7β-Methoxy-Mogroside V - ≥94%

Cat. No.: M664162

GRADE & PURITY ≥94%

Storage

Room temperature

Shipped In

Normal

Specifications

Spécifications et pureté

≥94%

Conditions de stockage de stockage

Room temperature

Expédié en

Normal

Pureté

≥94%

Application Protocols

No manufacturer-validated application protocols are provided for this item. Use cases will depend on your assay and analytical platform.

General starting points (informational; adjust to your system):

• Stock solution preparation: 10–50 mg/mL in DMSO, or 1–10 mg/mL in water. Warm (≤40 °C) and sonicate to fully dissolve. Filter (0.22 µm) if clarity/sterility is required.
• LC–MS quantification: Reverse-phase C18, water–acetonitrile (or water–methanol) gradient, 0.1% formic acid optional for improved peak shape. Consider ELSD/CAD if UV response is weak. Prepare calibration curves across your expected concentration range using matrix-matched standards.
• Enzymatic assay setup: Prepare in acetate or phosphate buffer (pH 5–7.5). Include appropriate controls (heat-inactivated enzyme, blank matrix). Monitor reaction progress by LC–MS.

These are general literature-informed practices and not validated for this specific catalog item. Always perform pilot experiments to optimize conditions.

Biological Roles

General biochemical context (literature; not product-specific claims):

• Mogrosides are cucurbitane-type triterpene glycosides found in Siraitia grosvenorii (monk fruit/luo han guo). They function in planta as specialized metabolites likely involved in defense and ecological interactions.
• Sensory biology: Mogroside V and related congeners are intensely sweet and can activate human sweet taste receptors (T1R2/T1R3) in vitro (literature). The impact of a 7β-methoxy substitution on receptor engagement is of research interest for SAR studies.
• Metabolic fate: Glycosides are often hydrolyzed by intestinal microbiota to aglycones and sugars; aglycones can undergo further phase I/II metabolism (glucuronidation/sulfation) before excretion (general natural product metabolism literature).
• Physicochemical profile: High polarity and multiple hydroxyls confer aqueous solubility and limited passive membrane permeability, often necessitating transporter-mediated or paracellular routes in biological systems.

Research utility:

• Serves as a tool compound for probing carbohydrate–protein interactions, glycosidase activities, and transport phenomena.
• Suitable as a matrix component or spike-in standard for metabolomics/natural products profiling, enabling MS/MS library building and retention indexing.

Note: All uses are for research purposes only. This section summarizes literature knowledge and should not be interpreted as safety, nutritional, or clinical guidance.

Buffer Applications

This compound is not a buffering agent and does not form classical buffer systems. It is typically dissolved in pre-made buffers for assays rather than being used to control pH.

Practical guidance (general):

• Compatible buffers: Phosphate-buffered saline (PBS), HEPES, and citrate–phosphate buffers at neutral pH are commonly used vehicles for aqueous solutions. Maintain pH ~6–8 to minimize glycosidic hydrolysis during extended incubations.
• Preparation: Dissolve the compound in a small amount of DMSO or warm water, then dilute into buffer with gentle mixing. Filter through 0.22 µm if sterility or clarity is required.
• Storage in buffer: For multi-day use, refrigeration can help maintain stability; minimize freeze–thaw cycles by aliquoting. Avoid strong basic buffers (pH >9) or hot acidic solutions, which can cleave glycosidic bonds.

If you require a buffering system for your experiment, select one based on your assay pH and ionic strength needs (e.g., phosphate, HEPES, MOPS).

Green Alternatives

Although 7β-methoxy-mogroside V is not a solvent or reagent used in bulk processing, greener choices apply to its handling and analysis:

Greener solvent choices for dissolution/extraction (general guidance):

• Prefer water or aqueous ethanol for dissolution and preparative work, minimizing reliance on DMSO or chlorinated solvents.
• For LC separations, water–ethanol can sometimes substitute for water–acetonitrile or water–methanol, though backpressure and selectivity may differ.

Comparison (general; not item-specific specs):

• Water/EtOH: Renewable, low toxicity, low environmental impact; may require higher temperatures/volumes for full dissolution.
• Methanol: Effective, but more toxic; good volatility for drying.
• Acetonitrile: Excellent chromatographic performance; higher EHS burden and supply volatility.
• DMSO: Outstanding solvency; persists in waste streams, use sparingly.

Operational tips for greener workflows:

• Use solid-phase extraction (SPE) with water/EtOH eluents to minimize solvent volumes in sample cleanup.
• Adopt MS-compatible, low-UV-gradient systems to reduce need for high-organic phases.
• Recover and recycle alcohol solvents when feasible via distillation.

