom Count
19
Formal Charge
0
Complexity
409.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
4
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
Calculadoras de soluciones
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Application Protocols
No item-specific tested application protocols are provided. For general laboratory use with hydrophobic small molecules:
LC–MS/HPLC reference solutions: Prepare a stock in a suitable solvent (e.g., DMSO, MeOH, or ACN; verify solubility). Dilute with mobile phase to working concentrations; filter through 0.2 µm PTFE/NYLON as appropriate.
Bioassay dosing: Prepare concentrated DMSO stocks and serially dilute into assay media, keeping final DMSO within assay tolerance (commonly ≤0.5–1% v/v). Include vehicle controls.
NMR sample: Dissolve in CDCl3 or DMSO-d6 depending on solubility; typical concentration 5–20 mg/mL. Add TMS or residual solvent peaks for referencing.
Always tailor protocols to your specific assay or instrument and consult your internal SOPs.
Biological Roles
Scope note: No biological/clinical claims are made for this product; content below reflects general literature context for furanosesquiterpenes.
Literature/general context (not item-specific)
Origin: Zedoarofuran is reported in the literature as a natural product from Curcuma species (e.g., C. zedoaria), part of their complex sesquiterpenoid metabolome.
Biosynthesis: Sesquiterpenes arise from the mevalonate or MEP pathways via farnesyl pyrophosphate (FPP) cyclization, followed by rearrangements and oxidative tailoring that can introduce heterocycles such as furan.
Ecological roles: Sesquiterpenes in plants often contribute to chemical defense, allelopathy, and signaling, with volatility and hydrophobicity aiding distribution in tissues and the rhizosphere.
Physicochemical behavior in biology: High lipophilicity can favor membrane association and low aqueous solubility; proteins such as P450s commonly metabolize terpenoids in vivo.
Analytical profiling: In metabolomics, zedoarofuran-like compounds are tracked by MS/MS fragmentation patterns associated with furan ring cleavage and terpenoid backbone ions.
Applications in research
Standards for botanical authentication and quality control.
Probes in structure–activity studies comparing oxidation state, saturation, and ring topology within sesquiterpenoid series.
Note: Any biological activity reported in the literature is highly context-dependent and should not be inferred as performance characteristics of this catalog item.
Buffer Applications
Not typically applicable. Zedoarofuran is a hydrophobic small molecule and is not used to prepare biological buffers. For laboratory work involving this compound in buffered systems, prepare a concentrated stock in a miscible organic solvent (commonly DMSO or ethanol; confirm solubility experimentally) and dilute into the desired buffer while keeping final organic content within assay-tolerable limits.
Green Alternatives
Context: Zedoarofuran is a target molecule rather than a solvent or reagent. Green considerations therefore focus on extraction, handling, and transformations rather than substitution of the molecule itself.
Greener solvent choices (general guidance)
Replace chlorinated solvents (DCM/CHCl3) with ethyl acetate, 2-MeTHF, CPME, or Me-THF/EtOH mixtures where feasible.
For stock solutions, ethanol can sometimes substitute for DMSO in bioassays, subject to solubility and assay tolerance.
Supercritical CO2 or pressurized ethanol/water can be explored for preparative extraction/purification from botanicals.
Comparison (general; not item-specific)
DCM vs Ethyl acetate: EtOAc offers lower toxicity and better biodegradability; may require larger volumes or altered gradients.
THF vs 2-MeTHF: 2-MeTHF is biorenewable and less peroxide-prone than THF; check solubility and UV background for analytics.
MeCN vs EtOH/EtOAc: MeCN provides sharper HPLC peaks but is petro-derived and toxic; partial replacement with greener solvents is possible depending on method.
Process considerations
Minimize air/light exposure during reactions to limit oxidative waste.
Use catalytic rather than stoichiometric oxidants where possible; explore electrochemical or photooxidation methods that avoid heavy metals.
Implement microscale/flow chemistry to reduce solvent load and improve heat/mass transfer for sensitive furan chemistry.
Pharmaceutical Uses
No therapeutic or clinical claims are made. This product is for research use only.
General formulation/analytical contexts (literature/general)
Reference/analytical standard: Useful for developing and validating chromatographic assays (HPLC/LC–MS) for Curcuma-derived materials and natural product mixtures.
