Longistylin C - ≥98% , CAS No.64125-60-6

CAS: 64125-60-6 Cat. No.: L1048422 PubChem CID: 6446720

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

• Sorrisi canonici: CC(=CCC1=C(C=C(C=C1OC)O)C=CC2=CC=CC=C2)C
• IUPAC Name: 3-methoxy-4-(3-methylbut-2-enyl)-5-[(E)-2-phenylethenyl]phenol
• InChIKey: NFAWEPOBHKEHPO-ZHACJKMWSA-N
• INCHI: 1S/C20H22O2/c1-15(2)9-12-19-17(13-18(21)14-20(19)22-3)11-10-16-7-5-4-6-8-16/h4-11,13-14,21H,12H2,1-3H3/b11-10+
• Isomeri SMILES: CC(=CCC1=C(C=C(C=C1OC)O)/C=C/C2=CC=CC=C2)C
• CAS alternativo: 64125-60-6
• PubChem CID: 6446720
• Termini MeSH: longistyline C

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Stilbenes

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Stilbenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Stilbenes
• Alternative Parents: Methoxyphenols Styrenes Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Stilbene - Methoxyphenol - Phenoxy compound - Anisole - Phenol ether - Methoxybenzene - Styrene - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Benzenoid - Ether - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 294.400 g/mol
• XLogP3: 5.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 294.162 Da
• Monoisotopic Mass: 294.162 Da
• Topological Polar Surface Area: 29.500 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 375.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Application Protocols

No validated application protocols are provided in the Product Data for SKU L1048422. As a general starting point for handling similar small molecules in research workflows:

• Preparation of stock solutions (typical, literature/general): Dissolve in DMSO at 10–50 mM. Vortex and, if needed, sonicate briefly. Filter through a 0.2 μm PTFE filter for particulate removal.
• Working solutions: Dilute stocks into assay medium to the desired final concentration, keeping DMSO ≤0.5–1.0% v/v unless your assay tolerates higher.
• Light protection: Use amber vials and minimize exposure during preparation and storage.
• Analytical QC: Verify identity/purity by HPLC and MS before critical experiments. Record retention time and UV spectrum for batch-to-batch comparability.

Please consult your internal SOPs and adapt conditions to your specific assay, instrumentation, and regulatory framework.

Biological Roles

Scope note: No biological activity data are provided in the Product Data for this specific item. The following are literature/general considerations for prenylated stilbene-type natural products and are not product specifications or claims.

Literature/general context:

• Natural origin: Prenylated stilbenes such as Longistylin C have been reported from Moraceae plants. Prenylation typically enhances membrane affinity and can influence interactions with proteins and membranes.
• Biochemical behavior: Phenolic –OH groups can undergo redox cycling and metal chelation in vitro; conjugated systems absorb UV light and may act as photoreactive chromophores.
• Metabolism (in vitro expectations): Phase II conjugation (glucuronidation/sulfation) on phenols; possible oxidative metabolism (e.g., aromatic/allylic hydroxylation) by microsomal enzymes.
• Assay handling: Adsorption to plastics can occur for lipophilic phenolics; precondition assay plates with protein or use low-binding plastics. Maintain consistent DMSO concentration across assay wells to avoid solvent artifacts.

Important: Any discussion of biological effects is general background and not an endorsement of suitability for medical use. This product is supplied strictly for research use only.

Buffer Applications

Not typically applicable. Longistylin C is a small-molecule natural product, not a buffering agent. It does not constitute a defined acid–base buffer system.

Practical guidance (for dissolution into buffers):

• Prepare a concentrated DMSO or ethanol stock and dilute into the desired assay buffer (e.g., phosphate, HEPES) under vigorous mixing to prevent precipitation.
• Maintain a constant final organic co-solvent percentage (commonly 0.1–2% v/v) across controls and treated samples.
• If higher apparent solubility is needed in aqueous media, consider cyclodextrin inclusion, micelles (e.g., 0.01–0.1% Tween-80), or protein carriers (BSA) as appropriate for the assay design.

Green Alternatives

While Longistylin C itself is a target compound rather than a process solvent, greener choices can be made for handling, purification, and derivatization.

Greener solvent considerations (literature/general):

• Replace dichloromethane with ethyl acetate or 2-MeTHF for extractions and reactions where feasible.
• Use MeCN or EtOH in place of THF/DMF where method compatibility allows; consider Cyrene or propylene carbonate as high-boiling dipolar alternatives in certain transformations.
• Prefer water–ethanol mobile phases for preparative chromatography when resolution permits.

