≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Store at 2-8°C Ships Wet ice Check lot-specific COA for exact specifications.
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Quality documents
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
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Literature proof
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Vue d’ensemble
Application：
4-Indolyl acetate has been employed as standard in a protocol for the optimization of gradient reversed phase chromatographic peak capacity for separation of small molecules：Reactant for preparation of: 1) Inhibitors of HIV-1 attachment; 2)Prostanoid EP3 receptor antagonist, as a novel antiplatelet agent; 3) Indolyl-nitroalkanes via N-bromosuccinimide catalyzed synthesis; 4) Psilocybin as a medicinal agent;
This compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
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 vendor-validated, item-specific application protocols are provided for this product. The following general procedures illustrate common research uses; they require optimization by the user.
Preparation of DMSO stock for enzymatic assays (general):
Dissolve 4-indolyl acetate in anhydrous DMSO to 50–100 mM. Filter (0.2 μm PTFE) if necessary. Store small aliquots at 2–8 °C, protected from light. Use within several days for best consistency.
For assays, dilute the stock into pre-warmed buffer (e.g., 50 mM phosphate, pH 7.4) to a final substrate concentration of 50–500 μM; keep final DMSO ≤1% v/v. Initiate with enzyme and monitor absorbance/appearance of color at appropriate wavelengths or by end-point extraction and HPLC.
Chemical deprotection (illustrative):
To a solution of the substrate (1.0 equiv) in MeOH, add K2CO3 (1.5 equiv) at 0 °C. Stir 1–2 h while warming to rt. Monitor by TLC/HPLC. Quench with saturated NH4Cl, extract with EtOAc, dry, and concentrate under reduced pressure at ≤30 °C.
TLC/HPLC monitoring:
Use UV 254–280 nm for detection. Increasing polarity suggests deacetylation to 4-hydroxyindole. Avoid oxidants that may form colored indigoids.
These are starting points only; adapt conditions to the scale, enzyme source, and purity constraints of your application.
Biological Roles
Scope note: This product is for research use only. The following information is general, literature-based background on indole chemistry and aryl indolyl acetates; it is not a statement of biological performance of this specific item.
Indole framework in biology (literature):
Indole is a privileged scaffold found in tryptophan, tryptamines, indole alkaloids, and many signaling molecules across bacteria, plants, and animals. It participates in π–π stacking, hydrogen bonding (via N–H), and hydrophobic interactions in proteins.
Phenolic indoles and acetates:
4-Hydroxyindole derivatives are oxidative metabolites in some pathways and can undergo enzymatic transformations. Masking the phenol as an acetate modulates lipophilicity and membrane permeability in model systems, enabling pro-substrate or pro-fluorophore strategies.
Aryl indoxyl/indolyl acetates are classical substrates for carboxyl esterases and lipases in vitro. Hydrolysis liberates the indolyl alcohol, which can undergo aerial oxidation to form intensely colored indigoid dimers; this chemistry underlies various colorimetric reporter assays used in microbiology and enzymology (positional isomers differ in kinetics and color yield; empirical validation is needed).
Assay considerations:
Use low co-solvent fractions (≤1–2% DMSO) to minimize enzyme inhibition.
Oxygen and pH influence the downstream oxidation of the liberated indolyl species; for reproducibility, control headspace, mixing, and include antioxidants when avoiding dye formation is desired.
No medical or clinical claims are made or implied.
Buffer Applications
4-Indolyl acetate is not a buffering reagent and is not used to prepare defined pH buffer systems. Its relevance to buffers is limited to being dissolved or diluted in them for enzymatic assays.
Practical notes for assay buffers (general guidance):
Typical esterase assay buffers: 50 mM phosphate, Tris, or HEPES, pH 7.0–8.0.
Maintain final organic co-solvent (e.g., DMSO) at ≤1–2% v/v to protect enzyme activity.
Include 0.01–0.05% non-ionic surfactant only if needed to stabilize dispersion; verify it does not inhibit the enzyme or interact with the indole chromophore.
Protect solutions from strong light and extended air exposure to minimize background oxidation to indigoid dyes.
