Flavone glycoside from Robinia with antibacterial and diuretic properties; derived from kaempferol. The ability of robinin to reverse the multidrug resistance of the human colon cancer cell line Colo 320 expreβing MDR1/LRP was explored by monitoring their
Condições de armazenamento de armazenamento
Protected from light,Store at -20°C
Enviado em
Ice chest + Ice pads
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This compound belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
External Descriptors
flavonols
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.
Soluble：DMSO，Pyridine, Methanol, Ethanol etc. ( < 1 mg/ml refers to the product slightly soluble or insoluble )
Sensibilidade
Light sensitive
Ponto de inflamação (°F)
Not applicable
Ponto de inflamação (°C)
Not applicable
Peso molecular
740.700 g/mol
XLogP3
-2.200
Hydrogen Bond Donor Count
11
Hydrogen Bond Acceptor Count
19
Rotatable Bond Count
8
Exact Mass
740.216 Da
Monoisotopic Mass
740.216 Da
Topological Polar Surface Area
304.000 Ų
Heavy Atom Count
52
Formal Charge
0
Complexity
1260.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
15
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
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Application Protocols
No manufacturer-tested biological assay protocols are provided for this SKU. The following are general, literature-based examples to guide laboratory use; optimize for your system.
Preparation of stock solutions:
Weigh robinin quickly under low light. Dissolve in DMSO to 10–50 mM or in methanol to 1–10 mg/mL. Vortex and sonicate gently if needed. Filter (0.22 µm PVDF) for LC applications.
LC–UV/LC–MS calibration curve (illustrative):
Mobile phase A: H2O + 0.1% formic acid; B: MeOH.
Column: C18, 2.1 × 100 mm, 1.7–3 µm. Flow: 0.3 mL/min. Gradient: 10–60% B in 15 min.
Prepare standards 0.05–50 µg/mL by serial dilution in initial mobile phase. Inject 2–5 µL; detect at 350 nm (band I) and confirm by MS (ESI−).
Prepare 0.1 mM DPPH in methanol. Mix 100 µL robinin solution with 3.9 mL DPPH solution to achieve 5–100 µM final. Incubate 25°C, dark, 30 min; read A517 against blank. Include standard antioxidant for comparison.
Enzymatic deglycosylation mapping:
Buffer: 50 mM sodium acetate, pH 5.0. Add α-L-rhamnosidase (and subsequently β-galactosidase). 25–37°C, 2–16 h. Analyze aliquots by HPLC for intermediate glycosides and kaempferol.
These examples are for research use only and should be validated for precision, accuracy, and robustness in your laboratory.
Biological Roles
Literature/general background (no medical claims):
Chemical class: Robinin is a kaempferol triglycoside—kaempferol 3-O-robinoside-7-O-rhamnoside—comprising one β-D-galactose and two α-L-rhamnose units. Glycosylation modulates solubility, stability, and bioavailability relative to the aglycone.
Plant metabolism: Flavonol glycosides are end-products of the phenylpropanoid pathway. Glycosyltransferases add sugars that aid vacuolar sequestration, transport, and photoprotection. Rhamnosylation/galactosylation patterns are species- and tissue-specific; robinin occurs notably in Robinia spp. and related taxa.
Physiological functions in plants: Roles include UV screening, antioxidant defense, modulation of auxin transport, and interaction with proteins and membranes. Sugar moieties can target compounds to specific cellular compartments and affect recognition by transporters.
Biotransformation: In biological systems, glycosidases can cleave sugars stepwise to release kaempferol. Microbiota-mediated deglycosylation is common in gut or microbial communities. Conjugation (methylation, sulfation, glucuronidation) of aglycone may follow in animal metabolism.
Biophysical properties: Multiple phenolic OH groups confer metal-chelation potential (e.g., Fe3+, Cu2+) and radical-scavenging activity; however, the sugar shell can sterically and electronically modulate chelation and redox behavior.
Analytical biology: Used as a marker for assessing plant stress responses, cultivar chemotypes, and the efficacy of extraction or enzymatic treatment protocols in plant biochemistry.
Note: The above describes general biological roles of flavonol glycosides and robinin as reported in the literature; it does not imply any therapeutic or clinical utility.
Buffer Applications
Robinin is not a buffering agent. It does not establish a defined pH range or buffering capacity.
