Cacticin - ≥98% , CAS No.6743-92-6

CAS: 6743-92-6 Cat. No.: C1042724 Formula: C₂₂H₂₂O₁₂ Peso molecolare: 478.41 PubChem CID: 5318644

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: COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• InChIKey: CQLRUIIRRZYHHS-UVHBULKNSA-N
• INCHI: 1S/C22H22O12/c1-31-12-4-8(2-3-10(12)25)20-21(17(28)15-11(26)5-9(24)6-13(15)32-20)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3/t14-,16+,18+,19-,22+/m1/s1
• Isomeri SMILES: COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O
• PubChem CID: 5318644
• Peso molecolare: 478.41

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Flavonoids
      • Subclass Flavonoid glycosides
        • Level5 Flavonoid O-glycosides
          • Level6 Flavonoid-3-O-glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Flavonoids
• Subclass: Flavonoid glycosides
• Intermediate Tree Nodes: Flavonoid O-glycosides
• Direct Parent: Flavonoid-3-O-glycosides
• Alternative Parents: 3'-O-methylated flavonoids 7-hydroxyflavonoids Flavones 5-hydroxyflavonoids 4'-hydroxyflavonoids Hexoses Chromones O-glycosyl compounds Methoxyphenols Anisoles Phenoxy compounds Methoxybenzenes Alkyl aryl ethers Pyranones and derivatives 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Oxanes Heteroaromatic compounds Vinylogous acids Secondary alcohols Polyols Oxacyclic compounds Acetals Organic oxides Hydrocarbon derivatives Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Flavonoid-3-o-glycoside - 3p-methoxyflavonoid-skeleton - Hydroxyflavonoid - Flavone - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Hexose monosaccharide - Chromone - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - Methoxyphenol - Methoxybenzene - Anisole - Phenoxy compound - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - 1-hydroxy-4-unsubstituted benzenoid - Pyranone - Phenol - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Pyran - Oxane - Monosaccharide - Vinylogous acid - Heteroaromatic compound - Secondary alcohol - Ether - Organoheterocyclic compound - Oxacycle - Polyol - Acetal - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Alcohol - Primary alcohol - Organooxygen compound - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
• External Descriptors: monosaccharide derivative - beta-D-galactoside - monomethoxyflavone - glycosyloxyflavone - trihydroxyflavone

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: 478.400 g/mol
• XLogP3: 0.700
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 5
• Exact Mass: 478.111 Da
• Monoisotopic Mass: 478.111 Da
• Topological Polar Surface Area: 196.000 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 773.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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 manufacturer protocols were provided for this SKU. The following general, non-item-specific procedures are offered for research planning. Adjust to your application and verify with small-scale tests.

1. Preparing an analytical stock solution

• Weigh accurately into an amber vial. Add dry DMSO or methanol to achieve 1–10 mg/mL. Vortex and sonicate gently if needed. Record exact concentration by mass and volumetry. Store aliquots to minimize freeze–thaw.

2. LC–UV/LC–MS calibration

• Dilute stock with initial mobile phase (e.g., water/ACN + 0.1% formic acid) to 0.5–100 µg/mL. Filter 0.22 µm PTFE. Inject a 5–7 point curve. Monitor two wavelengths (e.g., 254 and 350 nm) and MS SIM/MRM if available.

3. Acid hydrolysis check (aglycone confirmation)

• Dissolve sample in 50% MeOH with 1 M HCl to 1–2 mg/mL. Heat at 80°C for 1 h. Quench, neutralize, extract with EtOAc, and analyze both layers by LC–MS to verify aglycone formation and sugar release.

4. Stability screening

• Incubate replicate solutions at RT, 4°C, and 40°C (ambered) for 1–7 days. Assess by HPLC for degradation. Include pH 3–7 buffers with 5–20% MeOH to map stability domain.

These protocols are generic and must be adapted after reviewing the lot-specific CoA and SDS for this product.

Biological Roles

Context from literature (no clinical claims): Cacticin is referenced as a plant secondary metabolite of the flavonoid glycoside class, reported in cactus species. Exact structural assignment can vary by source; confirm the aglycone/sugar identity for this SKU via CoA.