Impurity profiling: Can serve as a marker compound in botanical raw-material qualification or process development research.
Preformulation studies: As a hydrophobic small molecule, zedoarofuran may be evaluated in research settings for solubilization strategies (cyclodextrins, lipid vehicles), though such studies are outside the scope of the product’s intended use.
Regulatory status
No pharmacopeial monograph is implied. Item-specific regulatory or compendial status is not provided; consult CoA/Spec Sheet if required by your workflow.
Manufacturing note
When used as a process-development reference, document lot-specific purity, residual solvents, and storage history, as furan-containing compounds may slowly oxidize under harsh conditions.
Physical Properties
Item-specific specifications
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.
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.
Literature/general expectations for furanosesquiterpenes (non-specification)
Physical state: Frequently low-melting solids or viscous oils depending on substitution and purity.
Solubility profile: Typically poorly soluble in water; soluble in common organic solvents (e.g., dichloromethane, chloroform, ethyl acetate, acetone). DMSO/MeOH often used for analytical stocks. Confirm for this item experimentally.
LogP: Sesquiterpenes commonly exhibit high lipophilicity (logP > 3), but exact value for zedoarofuran must be verified in primary data.
UV characteristics: Furan chromophore shows UV absorbance in the near-UV; exact λmax depends on substitution. Not specified for this item.
Stability: Furan rings can be sensitive to strong acids/oxidants and prolonged light/air exposure; actual stability for this item is not specified.
Note: For any numerical property required by your workflow, rely on the item’s CoA/Spec Sheet or measure under your conditions.
Quality and Grades
Item-specific quality details
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret typical grades (general guidance)
Research grade: Suitable for discovery chemistry and screening. Purity often confirmed by HPLC/LC–MS and/or NMR; exact threshold varies by supplier.
Analytical/Reference standard grade: Intended for quantitative work; accompanied by detailed purity assay, residual solvents, and impurity profiles.
HPLC grade (solvents): Defined by low UV absorbance and low residue; not applicable to this compound unless sold as a solution.
Recommended quality checks on receipt (best practices)
Identity confirmation: 1H/13C NMR (furan protons typically downfield), HRMS, and retention time match to reference if available.
Purity assessment: RP-HPLC or GC (if volatile/thermally stable); monitor for oxidative byproducts of the furan.
Water content/residual solvents: Karl Fischer/GC–HS as required by your application.
Implications of stabilizers (if present)
Antioxidants or inert-atmosphere packaging are sometimes used to protect furan-containing terpenoids. If any stabilizer is listed on the CoA, consider its impact on downstream assays and remove (e.g., by preparative chromatography) if necessary.
Reaction and Applications
Manufacturer Applications (catalog): Not provided; this item is listed within a small-molecule/compound library and is intended for research use only.
General research uses (non-item-specific)
Reference standard: For method development and profiling of Curcuma-derived sesquiterpenoids by LC–MS/GC–MS.
Screening libraries: Employed in phenotypic or target-agnostic screening as a structurally diverse natural-product scaffold.
Metabolomics/natural products: Spike-in controls for extraction/recovery studies from botanical matrices.
Representative transformations on furanosesquiterpenes (literature)
Oxidation of the furan ring to 1,4-dicarbonyls/lactones using singlet oxygen, m-CPBA (careful), or Ru/Os-mediated protocols.
Electrophilic substitution at the furan 2-/5-positions under mild Lewis/Brønsted acidic conditions.
Hydrogenation of olefinic sites on the terpenoid backbone using Pd/C or Rh catalysts to study SAR of saturation.
Halogenation (e.g., NBS) at activated allylic positions; regioselectivity depends on substitution pattern.
Use inert atmosphere and low temperatures when conducting electrophilic substitutions on furan to minimize polymerization/overreaction.
Monitor reactions by TLC with anisaldehyde/sulfuric acid stains, or by LC–MS using soft ionization to track minor oxidation products.
Reaction Conditions
Guidance below is literature/general for furan-containing sesquiterpenes and not a specification for this item. Optimize for your substrate and scale.
