Myricananin A - ≥95% , CAS No.1079941-35-7

CAS: 1079941-35-7 Cat. No.: M942874 PubChem CID: 74394447

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Aktionsart

INHIBITOR

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

COC1=CC2=CC(=C1O)C3=C(C=CC(=C3)CC(C(CCCC2)O)O)O

IUPAC Name

16-methoxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),14(18),15-hexaene-3,8,9,17-tetrol

InChIKey

ZABHYVQENRBSDL-UHFFFAOYSA-N

INCHI

1S/C20H24O5/c1-25-19-11-12-4-2-3-5-17(22)18(23)10-13-6-7-16(21)14(8-13)15(9-12)20(19)24/h6-9,11,17-18,21-24H,2-5,10H2,1H3

Isomere SMILES

COC1=CC2=CC(=C1O)C3=C(C=CC(=C3)CC(C(CCCC2)O)O)O

PubChem CID

74394447

Chemische und physikalische Eigenschaften

• Molekulargewicht: 344.400 g/mol
• XLogP3: 3.100
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 344.162 Da
• Monoisotopic Mass: 344.162 Da
• Topological Polar Surface Area: 90.200 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 417.000
• 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 application protocols are provided in the Product Data for this item. The following general protocols may be adapted, with appropriate validation, for small-molecule standards:

• Preparation of a screening stock solution (general)

  • Weigh analytically to prepare a 10–50 mM stock in anhydrous DMSO. Vortex and briefly sonicate if needed. Aliquot into amber, low-bind microtubes. Store sealed to limit moisture ingress.

• LC/UPLC-MS reference standard preparation (general)

  • Prepare 1 mg/mL in MeOH or ACN. Serially dilute to 1–1000 ng/mL in 50:50 MeOH:water (±0.1% formic acid or ammonium acetate as compatible). Filter through 0.2 µm PTFE. Record retention time and MS/MS fragments for your instrument.

• Cell-based assay dosing solution (general)

  • Dilute DMSO stock into pre-warmed media to achieve final solvent ≤0.5–1% v/v. Mix gently to avoid precipitation; visually inspect. Include vehicle controls and, where possible, orthogonal assay readouts.

All protocols require optimization for your specific lot, instrumentation, and biological system. Validate identity and purity in-house prior to critical experiments.

Biological Roles

• Scope and caveat

  • No item-specific biological data are provided in the Product Data. Statements below are general to small-molecule natural products and should not be construed as established for this item. Consult the primary literature for Myricananin A (e.g., via PubChem CID 74394447) for definitive information.

• General context for natural products

  • Many plant-derived small molecules function as secondary metabolites involved in defense, signaling, or stress response. They often feature multiple oxygenated functionalities that can influence redox behavior and metal chelation in vitro.
  • In research, purified natural products are used as chemical probes to interrogate biochemical pathways in cell-free or cellular assays. Appropriate controls (vehicle, inactive analogs) and orthogonal readouts are essential.

• Practical considerations for bioassays (general)

  • Ensure accurate dosing by preparing concentrated stocks in a fully compatible solvent (commonly DMSO) and maintaining final solvent below cytotoxic thresholds (often ≤0.5–1% v/v in cell-based assays).
  • Assess compound stability under assay conditions (temperature, light, pH, presence of serum) using LC-MS or HPLC to avoid confounding by degradation.
  • Non-specific binding to plastics can reduce free concentration; precondition plastics with media or use low-binding consumables.

Research use only: not for human or veterinary use, diagnostics, or therapeutics.

Buffer Applications

This product is a discrete small molecule standard and is not a buffering agent. Consequently, classical buffer-system guidance (e.g., phosphate, Tris, HEPES recipes, pH ranges) does not directly apply.

• Practical notes (general)
  • If the compound must be formulated into aqueous buffers for assays, use cosolvent strategies (e.g., ≤1% DMSO or ethanol) or cyclodextrin inclusion where compatible to aid apparent solubility.
  • Maintain buffer components that do not react with the analyte’s functional groups; avoid strong acids/bases or oxidants unless stability has been demonstrated experimentally.

For precise pH control, select an independent buffer system appropriate to your assay; this catalog item does not itself provide buffering capacity.

Green Alternatives

This entry is a discrete small molecule, not a process solvent. Green chemistry considerations therefore focus on the solvents and auxiliaries used to dissolve, purify, or analyze it.

