Osmanthuside B - ≥98% , CAS No.94492-23-6

CAS: 94492-23-6 Cat. No.: O1445779 Formule: C₂₉H₃₆O₁₃ Poids moléculaire: 592.59

GRADE & PURITY ≥98%

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Vue d’ensemble

Osmanthuside B can be isolated from Pseuderanthemum carruthersii (Seem.) Guill. var. atropurpureum (Bull.) Fosb and has weak acetylcholinesterase inhibitory activity.

Specifications

Spécifications et pureté

≥98%

Conditions de stockage de stockage

Store at 2-8°C,Protected from light

Expédié en

Wet ice

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Type d'action

INHIBITOR

Pureté

≥98%

Noms et identifiants

Poids moléculaire

592.59

Application Protocols

No manufacturer-validated protocols are provided for this item. The following are literature-based, general-purpose outlines to assist method development; they are not product specifications.

• Preparation of analytical stock solution:

  1. Warm vial to room temperature protected from light.
  2. Dissolve in methanol or DMSO to 10–20 mg/mL; vortex until homogeneous.
  3. Aliquot into amber vials; purge headspace with nitrogen; store as indicated under Storage.

• LC-MS purity check:

  • Column: C18, 100 × 2.1 mm, 1.7–3 µm.
  • Mobile phase A: water + 0.1% formic acid; B: acetonitrile.
  • Gradient: 5%→40% B over 10–15 min; flow 0.3 mL/min; 30–40°C.
  • Detection: UV 280/330 nm; ESI− scan 150–1500 m/z.

• DPPH antioxidant assay (example):

  • Prepare 0.06 mM DPPH in methanol. Mix 1 part sample solution (serially diluted in MeOH) with 19 parts DPPH, incubate 20 min in dark, read at 517 nm. Include Trolox as a positive control.

Adapt and validate all conditions for your specific instrumentation and research objectives.

Biological Roles

Literature/general information (not a statement of therapeutic use):

• Natural occurrence: Osmanthuside B is a phenylethanoid glycoside reported from Osmanthus fragrans and allied Oleaceae species as part of their specialized metabolite profile.
• Putative plant functions: Phenylethanoid glycosides are implicated in defense against oxidative stress and herbivory, acting as radical scavengers and UV screens within plant tissues.
• Chemical features underlying activity: Multiple phenolic hydroxyls and a conjugated cinnamoyl system confer electron-donating capacity, enabling radical stabilization in redox assays.
• Biotransformation (general): In biological systems, glycosides can undergo enzymatic hydrolysis (β-glucosidases) to release aglycones; cinnamoyl esters are susceptible to esterases. Subsequent phase II conjugation (glucuronidation/sulfation) is common for phenolics (literature).
• Analytical biomarkers: As a chemotaxonomic marker, it aids in profiling of Osmanthus extracts, supporting source authentication and quality evaluation.

Note: These points describe biochemical context and should not be interpreted as medical or clinical claims. This product is intended strictly for research use.

Buffer Applications

Osmanthuside B is not a buffering agent and is not used to control solution pH. However, it is frequently handled in aqueous buffers for biochemical assays and stability studies.

• Practical guidance (literature/general):

  • Use near-neutral buffers (e.g., 10–50 mM phosphate, HEPES, or acetate around pH 6.0–7.4) to limit ester and glycosidic cleavage.
  • Minimize buffer ionic strength for certain binding/transport assays to reduce matrix effects.
  • Include antioxidants (e.g., ascorbate, sodium metabisulfite) only if compatible with detection; note they interfere with redox assays.
  • Filter sterilize (0.22 µm) and prepare fresh immediately before use; phenolic oxidation is light- and oxygen-promoted.

• Avoid:

  • Strongly basic buffers (≥ pH 9), which accelerate saponification and phenolate formation.
  • Strongly acidic buffers (≤ pH 3), which promote glycosidic hydrolysis.

For precise pH-stability profiles and buffer compatibility, consult your method development data; item-specific buffer specifications are not provided.

Green Alternatives

Because Osmanthuside B functions primarily as an analyte/standard rather than a process solvent or reagent, “greener alternative” considerations focus on solvent systems and sample-prep choices used with it.

• Greener solvent choices for dissolution and chromatography (literature/general):

  • Prefer ethanol–water over methanol–water when performance is acceptable; ethanol is less toxic and bio-based.
  • Replace acetonitrile with aqueous ethanol or acetone–water where chromatographic selectivity permits.
  • Use supercritical CO2 is generally unsuitable due to high polarity of phenylethanoid glycosides; requires polar modifiers.