Trade-offs:

• Switching to ethanol from acetonitrile may alter selectivity and resolution; method re-optimization (gradient, temperature, stationary phase) is often required.

Pharmaceutical Uses

No pharmacopeial status, excipient designation, or dosage-form role is specified for this catalog item; it is supplied strictly for research use only.

Context for formulation research (general, non-clinical):

• As a high-polarity glycoside, 7β-methoxy-mogroside V can be evaluated as a reference standard in quality-control methods for botanical ingredients or as a model compound to study glycoside stability in formulation-relevant environments (pH, temperature, ionic strength).
• Solubilization approaches for test articles: Aqueous vehicles (water, buffers) or cosolvent systems (water–ethanol or small % DMSO) are typically effective. Cyclodextrin inclusion complexes can be explored as a formulation tool for taste-active glycosides (literature concept), though not specific to this item.
• Analytical development: Suitable for establishing specificity, recovery, and robustness of HPLC/UPLC methods in complex matrices.

Compliance note: This product is not intended for use in humans or animals, not a drug substance, and not an excipient for manufacturing. Do not cite it in clinical or nutritional contexts without appropriate regulatory qualification.

Physical Properties

Item-specific numerical specifications (this listing):

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

General/typical properties for mogroside V–type glycosides (literature/experience; not item specifications):

• Physical state: Non-volatile, high-molecular-weight organic solid (often amorphous to microcrystalline), hygroscopic tendency due to multiple hydroxyls.
• Melting/decomposition: Many cucurbitane glycosides show broad melting with decomposition typically >180–220 °C (literature). Exact value depends on hydration/crystallinity.
• Solubility: Readily soluble in water and aqueous buffers; also soluble in polar protic solvents (methanol, ethanol) and DMSO. Poorly soluble in nonpolar media (hexanes, toluene).
• Partitioning: Expected low logP at neutral pH due to multiple hydroxyls and sugars; behaves as highly polar surface-active small molecule rather than classical lipophile (literature inference).
• Optical rotation: Mogrosides are often optically active; sign/magnitude are structure-dependent (literature).
• UV/Vis: Weak π–π* absorption above 200 nm; no strong chromophores beyond oxygenated rings and saccharides. For analytical work, detection is commonly by ELSD/CAD or MS; UV detection may require low-wavelength monitoring (195–210 nm) (literature).

Practical notes (general):

• Aqueous solubility facilitates bioassay and analytical standard preparation; gentle warming and sonication can speed dissolution.
• Avoid strong bases/acids at elevated temperatures to prevent glycosidic hydrolysis or acetal cleavage.

Quality and Grades

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

Interpretation and guidance (general):

• Natural-product glycosides such as mogroside derivatives are commonly offered as research-grade materials for discovery chemistry and analytical reference. Purity is typically assessed by HPLC/UPLC with ELSD/CAD/UV and corroborated by MS and NMR.
• If annotated as “analytical standard” or “reference standard” (not specified here), this would imply tight assay/purity bounds, identity confirmation by orthogonal techniques, and defined water/ash limits. In the absence of a declared grade, rely on the CoA chromatogram and assay method for suitability in your workflow.
• Residual solvents, ash, and water/hygroscopicity can influence assay response; confirm with Karl Fischer or TGA if your application is moisture-sensitive.
• Stabilizers: Not expected/typical for mogroside solids; none are declared for this item. If stabilizers were used, they would be listed on the CoA.

What to check on receipt (best practices):

• Review CoA for identity (HRMS/NMR), purity (area %), and residual solvent profile.
• Inspect material visually for caking (moisture uptake) and re-homogenize if needed.
• For quantitative methods, perform a quick potency check by qNMR or external-standard HPLC to confirm assay against your internal standard set.

Reaction and Applications

This product is listed under “small molecules and compound libraries,” making it suitable for discovery chemistry, assay development, and analytical standards. While not a classical reagent, 7β-methoxy-mogroside V can be used in the following contexts (general literature guidance):

• Analytical reference/standard: Benchmark for quantifying mogrosides in botanical extracts (HPLC–ELSD/CAD/MS). Useful for method validation (linearity, precision, recovery) in food/natural product chemistry.
• Structure–activity studies: Comparing 7β-methoxy substitution with parent mogroside V to probe effects on receptor interactions, solubility, and stability (biochemical assays; no clinical claims).
• Chemical derivatization: Controlled acetylation, benzoylation, or silylation of hydroxyl groups for MS or GC derivatization; selective deprotection strategies illuminate hydroxyl reactivity.
• Enzymatic transformations: Glycosidase-mediated partial hydrolysis to access lower glycosides; glycosyltransferase-catalyzed modification of sugar chains for SAR libraries.
• Stability studies: pH- and temperature-dependent hydrolysis kinetics of glycosidic bonds; comparison of methoxy protection at C-7 vs native hydroxyl.

