Epinortrachelogenin , CAS No.125072-69-7

CAS: 125072-69-7 Cat. No.: E981868 PubChem CID: 14159539

Storage

Room temperature

Specifications

Condições de armazenamento de armazenamento

Room temperature

Nomes e identificadores

• Sorrisos canónicos: COC1=C(C=CC(=C1)CC2COC(=O)C2(CC3=CC(=C(C=C3)O)OC)O)O
• IUPAC Name: (3R,4S)-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
• InChIKey: ZITBJWXLODLDRH-VBKZILBWSA-N
• INCHI: 1S/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-11-27-19(23)20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3/t14-,20+/m0/s1
• SMILES isoméricas: COC1=C(C=CC(=C1)C[C@H]2COC(=O)[C@]2(CC3=CC(=C(C=C3)O)OC)O)O
• CAS alternativo: 125072-69-7
• PubChem CID: 14159539

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lignans, neolignans and related compounds
    • Classe Furanoid lignans
      • Subclass Tetrahydrofuran lignans
        • Level5 9,9'-epoxylignans
          • Level6 Dibenzylbutyrolactone lignans

• Kingdom: Organic compounds
• Superclass: Lignans, neolignans and related compounds
• Classe: Furanoid lignans
• Subclass: Tetrahydrofuran lignans
• Intermediate Tree Nodes: 9,9'-epoxylignans
• Direct Parent: Dibenzylbutyrolactone lignans
• Alternative Parents: Lignan lactones Methoxyphenols Phenoxy compounds Anisoles Methoxybenzenes 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Gamma butyrolactones Tertiary alcohols Oxolanes Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Carbonyl compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Dibenzylbutyrolactone - Lignan lactone - Methoxyphenol - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Monocyclic benzene moiety - Gamma butyrolactone - Benzenoid - Oxolane - Tertiary alcohol - Carboxylic acid ester - Lactone - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Ether - Monocarboxylic acid or derivatives - Alcohol - Carbonyl group - Organic oxygen compound - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propriedades químicas e físicas

• Peso molecular: 374.400 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 374.137 Da
• Monoisotopic Mass: 374.137 Da
• Topological Polar Surface Area: 105.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 513.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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

Application Protocols

No tested biological or analytical protocols are provided in the Product Data for this SKU.

General preparation and handling protocols (research-use guidance):

• Stock solution preparation: Dissolve in anhydrous DMSO to 10–50 mM. Sonication or gentle warming (≤40 °C) can aid dissolution. Filter (0.22 µm PTFE) if preparing for HPLC/LC-MS.
• HPLC analysis: Reversed-phase C18; gradient 10–90% MeOH/H2O or MeCN/H2O, 0.1% formic acid as needed. Detect at 280 nm and scan 200–400 nm for peak purity. For MS, use ESI in negative and positive modes; phenolate forms readily in negative mode.
• Solid handling: Minimize exposure to ambient humidity and light; cap promptly after weighing. For microgram quantities, weigh by differential method into pre-tared vials.
• Stability checks: Run a quick LC at t=0 and after 24–72 h in your chosen solvent system to confirm solution stability (look for oxidative byproducts or dimerization in air-exposed solutions).

These are general recommendations and not validated protocols for this item. Adjust to your instrumentation and assay requirements.

Biological Roles

General background (literature; not specific performance claims for this SKU):

• Chemical class: Epinortrachelogenin is a lignan/norlignan-type plant metabolite related to trachelogenin and nortrachelogenin. Lignans arise via oxidative dimerization of coniferyl alcohol-derived phenylpropanoids.
• Putative roles in plants: Phenolic lignans often contribute to defense, UV protection, and modulation of oxidative stress. They may occur glycosylated or as aglycones in various tissues.
• Biochemical properties: The presence of phenolic hydroxyls confers radical-scavenging and metal-chelating capacities in model systems. Some lignans interact with membrane interfaces due to amphiphilic character (aromatic core vs. polar phenols/lactone).
• Metabolism (general): In mammals, lignans can undergo phase I (O-demethylation, reduction, lactone hydrolysis) and phase II (glucuronidation, sulfation) metabolism. In the gut, microbial biotransformation may generate enterolignans; exact pathways depend on substitution and stereochemistry.
• Assay relevance: Researchers evaluate lignans for binding to biomacromolecules (proteins, lipids) and for modulation of enzymatic redox processes in vitro. Stereochemical inversion (“epi-”) can markedly alter binding and physicochemical behavior, making epimers valuable for mechanistic comparison.