• Sample preparation:

  • Solid-phase extraction using water/ethanol elution reduces chlorinated solvent usage.
  • Employ aqueous two-phase systems (ATPS) for plant matrix partitioning as a greener alternative to LLE with dichloromethane.

• Comparison snapshot (general guidance):

  • Methanol vs ethanol: similar elution strength on RP-LC; EtOH is greener but raises backpressure; verify pump limits.
  • Acetonitrile vs ethanol: ACN offers lower viscosity and sharper peaks; EtOH is greener but may require higher temperature or lower flow to manage viscosity.

Trade-offs are method-dependent; verify analyte stability and detector response when changing solvent systems. These are literature-based recommendations, not item specifications.

Pharmaceutical Uses

No pharmacopeial status or excipient grade is specified for this item. This product is supplied for research use only.

• Research/manufacturing context (literature/general):

  • Reference standard in herbal/raw-material QC for Osmanthus-derived ingredients.
  • System suitability and retention marker in RP-LC analyses of botanical extracts.
  • Impurity/degradation marker in stability-indicating methods for complex natural product mixtures.

• Formulation relevance (general):

  • Due to high polarity and multiple phenolic groups, Osmanthuside B serves as a challenging analyte to test extraction efficiency, matrix effects, and recovery in bioanalytical method validation.

No claims are made regarding therapeutic application, dosage, or clinical performance. For regulated use, establish method-specific validation with appropriate certified reference materials as required.

Physical Properties

Item-specific physical data were not supplied for this catalog entry. Do not treat the following literature guidance as specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Phenylethanoid glycosides often decompose upon heating; discrete melting transitions are uncommon (literature, qualitative).
• Boiling point: Not applicable (nonvolatile polyol; literature).
• Solubility (literature/general):
  • Highly soluble in polar protic solvents (water, methanol, ethanol) and DMSO.
  • Poorly soluble in nonpolar solvents (hexanes, toluene) due to multiple hydroxyls and glycosidic functionality.
• Partition behavior (literature): Strongly hydrophilic; expected low logP and high H-bonding capacity; favors reversed-phase retention with aqueous-organic eluents.
• Optical activity: Expected due to chiral sugar residues; specific rotation is compound- and solvent-dependent (literature).
• UV/Vis (literature): Cinnamoyl chromophore typically shows λmax around 325–335 nm (π–π* of caffeoyl) with additional absorbance near 280 nm from phenolics; exact maxima depend on substitution and pH.
• Stability considerations (general): Sensitive to strong acid or base (glycosidic hydrolysis/ester saponification). Phenolic oxidation can occur; exclude light and oxygen for best stability.

For absolute, item-specific values (mp, optical rotation, water content, UV cutoff, and metal/peroxide limits), consult the product’s CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet for purity, residual solvents, water content, and chromatographic criteria.

• Typical quality expectations for a research-grade natural product standard (general guidance):

  • Identity confirmation by HPLC/UPLC retention, MS, and/or NMR.
  • Purity often reported by HPLC area % at specified detection wavelengths (e.g., 254/330 nm for phenylethanoid chromophores).
  • If present, stabilizers/antioxidants should be declared on the CoA; none are specified here.

• What the grade implies (general definitions):

  • Analytical/reference grade: suitable as a reference standard for method development, system suitability, and quantitative assays.
  • Research grade: intended for R&D; not manufactured under GMP unless otherwise noted.

• Chromatography considerations (general):

  • Low UV background and defined λmax aid in sensitive detection for QC.
  • For quantitative work, use calibrated balances, verified purity, and correct response factors; consider water-of-crystallization where applicable.

Refer to the product’s CoA/Spec Sheet for definitive acceptance criteria, impurity profiles, and any stabilizer or counter-ion information.

Reaction and Applications

Primary use of Osmanthuside B in research is as a phytochemical reference standard and as a probe compound in antioxidant, radical-scavenging, and enzyme-modulating assay platforms. The following are research-oriented, literature-based applications (not product specifications):

• Analytical/QC applications:

  • Marker compound for Osmanthus fragrans and related herbal matrices; supports authentication and standardization.
  • LC-UV/LC-MS method development leveraging cinnamoyl chromophore (detect at ~330 and 280 nm; literature).
  • Stability-indicating studies: monitors ester/glycosidic integrity under stress (pH, heat, light).

