Lansiumarin C - ≥97% , CAS No.205115-75-9

CAS: 205115-75-9 Cat. No.: L956733 PubChem CID: 10498320

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Specifications & Purity

≥97%

Storage

Room temperature

Purity

≥97%

Names and Identifiers

Canonical Smiles

CC(=C)C(CCC(=CCOC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)C)O

IUPAC Name

9-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dienoxy]furo[3,2-g]chromen-7-one

InChIKey

DBHLROWQWPSCQG-RIYZIHGNSA-N

INCHI

1S/C21H22O5/c1-13(2)17(22)6-4-14(3)8-10-25-21-19-16(9-11-24-19)12-15-5-7-18(23)26-20(15)21/h5,7-9,11-12,17,22H,1,4,6,10H2,2-3H3/b14-8+

Isomeric SMILES

CC(=C)C(CC/C(=C/COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)/C)O

Alternate CAS

205115-75-9

PubChem CID

10498320

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives
      • Subclass Furanocoumarins
        • Level5 Linear furanocoumarins
          • Level6 Psoralens

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Furanocoumarins
• Intermediate Tree Nodes: Linear furanocoumarins
• Direct Parent: Psoralens
• Alternative Parents: 1-benzopyrans Fatty alcohols Benzofurans Pyranones and derivatives Alkyl aryl ethers Benzenoids Heteroaromatic compounds Furans Secondary alcohols Lactones Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Psoralen - Benzopyran - 1-benzopyran - Benzofuran - Fatty alcohol - Alkyl aryl ether - Pyranone - Fatty acyl - Benzenoid - Pyran - Heteroaromatic compound - Furan - Secondary alcohol - Lactone - Ether - Oxacycle - Organoheterocyclic compound - Alcohol - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.
• 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: 354.400 g/mol
• XLogP3: 4.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 354.147 Da
• Monoisotopic Mass: 354.147 Da
• Topological Polar Surface Area: 68.900 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 593.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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

Item-specific tested applications and protocols: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for common research workflows with small-molecule standards:

• Stock preparation:
  • Weigh accurately using an analytical balance (record temperature and humidity if moisture-sensitive behavior is suspected).
  • Prepare a primary stock in DMSO, MeOH, or ACN at 5–20 mM; filter (0.2 µm PTFE/PES) if needed.
  • Store aliquots to avoid repeated freeze–thaw or evaporation cycles.
• LC–MS analytical check:
  • Start with a water/ACN + 0.1% formic acid gradient (or ammonium acetate for negative mode). Inject 1–10 µL of a 10–50 µM solution.
  • Record full-scan and MS/MS spectra to establish a reference for future analyses.
• Bioassay setup (research use only):
  • Dilute stock into assay media to the working concentration, maintaining low final organic solvent content (typically ≤0.5% DMSO for cells).
  • Include vehicle controls and, if available, a structurally related reference compound.

Note: Tailor these steps to your laboratory SOPs after confirming the compound’s exact identity and stability.

Biological Roles

Item-specific biological annotations: Not specified for this item; refer to primary literature and CoA.

General context (no medical or clinical claims):

• Lansiumarin C is cataloged as a plant-derived small molecule in a compound library. Natural products of this class are often investigated as secondary metabolites that may participate in plant defense, signaling, or storage, depending on the exact structure and biosynthetic origin.
• Research use cases (non-therapeutic):
  • Probe molecule for studying phytochemical diversity in Lansium domesticum and related taxa via metabolomics/dereplication.
  • Analytical standard for quantifying its abundance in plant tissues or fractions.
  • Tool compound in biochemical assays exploring structure–activity relationships within a natural product family, without implying any physiological efficacy.

Practical guidance:

• For cellular or enzymatic assays, establish solubility limits and vehicle tolerances (e.g., ≤0.5% DMSO) prior to screening.
• Confirm identity and purity for each lot to ensure reproducibility across biological experiments.
• Monitor stability in assay buffers (pH 6–8 commonly used) using LC–MS; avoid high pH unless stability is demonstrated, as many natural products can hydrolyze or oxidize under basic or strongly oxidative conditions.

Buffer Applications

Not typically applicable as a buffer component.

Practical guidance when buffers are involved in assays with small organic molecules:

• Stock solutions: Prepare concentrated stocks in DMSO, methanol, or ethanol, then dilute into the working buffer to the desired final concentration while keeping organic cosolvent low (typically ≤0.5% v/v for cell-based assays, ≤2% for many enzyme assays), unless your system tolerates more.
• Common assay buffers (general, not product-specific):
  • Phosphate-buffered saline (PBS, pH ~7.4) for general cell compatibility.
  • HEPES (pH 6.8–8.2) for biological assays requiring stable pH under CO2-independent conditions.
  • Ammonium acetate/formate (pH 3.5–6.5) for LC–MS-friendly workflows; volatile and compatible with ESI.
• Adsorption considerations: Hydrophobic analytes may adsorb to plastic; consider low-bind tubes or glass vials. Include carrier protein or surfactant only if validated not to confound the assay.