Note: No biological activity, potency, or selectivity is claimed for this catalog item. Use strictly for research and method development as indicated by the Product Data (Research Use Only).

Buffer Applications

Not typically applicable. Epinortrachelogenin is a neutral/weakly acidic, poorly water-soluble small molecule and does not function as a buffering agent.

Practical notes for aqueous work (general guidance):

• If incorporation into aqueous buffers is required for an assay, dissolve first in DMSO or ethanol to make a concentrated stock (e.g., 10–50 mM), then dilute into buffer keeping the final organic co-solvent fraction low (commonly ≤0.1–0.5% v/v, per assay tolerance).
• Surfactants (e.g., 0.01–0.05% Tween 80) or cyclodextrins may improve apparent solubility. Validate that additives do not interfere with the assay readout.
• Adjusting pH above the phenolic pKa can increase solubility via phenolate formation, but may also alter molecule integrity and assay conditions; use with caution and confirm reversibility upon neutralization.

Green Alternatives

Sustainability considerations for handling and analysis of phenolic lignans:

• Solvent choice: Replace DMF and dichloromethane where possible.
  • Prefer ethanol, methanol (with caution), 2-propanol, ethyl acetate, or acetone for workup and recrystallization when solubility permits.
  • For chromatography, consider MeOH/H2O or MeCN/H2O with 0.1% formic acid; where feasible, use MeOH instead of MeCN (renewable origin options exist for MeOH).
• Reaction media: O-alkylations and esterifications may proceed in greener solvents (2-MeTHF, CPME, propylene carbonate) under phase-transfer or carbonate base conditions; verify solubility.
• Energy: Many derivatizations occur efficiently at ambient temperature; use microwave or flow chemistry to reduce time/energy when appropriate.
• Waste minimization: Implement mini-scale screens (0.01–0.1 mmol) to identify viable conditions before scale-up; use solid-supported scavengers to simplify workups and reduce solvent volumes.

Illustrative comparison (general; not item-specific):

• Traditional: DMF or DMSO for O-alkylation; DCM for chromatography.
• Greener option: Acetone or 2-MeTHF for O-alkylation; ethyl acetate/hexane or EtOAc/MeOH gradients for purification.

Trade-offs:

• Greener solvents may alter selectivity or rates; phenoxide formation and nucleophilicity can be lower in less polar media. Conduct small-scale trials to balance EHS benefits with performance.

Pharmaceutical Uses

Not applicable as a therapeutic claim. No pharmacopeial status or excipient role is provided in the Product Data for this item.

General research/formulation context (literature/typical for small-molecule standards):

• Natural product standard: Employed as a reference compound in analytical method development (e.g., HPLC identification/quantitation) of botanical materials.
• Preformulation studies: When evaluating lignan analogs, solubility screening can use co-solvents (DMSO, PEG 400, ethanol) or solid dispersions. These activities are research-only and exploratory.
• Encapsulation approaches (research level): Cyclodextrin inclusion complexes or lipid-based carriers are sometimes explored to enhance aqueous compatibility of phenolic natural products for in vitro testing.

No claims are made regarding therapeutic efficacy, safety in humans/animals, or regulatory acceptance. This product is supplied strictly for research use only as stated in the Product Data.