For actual pH control and buffering capacity, select a true buffer component (e.g., phosphate, HEPES).
Green Alternatives
While 4-indolyl acetate is a substrate/building block rather than a solvent, greener choices can be made in how it is used, processed, and deprotected.
Greener solvent choices (literature-informed):
Replace dichloromethane with ethyl acetate, 2-methyltetrahydrofuran (2-MeTHF), or cyclopentyl methyl ether (CPME) for workups and many reactions.
Use aqueous ethanol or isopropanol for precipitation/recrystallization where solubility permits.
For biocatalysis (esterase-catalyzed hydrolysis/transesterification), conduct reactions in buffered aqueous media with ≤1–2% DMSO or in deep eutectic solvents, reducing reliance on chlorinated organics.
Energy and waste minimization:
Favor enzymatic deprotection (esterases, lipases) at ambient temperature over strong acid/base hydrolysis to reduce energy input and neutralization waste.
Employ catalytic acyl transfer reagents (e.g., organocatalysts, immobilized enzymes) for transesterification instead of stoichiometric activating agents.
Comparison snapshot (qualitative):
DCM vs EtOAc: EtOAc offers lower toxicity and better biodegradability while often providing comparable solubility for indolyl esters.
Strong base hydrolysis vs esterase: Biocatalysis operates in water at near-neutral pH, minimizing corrosive waste, though substrate solubility and enzyme cost must be managed.
Trade-offs:
Greener solvents may alter reaction rates/selectivity; modest optimization of temperature, catalyst loading, and concentration is often required.
Enzymatic routes can be substrate-specific; preliminary screens for enzyme compatibility with the indole ring are advised.
Pharmaceutical Uses
Scope: No therapeutic claims are made. This product is intended for research use only.
4-Indolyl acetate is not a recognized pharmacopeial excipient. However, indole esters are sometimes used in discovery as pro-moieties to modulate solubility, permeability, or stability in prodrug models. In preformulation research, aryl acetates can serve as labile protecting groups to explore unmasking kinetics under physiological-like conditions (enzyme-mediated cleavage by esterases).
QC and analytical contexts:
Indolyl acetates can function as chromogenic esterase substrates in in-process testing or enzyme characterization studies (research scale). The post-hydrolysis oxidation to colored species allows rapid visual or spectrophotometric monitoring; positional isomers exhibit different kinetics that must be empirically calibrated.
Developability considerations (research stage):
Hydrolytic lability: Evaluate chemical stability in simulated gastric/intestinal fluids and human/rat plasma to understand esterase susceptibility.
Photostability: Indole chromophores can degrade or oxidize under UV; protect from strong light.
Solubility: Use co-solvents or solid dispersion approaches for screening; DMSO stock solutions are common for in vitro work.
Any application in regulated products would require separate qualification and compliance with appropriate pharmacopeial and regulatory standards.
Physical Properties
Item-specific physicochemical specifications are not provided in the Product Data. Where useful, literature-type values and qualitative behavior are summarized for planning purposes only.
Item-specific values (this catalog entry):
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 (item): Not specified for this item; refer to CoA/Spec Sheet. (Literature MW: 175.19 g/mol)
Literature/typical properties for 4-indolyl acetate (informational; not specifications):
Physical state: typically a crystalline solid or off-white powder for many aryl acetates.
Melting point: not widely standardized; consult primary literature or CoA. Often decomposes or melts in the ~100–200 °C range for related indolyl acetates (literature, indicative only).
Boiling point: not commonly reported (ester likely decomposes before distillation under ambient pressure).
Density: not commonly reported; solids typically near 1.2–1.4 g/cm3 for aryl esters (qualitative). Use pycnometry if needed.
Solubility profile (qualitative, literature):
Water: low solubility.
Organic: soluble in DMSO, DMF, acetone, ethyl acetate, dichloromethane, acetonitrile; sparingly to moderately soluble in alcohols; poor in alkanes/hexanes.
LogP: expected moderate (aromatic ester); experimental value not widely tabulated.
pKa: indole N–H pKa in DMSO ~17 (literature for indole); phenolic O is masked as an ester.