Typical solvents
Electrophilic substitutions and oxidations: DCM, CHCl3, or MeCN; for greener options, EtOAc or 2-MeTHF when compatible.
Hydrogenation: EtOH, EtOAc, or THF under H2 with Pd/C or Rh catalysts.
Representative conditions (examples)
Allylic bromination: NBS (1.1–1.5 equiv), AIBN initiation, reflux in CCl4 or safer solvent alternatives like acetonitrile under photoinitiation; 1–4 h. Quench and immediately purify to minimize rearrangements.
Epoxidation: m-CPBA (1.1–1.5 equiv) in DCM at 0 °C to rt, 0.5–3 h; pre-screen to minimize furan oxidation. DMDO in acetone at 0 °C often cleaner but requires on-site generation.
Hydrogenation: 5–10 wt% Pd/C (5–20 mol% metal), 1–3 bar H2, rt–40 °C, 1–6 h; monitor by TLC/LC–MS for selective alkene reduction without furan saturation.
Furan oxidation: Singlet oxygen via Rose Bengal (1–2 mol%), O2 bubbling, MeOH/DCM, 0–10 °C, light irradiation; 0.5–2 h to form oxygenated derivatives. Exercise photochemical safety.
Workup/purification
Avoid strong acid/base washes that can degrade the furan. Use neutral aqueous workups and silica gel buffered with 0.5–1% triethylamine if acid sensitivity observed.
Yields
Highly substrate-dependent; literature reports span moderate to good (30–80%) with careful control of overreaction and decomposition.
Safety and Handling
Authoritative source: Always consult the product’s SDS for definitive hazard, first aid, and disposal guidance.
Item-specific hazard data
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General laboratory precautions for hydrophobic natural products (non-specification)
PPE: Recommended use of lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Employ fume hood handling until volatility and irritancy are understood.
Avoid: Strong oxidizers and strong acids that may attack the furan ring; excessive heat, open flames, and prolonged UV exposure.
Inhalation/skin contact: Limit aerosol/vapor formation. Wash thoroughly after handling. In case of contact, rinse with water; remove contaminated clothing. Seek medical advice as per SDS.
Spills: Absorb with inert material (e.g., vermiculite), collect for disposal as organic chemical waste.
Fire safety: Treat as an organic combustible. Use CO2, dry chemical, or foam; water spray to cool containers. Verify specific extinguishing media on SDS.
Waste: Dispose in accordance with institutional and local regulations for organic laboratory waste.
Special notes
Furan motifs can undergo oxidation; store away from oxidants and light. If form is an oil, wipe threads and seal well to minimize air ingress.
Solvent Selection
Applicability: Zedoarofuran is a hydrophobic small molecule; solvent choice focuses on dissolution for analysis, screening, or reactions. Exact solubility for this item is not specified; validate experimentally.
General solvent behavior (literature/general)
Polarity class: Low-to-moderate polarity solute; favors medium polarity organic solvents.
Common solvents for dissolution: DMSO (for stock solutions), dichloromethane, chloroform, ethyl acetate, acetone, acetonitrile, methanol, ethanol. Poor water solubility expected for sesquiterpenes.
Dielectric considerations: Solubility typically increases with solvents that can stabilize the furan ring and any π-system interactions (e.g., DMSO, MeOH) without promoting rapid oxidation.
Selection guidance by use case
Analytical HPLC/LC–MS: Start with ACN/water or MeOH/water gradients; add 0.1% formic acid if positive-ion ESI is desired. Keep injection solvent ≤ sample solvent strength to maintain peak shape.
NMR: CDCl3 is often suitable for terpenoids. If solubility is limited, try CD2Cl2 or DMSO-d6.
Bioassays: Prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into assay buffer keeping final DMSO ≤ 0.5–1% v/v; confirm compatibility.
Synthesis: For electrophilic substitutions/oxidations on furan, use aprotic solvents (DCM, MeCN) under temperature control.
Quick comparison (general)
DMSO: Highest solvating power; can complicate MS and biological assays at high %.
MeOH/EtOH: Protic; convenient but can participate in reactions.
DCM/CHCl3: Excellent for nonpolar analytes; handle with ventilation and waste controls.