Physical Properties

Item-specific specifications from Product Data:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Literature/typical properties for lignans like epinortrachelogenin (non-spec for this item):

• Physical state: typically a pale amorphous solid or crystalline powder for purified lignans.
• Solubility profile: sparingly soluble in water; soluble in polar aprotic and protic organic solvents such as DMSO, DMF, methanol, and ethanol; moderate solubility in ethyl acetate and acetone; poor solubility in alkanes and hexanes.
• LogP/logD: phenolic lignans often exhibit moderate to high lipophilicity (logP ~2.5–4.5, literature ranges vary with substitution).
• UV: aromatic phenols typically show strong absorbance around 210–230 nm and 270–290 nm (π→π*), useful for HPLC-UV detection.
• Melting point, boiling point, density, refractive index, pKa: Not specified for this item; refer to CoA/Spec Sheet. For phenolic lignans, phenolic pKa values often lie in the ~9–10 range (literature), and lactone carbonyls show IR C=O bands ~1760–1780 cm−1.

Important: Do not treat the above literature values as specifications. Verify exact values for this SKU on the product CoA/Spec Sheet.

Quality and Grades

Item-specific grade/purity from Product Data:

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on quality for research-grade small molecules (general):

• Research-use grade: Suitable for discovery chemistry, method development, SAR screening, and as a reference material. When purity is not explicitly stated, verify by CoA (HPLC/GC area %, NMR, water/ash content if applicable).
• Chromatographic purity vs. assay: HPLC area % is commonly reported for natural products. Minor co-eluting congeners may be present in lower grades; NMR offers orthogonal confirmation of identity and purity.
• Stabilizers: None indicated for this item. If phenolic oxidation is a concern, small amounts of inert atmosphere packing or light-protective containers are often used (check CoA if applicable).
• Implications for sensitive assays: For bioassays or photophysical studies, request a recent CoA and consider re-purifying or pre-qualifying by LC-MS to confirm single-component behavior and absence of UV-active impurities.
• Documentation: For regulated workflows, Aladdin can typically provide CoA, lot-specific purity, and test methods upon request.

Conclusion: Since the specific grade/purity is not listed in the Product Data, consult the CoA/Spec Sheet for this SKU prior to use in quantitative studies.

Reaction and Applications

Manufacturer applications: Not provided in Product Data.

Research-use applications (general for lignans; literature-based, not specific to this item):

• Reference standard: Useful as a calibrant/marker compound when profiling plant extracts containing trachelogenin/nortrachelogenin-type lignans by HPLC-UV/LC-MS.
• SAR and probe development: The phenolic and (if present) lactone functionalities offer handles for selective derivatization (O-alkylation, O-acylation, etherification, reduction/oxidation) to explore structure–activity relationships in biochemical screening.
• Antioxidant and redox assays: Phenolic scaffolds are commonly evaluated in DPPH/ABTS and FRAP assays. Epinortrachelogenin can serve as a comparator standard in such method development (no performance claimed for this SKU).
• Chiroptical studies: Epimers such as “epi-” analogs are frequently used to study stereochemical effects on CD/ORD and chiral separations.

Practical tips:

• Handle under inert atmosphere and protect from strong light to minimize slow oxidative discoloration of phenols.
• For selective O-derivatization, use mild bases (K2CO3, Cs2CO3) in polar aprotic solvents (acetone, DMF) with alkyl/aryl halides; control equivalents to avoid over-alkylation.
• For analytical quantitation, prefer LC-MS with soft ionization (ESI) and reversed-phase gradients; phenolic adducts (Na+, NH4+) may appear—optimize mobile phase additives accordingly.

Always validate any application conditions experimentally for this specific batch.

