This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
550.500 g/mol
XLogP3
-1.300
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
15
Rotatable Bond Count
8
Exact Mass
550.143 Da
Monoisotopic Mass
550.143 Da
Topological Polar Surface Area
247.000 Ų
Heavy Atom Count
39
Formal Charge
0
Complexity
1060.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
7
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
1
Covalently-Bonded Unit Count
1
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Recensioni
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Application Protocols
Item-specific tested protocols are not provided in the Product Data. The following are general, literature-based procedures suitable for research use with betanin; adjust to your application and validate locally.
Preparation of a betanin stock solution (spectrophotometry)
Dissolve betanin in acidified water (e.g., 10 mM acetate buffer, pH 4.5) to ~1–2 mM. Protect from light and cool to 4–8 °C during preparation.
Verify concentration by UV–Vis using ε at ~535–540 nm appropriate for your buffer; filter (0.22 µm) to remove particulates.
UV–Vis calibration curve (λmax ~535–540 nm)
Prepare serial dilutions (e.g., 2–20 µM) in the same buffer. Measure absorbance in amber cuvettes, recording baseline with buffer only. Plot A vs. c and confirm linearity (R² ≥ 0.999) within the chosen range.
HPLC analysis (qualitative)
Column: C18, 150 × 4.6 mm, 5 µm; 30 °C.
Mobile phase A: Water + 0.1% formic acid; B: Acetonitrile.
Gradient: 5%→20% B over 15 min; flow 1.0 mL/min.
Injection: 5–20 µL of ~10–50 µM solution. Detect at 535 nm. Include system-suitability check using retention time and spectral purity.
Antioxidant assay (ABTS•+ example)
Generate ABTS radical cation per standard protocols. Mix with betanin solutions (acidified buffer), incubate in dark 6–10 min, measure ΔA734. Express activity relative to a standard curve, noting pH and ionic strength.
Always document buffer composition, pH, temperature, and light exposure to ensure reproducibility.
Biological Roles
General biochemistry (literature; not item-specific and not clinical):
Natural occurrence: Betanin is the predominant betacyanin pigment in beetroot (Beta vulgaris) and related Caryophyllales species. It belongs to the betalain family, which replaces anthocyanins in this clade.
Biosynthesis: Derived from L-tyrosine via L-DOPA to betalamic acid, which condenses with cyclo-DOPA glycosides (here, D-glucosylated) to form the red–violet betacyanins. Glycosylation enhances solubility, vacuolar storage, and stability.
Physiological roles in plants:
Pigmentation: Provides vivid coloration for pollinator/seed disperser attraction and photoprotection.
Stress responses: Acts as an antioxidant/osmoprotectant; may mitigate oxidative stress under high light, salinity, or drought conditions through ROS scavenging.
Chemical features relevant to biology:
Zwitterionic nature and multiple phenolic OH groups facilitate strong hydrogen bonding and metal chelation in aqueous cellular environments.
The conjugated iminium system underlies intense absorption in the green region, contributing to photoprotective screening.
Stability and turnover: Susceptible to enzymatic and non-enzymatic degradation at alkaline pH and elevated temperatures; vacuolar acidity in plant cells helps preserve pigment integrity.
Laboratory relevance:
Used as a biological marker for betalain pathway activity and as a calibration standard in plant metabolomics (HPLC-DAD/MS). Its pH-dependent spectral properties are exploited to monitor microenvironmental changes in model systems.
Note: All statements above relate to biochemical function and research context; no medical or clinical claims are implied.
Buffer Applications
Applicability: Betanin is not a buffering agent. However, its color and absorbance are strongly pH-dependent, so buffers are essential to maintain stability and reproducible spectra in experiments involving betanin.
Practical guidance (literature/general):
Recommended pH range: Maintain mildly acidic conditions (pH ~4–6) to limit degradation. Avoid alkaline media where rapid decolorization and structural changes occur.
Common buffer systems for analytical work:
Acetate buffer (pH 4–5.5): 10–50 mM sodium acetate adjusted with acetic acid; good general-purpose system.
Citrate buffer (pH 3–6): 10–50 mM trisodium citrate/citric acid; can also serve as a chelator to limit metal-catalyzed oxidation.
