3α-Hydroxymogroside IA1 , CAS No.H1453548

CAS: H1453548 Cat. No.: H1453548 Fórmula: C₃₆H₆₂O₉ Peso molecular: 638.87

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

3α-Hydroxymogroside IA1 is a mogroside derivative.

Specifications

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

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Nombres e identificadores

• Peso molecular: 638.87

Application Protocols

No validated, item-specific protocols are provided for this SKU. The following general, non-binding guidance can support common research workflows.

• Preparation of analytical stock (general)

  • Dissolve the solid in DMSO or MeOH to prepare a concentrated stock (e.g., 10–50 mg/mL). Sonication and gentle warming (≤40 °C) can aid dissolution. Filter (0.2 µm PTFE/PVDF).
  • For LC–MS, dilute the stock into water/ACN or water/MeOH with 0.05–0.1% formic acid or ammonium acetate.

• HPLC method sketch (general)

  • Column: C18, 2.1 × 100 mm, 1.7–3 µm.
  • Mobile phase A: water + 0.1% FA; B: ACN.
  • Gradient: 10%→40% B over 15 min; flow 0.3 mL/min; 30 °C.
  • Detection: ELSD/CAD or MS (ESI+). Use negative controls and system suitability standards.

• NMR sample prep (general)

  • 5–15 mg in DMSO-d6 or CD3OD; acquire 1H, 13C, HSQC, HMBC, COSY/TOCSY for full assignment.

• Note: These are generalized procedures. Optimize for your instruments and matrices. For research use only.

Biological Roles

This section summarizes general, literature-based biology of mogroside-class triterpene glycosides; it is not specific to the supplied batch and makes no clinical claims.

• Natural origin (literature)

  • Mogrosides are cucurbitane-type triterpenoid saponins from Siraitia grosvenorii (monk fruit), where they function as specialized metabolites likely involved in plant defense and attraction.

• Biochemical characteristics (literature)

  • Exhibit amphiphilic behavior (hydrophobic aglycone + hydrophilic sugars), enabling interactions with membranes and proteins.
  • Undergo phase II metabolism (e.g., glucuronidation/sulfation) and deglycosylation by glycosidases in biological systems; specific pathways depend on glycan pattern.

• Receptor interactions (biophysical context)

  • Sweet-tasting mogrosides are known to engage the T1R2/T1R3 sweet taste receptor complex in taste assays. Substituent and glycosylation patterns modulate potency and receptor engagement; the 3α-hydroxyl may influence conformation and hydration shell.

• Experimental utilities

  • Serve as standards for quantifying mogroside content in botanical materials.
  • Useful substrates for enzyme specificity studies (β-glucosidases, glycosyltransferases) to elucidate glycosidic bond stability and regioselectivity.

• Note: Specific bioactivity magnitudes, ADME parameters, or in vivo outcomes are highly context-dependent and are not provided here. For laboratory research use only.

Buffer Applications

This compound is not a buffering reagent and has no defined buffering range. Typical biological buffers (e.g., phosphate, HEPES, MES) should be selected independently for assays involving 3α-hydroxymogroside IA1. See Solvent Selection and Application Protocols for dissolution and handling guidance.

Green Alternatives

For this hydrophilic glycoside, greener practice centers on solvent choice during analytics and purification rather than replacing the compound itself.

• Preferable solvent systems (general guidance)

  • Water–ethanol or water–methanol mixtures for extraction and prep work, avoiding chlorinated solvents.
  • Aqueous mobile phases with volatile modifiers (e.g., formic acid, ammonium acetate) for LC–MS to reduce hazardous waste.

• Comparison (general; not item-specific) | Use case | Greener option | Conventional alternative | Trade-offs | |---|---|---|---| | Extraction of plant matrices | 50–80% ethanol–water | Methanol, acetone, CH2Cl2 | EtOH-water safer, but may co-extract more polar impurities; requires defatting step | | Analytical HPLC | Water/ACN with 0.1% FA | Water/MeOH (flammable), buffers with phosphate | ACN has higher cost/tox profile vs MeOH; both volatile and MS-friendly | | Sample dissolution | Water or EtOH (if soluble) | DMSO | Water/EtOH greener; DMSO offers superior solubility and stability |

• Operational improvements

  • Scale down method development (microbore LC, UHPLC) to reduce solvent consumption.
  • Implement solvent recycling for ACN/MeOH streams where validated.
  • Use room-temperature crystallizations/evaporation under reduced pressure rather than high-temperature drying.