Storage and Reconstitution
Item-specific storage conditions
Storage Conditions: Room temperature (as provided). Protect from excessive heat and direct light.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General best practices for furan-containing terpenoids
Container: Store in an amber, tightly sealed vial to limit light and air exposure. If the compound is an oil, consider argon/nitrogen headspace.
Atmosphere: Inert gas padding can mitigate slow oxidative degradation of furan rings during long-term storage.
Moisture: Keep dry; avoid humid environments that may promote hydrolysis/oxidation.
Reconstitution and solution handling
Solubility: Not specified for this item; assess empirically. Common approach is to dissolve in DMSO, MeOH, EtOH, or CH2Cl2 depending on the application.
Stock solutions: Prepare aliquots at convenient concentrations (e.g., 10–50 mM for screening in DMSO) to avoid repeated freeze–thaw cycles.
Stability of solutions: Store working solutions at 2–8 °C for short periods or at −20 °C for longer-term, protected from light; verify stability by LC–MS/HPLC over time.
Shelf-life and QC
Periodically re-check purity and identity (HPLC, NMR, MS) if stored for extended periods.
Follow the SDS and institutional guidelines for storage segregation away from oxidizers and strong acids.
Structure and Identity
Brief overview: Zedoarofuran is listed as a small-molecule natural-product–derived compound (library member). Item-specific structural identifiers are largely not provided in the Product Data; consult CoA/SDS for definitive identifiers.
Item-specific (from Product Data)
SKU: Z952157
Product Name: Zedoarofuran
CAS: 213833-34-2
InChIKey: 308845 (as provided)
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.
Literature/general context (not item-specific)
Compound class: Often described in literature as a sesquiterpenoid bearing a furan ring (a “furanosesquiterpene”) isolated from Curcuma species (e.g., C. zedoaria). Exact substitution patterns can vary by isomer/source.
Structural features (typical for furanosesquiterpenes):
One five-membered aromatic heterocycle (furan, C4H3O) potentially fused or attached to a C15 terpenoid framework.
Multiple sp2 carbons (alkenes) and an ether-like oxygen within the furan ring.
No formal stereochemistry can be asserted here; sesquiterpenes often display multiple stereocenters. Verify on the CoA.
2D structure (descriptive, literature-based)
A five-membered O-heteroaromatic ring (furan) attached to a hydrophobic sesquiterpene carbon skeleton (typically bicyclic or monocyclic with isoprenoid branching). Without the exact item-specific SMILES/InChI, the precise linkage and stereochemistry cannot be stated.
Synthetic Utility
Conceptual utility (general, not item-specific)
Scaffold for derivatization: The furan ring offers handles for electrophilic substitution, oxidation to 1,4-dicarbonyl motifs, and cycloaddition chemistry; the terpenoid backbone presents allylic/benzylic C–H positions for selective functionalization.
Semisynthesis: Oxidation, halogenation, hydrogenation, and cross-coupling (after suitable activation) enable generation of analog libraries for SAR.
Retrosynthetic leverage: Disconnections may target late-stage furan installation onto a sesquiterpene core, or vice versa via Paal–Knorr-type strategies on prefunctionalized backbones.
Representative transformations (literature)
m-CPBA or DMDO epoxidation at isolated double bonds; careful to avoid over-oxidation of furan.
NBS/NCS allylic halogenation, followed by substitution (SN1/SN2) or metalation for cross-coupling after conversion to organoboron/organostannane derivatives.
Photooxygenation (1O2) of the furan to endoperoxides/oxo derivatives, giving access to lactones and butenolides.
Acid-catalyzed Friedel–Crafts-type additions at the furan ring under low temperature; control over 2- vs 5-substitution is substrate dependent.
Practical considerations
Protect the furan from harsh acidic/basic conditions unless targeted; use low temperatures and short reaction times.
Employ inert atmosphere and antioxidant additives when needed to suppress autoxidation during scale-up.
Monitor by LC–MS to detect minor over-oxidation products early.
Target Specificity
Not applicable. This product is a small molecule and not an antibody, enzyme, or nucleic acid probe. No target specificity, isotype, clone, or species reactivity data are associated with this catalog item.
Preguntas frecuentes
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 213833-34-2. InChIKey QXEXMTIZXNCRJO-BSLXNSKLSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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