Practical notes:

• Maintain neutral pH and mild temperatures during handling to preserve native glycosidic architecture.
• For derivatizations, use anhydrous conditions and monitor by LC–MS to avoid over-reaction across multiple hydroxyls.
• When serving as an internal/external standard, verify purity/assay by orthogonal methods (qNMR and LC area%).

Reaction Conditions

General guidance for typical transformations of mogroside-type glycosides (literature-based; not item-specific specifications):

• Per-O-acetylation: Ac2O (10–20 equiv per OH), pyridine or DMAP catalysis, 0–25 °C, 1–12 h. Workup with aqueous NaHCO3. Monitor by LC–MS. Yields commonly >70% on a per-step basis, though product mixtures may arise from partial acylation.
• Selective acylation: Bulky anhydrides (isobutyric, pivalic) with DMAP in CH2Cl2 or MeCN, 0–25 °C; exploit differential reactivity of primary vs secondary hydroxyls on sugars.
• Acidic hydrolysis of glycosides: Aqueous HOAc or dilute mineral acid (0.01–0.1 M HCl), 40–80 °C, hours to days; generates lower glycosides and aglycone. Over-acidification or higher temperatures can cause degradation.
• Enzymatic trimming: β-Glucosidase in acetate buffer pH 4.5–5.5, 25–40 °C, 2–48 h; products analyzed by LC–MS. Enzyme selectivity can yield regioselective cleavage.
• Formation of analytical derivatives: TMS ether formation with BSTFA + 1% TMCS in anhydrous pyridine, 60–70 °C for 30–120 min following prior hydrolysis to monosaccharides/aglycone if GC–MS is required.

Solvent and stability notes:

• Avoid strong base (e.g., NaOMe/MeOH) unless specifically targeting transesterification/methylation; base can induce elimination or glycosidic cleavage over time.
• Protect from moisture for acylation/silylation steps; use anhydrous solvents and inert atmosphere as needed.

Always tailor conditions to your selectivity goals and confirm outcomes by high-resolution analytics.

Safety and Handling

Manufacturer-provided hazard data for this item:

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

General laboratory safety guidance for carbohydrate-rich triterpene glycosides (informational; always defer to the SDS):

• PPE: Wear lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Handle powders in a fume hood or ventilated enclosure to minimize dust inhalation.
• Inhalation/ingestion: Avoid generating dust; do not inhale. Do not ingest. If inhaled, move to fresh air; if swallowed, rinse mouth with water. Seek medical advice as per SDS.
• Skin/eye contact: Rinse with water for several minutes. Remove contaminated clothing. Obtain medical attention if irritation persists.
• Fire safety: Treat as a combustible organic solid. Use CO2, dry chemical, or water spray for small fires. Avoid dust accumulation near ignition sources.
• Chemical incompatibilities: Strong oxidizers (risk of exotherm), strong acids/bases at elevated temperature (can hydrolyze glycosidic bonds). Avoid prolonged exposure to high pH or mineral acids, especially when warm.
• Stability: Typically stable at ambient conditions when kept dry and protected from light. Hygroscopic uptake of moisture can lead to clumping or altered handling characteristics.

Always consult the product-specific SDS and CoA for definitive hazard classifications and first-aid measures.

Solvent Selection

Solubility/miscibility profile (general for mogroside-type glycosides):

• Highly polar, hydrogen-bonding compound. Dissolves well in water, aqueous buffers, methanol, ethanol, isopropanol (to a lesser extent), and DMSO.
• Poor solubility in nonpolar and weakly polar aprotic solvents (hexanes, heptane, toluene, MTBE, CPME). Limited solubility in acetonitrile; often improved with water content.

Recommended choices by application:

• Bioassay stocks: DMSO (10–50 mg/mL) or water; for water, gentle warming (≤40 °C) and sonication help. Dilute DMSO stocks into buffered media slowly to avoid precipitation.
• Preparative handling: Aqueous ethanol (50–80%) balances solubility and volatility for lyophilization or rotary evaporation.
• Analytical HPLC: Water–acetonitrile or water–methanol gradients with 0–0.1% formic acid. Detection via ELSD/CAD/MS; UV at 195–210 nm if needed.

Comparative notes:

• Water vs methanol: Water maximizes biocompatibility but may need higher volumes; methanol speeds drying and can sharpen chromatographic peaks.
• DMSO: Highest solvating power for stock solutions; use minimal volumes to limit DMSO in biological assays.

Practical tips:

• Filter solutions through 0.22–0.45 µm PTFE or PES to remove undissolved particulates prior to quantitative work.
• Avoid strong basic aqueous solutions and hot mineral acids, which can hydrolyze glycosidic bonds and alter composition.