Item-specific buffer compatibility, pKa, and aqueous solubility: Not specified for this item; refer to CoA/Spec Sheet and perform pilot solubility tests.

Green Alternatives

While compound identity-specific solvent choices are not provided for this item, greener practices can be applied to handling and analysis of Lansiumarin C.

• Prefer greener solvents where feasible:

  • Replace dichloromethane/chloroform with ethyl acetate, 2-MeTHF, CPME, or toluene (as appropriate to solubility and stability).
  • Use ethanol or isopropanol in place of methanol when chromatographic sensitivity allows, noting their favorable safety and environmental profiles.
  • For HPLC, consider water/ethanol or water/ACN (ACN has favorable UV transparency but is a petrochemical; ethanol is greener yet higher viscosity).

• Small comparison (general):

  • 2-MeTHF vs THF: 2-MeTHF is partially bio-based, lower peroxide risk than THF, and has higher immiscibility with water—useful for extractions.
  • CPME vs DCM: CPME is less volatile/toxic and offers broad solvation with good phase separation; check for peroxidation over time and store properly.

• Operational green tactics:

  • Minimize solvent volumes via microscale sample prep and UPLC where compatible.
  • Employ closed-transfer and low-evaporation workflows to reduce emissions.
  • Validate solid-phase extraction (SPE) to cut solvent use in cleanup.

Note: Always balance green choices with compound stability and analytical requirements; verify recovery and integrity by LC–MS/NMR after any solvent substitution.

Pharmaceutical Uses

No pharmacopeial monograph or excipient role is provided for this item. This product is supplied strictly for research use only.

General, non-clinical context:

• Natural product standards like Lansiumarin C may serve as analytical reference materials in drug discovery workflows, e.g., LC–MS calibration, retention time matching, and MS/MS spectral library curation.
• In pre-formulation research settings (non-clinical), exploratory solubility/stability assessments can guide feasibility studies for derivatives or analogs, without implying therapeutic use of this specific compound.

Documentation and compliance reminders:

• Do not use in human or veterinary applications. Not for diagnostic procedures.
• If used to support regulated analytical work, ensure traceability: maintain CoA, lot-specific purity, and validated analytical methods (qNMR, HPLC) for any reference standard role.

Item-specific excipient/formulation information: Not specified for this item; refer to CoA/Spec Sheet if any additional details are provided.

Physical Properties

Item-specific (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.
• Other specifications (mp, bp, density, solubility, logP, refractive index): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general values and guidance (not item specifications):

• Many plant secondary metabolites are solids with decomposition prior to boiling; melting points and solubilities can vary widely depending on substituents and glycosylation state. Consult curated databases (e.g., PubChem record for CID 10498320) and primary literature that explicitly references CAS 205115-75-9 for any reported constants.
• Practical solubility screening strategy (general):
  • Begin with high-permittivity, protic/aprotic solvents commonly used for natural products: DMSO, methanol, ethanol, acetonitrile, acetone.
  • If amphiphilic or glycosylated, aqueous miscibility may increase in water–organic cosolvent systems (e.g., 10–50% MeOH or ACN in water). Verify stability by LC–UV/MS.
  • For hydrophobic scaffolds, test EtOAc, dichloromethane, toluene, or CPME; avoid prolonged exposure if instability is suspected.

Notes:

• Do not treat literature values as product specifications. Use the item’s CoA/Spec Sheet and your in-lab measurements (DSC, TGA, Karl Fischer, UV–Vis, HPLC) to establish working properties for your application.

Quality & Grades

Item-specific (Product Data):

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

Guidance on interpreting grades and documentation:

• When grade is unspecified for a natural product standard, the CoA typically provides:
  • Purity assay method (e.g., HPLC/UPLC area %, qNMR) and batch-specific result.
  • Identity confirmation (e.g., HRMS, 1H/13C NMR, IR) and acceptance criteria.
  • Residual solvent levels and loss on drying (LOD) or water (KF) where applicable.
  • Appearance and color descriptors.
• Implications for use:
  • Bioassay screening: Prefer batches with quantitative purity determination and spectral identity matching a reference standard.
  • Analytical reference: Look for lot-specific purity ≥95% by orthogonal methods (e.g., qNMR plus LC).
  • Synthetic use: Confirm residual water/solvent and assess stability (DSC/TGA) if heating is anticipated.