• Chemical reactivity studies:

  • Controlled hydrolysis: acidic hydrolysis cleaves glycoside; basic conditions saponify the cinnamoyl ester—useful for structural confirmation.
  • Derivatization: per-O-acetylation of sugars (Ac2O/pyridine) or methylation of phenols (diazomethane or MeI/Ag2O) to simplify NMR/GC analysis (literature general practice).

• Bioassay platforms (in vitro research only):

  • DPPH/ABTS radical scavenging, FRAP assays as antioxidant benchmarks (mechanistic, non-clinical).
  • Enzyme interactions (e.g., tyrosinase, α-glucosidase) for mechanism studies; report activity context and controls.

• Practical tips:

  • Prepare fresh solutions, protect from light, and sparge with inert gas if long runs are anticipated.
  • Validate recovery in sample preparation; adsorption to plastics can occur at low µg/mL—use silanized glass where possible.

Reaction Conditions

General, literature-based conditions relevant to handling and derivatizing phenylethanoid glycosides such as Osmanthuside B (not product specifications):

• Hydrolysis:

  • Acidic glycosidic cleavage: 0.1–2 M HCl or TFA, aqueous or MeOH/H2O, 50–90°C, 0.5–6 h; monitor by LC-MS for aglycone release.
  • Basic saponification of cinnamoyl ester: 0.05–0.5 M NaOH or K2CO3 in MeOH/H2O or aqueous buffer, 0–25°C, minutes to hours.

• Derivatization for analytics:

  • Per-O-acetylation: Ac2O/pyridine or Ac2O/catalytic DMAP, 0–25°C, 1–12 h.
  • Phenolic methylation: MeI/K2CO3 (acetone, rt–50°C) or diazomethane (Et2O, 0–5°C; use extreme caution).
  • Silylation: BSTFA + 1% TMCS in anhydrous acetonitrile, 60–70°C, 30–60 min for GC.

• Antioxidant assays (in vitro set-up examples):

  • DPPH: 0.02–0.1 mM DPPH in MeOH; analyte 1–100 µM; measure at 517 nm after 10–30 min in dark.
  • ABTS•+: pre-generate radical; measure reduction at 734 nm; maintain pH ~7.4.

• Chromatography (RP-LC):

  • Mobile phase: water + 0.1% formic acid / acetonitrile or ethanol gradients.
  • Detection: 280 and ~330 nm; ESI-MS in negative mode often gives strong [M–H]− for phenolic glycosides.

Adjust conditions based on your equipment, safety protocols, and specific experimental goals.

Safety and Handling

• GHS information: Not specified for this item; refer to SDS for authoritative hazard classification, signal word, pictograms, and H-statements.
• General hazard profile (phenylethanoid glycoside; literature): Typically low volatility and low acute hazard; may cause irritation to eyes/skin/respiratory tract as fine powder. Avoid inhalation and contact.
• Recommended PPE: Lab coat, safety glasses or goggles, suitable gloves (e.g., nitrile). Use a dust mask or handle in a fume hood if particulate generation is possible.
• Handling notes:
  • Protect from light and air to minimize phenolic oxidation.
  • Avoid strong acids/bases that can cleave glycosidic or ester linkages.
  • Use clean, dry tools; minimize moisture ingress if weighing for analytical purposes.
• Incompatibilities (general): Strong oxidizers; strong acids/bases; enzymes that hydrolyze glycosides/esters if enzymatic stability is a concern.
• First aid (general guidance; consult SDS):
  • Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; seek medical advice.
• Spill/leak: Avoid dust formation; collect with inert absorbent; dispose according to institutional and local regulations.
• Fire safety: Use water spray, CO2, dry chemical, or foam as appropriate for surrounding materials.

Always defer to the product-specific SDS for definitive safety information.

Solvent Selection

Osmanthuside B is a highly polar, polyhydroxylated phenylethanoid glycoside. Solvent choice should reflect its hydrophilicity and phenolic character.

• Polarity/miscibility profile (literature/general):

  • Excellent solubility: water, methanol, ethanol, DMSO.
  • Moderate: aqueous acetonitrile or aqueous acetone mixtures.
  • Poor: nonpolar organics (hexanes, cyclohexane, toluene, MTBE).

• Practical choices by application:

  • Analytical stocks: 10–50 mg/mL in methanol or DMSO; dilute with water or buffer just before use to minimize hydrolysis/oxidation.
  • Preparative chromatography: dissolve in minimal methanol/water (e.g., 50–80% MeOH) for injection on reversed-phase columns.
  • Bioassays: prepare in aqueous buffer with a small percentage of ethanol or DMSO to aid dissolution; filter through 0.22 µm.

