Cedrelopsin - ≥95% , CAS No.19397-28-5

CAS: 19397-28-5 Cat. No.: C1002979 PubChem CID: 12302592

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CC(=CCC1=C2C(=CC(=C1O)OC)C=CC(=O)O2)C
• IUPAC Name: 7-hydroxy-6-methoxy-8-(3-methylbut-2-enyl)chromen-2-one
• InChIKey: IIEIJMSDKBAFFP-UHFFFAOYSA-N
• INCHI: 1S/C15H16O4/c1-9(2)4-6-11-14(17)12(18-3)8-10-5-7-13(16)19-15(10)11/h4-5,7-8,17H,6H2,1-3H3
• Isomeric SMILES: CC(=CCC1=C2C(=CC(=C1O)OC)C=CC(=O)O2)C
• PubChem CID: 12302592

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives
      • Subclass Hydroxycoumarins

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Hydroxycoumarins
• Intermediate Tree Nodes: Not available
• Direct Parent: 7-hydroxycoumarins
• Alternative Parents: 1-benzopyrans Anisoles Pyranones and derivatives Alkyl aryl ethers Heteroaromatic compounds Lactones Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 7-hydroxycoumarin - Benzopyran - 1-benzopyran - Anisole - Alkyl aryl ether - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Lactone - Oxacycle - Ether - Organoheterocyclic compound - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
• 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

Chemical and Physical Properties

• Molecular Weight: 260.279 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 260.105 Da
• Monoisotopic Mass: 260.105 Da
• Topological Polar Surface Area: 55.800 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 395.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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

• Item-specific (from Product Data):

  • No tested application protocols are provided for this item.

• General laboratory protocols (not item-specific; adapt to your system):

  • Stock preparation: Dissolve Cedrelopsin in DMSO to 10–50 mM, vortex, sonicate if needed, then sterile-filter (0.2 µm PTFE) for cell-free assays. Store aliquots to minimize freeze–thaw.
  • HPLC/UPLC assay: Develop a gradient (e.g., 5–95% MeCN in water with 0.1% formic acid over 10–15 min); monitor at 210–330 nm and by ESI± MS. Validate linearity, precision, and stability.
  • Stability testing: Subject solutions/solids to light, heat (40–60 °C), and oxidative stress (e.g., 0.1–1% H2O2) to establish degradation pathways; analyze by LC–MS.
  • Derivatization screen: If functional handles exist, run small-scale acylation/alkylation reactions and analyze by LC–MS/NMR for rapid SAR exploration.

• Documentation and QC:

  • Record batch number, preparation date, solvent/vehicle, and exact concentration. Attach chromatograms and spectra to your ELN entry.
  • Include vehicle controls in all assays and perform orthogonal confirmation (e.g., mass balance) where feasible.

Biological Roles

• Item-specific (from Product Data):

  • No biological role information is specified for this item; refer to primary literature and CoA as needed.

• General context (not item-specific; no medical/clinical claims):

  • Many plant secondary metabolites serve ecological functions such as defense, signaling, or allelopathy. In research, such molecules are commonly explored for interactions with enzymes, receptors, redox systems, or membranes.
  • Cedrelopsin, by name association, has been reported in the context of phytochemical studies of Meliaceae species. Researchers often investigate such compounds for binding to protein targets in vitro, modulation of enzyme activity, or as chemotaxonomic markers.

• Lab use guidance:

  • For biochemical assays, prepare fresh stock solutions in DMSO and assess compound stability in assay buffers across your pH and temperature window.
  • Include appropriate vehicle controls and, where possible, an orthogonal readout (e.g., mass balance by LC–MS) to rule out assay interference.

• Omics and profiling:

  • Use targeted MS/MS libraries and retention indexing to confirm presence/levels in plant extracts; compare against authentic Cedrelopsin standard for unambiguous identification.

• Note:

  • Specific mechanistic or pathway roles for Cedrelopsin are not provided here. Avoid extrapolating biological effects beyond controlled laboratory experiments.