Formate buffer (pH 3–4): For LC-MS compatibility; volatile.
Preparation tips:
Degas buffers (vacuum or helium sparging) and cool to slow oxidation.
Light protection: Use amber bottles and minimize exposure during measurements.
Ionic strength: Keep consistent, as it can subtly shift λmax and absorptivity.
Electrophoresis/cell culture: Betanin is not typically used in electrophoresis running buffers or cell culture media as a buffer. If used as a tracer dye or colorant, ensure compatibility with the medium and avoid alkaline pH.
Reporting: Always state buffer identity, concentration, pH (at measurement temperature), and any additives (ascorbate, EDTA) when publishing spectrophotometric or chromatographic data involving betanin.
Green Alternatives
Context: Betanin itself is a bio-based, biodegradable natural pigment sourced from plant materials (e.g., beetroot). When the goal is to color or to probe redox/photophysical behavior in a “green chemistry” framework, betanin is often the greener alternative to many synthetic azo/xanthene dyes.
Comparison (general; literature-based, not item-specific):
Sustainability profile
Betanin: Renewable origin, readily biodegradable; extraction in aqueous ethanol; low intrinsic toxicity profile reported in food contexts.
Synthetic azo dyes (e.g., Red 40): Petrochemical origin; potential for persistent breakdown products; often require stronger organic solvents.
Performance tradeoffs
Stability: Betanin is less stable to heat, light, and alkaline pH than many synthetic dyes; requires acidic, low-oxygen handling.
Spectral properties: Strong visible absorbance but narrower stability window; synthetic dyes may offer broader pH stability and lightfastness.
Process considerations
Solvent systems: Acidified water or aqueous ethanol suffice for betanin, aligning with green solvent selection guides.
Waste minimization: Aqueous streams with low toxicity; avoid chlorinated oxidants that rapidly degrade betalains and complicate waste.
Alternatives within the natural dye space:
Other betalains (amaranthin, gomphrenin) or anthocyanins (cyanidin-3-glucoside) may provide different hues/stability profiles while remaining bio-based.
Bottom line: If durability under harsh conditions is required, synthetic dyes may still be chosen; otherwise, betanin supports greener analytical and materials workflows under mild, acidic, aqueous conditions.
Pharmaceutical Uses
Scope: No therapeutic claims are made. The following concerns formulation/excipient contexts only (literature/general).
Role as a colorant: Betanin is the principal chromophore of “beetroot red” (often labeled E162 in food applications) and may be considered in pharmaceutical and nutraceutical formulations as a natural colorant, subject to local regulatory approvals and specifications. Its intense hue allows low loadings in coatings and liquid preparations.
Formulation considerations:
pH sensitivity: Best suited for acidic liquid vehicles and film coatings with protective matrices. Alkaline excipients can bleach the color.
Light/oxygen: Incorporate antioxidants (e.g., ascorbate) and use oxygen-barrier packaging; employ light-protective containers.
Solvent systems: Aqueous or aqueous-ethanolic processes under mild temperatures are preferred to preserve color.
Interactions: The catechol moiety can chelate metals; control trace metals to avoid catalytic fading.
Analytical control:
Identity and assay by HPLC-DAD at ~535 nm; monitor isomer/oxidation profile (betanin/isobetanin/neobetanin).
Color strength can be standardized via E1% at λmax in specified solvent and pH.
Regulatory/compendial aspects: Acceptance and limits vary by jurisdiction and compendium; when used as an excipient colorant, adhere to regional monographs/standards (if applicable) and perform stability studies under ICH conditions to define shelf-life in the intended dosage form.
Note: For SKU B988544, no grade or regulatory status is specified; consult the CoA/Spec Sheet for item-specific suitability.
Physical Properties
Item-specific physical data:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Storage: Room temperature (per Product Data).
Other specifications (mp, water, UV cutoff, metal limits, etc.): Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties (for context; not item specifications):
Color/form: Deep red–violet solid; commonly obtained as powders or crystalline aggregates when purified from beetroot extracts.
Melting behavior: Typically decomposes on heating rather than exhibiting a sharp melting point (literature).
Solubility: Highly soluble in water; sparingly to moderately soluble in aqueous alcohols (methanol, ethanol) and glycerol; essentially insoluble in nonpolar solvents (literature).