UV-vis: indole chromophore shows π→π* absorption in near-UV (e.g., 270–290 nm region, literature for indoles). Exact cutoff not established here.
Always confirm working values experimentally or via the item’s CoA/SDS.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on typical grades (general information relevant to indole building blocks):
Research grade: suitable for synthetic chemistry, method development, and enzymology screens. Purity is typically defined by HPLC/GC and NMR. Residual solvents, inorganic ash, or trace metals are generally uncontrolled beyond fit-for-purpose ranges.
High-purity/assay ≥98–99% (when offered): minimizes background in analytical or enzymatic assays; reduces unknown impurities that can affect colorimetric/fluorometric readouts with indole chromophores.
Stabilizers: aryl esters are generally supplied without stabilizers. If an inhibitor is used (rare), it will be disclosed on the CoA. Absence/presence of stabilizers affects storage and assay background.
Recommended quality checks (best practices):
Identity confirmation by 1H/13C NMR and HRMS. Verify absence of 4-hydroxyindole (hydrolysis product) and acetic acid.
Purity by HPLC/UPLC with diode-array detection to monitor indole UV bands. Consider orthogonal methods (TLC, GC if volatile derivatives are made).
Water content by Karl Fischer if moisture sensitivity is critical (especially for kinetic esterase assays).
UV background for chromatography: If using as an analytical standard or in trace assays, consider lots characterized for low UV-absorbing impurities; HPLC-grade reagents help reduce baseline noise.
Consult the item’s CoA for definitive grade, stabilizer, and analytical specifications.
Protected phenol handle: 4-Indolyl acetate is the O-acetylated form of 4-hydroxyindole. It serves as a protected phenolic indole that can be unveiled under mild basic or acidic conditions (chemical deprotection) or by esterases (biocatalytic deprotection).
Enzymatic substrate: Aryl indoxyl/indolyl acetates are classical esterase substrates. Hydrolysis affords indolyl alcohols that oxidize/dimerize to deeply colored indigoid pigments, enabling colorimetric detection. 4-Indolyl acetate can be explored as a positional isomer substrate in esterase profiling and inhibitor screening (literature context).
Acyl transfer chemistry: Under transesterification or acylation conditions, the acetate can participate as an acyl donor to nucleophiles (alcohols, amines) in the presence of catalysts (e.g., DMAP, lipases), though reactivity is typically modest relative to activated esters.
Indole functionalization: The indole N–H allows N-protection (Boc, Cbz) prior to electrophilic substitution (e.g., Vilsmeier–Haack formylation at C-3, Friedel–Crafts acylation/alkylation). The O-acetyl protects the 4-phenolic site from undesired O-alkylation or metalation.
Practical tips:
Dry conditions limit premature hydrolysis. Include molecular sieves or work under inert gas for moisture-sensitive steps.
Monitor reaction progress by TLC/HPLC using UV at ~280 nm (typical indole absorption). Watch for formation of 4-hydroxyindole (more polar) and indigoid byproducts (strongly colored) upon exposure to oxidants.
For enzymatic assays, prepare fresh DMSO stocks and minimize light/air exposure to reduce background oxidation.
Reaction Conditions
The following are literature-type, general conditions for common operations involving aryl acetate-protected indoles. They are provided as planning guidance and are not product specifications.
Hydrolysis (deprotection to 4-hydroxyindole):
Base-catalyzed: K2CO3 (1–2 equiv) in MeOH or MeOH/H2O (9:1), 0–25 °C, 0.5–4 h; monitor by TLC/HPLC. Quench with acid, extract promptly to limit further indole oxidation.
Acid-catalyzed: Catalytic HCl or TsOH in MeOH, 0–25 °C, 0.5–2 h. Avoid strong mineral acid at high temperature to prevent indole degradation.
Enzymatic: Porcine liver esterase or CALB in phosphate buffer (pH 7.4–8.0), 25–37 °C, hours to overnight; ≤1–2% DMSO as co-solvent. Aerobic conditions can give colored indigoid species post-hydrolysis; control oxygen if undesired.