Typical roles of flavonoid glycosides in plants (general)

• Defense and signaling: Contribute to UV protection, oxidative stress mitigation, and deterrence of herbivores and pathogens.
• Transport and storage: Glycosylation enhances water solubility and allows vacuolar sequestration, modulating bioavailability of the aglycone.
• Pigmentation and attraction: Influence coloration and may participate in plant–pollinator interactions.

Biochemical properties (general)

• Redox-active phenolics: Phenolic OH groups can donate hydrogen atoms to quench reactive species; metal-chelation motifs are common within the flavonoid core.
• Metabolism: In planta, biosynthesized via the phenylpropanoid pathway; glycosyltransferases attach sugars (e.g., glucose, rhamnose) to specific hydroxyls on the aglycone.
• Biotransformation (in vitro/in vivo models): Deglycosylation by β-glucosidases or gut microbiota can convert glycosides to aglycones, altering absorption and distribution in model systems.

Laboratory relevance

• Used as a reference standard in metabolomics and natural products chemistry to track biosynthetic flux or to annotate peaks in LC–MS datasets.

Note: The above reflects general properties of flavonoid glycosides; do not infer specific biological potency or safety without consulting primary data and the SDS.

Buffer Applications

Not typically formulated as a buffering reagent. Cacticin (a flavonoid glycoside) lacks acid/base pairs with pKa values and capacity suitable for classical biological buffers.

Practical guidance

• If used in biochemical assays, dissolve in a compatible organic cosolvent (e.g., DMSO or ethanol) and dilute into the assay buffer at low organic content to avoid precipitation. Verify compatibility with buffer components (e.g., avoid strong alkaline buffers that may promote glycosidic cleavage).
• Monitor for adsorption or precipitation in phosphate-containing buffers; pre-wet plasticware and include inert protein (e.g., BSA) only if appropriate for the assay design.

For actual buffer preparation needs, consider standard buffers (e.g., phosphate, HEPES, MOPS, acetate) chosen for their target pH range and ionic strength.

Green Alternatives

Green chemistry considerations generally relate to solvent choice and processing rather than the compound itself.

Greener solvent options for handling and analysis (general)

• Replace chlorinated solvents with alcohols or water–alcohol mixtures for extraction and dissolution when feasible.
• Prefer ethanol over methanol where compatibility allows (renewable feedstock, lower toxicity). For LC methods, water–ethanol gradients can sometimes substitute for water–acetonitrile with method re-optimization.

Comparison (general guidance, not item-specific)

• Methanol vs Ethanol: Ethanol offers improved safety profile and sustainability; slight decrease in elution strength and higher viscosity may require temperature/flow adjustments in LC.
• Acetonitrile vs Ethanol: ACN provides sharper peaks and lower backpressure; ethanol is greener but may necessitate elevated column temperature (35–45°C) to manage viscosity.
• DMSO vs PEG 400/glycerol (for stocks): DMSO is highly effective but not particularly green; viscous polyol alternatives are greener but often less suitable for analytical workflows.

Process considerations

• Employ room-temperature operations and avoid prolonged reflux where possible (e.g., enzymatic deglycosylation rather than acid hydrolysis).
• Minimize waste by preparing concentrated stocks and diluting as needed; use micro-scale reactions/assays to reduce solvent volumes.

Note: Any change in solvent system can affect solubility, stability, and analytical response. Validate greener substitutions for your specific method and matrix.

Pharmaceutical Uses

No pharmacopeial or excipient status is specified for this item. Do not use for human or veterinary applications.

Research/formulation context (general, non-clinical)

• Analytical reference: Can serve as a reference standard in quality control of botanical raw materials and extracts where this metabolite is a marker.
• Preformulation research: Solubility and stability screening in various solvent systems to inform botanical extract handling or in vitro assay design.
• Compatibility testing: Interaction studies with excipient matrices (e.g., cellulose derivatives, polyvinylpyrrolidone) may be performed in research settings to understand adsorption or stabilization behavior of phenolic glycosides.

Regulatory note

• This product is for research use only (per Product Data). It is not intended for use in diagnostic, therapeutic, or any clinical applications.

Documentation

• For any regulated workflow (e.g., GMP-adjacent analytics), obtain and retain the lot-specific CoA indicating identity tests, purity, and residual solvent/moisture if applicable.

