Indolelactic acid-d - ≥98% , CAS No.2470130-19-7

CAS: 2470130-19-7 Cat. No.: I1440120 Formula: C₁₁H₆D₅NO₃ Molecular Weight: 210.24

GRADE & PURITY ≥98%

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Indolelactic acid-d 5 is the deuterium labeled Indolelactic acid. Indolelactic acid is a tryptophan (Trp) catabolite in Azotobacter vinelandii cultures.

Specifications

Specifications & Purity

≥98%

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

Molecular Weight

210.24

Application Protocols

No item-specific, validated protocols are provided. The following is general guidance for using deuterated small-molecule standards in LC–MS/MS quantitation of indolelactic acid (research use only):

• Stock preparation:
  • Dissolve the material in dry DMSO or MeOH to prepare a primary stock (e.g., 1–10 mM as method permits). Filter if needed (PTFE, 0.2 μm). Record the exact concentration gravimetrically where possible.
• Working solutions and spiking:
  • Dilute the stock into water or mobile phase to create an internal standard (IS) working solution. Add IS to samples before extraction (protein precipitation, SPE, or LLE) to correct for recovery and matrix effects.
• Sample preparation (examples):
  • Protein precipitation: add IS, then 3–4 volumes of cold ACN or MeOH; vortex, centrifuge, collect supernatant.
  • SPE: condition cartridge, load sample containing IS, wash, elute with MeOH or MeOH/aqueous base, evaporate, and reconstitute in initial mobile phase.
• LC–MS settings (general):
  • Column: C18 or phenyl-hexyl. Mobile phases: water + 0.1% formic acid or ammonium formate; organic: MeOH/ACN. Monitor both analyte and IS transitions with appropriate mass offsets; verify absence of in-source H/D exchange.
• Calibration and QC:
  • Construct matrix-matched calibration curves with constant IS concentration across standards and QCs. Assess linearity, accuracy, precision, carryover, and stability (bench-top, autosampler, freeze–thaw).

Always tailor parameters to your instrument and matrix, and verify the isotopic label and purity on the CoA.

Biological Roles

This section summarizes literature knowledge about the unlabeled analyte (indole-3-lactic acid, ILA); the deuterated version is chemically analogous and used as a tracer/internal standard.

• Origin and pathways (literature):
  • ILA is a downstream product of tryptophan metabolism via the indolepyruvate pathway. It can be formed by microbial and host enzymes through reduction of indole-3-pyruvate to the α-hydroxy acid.
  • It is detected in diverse biological matrices (plasma, urine, feces, culture media) as part of the indole metabolome.
• Chemical features relevant to biology:
  • Amphipathic molecule with an indole aromatic system; exists predominantly as a carboxylate at physiological pH, influencing transport and protein binding.
  • The indole moiety can participate in noncovalent interactions (π–π, cation–π, H-bonding) with proteins and membranes.
• Research applications of the D-labeled analog:
  • Internal standard for targeted metabolomics to correct for matrix effects, ion suppression, and extraction variability.
  • Isotope tracing to follow uptake, interconversion, and clearance in in vitro systems and model organisms, provided the deuterium atoms are retained at relevant positions.

Important: Biological activities and signaling roles reported for ILA are context-dependent and outside the scope of this product description. This product is supplied strictly for research use only and is not intended for diagnostic or therapeutic applications.

Buffer Applications

Indolelactic acid-d is not a buffering reagent and does not constitute a standard biochemical buffer system.

• Practical note:
  • If dissolution in aqueous media is required, use a compatible buffer (e.g., phosphate, HEPES, carbonate) and adjust pH to maintain the compound in its carboxylate form for improved solubility. Validate that the buffer does not promote H/D exchange if deuterium retention is critical.
• For electrophoresis, cell culture, or enzyme assays:
  • Treat the compound as an analyte/standard added to pre-existing buffer systems rather than as a component that controls pH.

Refer to the Solvent Selection and Application Protocols sections for guidance on preparing stock solutions and spiking into buffered systems.

Green Alternatives

For analytical standards, the "green" dimension focuses on solvent choices and workflow design rather than replacing the analyte. Nevertheless, you can reduce environmental impact by optimizing media and derivatization.

• Solvent choice:
  • Prefer water/aqueous buffers when feasible by adjusting pH to solubilize the carboxylate form, thereby reducing reliance on high-boiling aprotic solvents.
  • When organic is required, MeOH or EtOH are greener alternatives to DMF/NMP. DMSO is relatively benign but challenging to remove.
• Sample preparation:
  • Minimize sample volumes and implement microextraction or 96-well SPE/precipitation to reduce solvent consumption.
  • Avoid chlorinated solvents in extraction; consider MeOH/ACN with water and buffered systems. If ACN use is heavy, evaluate EtOH/MeOH replacements for protein precipitation where method performance allows.
• Derivatization:
  • Choose less hazardous silylating/acylating agents when possible and conduct reactions at ambient temperature to minimize energy input.