Buffer Applications

Cedrelopsin is a small-molecule natural product and is not itself a buffering agent.

• Item-specific: No buffer system guidance is specified for this item; refer to CoA/Spec Sheet for any formulation notes.

• Practical notes (general, not item-specific):

  • For biochemical assays, dissolve Cedrelopsin in DMSO or MeOH, then dilute into your working buffer (e.g., phosphate, HEPES, or Tris) while vortexing to avoid precipitation.
  • Verify compound stability across your buffer pH range and ionic strength; many natural products can hydrolyze or oxidize at extremes of pH.
  • If solubility is limiting, consider co-solvents (≤1–2% DMSO) or surfactants compatible with your assay. Always include matched vehicle controls.

• Not typically applicable:

  • No dedicated buffer recipes, pKa-based buffering ranges, or electrophoresis buffer roles apply directly to Cedrelopsin.

Green Alternatives

This section discusses greener choices around the use, processing, and analysis of Cedrelopsin. Item-specific solvent or hazard data are not provided; the following are general recommendations.

• Solvent strategy (general):

  • Replace chlorinated solvents (DCM, CHCl3) with greener options where feasible: ethyl acetate (EtOAc), 2-MeTHF, cyclopentyl methyl ether (CPME), or dimethyl carbonate (DMC).
  • For analytical LC, prefer MeOH over acetonitrile where method performance allows, or adopt water-rich gradients to minimize solvent consumption.

• Workup and purification:

  • Favor liquid–liquid pairs such as EtOAc/water or MTBE/brine instead of chlorinated solvents.
  • Use normal-phase or reversed-phase flash chromatography with greener eluents (heptane/EtOAc; MeOH/H2O with volatile buffers).

• Energy and waste minimization:

  • Run reactions at ambient temperature and exploit catalytic methods where applicable.
  • Concentrate under reduced pressure at moderate bath temperatures; recover and recycle solvents when allowed by your quality system.

• Small comparison (general; not item-specific):

  • DCM vs EtOAc: EtOAc offers lower toxicity and better biodegradability, though it is more polar—may change selectivity.
  • THF vs 2-MeTHF: 2-MeTHF has a higher boiling point, is bio-based, and forms fewer peroxides; may alter solubility and rates.

• Documentation:

  • Record solvent selection rationale per ACS Green Chemistry guidance; include waste codes and recycling notes in batch records.

Pharmaceutical Uses

No pharmacopeial or excipient status is specified for this item; Cedrelopsin is offered for research use only.

• Item-specific (from Product Data):

  • Research Use Note: For research use only.

• General formulation context (not item-specific; no therapeutic claims):

  • In pre-formulation research, small-molecule natural products may be evaluated for solubility, stability, and compatibility with excipients to enable in vitro testing.
  • Solubilization strategies commonly explored in the lab include DMSO stocks, cosolvent systems (EtOH/PEG400/water), cyclodextrin inclusion complexes, or lipid-based vehicles—subject to the needs of in vitro models.

• Analytical control in formulations:

  • Use stability-indicating HPLC/UPLC methods to monitor degradation under ICH-like stressors (light, heat, humidity, oxidative conditions), acknowledging that this product is not intended for therapeutic use.

• Regulatory note:

  • This product is not accompanied by pharmacopeial monograph compliance (USP/EP/JP) or GMP release data. It should not be used in human or veterinary applications.

Physical Properties

• Item-specific (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.
  • Storage Conditions: Room temperature.

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

  • Melting point (MP)
  • Boiling point (BP)
  • Density
  • Refractive index
  • UV/Vis profile or cutoff
  • Water content, residual solvents, or elemental limits
  • Solubility profile (aqueous/organic)
  • LogP/logD, pKa

• Literature/general guidance (not item-specific):

  • Many plant secondary metabolites exhibit limited aqueous solubility and dissolve in common organic solvents (MeOH, EtOH, DMSO, CHCl3, acetone). Start with DMSO or MeOH stock solutions for analytical work, then dilute into assay media with mixing to avoid precipitation.
  • For analytical method development, screen LC solvents such as MeCN/H2O and MeOH/H2O with 0.1% formic acid or ammonium acetate buffers; assess peak shape and ionization in ESI±.
  • Record a DSC or melting range to aid identity checks and to flag polymorphs or solvate forms.
  • Establish a solubility baseline at room temperature in key solvents (water, buffer pH 2–10, DMSO, MeOH, acetonitrile) to inform handling and formulation.