• pH considerations: Avoid strong acid/base; near-neutral pH reduces risk of ester/glycoside cleavage. Phenolic ionization at high pH increases hydrophilicity but compromises stability.

• Comparison (general):

  • Methanol vs ethanol: MeOH offers slightly higher solvating power; EtOH is a greener, less toxic alternative with similar performance for most uses.
  • DMSO: maximal solvency for concentrated stocks; consider final DMSO % limits in bioassays.

Always verify solubility empirically for the specific batch; the above are literature-based guidelines, not product specifications.

Storage and Reconstitution

• Supplied storage guidance (item-specific):

  • Store at 2–8°C, protected from light (provided).
  • Shipped on wet ice (provided).

• General handling to maintain integrity:

  • Allow container to equilibrate to room temperature before opening to minimize moisture condensation.
  • Work under subdued light; reseal promptly. Consider inert gas backfill after each use.

• Reconstitution (general/literature):

  • Dissolve in methanol, ethanol, water, or DMSO depending on application. Start with small volumes and increase as needed to achieve target concentration.
  • Filter sterilize solutions (0.22 µm) for bioassays.

• Solution stability:

  • No item-specific stability data are provided. In absence of data, prepare fresh solutions for critical assays and store short-term at 2–8°C protected from light.
  • Avoid strong acid/base to prevent hydrolysis; minimize freeze–thaw cycling by aliquoting.

For definitive shelf-life, solution stability, and any special stabilizers, consult the product’s CoA/Spec Sheet and SDS. This product is for research use only.

Structure and Identity

Osmanthuside B is a plant-derived phenylethanoid glycoside isolated from Osmanthus species and related taxa. It belongs to the multifunctional glycosylated cinnamyl alcohol/catechol family commonly encountered in chemotaxonomic studies of Oleaceae.

• Item-specific identifiers

  • CAS: 94492-23-6 (provided)
  • 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, not item-specific specifications)

  • Core scaffold: a phenylethanoid (hydroxy-phenethyl) unit esterified with a hydroxycinnamoyl (e.g., caffeoyl) group.
  • Glycosylation: typically a disaccharide (glucosyl-linked) attached via O-glycosidic linkage to the phenylethanoid; multiple phenolic hydroxyls are present.
  • Functional groups: phenols, an ester (cinnamoyl), primary/secondary alcohols in sugar residues, and acetal linkages.
  • Stereochemistry: multiple defined stereocenters reside in the sugar moieties (D-pyranoses); E-geometry across the cinnamoyl double bond is typical in phenylethanoid glycosides (literature).

• 2D structure (verbal depiction; literature)

  • A hydroxycinnamate aryl ring (often catechol) bearing an E-CH=CH-COO– linkage that esterifies a glucopyranose; the sugar is further O-glycosidically linked to a hydroxyphenethyl ring system, generating a compact, polyhydroxylated amphipathic molecule.

Synthetic Utility

Although not commonly used as a synthetic building block, Osmanthuside B can inform or participate in synthetic studies focused on glycosylation, protection strategies, and phenolic chemistry (literature/general):

• Functional group handles:

  • Multiple alcohols (sugar hydroxyls) amenable to selective protection (Ac, Bz, TBDMS) for structural elucidation.
  • Phenolic OH groups allowing etherification/esterification to generate derivatives for SAR or analytical derivatization.
  • Cinnamoyl ester that can be selectively hydrolyzed (base) or migrated under specific conditions.

• Typical transformations:

  • Per-O-acetylation/per-O-benzoylation for NMR/GC amenability and crystallinity improvement.
  • Methylation or silylation of phenols for volatility and MS ionization modulation.
  • Enzymatic or acidic hydrolysis to access aglycone or monosaccharide conjugates for comparative studies.

• Synthesis context:

  • Serves as a target or intermediate benchmark in total/semi-synthesis of phenylethanoid glycosides, helping optimize glycosyl donors, protecting-group patterns, and esterification sequences.

These points are literature-based and intended for planning of research-scale transformations; no item-specific reactivity guarantees are implied.

Target Specificity

This product is a small-molecule natural product, not a biological targeting reagent or antibody. No antigen, epitope, clone, isotype, or species reactivity applies.

• Item-specific targeting data: Not applicable.
• If used in biochemical assays, any observed “specificity” pertains to assay design (e.g., enzyme selectivity) and must be empirically determined for the system under study.

Foire aux questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C, protected from light. The material is light-sensitive — keep it in its original opaque or amber container.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 94492-23-6, the molecular formula is C29H36O13, and the molecular weight is 592.59 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.