• Always balance green choices with analytical fitness, recovery, and compound stability.

Pharmaceutical Uses

No pharmacopeial monograph or excipient grade is specified for this item; refer to the CoA/Spec Sheet. The following are general, literature-based contexts for mogroside-class materials and do not constitute medical claims.

• Reference and QC standard

  • Applied as a reference standard for raw-material identity/purity testing and content uniformity in botanical-derived products.

• Formulation-relevant properties (general)

  • High aqueous/alcohol solubility of glycosides can aid preparation of analytical standards or laboratory prototypes.
  • As non-volatile, low-UV saponins, mogrosides often require ELSD/CAD or MS for QC release testing.

• Manufacturing considerations (general)

  • Hygroscopicity and susceptibility to hydrolysis under strong acid/base necessitate neutral pH handling and low-temperature storage.
  • For method transfer, verify system suitability using retention time windows and MS transitions characteristic of the target mogroside family.

• No therapeutic indications, dosage forms, or clinical utilities are provided here. Product is for research use only.

Physical Properties

• Item-specific properties

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

• General/literature expectations for mogroside-type saponins (not item specifications)

  • Physical state: Typically isolated as off-white to pale amorphous solids or microcrystalline powders.
  • Solubility: Good in water, methanol, ethanol, and DMSO; poor in nonpolar solvents (e.g., hexanes, toluene) due to extensive hydroxylation and glycosylation.
  • Melting/Decomposition: Often show broad melting with pre-decomposition rather than a sharp mp.
  • LogP/logD: Apparent lipophilicity is low because of sugar residues; partitioning favors aqueous or alcohol phases.
  • Optical rotation: Typically exhibits significant specific rotation from multiple stereocenters (value is structure- and sample-dependent).
  • UV: Weak chromophores; absorb mainly in deep UV (<210–220 nm). Derivatization (e.g., with chromophoric reagents) or ELSD/CAD often preferred for HPLC.

• Analytical hints (general)

  • HPLC: Reverse-phase C18 with aqueous ACN/MeOH and volatile modifiers (e.g., 0.1% formic acid) common; detection via ELSD/CAD/MS.
  • MS: Positive-mode ESI typically yields [M+H]+/[M+Na]+; multiple neutral losses of hexose units are diagnostic.
  • These are literature-based generalities; consult the item’s CoA for definitive specifications.

Quality and Grades

• Item-specific quality data

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

• What grade means in practice (general guidance)

  • For complex natural products like mogroside derivatives, suppliers typically report: purity by HPLC/ELSD or CAD, identity by HRMS and NMR (1H/13C), and water content (Karl Fischer) when relevant. Low-UV analytes often rely on ELSD/CAD % area for purity.
  • Absence of a named grade (e.g., “HPLC grade,” “analytical standard”) indicates researchers should verify fitness-for-use via their own analytical controls (HPLC-MS, NMR, optical rotation).

• Stabilizers/additives

  • Natural product reference materials are commonly shipped without stabilizers. If any stabilizer or counterion is present, it will be disclosed on the CoA. None are specified here.

• Batch-to-batch considerations (general)

  • Trace co-extracted congeners (other mogrosides) can co-elute; orthogonal methods (HILIC vs RP, different gradients, MS fragmentation) help confirm purity.
  • Monitor for hydrate content and microheterogeneity in saccharide substitutions; report purity on an anhydrous basis when comparing across lots.

• Recommendation

  • Prior to quantitative work (e.g., calibration standards), verify purity and assign an in-lab purity factor based on your chromatography method, referencing the item’s CoA.

Reaction and Applications

• Typical research uses (general for mogrosides; expand upon catalog context)

  • Analytical reference standard for profiling monk-fruit constituents in raw materials, extracts, and formulations via LC–MS/ELSD.
  • Metabolomics and biotransformation studies: substrate for glycosidases or oxidoreductases to map de-glycosylation and site-selective oxidations.
  • Structure–sweetness correlation studies (biophysical/biochemical) given the mogroside scaffold’s interaction with taste receptors; no clinical claims implied.

• Chemical manipulation (general transformations)

  • Per-O-acylation/benzoylation of sugar hydroxyls to aid chromatographic handling and crystallinity.
  • Selective deprotection or enzymatic trimming of glycosides to access series of analogs (IA, IIA, etc.).
  • Oxidation at secondary alcohols (TEMPO/BAIB or Dess–Martin) to carbonyls for derivatization; protect other OH groups as needed.