Acid–base/stability: More stable in mildly acidic media (pH ~4–6); undergoes degradation/color shift under alkaline conditions and at elevated temperatures or strong light (literature).
Spectral properties: Strong visible absorption with λmax ~535–540 nm in acidified aqueous media; molar absorptivity on the order of 5×10^4–7×10^4 L·mol⁻¹·cm⁻¹ depending on pH and ionic strength (literature).
Partitioning: Very hydrophilic (logP effectively very low/negative in neutral water due to zwitterionic/hydrophilic groups; literature qualitative assessment).
Practical notes:
Solutions are sensitive to light, oxygen, and heat; store protected from light and prepare fresh standards for quantitative spectrophotometry.
Color and spectral profile are pH-dependent; report pH and ionic strength alongside absorbance measurements for reproducibility.
Quality and Grades
Item-specific grade/purity details:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers or additives: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and best practices (general guidance for betalain pigments):
Purity considerations: “Analytical” or “reference” grades of betanin typically indicate high chromatographic purity (e.g., by HPLC/UPLC), low levels of isobetanin/neo derivatives, and controlled water/ash content. In contrast, “extract” grades may contain a mixture of betalains and phenolics.
UV–Vis suitability: For spectrophotometric standards (e.g., ε determination at ~535–540 nm), low UV-absorbing impurities and accurate moisture content are critical. Verify lot-specific extinction coefficients if provided.
Isomeric composition: Betanin can co-exist with isobetanin and oxidation products (e.g., neobetanin). If your application is quantitative or mechanistic, request chromatograms to confirm composition.
Stabilization: Acidified matrices (e.g., with citric or ascorbic acid) can enhance solution stability. If a stabilizer is present in a product, it may shift pH and spectral properties—adjust your calibration accordingly.
Quality control tests (typical for this class; not item-specific):
HPLC purity/profile with diode-array detection (DAD) at ~535 nm.
Moisture by Karl Fischer; ash/residue on ignition; identity by MS and NMR; color value (E1% at λmax) in specified solvent.
For regulated or method-validation work, rely on the batch CoA and methods specific to SKU B988544.
Reaction and Applications
Scope: Betanin is not a common synthetic reagent; instead, it is used as a natural chromophore/standard and as a redox-active phenolic pigment in analytical and materials contexts.
Representative applications (literature/general):
Spectroscopic standard: Used to calibrate instruments and methods for betalain quantitation. Strong absorbance near 535–540 nm enables sensitive colorimetric assays.
Antioxidant assays: Serves as a model substrate/standard in radical scavenging (DPPH, ABTS•+) and FRAP assays to benchmark antioxidant capacity of matrices. Report precise conditions due to pH/redox sensitivity.
Chromatographic method development: Employed to optimize HPLC/UPLC separations for betalains and related phenolics under acidic aqueous conditions with DAD or MS detection.
Photophysics and sensing: Investigated as a visible-light-harvesting dye and analyte in pH/oxidation-responsive sensors and dye-sensitized systems; spectral shifts with environment enable probe design.
Chemical transformations: Controlled acid/base or oxidative treatments yield derivatives such as neobetanin or deglucosylated betanidin for structure–activity studies.
Practical notes:
Avoid alkaline conditions to prevent rapid degradation/bleaching.
Use amber glassware and minimize headspace oxygen for kinetic or quantitative studies.
For electrochemical studies, use supporting electrolytes compatible with low pH (e.g., acetate buffers) to retain pigment integrity.
Manufacturer Applications: Not specified in Product Data; the above outlines typical research uses for betanin-class pigments.
Reaction Conditions
This section provides general laboratory conditions relevant to betanin handling, derivatization, and analysis (literature-based; not item-specific):
Stability and handling:
Work at pH 4–6, ≤25 °C when possible, and protect from light and oxygen. Add 0.01–0.1% acid (acetic/citric) to aqueous media to slow degradation.
Deglycosylation to betanidin:
Acidic hydrolysis in aqueous ethanol or water (e.g., 0.1–0.5 M HCl, 0–5 °C to limit chromophore damage); monitor by HPLC at ~535 nm. Neutralize and purify promptly.