Reaction Conditions

General conditions for common transformations on phenolic lignan scaffolds (literature guidance; optimize per substrate):

• O-Alkylation/O-Acylation: Phenol (1.0 eq), alkyl halide/acid chloride (1.1–1.5 eq), K2CO3 or Cs2CO3 (2.0 eq) in acetone, MeCN, or DMF, 20–60 °C, 2–16 h. For selective mono-alkylation, use weaker base, lower temperature, and slow addition.
• Demethylation of aryl methoxy groups: BBr3 (1–3 eq per OMe) in dry DCM at −78 to 0 °C, 1–4 h; quench cautiously with MeOH/H2O. Alternative: AlCl3/thiophenol or HBr/AcOH under controlled conditions.
• Lactone opening (if applicable): RO− (1.5–2.5 eq) or RNH2 (2–4 eq) in alcohol/THF at 0–25 °C, 1–6 h; re-lactonization via DCC/DMAP or acid-catalyzed cyclization in toluene with azeotropic water removal.
• Hydrogenation: Pd/C (5–10 wt%) in EtOH or EtOAc/H2, 1–3 bar, 20–40 °C; monitor for over-reduction of aromatic rings.
• Oxidation at benzylic positions: DDQ (1.1–1.5 eq) in toluene/CH2Cl2 at 0–25 °C; or MnO2 (excess) in DCM. Test small scale first to avoid phenolic over-oxidation.
• Analytical controls: Use LC-MS and 1H/13C NMR to monitor selectivity; phenolic protection may be required to avoid side reactions during multi-step sequences.

These conditions are representative starting points and not specifications for this product. Verify substrate compatibility and scale prudently.

Safety and Handling

Item-specific hazard information from Product Data:

• Signal word: Not specified for this item; refer to SDS.
• H-statements: Not specified for this item; refer to SDS.
• GHS classification and pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance for small-molecule phenolic lignans (literature/typical):

• Potential hazards: May cause skin/eye irritation and respiratory tract irritation if dust is generated. Phenolic groups can be irritants. Avoid ingestion and inhalation.
• PPE: lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust exposure.
• Storage incompatibilities: Avoid strong oxidizing agents (can oxidize phenols), strong bases in the presence of air (phenolate formation and potential oxidative darkening), and strong acids for prolonged periods if a lactone is present (possible hydrolysis/transesterification under forcing conditions).
• Hygroscopicity/light sensitivity: Many phenolic natural products discolor upon prolonged light/air exposure; store in tightly closed, light-protected containers.
• First-aid (overview; defer to SDS): Inhalation—move to fresh air; Skin—wash with soap/water; Eyes—rinse cautiously with water for several minutes; Ingestion—rinse mouth, seek medical advice.
• Spill response: Avoid dust, collect mechanically or dampen and wipe, dispose according to institutional and local regulations.

Always consult the Aladdin SDS for authoritative hazard classifications and response measures before use.

Solvent Selection

Applicability: Epinortrachelogenin is a neutral/weakly acidic phenolic natural product with limited aqueous solubility. Solvent choice strongly impacts handling, weighing solutions, and analytical methods.

General solvent behavior (literature/typical for phenolic lignans; not specifications):

• Highly recommended for stock solutions: DMSO (10–100 mM), DMF. Warm ethanol or methanol for lower concentration working solutions.
• Moderately suitable: Acetonitrile, ethyl acetate, acetone—use for sample transfer and chromatography; solubility may be limited at room temperature.
• Poor: Water and buffered saline; consider co-solvents (≤1–2% DMSO) or cyclodextrin inclusion if aqueous work is required.
• Acid/base: Deprotonation of phenolic OH with strong base (e.g., NaOMe) greatly increases solubility in alcohols but may induce side reactions/oxidation.

Selection tips:

• Bioassay prep: Prepare a concentrated DMSO stock (e.g., 10 mM), then dilute into media or buffer keeping final DMSO ≤0.1–0.5% v/v as assay permits.
• Purification: Normal-phase silica can lead to tailing for phenols; pre-add 0.1–1% AcOH to mobile phase or switch to reversed-phase (MeCN/H2O or MeOH/H2O with 0.1% formic acid) for sharper peaks.
• NMR: Acquire in DMSO-d6 or CD3OD. Phenolic OH may exchange and appear broad; add a drop of D2O to confirm OH assignments.

When to choose alternatives: If precipitation occurs on dilution, increase co-solvent fraction, gently warm, or use solubilizing excipients.