Comparison snapshot (general):

• 2-MeTHF vs THF: similar polarity; 2-MeTHF is partially bio-based, less miscible with water, and forms peroxides more slowly.
• EtOAc vs DCM: EtOAc is biodegradable, lower toxicity; higher boiling point may lengthen concentration times.
• EtOH vs MeOH: EtOH is less toxic and bio-based; slightly different elution strength in RP-HPLC.

Operational practices:

• Minimize solvent volumes via micro-scale reaction design and efficient workups.
• Use amber glassware and energy-efficient cooling/heating to reduce photolysis risks and energy consumption.
• Implement solvent recycling for common eluents (EtOAc, hexanes, MeOH) where purity requirements allow.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided in the Product Data. This product is supplied for research use only and is not intended for human or veterinary use.

General formulation considerations for research materials of this class (literature/general):

• Preclinical formulation (in vitro/in vivo research only): DMSO/PEG-400/saline co-solvent systems, lipid-based vehicles, or cyclodextrin complexes are commonly explored for stilbene-like, lipophilic phenolics.
• Stability: Protect from light to reduce E/Z isomerization and oxidative degradation; consider inert-atmosphere handling for long-term solutions.
• Analytical support: Employ stability-indicating LC–MS methods that can resolve geometric isomers and oxidative products.

Important: No clinical, therapeutic, or diagnostic claims are made or implied for this product.

Physical Properties

Item-specific properties (from Product Data):

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

Storage and logistics (from Product Data):

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

Safety/Regulatory fields (from Product Data):

• GHS classification / pictograms: Not specified for this item; refer to SDS.

Literature/general physicochemical expectations for prenylated stilbenes (for context only):

• Physical state: Often a pale solid or amorphous powder; strongly light-sensitive due to conjugated double bond (literature/general).
• Solubility: Typically sparingly soluble in water; soluble in organic solvents such as DMSO, DMF, acetone, methanol/ethanol, and ethyl acetate (literature/general). Actual solubility for this item is not specified; verify experimentally.
• Lipophilicity: Prenylation increases logP relative to non-prenylated stilbenes (literature/general).
• UV/Vis: Conjugated stilbene chromophore absorbs in near-UV; phenolic substituents can shift λmax (literature/general).

Important: Do not treat the above literature notes as specifications. For exact values (mp, purity, solubility, water/peroxide/metal limits, refractive index), consult the CoA/Spec Sheet for SKU L1048422.

Quality and Grades

Item-specific (from Product Data):

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

Guidance on interpreting quality information (general):

• Reference standards: For library/natural product compounds, identity is commonly supported by 1H/13C NMR, MS, and HPLC/UPLC purity. UV profiles can be diagnostic for stilbenes due to their conjugated chromophore.
• HPLC/UPLC area%: Higher area% indicates fewer UV-active impurities; co-eluting non-UV-active impurities must be assessed by orthogonal methods (e.g., ELSD or quantitative NMR).
• Isomeric purity: Stilbenes can exist as E/Z isomers; confirm E-isomer content by NMR coupling constants (e.g., J ~16 Hz for trans) or by chiro/achiral HPLC where relevant.
• Residual solvents/water/metals: Not specified for this item; refer to CoA/Spec Sheet. If critical for your application (e.g., bioassays), request detailed impurity profiling.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Many phenolics are supplied without stabilizers; if antioxidants are added, they should be declared on the CoA.

Recommendation: For sensitive biological assays or SAR work, request full analytical documentation (chromatogram, NMR, HRMS) for SKU L1048422 to verify identity, isomer ratio, and purity prior to use.

Reaction and Applications

Manufacturer applications (from Product Data):

• Not provided. This product falls under a “small molecules and compound library” category and is intended for research use only.

Research and application contexts (literature/general for prenylated stilbenes):

• Chemical biology/SAR: Utilized as a reference compound in natural product libraries for target deconvolution, binding screening, or phenotypic assays.
• Analytical standards: Employed for method development in LC–MS metabolite profiling of Moraceae extracts.
• Photochemistry/isomerization studies: Stilbene scaffold enables E/Z photoisomerization; useful in studying conjugation and reactivity under UV.

Transformations and derivatizations (literature/general):

• O-Acylation/O-alkylation of phenolic groups (e.g., using acyl chlorides/anhydrides or alkyl halides with base such as K2CO3) to modulate lipophilicity.
• Hydrogenation of the central C=C to yield bibenzyl analogs; catalytic Pd/C or Raney Ni under H2.
• Electrophilic substitution on activated aromatic rings (e.g., halogenation/nitration under controlled conditions).
• Oxidative couplings (e.g., with FeCl3 or hypervalent iodine reagents) to access dimers.

