This compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
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.
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Application Protocols
No item-specific, validated application protocols are provided in the Product Data. The following general, non-binding examples illustrate typical laboratory uses:
Preparation of stock solutions:
Dissolve at 10–100 mM in DMSO or methanol; for aqueous stocks, pre-wet with ethanol or warm buffer to aid dissolution. Filter (0.22 μm) if sterile solutions are required.
Enzymatic hydrolysis assay (example outline):
Buffer: 50 mM sodium acetate, pH 5.0; temperature 37 °C.
Substrate: 0.5–2 mM β-phenylethyl β-D-glucoside.
Enzyme: β-glucosidase at activity chosen to complete reaction in 1–2 h.
Quench aliquots with equal volume of MeOH; analyze by HPLC-UV at 254 nm.
HPLC method sketch (reversed phase):
Column: C18, 150 × 4.6 mm, 5 μm.
Mobile phase: water (0.1% formic acid)/MeOH gradient from 90:10 to 40:60 over 20 min.
Detection: 210–254 nm; or LC-MS in positive mode.
These examples are provided for research guidance only and are not validated for this specific lot. Optimize conditions for your equipment and objectives.
Biological Roles
General literature context (non-clinical):
Plant metabolite: β-Phenylethyl β-D-glucoside is reported as a glycosidically bound form of 2-phenylethanol in various plants. Glycosylation increases water solubility and enables storage/transport without volatilization or toxicity associated with the free aglycone.
Precursor reservoir: Upon tissue damage, fermentation, or processing, endogenous β-glucosidases can hydrolyze the glycoside to release 2-phenylethanol, contributing to floral/fruity aromas.
Detoxification and homeostasis: Glycosylation is a common phase II metabolic modification in plants, channeling small aromatic alcohols into vacuoles for sequestration.
Enzymatic specificity probes: As a defined β-D-glucoside with an aryl-alkyl aglycone, it serves as a substrate to study β-glucosidase active-site preferences (aryl vs alkyl substituents, leaving group effects) and to benchmark catalytic efficiency across enzyme sources.
Transport and compartmentalization: The increased hydrophilicity relative to 2-phenylethanol favors vacuolar localization; hydrolysis is often pH- and compartment-controlled (literature).
Note: The above reflects general biochemical roles reported for aryl O-β-D-glucosides; it is provided for research context only and does not imply biological activity claims for this specific catalog item.
Buffer Applications
This compound is not a buffering reagent. However, buffer conditions are relevant for its stability and enzymatic assays (general literature guidance):
pH control for stability: β-O-glycosidic bonds are most stable near neutral pH. For storage and handling in solution, use buffers in the pH 5.5–7.5 range (e.g., 50 mM sodium phosphate, citrate, or acetate depending on target pH).
Enzymatic hydrolysis assays (β-glucosidase): Citrate/phosphate buffers between pH ~4.5–6.5 are commonly used to optimize enzyme activity while limiting non-enzymatic hydrolysis.
Ionic strength: Moderate ionic strength (50–150 mM) supports enzyme stability; include BSA (0.1 mg/mL) if nonspecific adsorption is observed.
Cosolvents: Keep organic cosolvent (e.g., EtOH, MeOH, DMSO) at minimal levels compatible with solubility and enzyme tolerance, typically ≤5% v/v.
Recipes (illustrative; not product specifications):
50 mM sodium phosphate, pH 7.0; 50 mM sodium acetate, pH 5.0. Filter-sterilize and store at 2–8 °C.
Green Alternatives
The compound itself is a target analyte/building block rather than a solvent. Greenness considerations center on the media and methods used with it.
Prefer water or aqueous ethanol for enzymatic and extraction workflows when feasible.
Use bio-based solvents (EtOH, 2-MeTHF) for workups over halogenated solvents when compatible.
Avoid excessive DMSO/DMF when aqueous systems suffice for solubility.
Comparison snapshot (general):
| Use case | Conventional choice | Greener alternative | Trade-offs |
|---|---|---|---|
| Stock solution | DMSO | Water or EtOH (food-grade) | Solubility lower in water; EtOH may affect enzymes at >5–10% v/v |
| RP-HPLC | ACN | EtOH or MeOH | EtOH increases backpressure; MeOH less toxic than ACN but changes selectivity |
| Extraction | CH2Cl2/EtOAc | EtOAc or aqueous EtOH | EtOAc acceptable; aqueous EtOH may co-extract polar matrix components |
Process considerations:
Enzymatic hydrolysis at ambient temperatures in water minimizes energy input and avoids corrosives.