Practical handling in buffered systems (literature/general):
Preparation for biochemical assays: Dissolve robinin first in a suitable organic solvent (commonly DMSO or ethanol) to prepare a concentrated stock. Dilute into the working buffer with vigorous mixing to achieve the final concentration while maintaining cosolvent ≤1% v/v to preserve protein/enzyme activity.
Compatible buffers: Phosphate, HEPES, MOPS, and acetate buffers at pH 6.0–7.5 are commonly used in assays evaluating polyphenols. Avoid strong basic buffers (pH > 8) that can promote glycosidic hydrolysis and phenolate formation, potentially altering activity and spectra.
Adsorption concerns: Polyphenols can adsorb to plastic surfaces at low concentrations. Use low-bind plastics or glass vials and include minimal nonionic surfactant (e.g., 0.01% Tween 20) if validated not to interfere with the assay.
Filtration: If sterile filtration is required, use hydrophilic PTFE or PVDF membranes. Pre-rinse filters with buffer containing the same cosolvent to minimize analyte loss.
If you require a buffering component for your experiment, select an appropriate buffer system separately; robinin should be treated as an analyte/ligand within that buffered medium.
Green Alternatives
This section typically compares greener substitutes for hazardous solvents or reagents. Robinin is a target analyte/standard rather than a process solvent or bulk reagent, so direct “replacement” is not applicable.
Prefer sustainable solvents for dissolution and workups when compatible with your methods:
Ethanol (bio-based) and water mixtures can replace methanol or acetonitrile for many extraction or preparative chromatography steps when detection sensitivity permits.
2-Propanol/water or ethanol/water can be effective for sample preparation of plant matrices containing robinin, reducing the need for chlorinated solvents.
Chromatography:
For HPLC, consider aqueous ethanol or MeOH in place of MeCN where resolution allows; greener eluents reduce environmental burden.
Energy and waste:
Prepare concentrated stocks (e.g., in DMSO or ethanol) and aliquot to minimize repeat dissolutions and solvent waste.
Safety:
Avoid unnecessary use of strong acids/bases during extraction to limit hazardous neutralization waste and prevent glycoside hydrolysis.
Trade-offs:
Greener solvents may alter selectivity, UV background, or ionization efficiency in LC–MS. Validate method performance (LOD/LOQ, resolution, recovery) when substituting.
Summary: While robinin itself is not replaceable in studies specifically targeting this molecule, greener solvent choices and minimized solvent volumes can significantly improve the sustainability of workflows involving this analyte.
Pharmaceutical Uses
No therapeutic or clinical claims are made for this product. For research use only.
Contextual, literature-based information relevant to formulation and analysis:
Role in pharma labs: Robinin may be used as a reference standard in analytical method development and validation (e.g., identification/quantification of flavonol glycosides in botanical raw materials or complex mixtures that might be used in nonclinical research).
Excipient status: Robinin is not a common pharmaceutical excipient.
Formulation considerations for research prototypes:
Solubility enhancement strategies include cosolvents (ethanol, propylene glycol), complexation (cyclodextrins), or nanoformulations; however, such approaches must be validated for stability because glycosidic bonds are acid/base labile.
pH sensitivity: Avoid high pH during aqueous processing to prevent deglycosylation; maintain neutral to mildly acidic conditions.
Analytical compatibility:
Robust LC–UV/LC–MS methods can monitor robinin alongside related glycosides; use gradient elution with aqueous formic acid and MeCN/MeOH. Track aglycone (kaempferol) formation as a degradation marker under stress conditions.
Regulatory note: If used in regulated environments, ensure traceability to qualified reference materials and maintain full documentation (CoA, SDS, stability data). Any pharmacopeial status for robinin per se is not established (literature); rely on internal method suitability.
All uses must remain within research, development, and quality control contexts without implying therapeutic benefit.
Physical Properties
Item-specific physico-chemical specifications (mp, bp, density, water/peroxide/metal limits, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties for robinin (kaempferol 3-O-robinoside-7-O-rhamnoside):
Physical state/appearance: yellow to yellow-brown amorphous to microcrystalline solid (literature, varies with source and hydration).
Molecular formula and mass: commonly reported as C39H42O20; Mr ≈ 834.7 g/mol (literature).