• Practical tip:

  • If material tends to oil out or shows partial crystallinity, seed crystallization or use anti-solvent addition (e.g., add water to MeOH solution) to obtain a defined solid for MP and purity checks.

Quality & Grades

• Item-specific (from Product Data):

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

• How to interpret grade (general guidance):

  • If labeled as analytical or reference standard grade, expect tighter controls on identity (NMR, HRMS), purity (HPLC/UPLC assay), and residual solvents. If labeled as research grade, the material is suitable for discovery work but may not include pharmacopeial testing.
  • For chromatographic applications, low-UV-absorbing impurities and residual solvent profiles impact baseline and quantitation. Request HPLC chromatograms with detection wavelengths matching your method (e.g., 210–330 nm for aromatic/natural products) where possible.

• Verification checklist (recommended for this item):

  • Obtain and review the CoA for: assay method and % purity, water content (Karl Fischer) where applicable, residual solvents (GC), and identity spectra (1H/13C NMR, MS, IR).
  • Confirm batch-to-batch consistency by retaining a reference spectrum and an HPLC trace under your in-house method.
  • If stereochemistry is relevant, confirm by optical rotation and/or chiroptical methods (ECD), or compare against an authenticated reference standard.

• Impurities and stabilizers:

  • Stabilizers, metal content, and specific impurity limits are not specified for this item; refer to CoA/Spec Sheet.
  • If your application is stability-sensitive, request information on antioxidant use, moisture control, or recommended headspace conditions.

Reaction & Applications

• Item-specific (from Product Data):

  • Manufacturer Applications: Not specified.

• Research applications (general, not item-specific):

  • Natural product standards: Cedrelopsin can be used as a reference material in phytochemical profiling, dereplication workflows, and quality control of botanical extracts using LC–MS or HPLC–UV.
  • Analytical method development: Develop and validate retention, detection wavelength, and MS transitions for targeted quantitation in complex matrices.
  • Chemical biology screening: Utilize as a test article in biochemical or biophysical assays to map structure–activity relationships, after verifying purity and identity.

• Synthetic/derivatization ideas (general):

  • If functional groups permit (e.g., phenolic, lactone, enone common to many natural products), consider O-alkylation/acylation, hydrogenation, or Michael additions to prepare analogs for SAR.
  • Establish stability-indicating conditions to monitor potential hydrolysis, oxidation, or photolysis during reactions and storage.

• Practical considerations:

  • Drying and atmosphere: Absent specific sensitivity data, handle under dry, inert atmosphere for moisture-/oxygen-sensitive steps. Use anhydrous solvents when performing derivatizations.
  • Analytical tracking: Use UPLC with diode-array detection and MS to track conversions; confirm product identity by NMR.
  • Workup: Partitioning between water and EtOAc/MTBE is typical; adjust pH if acid/base functionalities are present to optimize recovery.

Reaction Conditions

Item-specific reaction condition data are not provided. The following guidance is general and must be adapted to the confirmed structure and functional groups of Cedrelopsin as verified by your CoA and in-house analysis.

• General condition mapping:

  • Protection/deprotection: Use mild base (K2CO3) in acetone/MeCN for O-alkylations; DMAP/Ac2O in pyridine or DCM for acetylations; hydrogenolysis for benzyl groups if present.
  • Reductions: For enone/lactone systems, consider selective 1,4-reduction (Stryker’s reagent, Rh/C under H2) versus 1,2-reduction (NaBH4, DIBAL-H) depending on target.
  • Couplings: If aryl/alkenyl halides are available on the scaffold, apply Suzuki–Miyaura (Pd catalyst, base, aqueous-organic solvents) or Buchwald–Hartwig amination for diversification.
  • Oxidations: TEMPO/bleach for alcohol to aldehyde/acid; mCPBA for epoxidation of alkenes—evaluate compatibility with other oxidizable motifs.