Practical tips:

• Protect from light during reactions and workup to minimize isomerization/oxidation.
• Employ anhydrous, oxygen-limited conditions for sensitive steps; degas solvents when necessary.
• Monitor by HPLC with UV and, where possible, MS detection to distinguish isomers and oxidative byproducts.

Reaction Conditions

General literature guidance for transforming stilbene-type, prenylated phenolics (not product specifications):

Common conditions:

• O-Acylation: Phenol + acyl chloride (1.2–2.0 equiv), Et3N or pyridine, 0–25 °C, DCM or EtOAc, 1–4 h. Work under subdued light; monitor by TLC/HPLC.
• O-Alkylation: Phenol + alkyl halide (1.2–1.5 equiv), K2CO3 or Cs2CO3, acetone/MeCN/DMF, 25–60 °C, 2–16 h. Avoid strong base if E/Z isomerization is problematic.
• Hydrogenation (C=C): H2 (1–3 atm), 10% Pd/C (5–10 wt%), EtOH/EtOAc, rt–40 °C, 1–6 h, yielding bibenzyl derivatives.
• Electrophilic halogenation: NBS/NCS (1.05–1.2 equiv) in DMF/MeCN at 0–25 °C to introduce handles for cross-coupling.
• Cross-coupling (if aryl halide present): Suzuki (Pd(PPh3)4, base: K2CO3), 60–90 °C, dioxane/H2O or MeCN/H2O; Buchwald–Hartwig for aryl amination with suitable ligands.

Analytical and stability considerations:

• Use amber glassware and wrap vessels in foil to limit photochemical isomerization.
• Degas solvents for oxygen-sensitive steps; consider inert gas backfill.
• Monitor isomer ratio and potential oxidative byproducts by HPLC–UV and LC–MS.

Expected yields: Highly substrate-dependent; for simple O-acylation/alkylation, isolated yields commonly range from moderate to high in the literature. Optimize conditions for the specific substitution pattern of the supplied compound.

Safety and Handling

Authoritative safety information should be taken from the product SDS. The following reflects only what is known from the Product Data and general good laboratory practice.

Item-specific (from Product Data):

• Signal word / H-statements / GHS pictograms / Classification: Not specified for this item; refer to SDS.
• Research Use Note: For research use only.

General handling guidance (literature/general for polyphenolic stilbenes):

• PPE: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood to minimize inhalation of dust/aerosols when weighing.
• Avoid: Strong oxidizers, strong bases/acids that can promote oxidation, isomerization, or O-alkylation; prolonged light exposure (risk of E/Z isomerization and oxidation); elevated temperatures for extended periods.
• Hygroscopicity/photolability: Stilbenes are often light-sensitive; store protected from light. Some prenylated phenols can slowly oxidize on air—minimize headspace oxygen and recap promptly.
• First aid (overview; consult SDS): If inhaled—move to fresh air; skin/eye contact—rinse with water for several minutes; ingestion—rinse mouth and seek medical advice. Provide the SDS to medical personnel.
• Spill response: Avoid dust generation. Contain with inert absorbent, collect into suitable container, and clean area with solvent compatible with your waste protocol.
• Waste: Dispose of in accordance with institutional hazardous organic waste procedures.

Always defer to the SDS and institutional EHS policies for definitive hazard, exposure limits, and emergency procedures.

Solvent Selection

Applicability: Longistylin C is a hydrophobic, phenolic natural product (stilbene class). Solvent choice primarily concerns dissolution for assay stock solutions and for synthetic derivatization.

General dissolution guidance (literature/general):

• Preferred for stock solutions: DMSO (often ≥10 mM), DMF, or ethanol; methanol and acetone are alternatives. Filter sterilize if used in cell-free enzymatic assays.
• Aqueous work: Use co-solvent strategies (e.g., 0.5–2% DMSO in buffer) or cyclodextrin encapsulation; avoid precipitation on dilution by premixing DMSO stock into vigorously stirred buffer.
• Chromatography: Reverse-phase methods commonly use water–acetonitrile or water–methanol with formic acid or ammonium acetate. Maintain low light exposure during prep/analytical runs.

Polarity/miscibility profile (literature/general for prenylated stilbenes):

• Polarity: Moderately lipophilic owing to prenyl substitution; phenolic –OH groups enable limited H-bonding.
• Miscibility: Miscible with polar aprotic organics (DMSO/DMF/acetone); soluble in alcohols and esters; low water solubility.