Solubility: sparingly soluble in water at ambient temperature; soluble in polar protic/apatitic organic solvents such as methanol, ethanol, and highly soluble in DMSO and dimethylformamide (literature). Aqueous solubility improves with mild heating or co-solvents (≤10% v/v DMSO or ethanol) and at alkaline pH where phenolic OH may partially ionize.
LogP/logD: expected low logP and high polarity due to three sugars (literature/estimated); behaves as a highly polar polyphenol.
pKa: multiple phenolic pKa values typically in the ~6–10 range for flavonols; glycosidic substitution can shift acidity modestly (literature, family trend).
UV–Vis: characteristic flavonol bands with λmax in band II (~260–280 nm) and band I (~345–370 nm) depending on solvent and pH (literature). Note: These are general chromophore features, not item specifications.
Thermal behavior: many flavonol glycosides darken and decompose on heating rather than exhibit a sharp melting point (literature). Avoid prolonged exposure to elevated temperatures.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Context for this product type:
Reference/analytical use: Robinin is commonly employed as a phytochemical reference standard in natural products analysis (HPLC/LC–MS) and for biochemical assays probing flavonoid glycosides. For such uses, analytical-grade material emphasizes identity confirmation (NMR/MS), narrow impurity profiles, and low residual solvent.
Chromatographic performance: When marketed for analytical workflows, “HPLC grade” reagents target low non-volatile residue and defined UV backgrounds. For small molecules (standards), the relevant attributes are purity by HPLC/UPLC (area%), water content (Karl Fischer), and residual solvents—none of which are specified here for this item.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Polyphenols are sometimes provided without stabilizers; if present, stabilizers should be disclosed on the CoA.
Identity verification: Typical orthogonal methods include 1H/13C NMR (DMSO-d6/methanol-d4), HRMS (ESI−/ESI+), and chromatographic retention vs. authenticated standards. Glycosidic pattern can be corroborated by MS/MS fragmentation (losses of 146 Da rhamnose, 162 Da hexose) and enzymatic/acid hydrolysis profiles.
Recommendation: Consult the batch-specific CoA for assay (HPLC area%), residual solvents, water content, and any stabilizer information relevant to your regulatory or analytical requirements.
Reaction and Applications
This product is most often used as a reference material and biochemical probe rather than as a commodity reagent.
Research and analytical applications (literature/general):
Phytochemical standard: Calibration of HPLC/UPLC/LC–MS methods for profiling flavonol glycosides in plant extracts. Diagnostic MS/MS losses (−146 rhamnose, −162 hexose) confirm glycosylation pattern.
Antioxidant/ROS-scavenging assays: Evaluated in cell-free systems (DPPH, ABTS, FRAP, ORAC) as a representative kaempferol triglycoside; glycosylation modulates redox properties and solubility. Use neutral buffers and minimize metals to avoid confounding redox cycling.
Enzymology: Substrate or probe for glycosidases (α-L-rhamnosidase, β-galactosidase) to study stepwise deglycosylation; monitoring by HPLC/MS yields kinetic/sequence information.
Stability studies: Acid/base hydrolysis to release aglycone (kaempferol) for quantification or structural confirmation; compare rates across pH and temperature.
Plant metabolism: Marker for biosynthetic and transport processes of flavonoid glycosides; used to validate extraction and sample-prep protocols.
Practical tips:
Use amber glassware and subdued light to limit photo-oxidation of the aglycone chromophore.
Include antioxidants/metal chelators (e.g., 0.1 mM EDTA) only if validated not to interfere with intended assays.
For LC–MS, avoid prolonged exposure to high-pH mobile phases; prefer formic acid (0.05–0.1%) or ammonium formate at pH ≤6.5.
Document exact solvent composition and temperature during dissolution; supersaturation and slow wetting can occur due to extensive hydrogen bonding in the sugar shell.
Reaction Conditions
General, literature-based conditions relevant to robinin and related flavonol glycosides. These are not item-specific specifications.
Acidic hydrolysis (deglycosylation):
Conditions: 0.5–2 M mineral acid (HCl or H2SO4) in 50–80% aqueous methanol or water, 60–90°C, 0.5–4 h.
Outcome: Stepwise cleavage of rhamnose/galactose to release kaempferol; monitor by HPLC (appearance of kaempferol, disappearance of parent).