Comparison (general perspectives):

• DMSO vs DMF/NMP: DMSO is less hazardous and often suitable for stock solutions, though it is not readily biodegradable; DMF/NMP carry reproductive toxicity concerns and should be avoided if alternatives meet performance requirements.
• Aqueous buffer at pH 8–9 vs strong base: Mild buffering achieves solubility with fewer safety and waste concerns than using concentrated NaOH or harsh amines.

Note: The analyte itself (indolelactic acid-d) has no practical “green substitute” in quantitative workflows; instead, greening focuses on solvents, scale, and waste minimization.

Pharmaceutical Uses

No excipient or compendial role is specified for this item; it is supplied for research use only.

• Typical research/formulation contexts (general):
  • Employed as a stable-isotope internal standard during method development and validation in bioanalytical assays that support pharmaceutical research (e.g., PK/PD studies in preclinical settings), aiding accuracy and precision of LC–MS/MS quantitation of indolelactic acid.
  • May be used to assess recovery and matrix effects in biological sample processing workflows (protein precipitation, SPE, or LLE) as part of method characterization.
• Regulatory note:
  • This product is not intended for human or veterinary use, not for diagnostic procedures, and not a drug substance or excipient. If an isotopically labeled internal standard is needed for regulated studies, confirm that documentation (CoA, isotopic enrichment data, stability information) meets your QA requirements.

Any pharmacopeial status, residual solvent profiles, or elemental impurity classifications are not specified for this item; refer to the CoA/Spec Sheet and SDS for details if required by your quality system.

Physical Properties

Only limited item-specific property data are provided for this catalog entry.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet (depends on degree/position of deuteration).
• Density, refractive index, water content, UV cut-off: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general/literature guidance for indole-3-lactic acid and its D-labeled analogs):
  • Freely soluble in polar aprotic solvents such as DMSO and DMF (literature/practice).
  • Sparingly to moderately soluble in water at neutral pH; solubility increases markedly in basic aqueous media due to carboxylate formation (literature).
  • Soluble in alcohols (MeOH, EtOH) and mixtures with water; limited in nonpolar hydrocarbons (literature).
• Acid–base behavior (literature):
  • Carboxylic acid pKa typically ~3–4 for α-hydroxy acids; phenyl/indole substituents may modestly modulate this value. Exact pKa for this isotopologue not specified.
  • The indolic N–H is weakly acidic; typically not deprotonated under neutral conditions.
• Partitioning (literature trend):
  • The indole ring imparts hydrophobic character, while the α-hydroxycarboxylic acid increases polarity, yielding amphipathic behavior; deprotonation strongly increases aqueous solubility.

Important: For exact numeric values (mp, bp, pKa, logP, solubility) of this specific deuterated item, consult the CoA/SDS or characterize under your method conditions.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and considerations for isotope-labeled small molecules:

• Isotopic enrichment: For quantitative mass spectrometry, the percent deuterium incorporation and the exact labeling pattern are as critical as chemical purity. Verify:
  • Total isotopic enrichment (e.g., ≥98 atom % D, if applicable; actual for this item not specified).
  • Site-specific labeling (ring vs side chain) to avoid H/D loss under assay conditions.
• Chemical purity and related substances: Review residual solvents, non-deuterated isotopologues, and synthetic by-products. For quantitation, the unlabeled analog content should be low enough to avoid bias at low analyte levels.
• Residual water/peroxide/metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Documentation: Request CoA and, if available, isotopic distribution spectrum and NMR/HRMS data that demonstrate the labeling pattern and enrichment.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Typically, no stabilizer is needed for solid α-hydroxyacids, but confirm for this item.

Use-case alignment:

• For LC–MS/MS internal standards, select an isotopologue with a mass shift that avoids overlap with natural isotopic envelopes and with fragmentation pathways that closely mirror the analyte. Ensure grade aligns with regulated method requirements if applicable (e.g., research vs. regulated bioanalysis; this product is for research use only).

Reaction and Applications

Primary uses of indolelactic acid-d are analytical and mechanistic rather than as a bulk reagent.