If pH adjustment is necessary, choose citrate or acetate buffers over strong mineral acids/bases when possible to limit waste hazards.
Pharmaceutical Uses
No pharmacopeial grade or excipient role is specified for this item. The following are general, non-clinical research contexts only:
Pro-fragrance concept studies: β-glucosides of aroma alcohols (like 2-phenylethanol) are investigated as latent fragrance donors; controlled enzymatic or chemical release can be profiled in formulation matrices.
ADME surrogates: Aromatic O-glucosides are sometimes used in in vitro systems to model glycosidase-mediated cleavage and to study permeability vs. stability trade-offs of glycosylated small molecules.
Stabilization in hydrophilic matrices: The glycoside’s increased aqueous solubility relative to the aglycone can aid formulation research that requires water-based systems.
Important: This product is for research use only. No medical, diagnostic, or therapeutic applications are claimed or supported. For any use in regulated products, appropriate grade qualification and regulatory assessment would be required.
Physical Properties
Item-specific numerical specifications are not provided in the Product Data. Do not treat the following as product specifications; they are general/literature guidance to aid method development.
State/appearance: Not specified for this item; refer to CoA/Spec Sheet. (Glycosides are typically crystalline solids, literature.)
Molecular weight: ~284.31 g/mol (literature/computed from C14H20O6)
Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Many aryl O-glucosides melt/decompose >100 °C, literature.)
Boiling point: Not applicable (glycosides generally decompose before boiling, literature).
Density: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (qualitative, literature):
Water: moderate to good solubility expected due to polyol character.
Polar organics: soluble in methanol, ethanol; high solubility in DMSO; limited in nonpolar solvents (e.g., hexanes).
Partitioning (literature): logP expected low-to-moderate negative/near 0 owing to sugar hydroxyls; actual value not specified.
pKa: No ionizable groups with pKa in physiological range; hydroxyls may have very high pKa (>12), literature.
Optical rotation: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable to solids; not specified.
Practical notes (general): Hygroscopicity can be observed for carbohydrate-rich solids; dry under vacuum over P2O5 or in a desiccator if precise weighing is required. Prepare aqueous or alcohol solutions freshly to minimize hydrolysis under harsh pH.
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and context (general guidance):
Without a stated grade (e.g., “≥98%,” “HPLC grade,” “BioReagent”), end-users should consult the batch-specific CoA for assay method (HPLC/GC/qNMR), purity, and impurity profile (residual solvents, moisture).
Carbohydrate glycosides may contain minor proportions of:
Residual solvents from crystallization (e.g., alcohols) — typically reported on CoA.
Water (adsorbed) — Karl Fischer values, if measured, will be CoA-specific.
Aglycone-related impurities (e.g., free 2-phenylethanol) — assess by HPLC/GC.
If optical rotation or enantiopurity is relevant (β-D configuration), CoA may include [α]D measurements. Absent an item-specific value, do not assume.
Stabilizers: None indicated in Product Data. If present for a specific lot, it will be listed on the CoA.
Recommendations:
For enzymology or biotransformation studies, verify low metal content and residual enzyme inhibitors if critical to your assay; request extended analysis if needed.
For synthetic applications, confirm moisture content and assay by HPLC prior to scale-up, as hydrolysis can increase free aglycone content during storage/handling.
Reaction and Applications
This glycoside is broadly useful as a substrate, standard, and building block in carbohydrate and flavor chemistry.
Enzymology and analytical applications (literature):
Substrate for β-glucosidases to study enzymatic release of 2-phenylethanol; monitor by HPLC/GC-MS.
Model compound for kinetic isotope effect and transition-state analysis of β-glycosidic bond cleavage.
Flavor/aroma research:
Represents a bound reservoir of 2-phenylethanol in plants; used to evaluate precursor pools and release under fermentation or processing.
Synthetic chemistry:
Protecting-group-free manipulations on the aglycone are possible under mild conditions; however, the glycosidic bond is acid/base labile.
Can serve as a leaving-group-modified acceptor in transglycosylation using glycosynthases or engineered β-glucosidases (literature).