Transesterification/acyl transfer:
DMAP (5–10 mol%) with anhydrides or alternative alcohols in MeCN or toluene, 25–60 °C, 2–16 h.
Lipase-mediated exchange in organic/aqueous biphasic systems at ambient temperature.
Electrophilic substitution on indole (protect O and often N):
Vilsmeier–Haack (POCl3/DMF) for C3-formylation at 0–25 °C.
Friedel–Crafts acylation with acid chlorides and Lewis acids (mild conditions) targeting C3; protect N with Boc to enhance regioselectivity.
Typical yields (qualitative):
Deacetylation often 70–95% if oxidation is minimized; enzymatic conversions vary with enzyme and cosolvent.
Workup tips:
Minimize exposure to air/light after generating the free indolyl alcohol; use antioxidants (e.g., ascorbate) if necessary for sensitive assays.
Safety and Handling
GHS classification and statements (this item):
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General hazards for indole aryl esters (literature/guidance):
May cause skin/eye irritation and respiratory irritation if dusts are generated. Avoid inhalation and contact.
Hydrolyzable ester: can liberate acetic acid under strong acid/base or enzymatic conditions; acetic acid is corrosive at high concentrations.
Oxidation: indoxyl-type species formed after hydrolysis can oxidize to colored indigoid products; minimize unintended exposure to strong oxidants.
Handling recommendations (professional practice):
Use in a fume hood with appropriate PPE: lab coat, nitrile gloves, safety glasses/goggles.
Avoid moisture when dry handling to limit premature hydrolysis. Prepare fresh solutions when possible.
For solution work, prefer anhydrous solvents for reactivity studies; for bioassays, use sterile, buffered systems.
Incompatibilities (general): strong acids/bases (accelerate hydrolysis), strong oxidizing agents, and prolonged exposure to light/air in solution.
First-aid overview (refer to SDS for authoritative guidance):
Eye/skin contact: Rinse with water for several minutes; remove contaminated clothing. Seek medical attention if irritation persists.
Inhalation: Move to fresh air; monitor for symptoms; obtain medical advice if needed.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Waste: Collect organic solutions as halogen-free organic waste unless solvent dictates otherwise. Follow institutional and local regulations.
Solvent Selection
4-Indolyl acetate is a moderately lipophilic aryl ester bearing an indole chromophore. It dissolves well in many polar aprotic organics and in DMSO for biological assays.
Synthetic transformations: dichloromethane, acetonitrile, or ethyl acetate often balance solubility and reactivity for ester hydrolysis, acyl transfer, or electrophilic aromatic substitution on the indole ring.
Enzymology/biochemical assays: prepare concentrated stocks in DMSO (e.g., 10–100 mM), then dilute into aqueous buffers keeping final DMSO ≤1–2% v/v to minimize enzyme inhibition. Include a non-ionic surfactant only if required.
Purification: normal-phase silica with EtOAc/hexanes or DCM/MeOH mixtures works well; reverse-phase (C18) using aqueous acetonitrile is suitable for analytical purity assessment.
When to choose alternatives:
If aqueous compatibility is essential, consider introducing a solubilizing co-solvent system (DMSO or MeCN) or derivatizing to a more polar analog for specific assays.
For peroxide-sensitive contexts, avoid ether-rich systems and store aprotic solvents properly; though 4-indolyl acetate itself is not a peroxide former, indole chromophores can be oxidation-sensitive.
Small comparison (qualitative):
DMSO: maximal solubility, enzyme-tolerable at low %.
MeCN: good solvent for kinetic studies and HPLC compatibility.
EtOAc: greener workup/purification solvent with adequate solubility.
Storage and Reconstitution
Storage conditions (item-specific):
Store at 2–8 °C (from Product Data).
Shipped on wet ice (from Product Data).
General storage guidance for aryl indolyl acetates (literature/practice):
Keep container tightly closed, in a dry place, protected from light. Moisture and prolonged light exposure can promote hydrolysis and oxidation.
For longer-term storage, consider an inert atmosphere (nitrogen/argon) and amber glass.