Physical Properties

Item-specific specifications

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

General literature characteristics for flavonoid glycosides (context—not item specifications)

• Physical state: Typically a yellow to yellow-brown amorphous powder or microcrystalline solid depending on hydration and counterions.
• Solubility: Often sparingly soluble in cold water; soluble in polar organic solvents such as methanol, ethanol, and DMSO; limited solubility in nonpolar solvents (hexanes, toluene). Solubility increases with gentle heating and in aqueous alcohols. Always determine actual solubility empirically for your lot.
• UV–Vis: Strong absorbance in the 250–380 nm region due to conjugated aromatic systems; distinct Band I/II patterns typical for flavonoids (useful for qualitative ID by UV spectral shifts with AlCl3/NaOMe—literature practice).
• Stability: Phenolic glycosides are generally stable as dry solids under ambient conditions but may undergo slow hydrolysis or oxidation in solution, accelerated by alkaline pH, high temperature, light, and trace metals.

Practical notes

• Prepare fresh solutions for quantitation assays. Use amber glassware or wrap containers in foil to minimize photodegradation.
• If exact extinction coefficients or partition data are required, determine experimentally for the specific SKU.

Quality and Grades

Item-specific quality information

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet for assay method (e.g., HPLC area %), residual solvents, and related substances.
• Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting quality for flavonoid standards and research materials

• Typical characterization set: Identity confirmation by 1H/13C NMR, HRMS, and HPLC purity profile; UV–Vis spectrum consistent with flavonoid chromophore. Where applicable, sugar composition may be confirmed by acid hydrolysis followed by GC or LC of monosaccharides.
• Chromatographic purity vs. assay: HPLC area % at a specific wavelength may over- or under-represent true content if impurities have different absorptivities. Consider quantitative NMR (qNMR) for absolute content.
• Water and residual solvents: Glycosides can be hygroscopic and may retain bound solvent or water of crystallization. Karl Fischer water content, if reported, informs accurate massing for quantitative work.
• Reference standard use: For analytical calibration (e.g., LC–UV/LC–MS in natural product profiling), verify lot-specific purity/assigned value and uncertainty when establishing calibration curves.

Practical tips

• Equilibrate solid to room temperature in a desiccator before opening to minimize moisture uptake.
• If low-UV applications (HPLC baseline) are critical, review the UV absorbance specification or perform a baseline scan on your system.

Reaction and Applications

This product is primarily used as a research chemical and analytical reference for plant metabolite studies. While detailed manufacturer applications were not provided, the following uses align with literature practice for flavonoid glycosides.

Analytical and profiling

• Marker/standard in phytochemical fingerprinting of cactus and related botanical matrices via HPLC–UV or LC–MS.
• Quality control of extracts: retention time/UV spectra matching; quantitative determination using calibration curves.

Chemical transformations (general)

• Acid-catalyzed hydrolysis: Cleaves O-glycosidic bond(s) to release the aglycone (flavonoid) and sugar(s). Typically performed with aqueous mineral acids (e.g., 1–2 M HCl) under reflux; monitor by TLC/LC.
• Enzymatic deglycosylation: Glycosidases (e.g., β-glucosidase or rutinosidase depending on sugar) provide milder, selective cleavage preserving sensitive aglycones.
• Derivatization for analysis: Silylation or acetylation of phenolic OH groups to improve GC behavior of aglycones post-hydrolysis; sugar monomers can be derivatized for GC analysis.

Stability and handling in reactions

• Avoid strong bases and high pH which can induce rearrangements and oxidation of phenolic moieties.
• Use antioxidants (e.g., ascorbate) and inert atmosphere for extended reactions if oxidation is a concern.

Practical tips

• To suppress on-column degradation in LC, employ mildly acidic mobile phases (0.05–0.1% formic or acetic acid) and minimize dwell time at high temperatures.