• Stable-isotope internal standard (LC–MS/MS, HRMS):
  • Employed for accurate quantification of endogenous indole-3-lactic acid in biological matrices (plasma, urine, feces, cell lysates). The deuterium label provides a mass shift with near-identical ionization and fragmentation behavior.
  • Selection of collision energies and transitions should mirror the unlabeled analyte; confirm absence of H/D scrambling under source conditions.
• Metabolic tracing (research):
  • Used in tracer studies to probe tryptophan–indole pathways, microbial metabolism, and transport processes. Isotope placement dictates interpretability; confirm site-specific labeling from the CoA.
• Derivatization chemistry for GC/LC:
  • Carboxyl function allows esterification (e.g., Me/Et esters via acidic alcohols) to tune volatility or LC retention.
  • α-Hydroxy group enables silylation (TMS, TBDMS) or acylation to increase detectability and improve chromatographic performance.
• Reactivity considerations:
  • The α-hydroxycarboxylic motif can undergo esterification, lactonization under dehydrating conditions (less favored here), and racemization under strong base/heat; preserve stereochemical integrity if relevant to your study.
  • The indole ring is nucleophilic at C3 (already substituted) and can undergo electrophilic substitution at other positions; however, such transformations will often compromise its identity as an internal standard.

Note: For quantitative bioanalysis, validate matrix effects, extraction recovery, and the stability of the deuterium label across all sample-prep steps.

Reaction Conditions

No item-specific reaction conditions are provided. The following general guidelines apply to transformations or analytical derivatizations of indolelactic acid and its deuterated analogs (literature/practice):

• Esterification of the carboxyl group:
  • Fischer conditions: alcohol solvent with catalytic mineral acid at ambient to reflux temperatures; for D-label retention, avoid prolonged heating in protic media if the labeled positions are exchangeable.
  • Steglich esterification: DCC/DMAP (or EDCI) in dry dichloromethane/DMF at 0–25°C provides milder conditions with better control over racemization.
• Silylation of the hydroxyl group (for GC/MS):
  • BSTFA or MSTFA with 1% TMCS in anhydrous acetonitrile or pyridine, 60–70°C for 15–30 min, yields TMS derivatives that enhance volatility and MS response.
• Amide coupling:
  • HATU/DIPEA or EDCI/HOBt in DMF or DCM at 0–25°C; monitor for potential racemization of the α-center under basic conditions.
• Oxidation of the secondary alcohol:
  • Dess–Martin periodinane or TEMPO/bleach at 0–25°C in aprotic media can give the corresponding keto acid; minimize aqueous exposure if D is at the α-position.
• LC–MS conditions (analytical, general):
  • Reversed-phase LC with aqueous buffer (0.1% formic acid or ammonium formate) and MeOH/ACN gradient; ESI(−) or ESI(+) depending on method. Validate that source conditions do not induce H/D exchange.

Always confirm label integrity by HRMS/NMR after transformations if the deuterium content is critical to the study.

Safety and Handling

Item-specific GHS and hazard details are not provided here; consult the SDS for authoritative information prior to use.

• GHS/Classification for this item: Not specified for this item; refer to SDS.
• Signal word, H-statements, pictograms: Not specified for this item; refer to SDS.

General laboratory guidance for indole-containing α-hydroxycarboxylic acids and their deuterated analogs:

• Handling: Avoid dust generation and inhalation. Prevent contact with eyes and skin. Work in a fume hood when weighing and preparing stock solutions, especially in organic solvents.
• PPE: Safety glasses, lab coat, and suitable chemically resistant gloves (e.g., nitrile). Use splash protection if preparing concentrated solutions.
• Storage incompatibilities: Keep away from strong oxidizers and strong bases/acids when neat. In solution, avoid prolonged exposure to strong base at elevated temperature to minimize potential racemization or decomposition of α-hydroxyacids.
• Stability considerations: Deuterated compounds can undergo H/D exchange at labile positions (e.g., exchangeable N–H, O–H, and sometimes benzylic/α positions under acidic/basic or catalytic conditions). Minimize exposure to protic media if retention of the deuterium label is critical; use dry, aprotic solvents when possible.
• First aid (overview; follow SDS): Inhalation—move to fresh air. Skin/eye contact—rinse with water for several minutes; remove contaminated clothing. Ingestion—rinse mouth, seek medical attention.
• Waste: Collect organic solutions and solids as hazardous chemical waste per institutional and local regulations.

Solvent Selection

As an amphipathic α-hydroxycarboxylic acid bearing an indole ring, indolelactic acid-d exhibits dual solubility behavior.