Reconstitution and solution handling:
Prepare concentrated stocks in anhydrous DMSO (e.g., 50–100 mM) or other suitable dry organic solvent (DMF, MeCN) immediately before use.
For biochemical assays, dilute into buffer to the desired concentration, keeping final organic co-solvent ≤1–2% v/v. Mix thoroughly to avoid localized precipitation.
Avoid repeated freeze–thaw of stock solutions; aliquot into single-use vials. Store solution aliquots at 2–8 °C for short periods (hours–days) or at −20 °C for longer, if stability is confirmed experimentally.
Stability notes:
Monitor for signs of hydrolysis (appearance of acetic acid odor, increased polarity on TLC/HPLC) and oxidation (development of color in solution). Prepare fresh solutions to ensure reproducibility.
Always consult the product’s CoA and SDS for definitive storage guidance and stability limits for the supplied lot.
Structure and Identity
4-Indolyl acetate is the O-acetyl ester of 4-hydroxyindole, combining an indole heteroaromatic core with a phenolic acetate protecting group.
Item-specific identifiers (from Product Data):
SKU: L115488
CAS: 5585-96-6
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identity (informational; not item specifications):
Core: bicyclic indole (benzofused pyrrole) with one ring nitrogen (pyrrolic N–H).
Substitution: an O-acetyl group at the 4-position of the benzenoid ring (i.e., the acetate ester of a phenolic OH on indole-4-ol). The acetate is –O–C(=O)–CH3.
Functional groups: heteroaromatic indole (weakly basic/acidic N–H), aryl ester (acid-labile/base-labile), and an amide-like carbonyl within the ester (electrophilic).
Stereochemistry: none (achiral; no stereocenters).
2D structural description in words (general):
An indole ring with the N–H in the five-membered ring. On the adjacent six-membered ring, the para-to-fusion carbon (position 4) bears an –OAc substituent (–O–C(=O)–CH3). The remainder of the ring is unsubstituted.
Note: Structural identifiers and exact tautomeric/structural data for this specific item should be confirmed from the CoA/Spec Sheet.
Synthetic Utility
4-Indolyl acetate is a versatile, protected-phenol indole building block. Its value lies in orthogonal functional group management and in leveraging the indole’s innate reactivity.
Protecting-group logic:
The O-acetyl group masks 4-hydroxyindole, enabling transformations that would otherwise suffer from phenolic O-attack or undesired chelation. It is removable under mild acid/base or via esterases, offering orthogonality to N-protecting groups (Boc, Cbz, Alloc).
Hydrolysis/deprotection: Na2CO3/MeOH-H2O, K2CO3/MeOH, or dilute HCl/MeOH at 0–25 °C to reveal 4-hydroxyindole.
Transesterification: catalytic DMAP or lipase-mediated exchange to other esters (e.g., pivalate, benzoate) to tune stability.
N-Functionalization: selective N-acylation/alkylation (e.g., Boc anhydride, alkyl halides) while OAc remains intact; subsequent electrophilic C3 functionalization (Vilsmeier–Haack formylation, Mannich, or Friedel–Crafts) proceeds with the phenol protected.
Cross-coupling (indirect): halogenate at C-3 or benzenoid positions after appropriate directing/protection; then perform Suzuki/Miyaura, Buchwald–Hartwig, or Sonogashira couplings. The OAc typically survives many Pd-catalyzed conditions.
Analytical handles:
Strong UV absorbance around 280 nm (typical for indoles) supports HPLC monitoring.
TLC visualizes under UV; post-stain with mild reagents to avoid inducing hydrolysis.
Caution:
Avoid strong bases at elevated temperature that could induce competing N-acylation migration or cleavage of OAc with side reactions.
Target Specificity
This product is a small-molecule reagent and does not have antibody/biological target specificity in the sense of immunoreagents.
Item-specific target details: Not applicable/not specified for this item.
Context (general): In enzymology research, aryl indolyl acetates can act as substrates for broad classes of carboxyl esterases and lipases. Any apparent “specificity” arises from enzyme-substrate kinetics and must be determined empirically for each enzyme preparation. No specific target, clone, or isotype information applies.
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