Practical tips:
For hydrolysis studies, use buffered aqueous systems (pH 4.5–6.5) and control temperature (25–50 °C) to tune rate; include internal standards.
When using as a calibration standard, prepare fresh solutions and store aliquots at ≤−20 °C to minimize degradation.
For chemical cleavage, mild acid (e.g., 0.01–0.1 M HCl) in aqueous alcohol at elevated temperature can effect hydrolysis; monitor to avoid overreaction of aglycone.
Detection/quantitation:
UV detection at ~254 nm leverages the aryl chromophore; MS-friendly eluents facilitate LC-MS quantitation of glycoside and released 2-phenylethanol (literature guidance).
Reaction Conditions
General literature guidance for typical transformations involving β-aryl O-glucosides; not item-specific specifications.
Enzymatic hydrolysis (β-glucosidase):
Solvent: aqueous buffer (50 mM acetate or citrate), pH 4.5–6.0.
Temperature: 25–40 °C.
Enzyme loading: varies by source; activity often in U/mL; titrate to achieve complete hydrolysis within 0.5–4 h.
Monitoring: HPLC-UV at 254 nm; LC-MS to confirm 2-phenylethanol formation.
Acid-catalyzed hydrolysis:
Solvent: water or aqueous alcohol (MeOH/EtOH).
Acid: HCl or H2SO4, 0.01–0.1 M.
Temperature: 50–80 °C accelerates; lower temperatures for kinetic studies.
Notes: Control time to avoid aglycone side reactions; neutralize and extract promptly.
Glycosylation to prepare the compound (for reference):
Donor: peracetylated glucosyl bromide or trichloroacetimidate; acceptor: phenethyl alcohol.
Promoters: Ag2CO3/AgOTf (bromide) or TMSOTf (imidate).
Solvent: DCM, toluene, or acetonitrile; −30 to 0 °C; then global deprotection (e.g., Zemplén methanolysis).
Derivatizations:
Selective acylation or silylation of primary C6-OH in pyridine/DMAP or imidazole/DMF at 0–25 °C.
Oxidation of the phenethyl side chain (e.g., to aldehyde/acid) using TEMPO or Dess–Martin with protection of sugar hydroxyls.
Reported yields and kinetics depend strongly on catalysts and protection schemes; consult primary literature for specific systems.
Safety and Handling
GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to the SDS for authoritative safety information.
Likely hazards (general for carbohydrate aryl glycosides): low acute toxicity expected; may cause eye/skin irritation; combustible organic solid. Dust may form combustible mixtures with air—avoid dust accumulation.
Handling recommendations (general best practice):
Use in a chemical fume hood to minimize dust inhalation and exposure.
PPE: lab coat, safety glasses or goggles, and suitable gloves (e.g., nitrile). Avoid contact with eyes/skin; wash thoroughly after handling.
Incompatibilities: Strong acids or bases may promote hydrolysis of the glycosidic bond; strong oxidizers can attack the aryl moiety or polyol portion.
First-aid (overview; see SDS):
Inhalation: move to fresh air; seek medical advice if symptoms persist.
Skin contact: wash with soap and water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention as appropriate.
Fire-fighting: Use water spray, CO2, dry chemical, or foam; combustion may produce CO/CO2; firefighters should wear self-contained breathing apparatus.
Spills: Avoid dust, sweep up carefully, and place in a suitable container for disposal according to local regulations.
Always defer to the product’s SDS for definitive hazard and response information.
Solvent Selection
β-Phenylethyl β-D-Glucoside is a polar, polyhydroxylated aryl O-glycoside. Solvent choice should balance hydrogen-bonding capacity with stability of the glycosidic bond.
Polarity/miscibility (general literature):
Water: good solvent for dissolution and enzymatic work; avoid extreme pH to minimize hydrolysis.
Alcohols (MeOH, EtOH): good solubility; useful for chromatography and prep solutions.
DMSO, DMF: excellent solubility for stock solutions; dilute promptly into buffered media to avoid prolonged exposure.
Poor solubility expected in nonpolar solvents (toluene, hexanes).
When to choose what:
Enzyme assays (β-glucosidase): aqueous buffers with minimal organic cosolvent (≤5–10% v/v MeOH/EtOH) to maintain enzyme activity.