Reaction Conditions

General literature conditions for transformations relevant to flavonoid glycosides (for method planning; not item-specific specifications):

• Acid hydrolysis (deglycosylation): 1–2 M HCl or H2SO4 in aqueous methanol or water, 70–100°C, 0.5–4 h. Monitor by TLC/LC–UV. Neutralize and extract aglycone into EtOAc. Gentle conditions (e.g., 0.1–0.5 M acid, 50–60°C) minimize aglycone degradation.
• Enzymatic hydrolysis: β-Glucosidase or specific rutinosidases in acetate or citrate buffer (pH 4.5–5.5), 25–40°C, 1–24 h. Advantages include selectivity and milder conditions; confirm enzyme specificity to the sugar linkage.
• Phenolic acylation (protection): Ac2O/pyridine or DMAP-catalyzed acylation in dichloromethane or acetonitrile, 0–25°C, 0.5–6 h. Protect sugars beforehand or work on the aglycone to avoid complex mixtures.
• Silylation (analytical derivatization): BSTFA or MSTFA with 1% TMCS, 60–70°C, 15–60 min, anhydrous conditions for GC–MS analysis of aglycones and sugars post-hydrolysis.
• Oxidation sensitivity: Avoid strong oxidants and elevated pH; conduct reactions under inert atmosphere if prolonged heating is required.

Solvent notes

• Methanol/ethanol and aqueous mixtures are common media; DMSO can dissolve highly polar substrates but may complicate downstream workup.

Yields and kinetics

• Reported yields vary widely with structure and conditions; optimize at small scale and quantify conversions by HPLC or qNMR.

Always validate conditions with the actual material from this SKU; minor structural differences can change reactivity.

Safety and Handling

Authoritative safety information must be taken from the product SDS. The following summarizes general good practice for phenolic glycosides.

Product Data (item-specific)

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.
• Storage: Room temperature (per Product Data).

General laboratory precautions (not a substitute for SDS)

• PPE: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid inhalation of dust and contact with skin/eyes. Use in a fume hood when weighing powders or preparing solutions.
• Incompatibilities: Strong oxidizers; strong bases (risk of glycosidic cleavage and phenolate formation); prolonged exposure to light and heat may promote degradation. Avoid metal contamination that can catalyze oxidation.
• First aid (general): Inhalation—move to fresh air, seek medical attention if symptoms persist. Skin/eye contact—rinse with water for at least 15 minutes, remove contaminated clothing, seek medical attention if irritation develops. Ingestion—rinse mouth, do not induce vomiting, seek medical advice.
• Spill/cleanup: Avoid dust generation. Sweep up with minimal dusting and place in suitable container for disposal. Wash spill area with water/ethanol as appropriate.
• Fire safety: Combustible organic solid; use CO2, dry chemical, or foam extinguishers. Thermal decomposition may produce irritating vapors; firefighters should wear SCBA.

Disposal

• Dispose of contents/container according to local/regional regulations for organic laboratory chemicals.

Solvent Selection

Applicability: Cacticin (a flavonoid glycoside by literature context) is polar and typically handled in polar protic or aprotic solvents.

General solvent behavior (literature context)

• Preferred solvents for stock solutions: DMSO (high solubilizing power), methanol, ethanol. Aqueous alcohols (e.g., 50–80% MeOH or EtOH) can aid dissolution while maintaining LC–UV compatibility.
• Water: Solubility can be limited at neutral pH; solubility improves modestly with warm water or in the presence of co-solvents. Avoid strong base which can cleave glycosidic bonds.
• Nonpolar solvents: Poorly soluble in aliphatic hydrocarbons and chlorinated nonpolars.

Selection guidance by application

• Analytical LC–UV/LC–MS: Prepare standards in MeOH, ACN, or DMSO, then dilute with initial mobile phase. Filter through 0.22 µm PTFE or PVDF; avoid nylon if strong hydrogen bonding leads to adsorption.
• Bioassays (in vitro): Make a concentrated DMSO or ethanol stock (e.g., 10–50 mM as solubility permits) and dilute into assay buffer to low final organic content. Verify precipitation visually and by light scattering.
• Isolation/purification: Reverse-phase systems (C18) with water–ACN or water–MeOH plus 0.1% formic or acetic acid are standard. Normal-phase silica often requires strongly polar eluents (CHCl3/MeOH/H2O mixtures) that can promote hydrolysis—monitor carefully.

Small comparison (general)

• DMSO: Highest solvency; not volatile; can interfere with some bioassays.
• Methanol/Ethanol: Good balance of solvency and volatility; compatible with most LC methods.
• Acetonitrile: Useful for LC dilutions; moderate solvency for glycosides; low viscosity enhances MS response.