• Preferred greener solvents for handling (general guidance)

  • Where feasible, use ethanol, isopropanol, methanol, or acetonitrile (all relatively manageable in waste streams for analytical workflows). Avoid chlorinated solvents unless necessary for solubility.

• Example comparison (general; choose based on your method)

  • Ethanol vs. DMSO: Ethanol is greener and LC-volatile but may have lower solubilizing power; DMSO excels at dissolution but is not volatile and can complicate assays at higher %.
  • MeOH vs. CH2Cl2: Methanol is preferred for LC sample prep due to lower toxicity and better waste profile; dichloromethane should be reserved for cases requiring strong nonpolar solvation.

• Purification considerations

  • For chromatographic purification or repurification, prefer EtOAc/EtOH/MeOH with heptane or ethyl acetate systems over halogenated solvents when separation allows.

• Waste minimization

  • Scale stock solutions to immediate needs; employ micro-scale workflows (96-well or 384-well plates) to reduce solvent consumption during screening.

Note: Item-specific green metrics (e.g., E-factor, PMI) are not applicable to a catalog standard supplied for research.

Pharmaceutical Uses

• Status and scope

  • No pharmacopeial status, excipient role, or formulation guidance is provided for this item. It is sold strictly for research use only.

• Typical research/manufacturing contexts for natural-product standards (general)

  • May be used as a reference chemical during analytical method development (e.g., LC-UV/LC-MS identification and quantitation) in discovery settings.
  • Potentially used as a marker compound for botanical raw-material characterization in R&D, subject to legal and regulatory frameworks; not intended for GMP drug product manufacture.

• Formulation considerations for lab studies

  • Stock in DMSO or ethanol for screening; for preclinical in vitro work, ensure solvent percentages remain within tolerated limits for the biological system under study. For any in vivo research (outside the scope of this catalog), institutional approvals and suitable grade are required—this item is not intended for such use.

• Documentation

  • For any regulated workflow, an authenticated reference standard with full traceability and acceptance criteria is necessary. Obtain and retain the CoA/Spec Sheet for your lot and verify identity/purity with orthogonal methods when appropriate.

Physical Properties

Item-specific specifications are not provided in the Product Data. Do not treat the following as lot specifications; consult the CoA/Spec Sheet for your purchased lot.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (exact): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not typically applicable for complex natural products (decompose on heating); item-specific value not specified.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable (solid) or not specified; refer to CoA/Spec Sheet.
• LogP/logD: Not specified for this item; refer to CoA/Spec Sheet.
• pKa(s): Not specified for this item; refer to CoA/Spec Sheet.
• UV/Vis profile: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility guidance (general/literature-style considerations, not specifications)
  • For small-molecule natural products, initial dissolution screening commonly includes DMSO, methanol, ethanol, acetonitrile, and 1:1 cosolvent–water mixtures. Begin at 1–10 mg/mL in DMSO, then dilute into aqueous buffers as needed.
  • If the compound is polyphenolic, it may exhibit limited solubility in pure water and better solubility in polar organic solvents; confirm empirically.

Handling note: Avoid prolonged heating during attempts to dissolve; gentle sonication and incremental solvent addition often help achieve clear solutions.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• What grade implies (general guidance)

  • Research grade natural-product standards are commonly qualified by NMR purity, HPLC/UPLC area% assay, and HRMS identity confirmation. When HPLC grade solvents are used during purification, the resulting material often exhibits low non-volatile residue—useful for analytical and bioassay contexts.
  • If “reference standard” is indicated (not specified here), expect detailed chromatographic purity metrics and retention-time match to literature or authenticated lots.

• Typical quality documentation you should expect

  • Certificate of Analysis (CoA) with assay method (e.g., HPLC area%), lot number, and acceptance limits.
  • Spectral package on request: 1H/13C NMR, HRMS, and sometimes IR/UV-Vis.

• Stabilizers/additives

  • Not specified for this item; refer to CoA/Spec Sheet. If provided as a neat solid, it is typically stabilizer-free. If supplied in solution, a defined solvent system will be listed on the CoA.

• Practical tips

  • Upon receipt, record lot identifiers and any purity figures from the CoA in your ELN. If your application is highly purity-sensitive (e.g., quantitative assays), verify purity by an orthogonal HPLC method in-house.

Reaction and Applications

• Manufacturer applications (from catalog)

  • Not specified in the Product Data. This product is categorized under small molecules/compound libraries and is supplied for research use only.