Synthetic transformations on the aglycone (e.g., selective oxidation on the phenethyl chain): polar aprotic solvents (DMSO/AcN) can be used with base/acid carefully controlled.
Purification: reversed-phase aqueous MeOH/ACN systems are effective; normal-phase silica requires alcohol modifiers to elute strongly retained polyols.
Practical tips:
Degas buffer/solvent if performing sensitive kinetics.
For weighing/dissolution, pre-wet with a small volume of alcohol before adding water to accelerate dissolution.
Avoid strong basic media in protic solvents for extended times, which can cleave the glycoside.
Storage and Reconstitution
Storage conditions (from Product Data): Store at −20 °C, argon charged.
Shipping (from Product Data): Shipped in ice chest with ice pads.
Research use note: For research use only.
General handling guidance:
Keep container tightly closed under inert gas (argon) to minimize oxidative or hydrolytic degradation. Allow the vial to equilibrate to room temperature before opening to reduce moisture condensation.
Hygroscopicity is possible for polyhydroxy compounds; recap promptly and return to cold storage after use.
Aliquoting: For solution work, prepare single-use aliquots to avoid repeated freeze–thaw and headspace moisture exposure.
Reconstitution (general suggestions; not specifications):
Solvents: water, ethanol, methanol, or DMSO depending on application. Start with a small volume of alcohol to wet, then add water/buffer if an aqueous solution is desired.
Concentrations: Prepare working stocks appropriate to your method (e.g., 10–100 mM in DMSO or 1–10 mg/mL in aqueous alcohol). Filter if sterile solutions are needed.
Stability in solution: Best used fresh. For short-term storage, keep solutions at 2–8 °C (hours to days) or at ≤−20 °C (days to weeks), protected from light and extreme pH.
Always refer to the CoA/SDS for lot-specific guidance and stability data.
Structure and Identity
β-Phenylethyl β-D-Glucoside is an O-glycoside linking a β-D-glucopyranose to a phenethyl (2-phenylethyl) aglycone via the anomeric oxygen in β-configuration.
Item identifiers (from Product Data):
SKU: P355558
Product name: β-Phenylethyl β-D-Glucoside
CAS: 18997-54-1
PubChem CID: 11289099
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers (for reference, not product specifications):
Typical molecular formula: C14H20O6 (literature)
Typical molecular weight: ~284.31 g/mol (literature/computed from formula)
Structural features (general description):
Carbohydrate core: β-D-glucopyranose ring (chair conformation), bearing four secondary hydroxyls and one primary hydroxyl.
Glycosidic linkage: β-anomeric O-glycosidic bond to the aglycone at C1 of glucose.
Aglycone: phenethyl group (–O–CH2–CH2–C6H5), comprising a benzenoid ring connected via an ethylene spacer.
Stereochemistry: glucose centers retain D-configuration with β-linkage at the anomeric center (general literature description).
2D structure in words: a six-membered glucopyranose ring with hydroxyls at C2, C3, C4, and C6; the anomeric oxygen (C1) bridges to a –CH2–CH2–phenyl moiety, giving an aryl-alkyl ether linked β-glycoside.
Synthetic Utility
As a defined β-D-glucoside of 2-phenylethanol, this molecule serves as a versatile handle in carbohydrate and aroma chemistry.
Substrate in β-glucosidase-catalyzed transglycosylations/glycosynthase reactions to construct new glycosidic bonds (literature).
Precursor to release 2-phenylethanol under controlled hydrolysis in model systems.
Starting point for preparing radiolabeled or isotopically enriched analogs for mechanistic studies.
Retrosynthetic perspective:
Disconnection at the anomeric center suggests access via glycosylation of phenethyl alcohol with an activated glucose donor (e.g., peracetylated glucosyl bromide/trichloroacetimidate), followed by deprotection to furnish the free polyol.
Purification/analytics:
Strong retention on silica; use methanol/dichloromethane or EtOAc/MeOH with base modifier (0.1–1% Et3N) to reduce tailing. Reversed-phase C18 with water/MeOH or ACN is effective.
Monitor by HPLC at 254 nm utilizing the aryl chromophore and by MS (M+H+ ~285, literature).
Target Specificity
Not an antibody, enzyme, or targeted biological reagent. No target specificity data apply to this catalog item. For biochemical work, see “Biological Roles” and “Reaction & Applications” for relevant enzyme-substrate context (β-glucosidase).
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