• Solvents and temperatures (general ranges):

  • Typical organic solvents: toluene, MeCN, DCM, EtOAc, THF/2-MeTHF, MeOH/EtOH. Temperature windows from 0 °C to reflux, contingent on stability.

• Analytical checkpoints:

  • Perform TLC or UPLC–MS time-course monitoring; collect aliquots to profile side-products.
  • Use buffered quench when acid/base-sensitive groups are present; include antioxidant (BHT) if oxidative degradation is observed.

• Yields/time (literature-general):

  • For small-scale derivatizations of natural products, 40–85% isolated yields over 0.5–6 h are typical, highly dependent on substrate and conditions.

• Note: Validate all conditions on milligram scale before scale-up.

Safety & Handling

• Item-specific (from Product Data):

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.
  • Storage Conditions: Room temperature.
  • Research Use: For research use only.

• General laboratory safety (not item-specific; always defer to SDS):

  • PPE: lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of dust or solvent vapors.
  • Avoid ingestion, inhalation, and skin/eye contact. Wash hands thoroughly after handling. Do not pipette by mouth.
  • Incompatibilities: Until confirmed by SDS, segregate from strong oxidizers/acids/bases and sources of ignition. Avoid prolonged exposure to heat, light, and moisture, which can accelerate degradation of many natural products.
  • First aid (general): If inhaled, move to fresh air; if on skin, wash with soap/water; if in eyes, rinse cautiously with water for several minutes; if swallowed, rinse mouth. Seek medical attention as needed. Provide SDS to responders.

• Spill and waste:

  • Small spills: Absorb with inert material, collect in chemical waste. Prevent dust generation.
  • Disposal: Treat as organic laboratory chemical waste; follow institutional and local regulations.

• Stability notes (general):

  • Natural products can be photosensitive or hydrolytically labile. Store in amber vials, tightly capped, under dry conditions. Minimize repeated warming/cooling cycles.

Solvent Selection

• Item-specific (from Product Data):

  • No solvent preferences or solubility data are specified for this item; refer to CoA/Spec Sheet.

• General guidance for small-molecule natural products (not item-specific):

  • Primary dissolution solvents: DMSO (analytical stocks up to 10–50 mg/mL), MeOH, EtOH, acetone, acetonitrile, ethyl acetate, dichloromethane, and chloroform often provide good solubility. Begin with DMSO or MeOH for bioassays and analytics.
  • Aqueous handling: If water solubility is low, prepare concentrated DMSO stocks and dilute into buffered media with vigorous mixing; keep final DMSO ≤1–2% for cell-free assays and adjust per your system.
  • Polarity considerations: If the compound contains multiple heteroatoms or conjugated systems, mixed solvent systems (e.g., MeOH/H2O, ACN/H2O with 0.1% FA) can balance solubility and chromatographic performance.

• Comparative selection (examples; literature/general):

  • For preparative chromatography, use EtOAc/hexanes or MeOH/CH2Cl2 systems, then refine via gradient flash or prep-LC (MeCN/H2O). Assess compound stability against protic vs aprotic conditions.
  • For NMR: CDCl3 is a common first choice for neutral, hydrophobic natural products; CD3OD or DMSO-d6 if hydrogen bonding or limited solubility occurs.

• Practical tips:

  • Test and document solubility across a small solvent panel at room temperature and at 37 °C.
  • Filter stock solutions (0.2 µm PTFE) before LC/UPLC to protect columns.
  • Avoid adsorption losses by pre-conditioning glassware and using low-binding tips/vials for low-dose work.

Storage & Reconstitution

• Item-specific (from Product Data):

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

• Solid handling (general; not item-specific):

  • Store tightly sealed in an amber vial at room temperature in a dry place. Protect from light, heat, and moisture.
  • If hygroscopic or light-sensitive behavior is observed, store under inert gas (argon) and consider refrigeration (2–8 °C) if compatible with vendor guidance; document any changes from labeled conditions.