• Analytical method development

  • Use MS/MS neutral-loss scanning (−162 Da for hexose) to fingerprint glycan count.
  • Implement ion-pair-free reverse-phase conditions for MS compatibility; consider HILIC for early eluters with minimal chromophores.

• Practical tips

  • Dry thoroughly under high vacuum over P2O5 or in a desiccator to constant mass before preparing standards.
  • Minimize exposure to strong acid to prevent hydrolysis of glycosidic linkages; maintain neutral to mildly acidic mobile phases for LC.

Reaction Conditions

The following are general literature conditions relevant to mogroside-class glycosides; they are provided as guidance for method development and are not item-specific specifications.

• Protection/Acylation

  • Reagents: Ac2O/pyridine or BzCl/DMAP; Solvent: pyridine or CH2Cl2 with catalytic DMAP; Temp: 0 °C to rt; Time: 2–18 h. Workup with aqueous NaHCO3; monitor by LC–MS.

• Selective Oxidation of Sugar OH

  • TEMPO (0.1–0.2 equiv), BAIB (1.5–2.0 equiv); Solvent: CH2Cl2/MeCN or water/MeCN; Temp: 0–25 °C; Time: 1–4 h. Quench with Na2S2O3; isolate by RP-HPLC.

• Dess–Martin Oxidation (secondary OH)

  • DMP (1.5 equiv) in CH2Cl2; 0–25 °C, 0.5–3 h. Avoid excess acid; promptly remove iodine byproducts.

• Sulfation

  • Reagent: SO3·pyridine complex (3–5 equiv); Solvent: DMF or pyridine; Temp: 0–25 °C; then neutralize to form sodium salts. Purify by desalting RP cartridges.

• Enzymatic Deglycosylation/Transglycosylation

  • Enzymes: β-glucosidase or engineered glycosyltransferases; Buffer: 50 mM phosphate or acetate, pH 5–7; Temp: 25–40 °C; Time: hours–days. Analyze by LC–MS/MS.

• Typical solvents

  • DMSO, MeOH, EtOH, MeCN, water mixtures suit dissolution; avoid prolonged strong acid/base to preserve glycosidic bonds.

• Expected outcomes

  • Yields and selectivity are substrate- and position-dependent; verify site-selectivity via 2D NMR and HRMS before scale-up.

Safety and Handling

• GHS classification (from Product Data)

  • 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.
  • GHS Classification: Not specified for this item; refer to SDS.

• General laboratory safety (not item-specific; follow your institutional SOPs)

  • PPE: Lab coat, safety glasses, and nitrile gloves. Use a chemical fume hood for weighing and solution prep to control dust/aerosols.
  • Handling: Avoid inhalation of powders; hygroscopic tendencies are common among glycosides—cap vials promptly. Prepare solutions with clean, dry glassware to avoid microbial contamination.
  • Incompatibilities: Strong oxidizers and strong acids/bases may degrade glycosidic linkages. Avoid prolonged exposure to elevated temperatures or direct light.
  • First aid (overview): If inhaled—move to fresh air; if on skin/eyes—rinse with water for several minutes; if ingested—rinse mouth. Seek medical attention per SDS guidance.
  • Waste: Collect solutions/solids in nonhalogenated organic or aqueous waste streams as appropriate; follow local regulations.

• Special risks (general for saponins)

  • Saponins can be surfactant-like; avoid foaming and aerosol formation. Thermal degradation can occur before melting; avoid hot plates for drying—use vacuum at ambient temperature.

• Always consult the product-specific SDS and your institution’s EHS guidance for authoritative hazard and response information.

Solvent Selection

• Polarity and solubility class (general for glycosides; not item-specific specs)

  • Highly polar compound due to multiple hydroxyls and sugars; typically soluble in water, methanol, ethanol, and DMSO; sparingly to insoluble in nonpolar solvents (hexanes, toluene, CPME).

• Recommended solvent systems by use case (general)

  • Analytical standard prep: DMSO stock (e.g., 10–50 mg/mL), then dilute into aqueous-organic mobile phase (ACN/H2O or MeOH/H2O) to minimize precipitation.
  • Preparative purification: Aqueous MeOH/ACN with volatile modifiers (0.05–0.1% FA or NH4OAc) for RP-HPLC; HILIC may aid separation from closely related mogrosides.
  • NMR: DMSO-d6 or CD3OD provide good solubility and well-resolved spectra for saccharide protons; exchangeable OH signals are temperature- and solvent-dependent.