Enzymatic hydrolysis:
α-L-Rhamnosidase and β-galactosidase in acetate/phosphate buffer (pH 4.5–6.5), 25–40°C, hours to overnight. Sequential additions can map linkage order.
Antioxidant assays (cell-free):
DPPH: ethanol or methanol, 25°C, 15–30 min incubation; measure A517; include Trolox or quercetin as controls.
ABTS: aqueous ethanol, pH ~7.4; pre-generate ABTS•+; read A734 after 6–10 min. Maintain cosolvent ≤1% v/v when diluting DMSO stocks.
LC–MS method development:
Mobile phase: water + 0.05–0.1% formic acid and MeOH/MeCN; column: C18, 2.1–4.6 mm ID; gradient 5→70% organic over 10–25 min.
Detection: UV 260–280 nm (band II) and 340–360 nm (band I); ESI− typically yields deprotonated [M−H]− with characteristic sugar losses.
Stability studies:
Photostability: Protect from UV/visible light; evaluate by storing replicate solutions in amber vs. clear vials.
pH stress: Assess at pH 2, 7, 9 at 25–40°C; anticipate faster degradation at basic pH.
Note: Validate each protocol for your matrix, scale, and instrumentation; adjust times/temperatures to meet your analytical endpoints.
Safety and Handling
Regulatory/GHS for this specific item: Not specified for this item; refer to CoA/Spec Sheet and the product SDS for authoritative safety data.
General laboratory safety guidance for polyphenolic glycosides (literature/best practice):
Hazards: Typically low volatility; dust may cause mechanical irritation to eyes/respiratory tract. Phenolic compounds can cause skin/eye irritation. Avoid inhalation of powders.
PPE: Wear lab coat, nitrile gloves, and safety glasses. Use a dust mask or handle in a fume hood/containment when weighing to minimize airborne particulates.
Handling: Minimize light and air exposure to reduce oxidative degradation. Prepare solutions immediately before use or store aliquots protected from light.
First aid overview: If inhaled—move to fresh air. Skin—wash with soap and water. Eyes—rinse cautiously with water for several minutes; remove contacts if present. Ingestion—rinse mouth and seek medical attention if unwell. Provide SDS to medical personnel.
Spill/leak: Avoid dust generation; sweep up with minimal agitation and collect for disposal. Clean area with water/ethanol. Dispose according to institutional and local regulations.
Fire: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2; firefighters wear self-contained breathing apparatus.
Always consult the product-specific SDS for full GHS classification, pictograms, and H/P statements.
Solvent Selection
Robinin is a highly polar flavonol triglycoside; solvent choice should balance solubility, stability of glycosidic bonds, and compatibility with the intended assay.
Polarity/miscibility profile (literature):
Highly soluble: DMSO, DMF.
Good solubility: methanol, ethanol; hot aqueous alcohols.
Limited solubility: cold water, acetonitrile (improves with water or alcohol cosolvent).
Analytical standards (HPLC/LC–MS): Prepare a concentrated stock in methanol or DMSO (e.g., 1–10 mg/mL), then dilute into initial mobile phase composition (e.g., water/MeCN with 0.1% formic acid). Avoid strong base in diluents to prevent hydrolysis.
Biochemical assays: Use DMSO stocks (e.g., 10–50 mM) and dilute into buffered aqueous media keeping final DMSO ≤1% v/v. For purely aqueous systems, pre-warm and sonicate; small ethanol content (≤2% v/v) aids dissolution.
NMR: DMSO-d6 or methanol-d4 typically provide well-resolved spectra; exchangeable phenolic/sugar OHs may broaden.
Stability considerations:
Acid/base-sensitive: Strong acids/bases can cleave glycosidic bonds; prefer neutral to mildly acidic organic mixtures (MeOH, EtOH, DMSO) for stock preparation.
Comparison (literature-based):
DMSO vs MeOH: DMSO offers superior solubility and long-term stock stability; MeOH is more volatile and MS-friendly but may support slow transesterification in strong acid/base conditions.
Storage and Reconstitution
Storage conditions (item-specific from Product Data):
Store at −20°C.
Protect from light.
Shipped in an ice chest with ice pads to maintain low temperature.
Research use only.