• Typical research applications for natural-product standards (general)

  • Analytical reference in LC/UPLC-MS method development and quantitation (calibration curves, retention/fragmentation benchmarking).
  • Chemical biology and screening: tool compound for phenotypic or target-based assays, subject to solubility and stability constraints.
  • Metabolomics/natural products studies: spike-recovery experiments, stability profiling, comparison with plant or microbial extracts.

• Synthetic/derivatization uses (general)

  • If functional groups permit, derivatives may be prepared for SAR, probe development (e.g., biotinylation/fluorophore tagging), or pro-analogs for mechanistic studies. Confirm functional group compatibility before attempting.

• Practical tips

  • Establish a validated analytical method (HPLC-UV or LC-MS) to monitor purity and concentration over time, particularly if performing biological assays.
  • Prepare fresh working solutions; minimize freeze–thaw cycles to reduce degradation and adsorption losses.
  • Consider light and air sensitivity tests (side-by-side storage in amber vs. clear vials, with/without inert atmosphere) to inform handling.

Reaction Conditions

No item-specific reactivity profile or transformation conditions are provided in the Product Data. The following are general considerations for handling and, if applicable, derivatizing small-molecule natural products:

• Solvent and atmosphere (general)

  • Conduct reactions in dry, oxygen-free solvents when sensitive functionalities are suspected; use inert gas (N2/Ar) and anhydrous alcohols or aprotic solvents (DCM, THF, MeCN) as appropriate. Prefer greener options (EtOAc, MeOH, EtOH) when feasible.

• Temperature and time

  • Many multifunctional natural products undergo side reactions at elevated temperatures; start at 0–25°C and scale up cautiously. Monitor by TLC/HPLC at short intervals.

• Catalysts and reagents

  • For acylations/alkylations of phenolic or alcoholic groups, employ mild bases (e.g., K2CO3) and activated reagents (acyl chlorides/anhydrides) under controlled conditions to maintain selectivity.
  • Avoid strong oxidants/reductants until stability is established; employ chemoselective reagents (e.g., Dess–Martin periodinane for sensitive oxidations) if needed.

• Workup and purification

  • Minimize exposure to strong acid/base during quench. Use rapid chromatography with volatile eluents. Protect from light and air when collecting fractions, and concentrate at reduced temperature.

• Expected yields (literature-general)

  • Yields for late-stage functionalization of complex natural products vary widely (30–90%) depending on substitution pattern and protecting-group strategy; consult compound-specific literature for Myricananin A for precedent.

Safety and Handling

• GHS/SDS status (item-specific)

  • Signal Word: Not specified for this item; refer to SDS.
  • Hazard Statements (H-): Not specified for this item; refer to SDS.
  • GHS Classification and Pictograms: Not specified for this item; refer to SDS.

• General laboratory precautions (best practice; defer to SDS for authoritative guidance)

  • Use in a chemical fume hood, avoid inhalation of dusts/aerosols, and prevent skin/eye contact.
  • Recommended PPE: lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile).
  • Hygiene measures: wash hands after handling; avoid eating/drinking in work area.

• Incompatibilities and stability (general)

  • Many natural products can be sensitive to strong oxidizers, strong acids/bases, and extended exposure to light/air. Store in tightly closed container; minimize repeated opening.
  • If preparing solutions, use clean, dry glassware; consider amber vials to limit light exposure.

• First-aid overview (general)

  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: wash with soap and water; remove contaminated clothing.
  • Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention if irritation persists.
  • Ingestion: rinse mouth; seek medical advice.

Note: Always consult the official SDS for your lot before use. Product is for research use only.

Solvent Selection

Because item-specific solubility data are not provided, begin with a structured solvent screening and document observations.

• General polarity considerations (general guidance)

  • Start with polar aprotic and protic solvents commonly effective for small-molecule natural products: DMSO, methanol, ethanol, acetonitrile. For partitioning into aqueous media, consider cosolvent systems (e.g., 5–20% DMSO or ethanol in buffer) or inclusion of minimal surfactant if compatible with your assay.

• Miscibility and dilution

  • Stock solutions in DMSO at 10–50 mM are typical for screening libraries; dilute into assay media immediately before use to minimize precipitation.
  • If aqueous workup is needed, pre-wet vessels with solvent to reduce adsorption losses of hydrophobic analytes.