Storage and Reconstitution

Manufacturer information for this item:

• Storage Conditions: Room temperature.
• Shipped In: Normal.

Additional handling guidance (general best practices for glycoside solids; not a specification):

• Protect from moisture and light. Store in a tightly closed container with desiccant if possible. Hygroscopic uptake can lead to clumping and minor potency drift by mass.
• For long-term storage, ambient conditions are acceptable per listing; refrigeration (2–8 °C) can be used as a precaution if local climate is hot/humid, provided the container is well sealed to prevent condensation upon warm-up.

Reconstitution (general suggestions):

• Solvents: Water, aqueous buffers (pH 6–8), methanol, ethanol, or DMSO. Begin with a small volume, then dilute to target concentration.
• Technique: Gently warm (≤40 °C) and sonicate to aid dissolution. Avoid strong base or hot mineral acid to preserve glycosidic integrity.
• Filtration: 0.22–0.45 µm syringe filter (PTFE or PES) recommended prior to quantitative analyses or cell-free assays.
• Aliquoting: For aqueous or DMSO stocks, prepare single-use aliquots to minimize freeze–thaw. If freezing solutions, store at −20 °C and thaw at room temperature; inspect for precipitation upon thawing and redissolve with gentle mixing.

Always consult the item’s CoA/SDS for any additional, product-specific instructions.

Structure and Identity

• Item: 7β-Methoxy-Mogroside V (SKU: M664162)
• CAS: 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.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general chemical knowledge for mogroside V derivatives):

• Core scaffold: A cucurbitane-type tetracyclic triterpenoid aglycone (mogrol skeleton), heavily oxygenated.
• Glycosylation: Multiple β-D-glucopyranosyl units attached via glycosidic linkages (mogroside V class typically bears two disaccharide chains at C-3 and C-24 of the mogrol core; literature).
• Substitution: 7β-methoxy indicates an O–CH3 substituent at the C-7 position with β-orientation on the triterpene core (literature rationale for naming; stereochemical drawing should show the methoxy axial/equatorial depending on local ring conformation).
• Functional groups: Multiple secondary alcohols, acetal-like glycosidic bonds, ether linkages (including the 7β-methoxy), numerous stereocenters (>10), and no formal charge at neutral pH.
• 2D description (literature-based): A compact fused-ring (A/B/C/D) triterpene nucleus with pendant glycosidic chains; the 7-position on the B-ring bears a methoxy substituent pointing β (up) relative to the steroid-like core plane; sugar residues are β-linked glucoses forming di- or tri-saccharide chains.

Notes:

• Exact stereochemical descriptors, atom numbering, and sugar attachment pattern for this 7β-methoxy derivative should be confirmed against the CoA/Spec Sheet for this catalog item.

Synthetic Utility

While primarily a natural-product tool compound rather than a general reagent, 7β-methoxy-mogroside V offers several avenues for synthetic and mechanistic studies (general literature guidance):

• Functional group landscape: Dozens of secondary alcohols (on sugars and aglycone), ether linkages (glycosides and 7β-methoxy), and multiple stereocenters enable chemoselectivity challenges and protecting-group strategy development.
• Derivatization chemistry: Per-O-acylation (Ac2O/pyridine or acyl chlorides) for lipophilicity tuning and spectral simplification; selective acylation using enzymes or bulky acyl donors; methylation/silylation for GC–MS derivatization (e.g., TMS ethers after hydrolysis).
• Glycosidic manipulation: Controlled acid-catalyzed hydrolysis to access sub-glycosides and the mogrol core; enzymatic trimming with β-glucosidases for SAR libraries.
• Conjugation strategies: Carbodiimide- or click-chemistry-based tagging after introducing handles (e.g., periodate oxidation of vicinal diols on glucose followed by oxime formation) to produce probes for affinity chromatography or imaging (in vitro research).
• Analytical synthesis: Isotopic labeling of select hydroxyls (e.g., 18O exchange under acidic conditions) for MS mechanistic studies.

Best practices:

• Employ orthogonal protection schemes to address differential reactivity of sugar vs aglycone hydroxyls.
• Monitor reactions by LC–MS and 1H/13C NMR due to the high density of similar functional groups and potential for microheterogeneity.

Target Specificity

Not applicable. This product is a small-molecule triterpene glycoside, not an antibody, probe with a defined protein target, or an engineered biologic. No antigen/epitope, clone, isotype, or species-reactivity information applies.

For researchers studying molecular interactions, any target engagement (e.g., with taste receptors or enzymes) should be established experimentally under your specific assay conditions and documented in your study rather than inferred from this catalog entry.