• Reconstitution (general guidance):

  • Prepare a concentrated stock solution in DMSO (e.g., 10–50 mM) or MeOH. Vortex and sonicate gently to ensure full dissolution. Filter if needed (0.2 µm PTFE) for analytical use.
  • For aqueous applications, add the organic stock to buffer slowly with vigorous mixing to prevent precipitation. Keep final organic solvent content minimal and consistent across samples.

• Stability and aliquoting:

  • Prepare single-use aliquots to minimize air/light exposure and freeze–thaw cycles. Record storage conditions and expiry in your ELN.
  • Periodically re-check purity by HPLC/UPLC, especially after prolonged storage at room temperature.

• Specifications not provided for this item:

  • Exact solubility, pH compatibility, and long-term stability data are not specified; consult the CoA/Spec Sheet and perform in-house verification before critical experiments.

Structure & Identity

Cedrelopsin is a plant-derived small molecule natural product offered for research use.

• Item-specific (from Product Data):

  • Product Name: Cedrelopsin (SKU: C1002979)
  • CAS: 19397-28-5
  • InChIKey: 141629 (as provided; note this is not in typical 27-character format—verify against 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.

• Literature/general notes (not item-specific):

  • “Cedrel-” prefixed names commonly refer to constituents originally reported from Cedrela spp. (Meliaceae). Cedrelopsin has been described in the natural products literature as a plant secondary metabolite; consult primary references for definitive structure assignment for your application.
  • If you require exact stereochemistry, confirm via vendor CoA, NMR, HRMS, and optical rotation.

• 2D structural description (generic guidance):

  • Without an item-specific structure, Aladdin recommends confirming the ring system(s), heteroatoms, and functional motifs via the CoA/SDS or by running an identity check (1H/13C NMR in CDCl3/CD3OD; LC–MS). Provide your team with an internal structure file (SDF/MOL) before method development.

• Identification best practices:

  • Cross-verify CAS 19397-28-5 in trusted databases (e.g., CAS Registry, PubChem CID if applicable) and reconcile with your internal inventory code.
  • Use orthogonal ID tests before scale-up: NMR, LC–MS (+/- HRMS), and FT-IR.

Synthetic Utility

Without an item-specific structural disclosure in the Product Data, synthetic planning must be guided by your confirmed structure (via CoA and in-house characterization). The following are general considerations for small-molecule natural products.

• Functional group leverage (general):

  • If phenolic or alcoholic groups are present: O-alkylation/acylation to modulate lipophilicity; carbonate/carbamate formation; selective protection for stepwise derivatization.
  • If conjugated enone/lactone motifs exist: Michael additions, conjugate reductions (e.g., triacetoxyborohydride or catalytic hydrogenation), or epoxidations; pay attention to stereocontrol.
  • If carboxylate/lactone present: Ring-opening to acids/esters; amide couplings using EDCI/HATU; late-stage diversification.

• Retrosynthetic value:

  • Cedrelopsin can serve as a scaffold for analog development. Late-stage functionalization via C–H activation or photoredox approaches may be feasible depending on aromaticity and substituent pattern.

• Purification and analytics:

  • Maintain a stability-indicating workflow: monitor by UPLC–MS and 1H NMR; avoid strong bases/acids if hydrolysis is suspected.
  • For chiral centers, employ chiral HPLC or derivatization to establish enantiopurity.

• Documentation:

  • Record full spectral data sets (1H, 13C, HSQC/HMBC, HRMS) for each intermediate and final analog to build an internal library aligned to the Cedrelopsin reference.

Target Specificity

Not applicable; Cedrelopsin is a small-molecule research chemical, not an antibody or affinity reagent.

• Item-specific (from Product Data):

  • No biological target, antigen, or epitope information is specified for this item.

• Guidance:

  • If your research involves protein binding, establish target engagement using biophysical assays (SPR, ITC, DSF) or enzymology, and report conditions alongside purity and identity verification.