Acylation of phenolic/sugar OH groups:
Use mild acyl donors (acid anhydrides/activated esters) in buffered aqueous-organic biphasic systems or DMF with catalytic base kept minimal; maintain low temperature and brief reaction times to avoid bleaching.
Oxidative conversion to neobetanin/quinonoid species:
Aerated aqueous solutions at neutral-to-slightly acidic pH under controlled light; or use very mild oxidants (e.g., ferricyanide) to track kinetics electrochemically/spectroscopically.
Mobile phase A: Water + 0.1% formic acid; B: Acetonitrile or methanol.
Gradient: 5–20% B over 10–20 min at 25–35 °C.
Detection: DAD at 535–540 nm; MS in positive mode can detect the iminium-bearing ion; maintain acidic conditions to limit on-column degradation.
Expected observations:
Rapid fading in alkaline conditions; bathochromic/hypsochromic shifts with solvent and pH.
Note: For quantitative or regulated work, validate and adjust conditions to your matrix and instrumentation.
Safety and Handling
Item-specific hazard information (per Product Data):
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
General safety guidance (literature/standard lab practice; not a substitute for the SDS):
Expected hazards: Betanin is a naturally occurring food colorant; typically regarded as of low acute toxicity. However, purity, formulation, and degradation products may alter hazards. Handle as a laboratory chemical.
Personal protective equipment (PPE): Use lab coat, safety glasses, and suitable gloves (e.g., nitrile). Avoid inhalation of dusts and contact with eyes/skin.
Handling: Work away from strong bases and oxidants. Minimize exposure to light and heat to limit degradation and potential formation of colored residues.
Incompatibilities: Strong bases (accelerate decomposition/bleaching), strong oxidizers, hypochlorite, and elevated temperatures. Metals/catalysts that promote oxidation can reduce stability.
First aid (overview):
Eye/skin contact: Rinse with water for several minutes; remove contaminated clothing. Seek medical attention if irritation persists.
Ingestion/inhalation: Move to fresh air; rinse mouth with water. Obtain medical advice if unwell.
Spill/leak response: Avoid creating dust; collect with damp disposable towels or HEPA-filtered vacuum. Wash area with mild acidified aqueous cleaner to remove stains.
Fire safety: Organic pigment; may burn if dried and heated strongly. Use water spray, CO2, foam, or dry chemical. Combustion may produce CO/CO2 and nitrogen-containing fumes.
Always consult the product-specific SDS for authoritative hazard classification and emergency procedures.
Solvent Selection
Applicability: Betanin is a highly polar, water-soluble zwitterionic pigment; solvent choice primarily concerns aqueous systems and aqueous-organic mixtures.
Polarity and miscibility (literature/general):
Primary solvent: Water (high solubility). Stability favored in mildly acidic aqueous media (pH ~4–6).
Aqueous-organic: Miscible in water–methanol, water–ethanol; modest solubility in pure lower alcohols; very low solubility in aprotic nonpolar solvents (e.g., hexane, toluene) and limited in pure acetonitrile.
Additives: Small amounts of food-grade acids (citric, acetic) can improve color stability. Ascorbate may serve as an antioxidant but can also participate in redox reactions; assess impact experimentally.
Practical selection by application:
Spectrophotometry: Use acidified water (e.g., 0.01–0.05 M acetate or citrate buffer, pH 4–5). Report the exact matrix (pH, ionic strength) to ensure reproducibility of λmax and ε.
HPLC: Aqueous mobile phases acidified with 0.1% formic acid or 0.05% TFA; organic modifier typically acetonitrile or methanol. Maintain low pH to limit on-column degradation/isomerization.
Extraction from plant matrices: Aqueous ethanol with 0.1–1% acid (citric/acetic) at low temperature and minimal oxygen exposure.
Comparison (general):
Water (acidified) — best stability/solubility.
Methanol/ethanol — workable with water present; may affect apparent molar absorptivity.
Nonpolar solvents — not recommended; negligible solubility and rapid fading.
Tip: Degassing and working under low light can markedly improve solution lifetime.
Storage and Reconstitution
Item-specific storage condition:
Store at room temperature (per Product Data for SKU B988544).