Recommendations:

• Request the latest CoA for this SKU to obtain purity, analytical methods, and stabilization/packing notes.
• If low UV background is required (e.g., HPLC UV detection), verify UV cutoff/absorbance profile—Not specified for this item; refer to CoA/Spec Sheet.
• If metal content is critical for catalytic studies, request ICP data—Not specified for this item; refer to CoA/Spec Sheet.

Reaction & Applications

Item-specific “Manufacturer Applications”: Not specified in the product data for this SKU.

General research uses for a cataloged natural product standard in a small-molecule/compound library:

• Reference material for analytical profiling:
  • LC–MS method development, retention index mapping, and MS/MS spectral library building.
  • Orthogonal identity confirmation via NMR, UV–Vis, and IR against literature for CAS 205115-75-9.
• Chemical biology and screening:
  • Inclusion in phenotypic or target-based screening decks to probe natural-product chemical space (dosing guided by solubility and cytotoxicity pilot tests; research use only).
• Comparative phytochemical studies:
  • Authentic standard for dereplication in extracts of Lansium domesticum and related species by LC–HRMS.
• Stability and degradation studies:
  • Evaluate susceptibility to hydrolysis/oxidation by forced-degradation protocols (acid/base, peroxide, light) to inform storage and assay conditions.

Practical tips (general):

• Verify identity against a trusted reference (CoA spectra vs. literature) before using as a standard.
• If chromatographing, start with water/ACN or water/MeOH gradients with 0.1% formic acid unless the compound is acid-labile; adjust pH modifiers based on observed stability.
• For quantitation, prefer qNMR or external calibration with gravimetrically prepared solutions; confirm response factors and linearity in the chosen detector.

Reaction Conditions

Item-specific reaction condition guidance is not applicable because no defined synthetic use or functional group specification is provided for this SKU.

General guidance for handling during chemical manipulations (if derivatization is attempted after confirming structure):

• Solvents: Start with anhydrous, oxygen-free solvents if the compound contains oxidizable motifs; otherwise use standard dry solvents (MeOH, EtOH, ACN, DCM, toluene) as dictated by solubility.
• Temperatures: Many natural products are sensitive to strong heat; keep ≤50 °C during routine operations unless stability is documented by DSC/TGA.
• Catalysts/reagents: Use neutral to mildly acidic conditions for transformations that risk base-promoted degradation (e.g., glycosidic cleavage or ester hydrolysis). Avoid strong oxidants without prior stability testing.
• Timelines and monitoring: Employ TLC with multiple stains (UV254/365, anisaldehyde, vanillin), and LC–MS for real-time tracking. Collect kinetic samples to evaluate degradation.

Expected yields: Not applicable—no literature yields specific to this item are provided here. Consult peer-reviewed sources specific to Lansiumarin C (CAS 205115-75-9) for any reported transformations and conditions.

Safety & Handling

Item-specific (Product Data):

• GHS Classification: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.
• Hazard statements (H-phrases): Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.
• Storage conditions: Room temperature (per product data). Protect from moisture and excessive heat.

General laboratory safety guidance (not a substitute for SDS):

• PPE: Wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure to dusts/aerosols.
• Incompatibilities (general for organic small molecules): Avoid strong oxidizers and strong acids/bases unless compatibility is confirmed. Prevent prolonged exposure to light and air if chromophores or oxidizable functionalities are suspected.
• First aid overview:
  • 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.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Hygiene measures: Avoid breathing dust. Do not eat, drink, or smoke when using this product. Wash hands thoroughly after handling.

Notes:

• Always defer to the product’s SDS for authoritative hazard classification, exposure limits, spill response, and disposal guidance.

Solvent Selection

Item-specific solubility and polarity: Not specified for this item; refer to CoA/Spec Sheet.

General approach for dissolving structurally complex natural products when properties are unknown:

• Stepwise solubility screen (small scale, ~1–2 mg):
  • Tier 1: DMSO, methanol, ethanol, acetonitrile (broadly compatible with LC-MS and bioassays).
  • Tier 2: Acetone, isopropanol, ethyl acetate (for moderately polar organics).
  • Tier 3: Dichloromethane, chloroform, toluene, CPME, MTBE (for nonpolar compounds; evaluate stability first).
  • Aqueous systems: If dissolution in neat organic fails, test 10–50% organic in water or buffers; avoid high pH unless stability is documented.