Storage and Reconstitution

Item-specific storage from Product Data:

• Storage conditions: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General best practices for this compound class (supplemental guidance; not specifications):

• Light/air protection: Store in a tightly closed, inert container, protected from light. If long-term storage is planned, consider desiccation and/or inert gas backfill (N2/Ar).
• Temperature: While room temperature is noted in Product Data, many phenolic natural products benefit from cool, dry storage. If solutions are prepared, store aliquots at −20 °C to limit degradation; avoid repeated freeze–thaw.
• Reconstitution: For bioassays, reconstitute in anhydrous DMSO to a high-concentration stock (e.g., 10–50 mM). Vortex and, if needed, sonicate briefly. Filter sterilize if required for cell-based work (0.22 µm PTFE). Record exact concentration by weight and solvent density, or by quantitative NMR for highest accuracy.
• Shelf life: Not specified for this item; verify stability periodically by HPLC/LC-MS, especially after first opening.

Always consult the product label and CoA/SDS for lot-specific storage and handling instructions.

Structure and Identity

Item-specific identifiers from Product Data:

• SKU: E981868
• Product name: Epinortrachelogenin
• CAS: 125072-69-7
• PubChem CID: 14159539
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists an incomplete key: "458134")
• 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.

General structural context (literature):

• Epinortrachelogenin is reported in the literature as a plant-derived lignan (norlignan) related to trachelogenin/nortrachelogenin scaffolds.
• Typical features of this family include a substituted biphenyl/bibenzylic framework bearing phenolic hydroxyl groups and, in some congeners, a butyrolactone (dibenzylbutyrolactone) motif with defined stereocenters. “Epi-” denotes an epimer relative to nortrachelogenin at one stereogenic center.
• 2D description (generic for this class): two aromatic rings with methoxy/phenolic substitution linked through a short aliphatic chain that may cyclize to a lactone; multiple hydrogen-bond donors/acceptors due to phenols and lactone carbonyl.

Notes:

• For definitive structural string identifiers (SMILES/InChI) and exact stereochemistry of this catalog item, consult the Aladdin CoA/Spec Sheet or SDS.

Synthetic Utility

General reactivity of epinortrachelogenin-like lignans (literature; not specific to this lot):

• Phenolic OH groups: Amenable to selective protection (Bn, MOM, TBDMS) and derivatization (O-alkylation/acylation, carbonate/urethane formation). Using mild bases (K2CO3/Cs2CO3) in polar aprotics enables mono- vs. di-derivatization control.
• Aromatic substitution: If methoxy groups are present, demethylation (BBr3, AlCl3/thiols) can access additional phenols for diversification; electrophilic substitutions are generally limited by deactivation patterns.
• Lactone (if present): The dibenzylbutyrolactone moiety can be opened under basic nucleophilic conditions (alkoxide, amine) to corresponding hydroxyacids or amides, then re-lactonized under dehydrating conditions. Stereochemistry at the lactone-bearing center can influence reactivity.
• Oxidation/reduction: Benzylic positions may be oxidized (e.g., DDQ) or reduced (NaBH4, catalytic hydrogenation) to adjust oxidation state and prepare analogs.
• Cross-coupling after halogenation: Strategic iodination/bromination of the aromatic rings allows Suzuki/Miyaura or Ullmann-type ether couplings to build libraries on the lignan core.

Retrosynthetic value:

• Serves as a chiral, polyfunctional scaffold to explore SAR by systematic modification at phenolic, benzylic, and lactone positions. The “epi-” stereochemistry offers an internal control for stereochemical effects in binding or physical properties.

Target Specificity

Not applicable. This product is a small-molecule lignan and is not an antibody, enzyme, nucleic acid, or targeted biological reagent. No target, epitope, or isotype information is associated with this SKU in the Product Data.

If planning biochemical assays, any observed “target specificity” should be empirically determined for your system, and appropriate controls (vehicle, inactive analogs, stereochemical controls like non-epi isomers) should be included.