Storage and Reconstitution

Item-specific storage

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

General guidance for flavonoid glycosides

• Protect from light and moisture. Store tightly capped in a desiccated environment (desiccant pouch or desiccator). Avoid prolonged exposure to elevated temperature.
• For long-term archiving, consider storing at 2–8°C in the dark if compatible with your use pattern, even if RT is acceptable, to minimize slow oxidation/hydrolysis.

Reconstitution and solution handling

• Solvents: DMSO, methanol, or ethanol are typical for stock solutions. Water solubility may be limited; use aqueous alcohols if needed. Determine solubility empirically for your lot.
• Concentration: Prepare concentrated stocks (e.g., 1–50 mg/mL as solubility allows) and dilute immediately before use. Filter solutions for analytical applications.
• Stability in solution: Use freshly prepared solutions when possible. Store aliquots in amber vials at 2–8°C; avoid repeated freeze–thaw. Discard solutions showing precipitation, discoloration, or unexpected LC peaks.

Documentation

• Consult the CoA/SDS for any lot-specific stability statements or special precautions. This product is for research use only.

Structure and Identity

Brief overview: Cacticin is a plant-derived small molecule commonly described in the literature as a flavonoid glycoside occurring in cacti (e.g., Opuntia spp.). Specific structural identifiers for this catalog item are limited in the Product Data; consult the CoA/SDS for definitive identity attributes.

Item-specific identifiers (from Product Data)

• CAS: 6743-92-6
• PubChem CID: 5318644
• InChIKey: 50979 (as provided; appears truncated—verify against 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 class and features (general literature context)

• Chemical class: Flavonoid glycoside (phenolic O-glycoside) reported from cactus species; exact sugar and aglycone composition should be verified for the specific material lot.
• Functional groups: Multiple phenolic hydroxyls on a flavone/flavonol-type scaffold; one or more O-glycosidic linkages to hexose/deoxyhexose units (typical of flavonoid rutinosides/glucosides). Contains conjugated aromatic rings (A- and B-rings) connected via heteroaromatic C-ring.
• 2D description: Two benzene rings connected through a heterocyclic pyranone ring (typical flavonoid core). One ring (B) bears phenolic substituents; O-glycosidic substituent(s) extend from the C- or O-position on the core, terminating in one or more sugar rings rich in hydroxyls.

Notes

• Because “cacticin” has been variably attributed in the literature, confirm exact structure (aglycone, sugar identity, substitution pattern) for this SKU via the provided CoA/SDS before method development or quantitation.

Synthetic Utility

Although primarily a natural product/analytical standard, cacticin can be leveraged as a synthetic handle in method development and in transformations centered on the flavonoid core and its glycosidic linkage(s).

Useful transformations (general)

• Selective deprotection/deglycosylation: Acidic or enzymatic hydrolysis to access the aglycone for structure–activity comparisons, followed by re-glycosylation with alternative sugars using glycosyl donors (trichloroacetimidates, thioglycosides) under Lewis acid catalysis.
• Phenolic derivatization: Acylation, alkylation, or silylation of phenolic OH groups for protection or analytical volatility enhancement.
• Metal-catalyzed modifications: Mild cross-coupling or O-arylation approaches on suitably protected aglycones; typically requires prior protection of phenols and removal of sugars.

Analytical method development

• Chromatographic selectivity probe: Serves as a polar aromatic analyte to challenge RP and HILIC selectivity, evaluate ion-pairing avoidance, and characterize column silanol activity.

Retrosynthetic perspective

• Disconnection at the glycosidic bond suggests accessing the aglycone from commercially available flavonoids, followed by regioselective glycosylation at the target hydroxyl. Protecting group strategy (e.g., benzyl/acetyl) is central to controlling O-glycosylation site-selectivity.

Notes

• The exact reactivity and protecting group strategy depend on the definitive structure of cacticin for this SKU; verify aglycone identity and sugar composition from the CoA.

Target Specificity

Not applicable. This product is a small-molecule natural product, not an antibody, enzyme, or targeted biologic.

• No antigen/epitope, clone, isotype, or species reactivity applies.
• If used in biochemical assays, any target interactions are exploratory research observations and are not specified for this item.