Practical tips:

• For screening libraries, prepare concentrated DMSO stocks (e.g., 10–20 mM) and dilute into assay media to ≤0.5% v/v DMSO to mitigate solvent effects.
• Warm gently (≤40 °C) and sonicate to aid dissolution. Avoid prolonged heating or basic conditions that might promote hydrolysis.
• Filter through 0.2 µm PTFE or PES for analytical injections; PVDF may be preferable for strongly organic systems.

Comparison (general):

• DMSO vs methanol: DMSO offers widest solubilization but is less volatile and may affect biology; MeOH is LC-friendly but can be less effective for highly lipophilic analytes.
• ACN vs EtOH: ACN is lower viscosity and UV-transparent; EtOH is greener and widely compatible but less volatile than MeOH/ACN.

Storage & Reconstitution

Item-specific (Product Data):

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

General best practices for small-molecule natural products:

• Protect from light and moisture; store in the original, tightly closed container with desiccant if provided.
• If long-term storage is planned, consider secondary containment in a desiccator or under inert gas, especially for oxidation- or hydrolysis-prone compounds.
• Upon first opening, record open date and lot number; if feasible, split into single-use aliquots to minimize headspace and repeated exposure.

Reconstitution guidance (when properties are unknown):

• Start with DMSO or methanol for primary dissolution at 5–20 mM. Sonicate gently or warm to ~30–40 °C to aid dissolution; avoid prolonged heating.
• For aqueous assays, dilute the organic stock into buffer with vigorous mixing to prevent precipitation. Verify clarity and stability by a quick test injection on LC–UV/MS.
• If precipitation occurs upon dilution, increase organic cosolvent fraction or reduce concentration; alternatively, use cyclodextrins or accepted solubilizing excipients only after compatibility tests.

Always refer to the lot-specific CoA/SDS for definitive handling, stability, and storage information.

Structure & Identity

Brief overview: Lansiumarin C is listed as a small-molecule natural product entry in our compound library. Item-specific identifiers are limited for this SKU; detailed structure should be confirmed from the CoA/Spec Sheet or primary literature before use.

• Item-specific (Product Data):

  • SKU: L956733
  • Product name: Lansiumarin C
  • CAS: 205115-75-9
  • PubChem CID: 10498320
  • InChIKey: 59006 (as provided; note this is non-standard format—verify against CoA/literature)
  • 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 (for orientation; verify against primary sources):

  • Lansiumarins are reported as plant-derived secondary metabolites originally isolated from Lansium domesticum (langsat). Specific sub-class and exact functional groups for “Lansiumarin C” should be verified in peer-reviewed reports corresponding to CAS 205115-75-9 and CID 10498320.
  • Typical features in related natural products may include polyoxygenation and glycosidic or phenolic moieties; however, do not assume these for this item without structural confirmation.

• Structural description (2D, general guidance):

  • Because the definitive structure (SMILES/InChI) is not provided in the product data, a reliable 2D depiction should be sourced from an authenticated database entry (e.g., PubChem CID 10498320) or the item’s CoA prior to method development, quantitation, or spectral assignment.

Synthetic Utility

Item-specific reactivity and functional groups are not provided for this SKU. Without a confirmed structure (SMILES/InChI), prescriptive synthetic transformations cannot be recommended.

General considerations for complex natural products (when structure is confirmed from CoA/literature):

• If glycosidic moieties are present: Protecting-group strategies (e.g., acetyl, benzyl) and selective glycosidic bond manipulations (Koenigs–Knorr, glycosyl donors/acceptors) may be relevant.
• If phenolic units exist: O-alkylation/acylation, oxidative coupling, or late-stage diversification (e.g., Mitsunobu etherifications, SNAr on activated rings) can be explored.
• If lactone/ester functions are present: Careful base selection to avoid transesterification; potential sites for hydrolysis or amidation.
• If multiple stereocenters: Consider derivatization routes that preserve configuration; use mild conditions and monitor by chiroptical methods or chiral HPLC.

Use as an analytical/synthetic benchmark:

• Serve as an authentic comparator in total synthesis or semisynthesis projects targeting the lansiumarin scaffold family—matching 1H/13C NMR, HRMS, and optical rotation to literature.

Caution:

• Do not assume functional groups or reactivity for this item without verifying the exact structure that corresponds to CAS 205115-75-9 and CID 10498320.

Target Specificity

Not applicable. This product is a small-molecule natural product entry and is not an antibody, protein, or nucleic acid reagent.

• Item-specific target/epitope/clone/isotype information: Not specified for this item; refer to CoA/Spec Sheet.
• If used in biological assays, any observed activity should be treated as exploratory and must be verified independently; no target specificity is claimed or implied by this listing.