• Comparison (general)

  • Water: green, biocompatible; limited stability for long-term storage due to hydrolysis/bioburden risk.
  • MeOH/EtOH: strong solvating power for glycosides; flammable; compatible with ELSD/CAD.
  • DMSO: excellent solvency and stability; viscous—use small aliquots and warm gently to aid dissolution.

• Tip

  • Filter through 0.2 µm PTFE or PVDF after dissolution to remove particulates; avoid nylon if using strong acidic modifiers due to potential interaction.

Storage and Reconstitution

• Item-specific storage/shipping (from Product Data)

  • Storage: Store at -20°C.
  • Shipped in: Ice chest + Ice pads.

• General storage guidance for mogroside glycosides (not item-specific)

  • Keep tightly sealed in an inert atmosphere (e.g., argon/nitrogen headspace) with desiccant to limit moisture uptake.
  • Protect from light and repeated freeze–thaw. If frequent access is needed, pre-aliquot into single-use vials.

• Reconstitution (general)

  • Preferred solvents: DMSO, methanol, ethanol, or water depending on application. Begin with a small volume, vortex, and sonicate briefly. Gentle warming (≤40 °C) may help.
  • After dissolution, store solutions at -20 °C (or lower) in amber vials. For aqueous solutions, consider adding sterile filtration and storing at 2–8 °C short-term to mitigate hydrolysis/bioburden.

• Stability notes (general)

  • Avoid prolonged exposure to strong acids/bases and elevated temperatures to preserve glycosidic bonds.
  • Document concentration and date of preparation on each aliquot; check for precipitation or degradation by HPLC–MS prior to critical use.

• For any missing item-specific details (e.g., exact solubility, concentration limits), please consult the product’s CoA/Spec Sheet.

Structure and Identity

A cucurbitane-type triterpenoid saponin derived from the mogroside family (monk-fruit glycosides), bearing an additional 3α-hydroxyl on the aglycone relative to mogroside IA1.

• Item-specific identifiers (from Product Data)

  • SKU: H1453548
  • Product Name: 3α-Hydroxymogroside IA1
  • CAS: H1453548 (catalog placeholder; Not a registry CAS)
  • InChIKey: 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 (general/literature description)

  • Core: Tetracyclic cucurbitane triterpene (mogrol-type) with multiple secondary/tertiary alcohols.
  • Glycosylation: One or more β-D-glucose residues (typical of mogrosides) ester/ether-linked at side-chain positions; precise glycan count/linkage pattern should match IA1 lineage (literature) but is not item-specified here.
  • Key modification: 3α-OH at C-3 of the aglycone (alpha configuration at the A-ring), distinguishing it from mogroside IA1.
  • Functional groups: Multiple alcohols (aglycone + sugars), glycosidic linkages, and possible acetal motifs within saccharides.

• 2D structure (verbal)

  • A compact four-ring hydrophobic nucleus (cucurbitane) bearing several hydroxyls, extended by a polar oligosaccharide tail attached via a glycosidic bond. The 3α-hydroxyl projects axially from ring A, while sugar hydroxyls create a dense hydrogen-bonding periphery.

Synthetic Utility

While primarily a natural-product standard, 3α-hydroxymogroside IA1 is a versatile scaffold for derivatization in carbohydrate and triterpenoid chemistry (general literature guidance below).

• Functional group handles

  • Multiple secondary alcohols (sugar + aglycone) enable selective acylation, carbamate formation, and carbonate installation.
  • Glycosidic linkages can be enzymatically cleaved or extended for chemoenzymatic synthesis of analog libraries.

• Strategic transformations

  • Per-O-protection (Ac, Bz) to modulate polarity and enable crystallization/X-ray.
  • Site-selective oxidation (e.g., TEMPO/BAIB for primary alcohols; Dess–Martin for secondary OH) to install carbonyls for further elaboration (e.g., reductive amination on sugar residues after oxidation to aldehydes).
  • Sulfation/phosphorylation of selected hydroxyls to probe transport/solubility changes.
  • Glycosylation remodeling via glycosyltransferases or transglycosylation to tune physicochemical properties and receptor interactions.

• Retrosynthetic value

  • Provides access to the mogrol aglycone (via controlled hydrolysis) and to a panel of partial glycosides, facilitating SAR mapping across sweetness receptor assays or biophysical binding models.

• Analytical control

  • Track modifications by LC–MS/MS with neutral-loss scans for hexose units; 1D/2D NMR (HSQC, HMBC, TOCSY) to assign regioselectivity of derivatization.

Target Specificity

Not applicable. This product is a small-molecule triterpene glycoside, not an antibody or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity applies.