When to choose alternatives:

• If DMSO-sensitive assays: Use ethanol or PEG-400 as a carrier, or prepare liposomal/micellar formulations (e.g., 0.1% Tween-80) for biochemical screening.
• If photolability is a concern: Prefer amber vials and minimize run times; use cooler autosampler temperatures to limit isomerization.

Storage and Reconstitution

Item-specific (from Product Data):

• Recommended storage: Room temperature.

Additional guidance (literature/general for stilbene-type phenolics):

• Light protection: Store in amber vials or foil-wrapped containers to mitigate photoisomerization/oxidation.
• Atmosphere: Keep container tightly closed; minimize headspace oxygen. For long-term storage, consider inert gas backfill (N2/Ar), especially for opened containers.
• Humidity: Store in a dry place; while many phenolics are not strongly hygroscopic, moisture can affect stability and handling.

Reconstitution (for laboratory use):

• Solvent: DMSO is commonly preferred for concentrated stocks; ethanol or DMF are alternatives. Begin with small volumes and incrementally add solvent while swirling to ensure complete dissolution.
• Typical stock concentration (guidance): 10–50 mM in DMSO. Adjust based on solubility and assay requirements.
• Aliquoting: Prepare single-use aliquots to minimize freeze–thaw and headspace exposure. Label with concentration, date, and lot.
• Storage of solutions: Refrigerated (2–8 °C) or frozen (−20 °C) DMSO stocks in amber vials can improve stability; equilibrate to room temperature before opening to reduce moisture uptake. Validate stability by periodic HPLC.

Always refer to the product’s CoA and SDS for item-specific stability data and handling instructions. For research use only.

Structure and Identity

Brief overview: Longistylin C is reported in the literature as a prenylated stilbene-type polyphenol isolated from certain Moraceae species. The specific structure and identifiers for this catalog item are not fully specified in the provided Product Data.

Item-specific identifiers (from Product Data):

• CAS: 64125-60-6
• InChIKey: 236879 (format appears non-standard; verify on CoA/SDS)
• 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 (literature/general):

• Core scaffold: Typically a trans-stilbene backbone (two phenyl rings linked by an ethene unit) with one or more prenyl/geranyl side chains and phenolic –OH groups.
• Functional groups: Phenols (H-bond donors/acceptors), conjugated alkene(s), and isoprenyl substituents that increase lipophilicity.
• 2D description: Two substituted aromatic rings joined through a C=C; one ring often carries phenolic hydroxyls, the other bears an isoprenyl (–CH2–C(CH3)=CH2) or similar unit.

Notes:

• Verify exact stereochemistry (E/Z at the stilbene double bond) and substitution pattern on the supplied CoA. Literature often reports the trans (E) configuration for analogous natural products.

Synthetic Utility

From a synthetic chemist’s perspective, a prenylated stilbene like Longistylin C is a versatile platform for generating analog series and probing structure–activity relationships.

Key functional groups (literature/general):

• Phenolic –OH: Amenable to O-alkylation (alkyl halides, Mitsunobu variants), O-acylation (acyl chlorides/anhydrides), or conversion to carbonates/urethanes.
• Stilbene C=C: Subject to hydrogenation (bibenzyl formation), epoxidation under peracids, or oxidative cleavage (e.g., ozonolysis) to benzaldehyde/benzoic acid derivatives.
• Aromatic rings: Directed electrophilic substitution relative to phenols or protected phenols; halogenation enables cross-coupling handles.
• Prenyl side chain: Offers allylic functionalization, hydroboration–oxidation, or oxidative rearrangements.

Applications (literature/general):

• Probe synthesis: Installation of reporter tags via carbonate/urethane linkers on phenols or via click-ready handles introduced through halogenation/cross-coupling.
• Prodrug strategies (research only): Phenolic ester/carbonate masking to tune solubility and permeability in in vitro systems.
• Dimerization/cyclization: Oxidative phenol coupling to access resveratrol-like oligomers for comparative studies.

Note: Exact reactivity may vary with substitution pattern and E/Z geometry; confirm structure and isomer ratio before planning transformations.

Target Specificity

Not applicable. This product is a small-molecule natural product, not a biological macromolecule or antibody. No target specificity data are provided in the Product Data.

For researchers investigating protein targets: any binding or selectivity information should be generated empirically under your assay conditions and cannot be inferred from this listing.