General guidance (literature/practice; complementing, not contradicting, the above):
Light/oxygen sensitivity: Keep the container tightly closed, under inert headspace if possible, and protected from light (amber bottle or foil wrap) to limit oxidation and color loss.
Humidity: Store in a dry place; moisture uptake can affect mass-based dosing and accelerate degradation.
Long-term considerations: Although room temperature storage is listed, cooler storage (e.g., 2–8 °C) and desiccation often improve shelf-life for betalains; assess stability for your use case and follow the item’s CoA if provided.
Reconstitution (for solid materials):
Solvent: Use acidified water (e.g., acetate or citrate buffer, pH ~4–5). Avoid alkaline solutions.
Concentration: Prepare a concentrated stock (e.g., 1–2 mM) and dilute freshly before use.
Technique: Add solvent gradually with gentle swirling under low light; filter through 0.22 µm if particulate matter is present.
Storage of solutions: Use amber vials, minimize headspace, and keep cold (e.g., 2–8 °C). Prepare fresh daily for quantitative measurements; extended storage may lead to fading or spectral shifts.
Always refer to the lot-specific CoA/Spec Sheet and SDS for definitive storage, stability, and handling instructions for SKU B988544.
Structure and Identity
Brief overview: Betanin is the major red–violet betalain pigment of beetroot, structurally a glycoside of the catecholic betacyanin aglycone (betanidin) with a glucose at the 5-O position.
Item-specific identifiers from Product Data:
CAS: 6540685 (as provided)
InChIKey: 53228 (as provided)
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.
Literature identity (for general reference; not item specifications):
Core features: Aromatic catechol ring fused to a dihydropyridinium-type chromophore (betalamic-derived), bearing a carboxylate, phenolic hydroxyls, and a glucopyranosyl substituent (typically 5-O-β-D-glucopyranose on the cyclo-DOPA moiety).
Charge state: Zwitterionic at neutral pH (iminium cation with carboxylate anion; phenolic groups partially deprotonated depending on pH).
2D structural description (general):
A highly conjugated, cationic betalamic-derived chain is condensed with a cyclo-DOPA unit. The catechol ring (1,2-dihydroxyphenyl) bears a glycosidic linkage to a D-glucose. The system includes one carboxylic acid, multiple phenolic OH groups, and an iminium nitrogen embedded in a polyene chain responsible for strong visible absorption (red–violet hue).
Note: Exact stereochemistry at the sugar is D-glucose (β-linkage); other stereocenters arise from the sugar only. Refer to CoA/SDS for definitive identifiers specific to SKU B988544.
Synthetic Utility
Perspective: Betanin is primarily a natural pigment/analytical standard rather than a general synthetic building block. Nevertheless, its functional groups enable selective transformations useful for structure–property studies (literature/general):
Functional group portfolio:
Phenolic catechol (ortho-dihydroxy) enabling oxidation to quinonoid species, metal chelation, and protective acylation/etherification.
Carboxylic acid amenable to esterification or salt formation under mild conditions.
Glycosidic linkage at the phenolic oxygen allowing enzymatic or acid-catalyzed deglycosylation to yield betanidin (aglycone).
Conjugated iminium/polyene core susceptible to isomerization and oxidative rearrangements (e.g., formation of neobetanin).
Representative transformations:
Hydrolysis: Controlled acid hydrolysis (low pH, low temperature) to remove glucose and access betanidin for comparative antioxidant/photophysical studies.
Acylation: Derivatization of phenolic or sugar OH groups to enhance lipophilicity or tune stability (often using mild acylating agents to avoid chromophore degradation).
Oxidation/rearrangement: Mild oxidants or light/oxygen to generate neobetanin or quinonoid species; used to probe degradation pathways.
Analytical synthetic context:
Isotopic labeling (e.g., 13C/15N in precursors) can be traced into the chromophore for metabolism studies in plants.
Caveat: The chromophore is sensitive; reaction design emphasizes low temperature, acidic conditions, exclusion of strong bases/oxidants, and minimal light to preserve the desired scaffold.
Target Specificity
Not applicable. SKU B988544 (Betanin) is a small-molecule pigment, not an antibody, enzyme, or targeted biological reagent. There are no antigen/epitope, clone, isotype, or species-reactivity attributes associated with this product.
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