• When to choose alternatives (general)

  • If precipitation occurs on aqueous dilution, increase organic fraction, reduce stock concentration, or use mixed solvents (e.g., MeOH:water 1:1) during preparation.
  • For LC-MS sample prep, prefer volatile solvents (MeOH, ACN, IPA) to facilitate evaporation and minimize ion suppression; add 0.1% formic acid or ammonium acetate as needed for ionization—confirm compatibility.

• Small comparison (general)

  • DMSO: highest solubilizing power; not LC-volatile; limit final assay %.
  • MeOH/EtOH: LC-volatile; moderate solubilizing power; watch for ester/acetals (if present) undergoing exchange in strongly acidic/basic media.
  • ACN: LC-volatile; good for nonpolar to moderately polar analytes; limited for strongly hydrogen-bonding solids.

Storage and Reconstitution

• Storage (item-specific from Product Data)

  • Store at room temperature. Keep container tightly closed in a dry, well-ventilated place. Protect from excessive heat and direct light as good laboratory practice.

• Shipping

  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• Stability considerations (general)

  • For natural products, limit exposure to air, light, and moisture. If long-term storage is planned, consider subdividing into single-use aliquots to avoid repeated container opening.

• Reconstitution guidance (general)

  • Initial solvent trial: add a minimal volume of DMSO or methanol and vortex/sonicate to achieve a clear concentrate (e.g., 10–50 mM). If needed, warm gently to 25–30°C; avoid prolonged heating.
  • For aqueous applications, dilute concentrate into compatible buffer immediately before use, maintaining low final organic percentages to prevent precipitation.
  • Record exact solvent, concentration, and preparation date on the vial/ELN. Assess solution stability by HPLC/LC-MS over the intended usage window.

• Freeze–thaw

  • If solutions are stored refrigerated or frozen, aliquot to minimize freeze–thaw cycles. Many small molecules tolerate –20°C storage in DMSO, but confirm stability empirically for your application.

Research Use Note: For research use only.

Structure and Identity

Brief overview: This listing refers to the discrete small molecule natural product standard Myricananin A.

• Item-specific identifiers (from Product Data)

  • Product Name: Myricananin A
  • SKU: M942874
  • CAS: 1079941-35-7
  • PubChem CID: 74394447
  • InChIKey: 451433 (as provided; note that full 27-character InChIKey is not specified for this item; refer to CoA/Spec Sheet.)
  • 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)

  • Myricananin A is reported in the natural products literature as a plant-derived small molecule; detailed functional groups and stereochemistry should be confirmed from primary literature and spectral data for the specific isomer.
  • For unambiguous structure confirmation in your lab, employ orthogonal methods: HRMS, 1D/2D NMR (1H, 13C, HSQC/HMBC), and, where possible, comparison with an authenticated reference chromatographic profile (HPLC/UPLC retention, UV).

• 2D structure description (general guidance)

  • Without an item-specific SMILES or InChI, a textual 2D description cannot be authoritatively provided here. Please consult the CoA/Spec Sheet or PubChem CID 74394447 for a definitive 2D depiction and connectivities.

Note: All structural assertions for regulated documentation should be based on the CoA/Spec Sheet accompanying your lot.

Synthetic Utility

Item-specific functional-group information is not provided, so the following is general guidance on employing small natural products in synthesis and derivatization.

• Roles in synthesis (general)

  • Serve as a scaffold for semisynthetic modification in structure–activity relationship (SAR) studies.
  • Provide a comparator for total synthesis efforts—used to validate stereochemical assignment and analytical equivalence of synthetic material.
  • Act as a chiral or polyfunctional building block if reactive handles are present (e.g., phenolic OH, carbonyls), enabling etherification/esterification, acylation, or selective oxidations/reductions.

• Analytical benchmarking

  • Authentic natural material allows calibration of NMR chemical shifts and LC retention for synthetic route development; co-injection and mixed-melting (if crystalline) help confirm identity.

• Practical notes

  • Protecting-group strategies may be required if multiple nucleophilic sites are present; select conditions that avoid rearrangement or oxidation.
  • Track isomerization or degradation under basic or acidic conditions by LC-MS.

For any planned transformations, consult primary literature specific to Myricananin A to ensure compatibility and to leverage precedent on chemoselectivity and yields.

Target Specificity

Not applicable to this catalog item. Myricananin A is a small molecule and not an antibody or affinity reagent; no antigen/epitope, clone, isotype, or species reactivity information applies.

• If used as a chemical probe in target-engagement studies, any “specificity” claims must be established experimentally for the system under study and are not provided here.