General guidance (literature/best practice):
Container: Keep tightly closed in amber glass or foil-wrapped container to minimize light and moisture ingress. Purge headspace with inert gas (nitrogen/argon) if feasible to reduce oxidation.
Solid stability: Maintain desiccation (e.g., with silica gel) at −20°C. Avoid repeated warming/cooling cycles that can introduce condensation.
Reconstitution:
Solvents: DMSO (preferred for highest solubility), methanol, or ethanol. Begin with a small volume, vortex, and expand to target concentration.
Working stocks: Prepare concentrated aliquots (e.g., 10–50 mM in DMSO) in amber vials. Store aliquots at −20°C protected from light; avoid freeze–thaw by using single-use portions.
Aqueous dilution: Add organic stock slowly to vigorously stirred buffer to avoid local supersaturation. Keep final DMSO/EtOH ≤1% v/v where biological compatibility is needed.
Stability of solutions: At 4°C and protected from light, methanolic or DMSO solutions are typically stable for days to weeks (literature); verify by HPLC before critical measurements. Discard solutions showing precipitation, color change, or degradation peaks.
Always consult the batch-specific CoA for any additional storage notes or stability data particular to the supplied lot.
Structure and Identity
Robinin is a polyphenolic flavonol triglycoside derived from kaempferol, bearing a disaccharide (robinosyl = α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranosyl) at the 3-OH and an additional α-L-rhamnose at the 7-OH.
SKU: R463279
Product Name: Robinin
CAS: 301-19-9 (literature)
PubChem CID: 5281693 (literature)
InChIKey (as provided in Product Data): 275099
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet. • Typical literature assignment: often reported as C39H42O20 for kaempferol 3-O-robinoside-7-O-rhamnoside.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet. • Literature value for C39H42O20 corresponds to ~834.7 g/mol.
Structural features (descriptive):
Core scaffold: kaempferol (4H-1-benzopyran-4-one) with a 3-hydroxyflavone backbone; A- and B-phenyl rings linked through a heterocyclic C-ring.
Functional groups: multiple phenolic hydroxyls, conjugated carbonyl (flavonol), three O-glycosidic linkages (one to galactose, two to rhamnose), numerous secondary alcohols within sugars.
Stereochemistry: multiple defined stereocenters in the pyranose rings (β-D-galactopyranosyl, α-L-rhamnopyranosyl units); aglycone is planar/aromatic with no stereocenters.
2D description: a planar kaempferol chromophore with extended conjugation (ring A–C–B) and sugar appendages at positions 3 and 7 that increase polarity and hydrogen-bonding capacity.
Synthetic Utility
Robinin is primarily an analytical standard/biochemical probe rather than a synthetic building block; nonetheless, its functional groups enable certain transformations for method development and structural studies (literature/general):
Hydrolytic transformations:
Acid- or enzyme-catalyzed cleavage of glycosidic bonds to yield the aglycone kaempferol and constituent sugars (rhamnose, galactose). Useful for confirming substitution pattern and for preparing comparative standards.
Selective deprotection/derivatization:
Phenolic OH groups on the aglycone can be selectively methylated/acylated under mild conditions (post-hydrolysis) to generate derivatives for SAR or chromatographic retention tuning.
Sugar hydroxyls may be peracetylated to facilitate MS detection or to study glycoside stability; care is needed to avoid cleavage.
Oxidation/reduction chemistry:
The conjugated flavonol chromophore undergoes electrophilic substitution and redox reactions; however, in the intact triglycoside, steric/electronic shielding from sugars reduces reactivity at the aromatic OH positions.
Conjugation:
Formation of noncovalent complexes (e.g., cyclodextrins) or covalent linking via carbonate/ester at phenolic OH (aglycone) can be explored after controlled deglycosylation.
For classical synthetic route planning, robinin is not typically used as a precursor; instead, chemists synthesize it from kaempferol via stepwise glycosylation with protected donors. As a purchased standard, its key value is in analytical benchmarking, stability studies, and enzymology rather than in building complex molecules.
Target Specificity
Not applicable. This product is a small-molecule flavonol glycoside, not an antibody, enzyme, or affinity reagent. There is no antigen/epitope, clone, isotype, or species reactivity associated with robinin.
Use this tab only if your application involves binding studies; in that case, define targets empirically (e.g., enzyme classes such as glycosidases) and report KD/Ki values from your own data or literature.
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C2619167