• Polarity class and miscibility (general/literature trends):
  • Highly soluble in polar aprotic solvents (DMSO, DMF, NMP) and protic alcohols (MeOH, EtOH).
  • Limited solubility in nonpolar solvents (hexanes, toluene) unless derivatized or ion-paired.
  • Aqueous solubility increases strongly above pH ~5 due to carboxylate formation; near-neutral water solubility may be modest.
• Practical stock preparation:
  • Prepare concentrated stocks in DMSO (e.g., 10–100 mM as method allows) and dilute into aqueous buffers immediately prior to use to limit precipitation; verify stability of the deuterium label in the chosen diluent.
  • For fully aqueous methods, adjust to basic pH (e.g., carbonate/bicarbonate) to keep the compound in its carboxylate form.
• When to choose alternatives:
  • For GC-based workflows, convert to volatile derivatives (e.g., silyl esters/ethers) to enable use of nonpolar carriers.
  • If H/D retention is critical, favor dry aprotic media over protic solvents that promote exchange at labile positions.
• Small comparison (general):
  • DMSO vs MeOH: DMSO maximizes solubility and minimizes rapid H/D exchange; MeOH aids quick dissolution but is protic.
  • Water (pH >7) vs neutral water: deprotonated form is more soluble and chromatographically distinct; neutral water may precipitate concentrated stocks.

Storage and Reconstitution

• Storage conditions (item-specific): Store at 2–8°C. Shipped on wet ice.
• Containerization: Keep tightly closed in the original container to minimize moisture uptake and atmospheric exchange that could promote H/D exchange at labile sites.
• Protection: Store desiccated, away from light and heat sources. If label integrity is critical, limit exposure to protic vapors and repeated opening.
• Reconstitution and stock solutions:
  • Use dry, oxygen- and moisture-limited conditions when preparing concentrated stocks. Preferred solvents are dry DMSO or MeOH; for maximum D-retention, favor aprotic media and avoid prolonged contact with water or basic solutions unless necessary for the application.
  • Prepare aliquots to avoid repeated freeze–thaw cycles. For aqueous working solutions, prepare fresh as needed.
• Stability guidance:
  • Long-term solid stability at 2–8°C is generally good for small aromatic α-hydroxyacids, but specific stability data for this isotopologue are not provided; monitor by LC–MS.
  • In solution, store at low temperature (e.g., 2–8°C for short term; −20°C for longer term) and protect from light. Validate stability in your intended matrix and solvent system.
• Research use note: For research use only. Not for human or veterinary use.

For definitive shelf life, retest intervals, and solution stability of this specific item, consult the product CoA and SDS.

Structure and Identity

Indolelactic acid-d is a deuterium-labeled analog of indolelactic acid, designed as a stable-isotope reagent for analytical and mechanistic studies.

• Item-specific identifiers:
  • CAS: 2470130-19-7
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Structural features (general/literature description):
  • Core scaffold: an indole ring (fused benzene–pyrrole) bearing a 3-substituted side chain.
  • Functional groups: secondary alcohol and carboxylic acid on the lactic-acid side chain (2-hydroxypropionic acid tethered at the 3-position of indole).
  • Isotopic label: one or more hydrogens in the molecule are replaced by deuterium (exact labeling pattern is item-specific; consult CoA for the D-count and positions).
  • Stereochemistry: the lactic acid center can be R or S in unlabeled material; isotope substitution does not introduce a new stereocenter but may specify enantiomeric form in some products (not specified here).
• 2D structure (described): an indole ring with the C3 carbon bearing a –CH(OH)–CH3–CO2H fragment; ring nitro­gen is unsubstituted. In the deuterated variant, selected hydrogen atoms on the side chain and/or ring are replaced by D to create a mass shift for MS-based quantification.

Note: Exact isotopic enrichment and labeling positions are critical for analytical use; verify on the product CoA before method development.

Synthetic Utility

While primarily an analytical standard, indolelactic acid-d can serve as a labeled building block or probe in synthesis and mechanistic experiments.

• Functional group handles:
  • Carboxylic acid: amenable to esterification (Fischer, Steglich), amidation (carbodiimide, HATU/EDC), and coupling to reporter tags or carriers while retaining a deuterium-derived mass signature.
  • Secondary alcohol: allows acylation, silylation, or oxidation to the corresponding keto-acid (indolepyruvic acid analog) for isotope effect studies.
  • Indole ring: electrophilic substitution (e.g., halogenation, N-acylation/alkylation), though modifications may defeat its use as an internal standard.
• Isotopic considerations:
  • Site-specific deuteration enables kinetic isotope effect investigations, mapping of hydrogen transfer steps, and MS-based tracking of fragment origin.
  • Avoid conditions that cause H/D exchange at labeled positions (strong acids/bases, metal-catalyzed exchange, protic solvents at elevated temperature) if label retention is required.
• Conjugation examples (general):
  • Preparation of deuterated esters/amides to tune chromatographic properties or to immobilize on solid supports for affinity studies.
  • Derivatization with chromophores or fluorophores for orthogonal detection while keeping MS traceability via the D label.

Before synthetic use, verify the exact labeling pattern and enrichment on the CoA to ensure the deuterium atoms reside at positions relevant to your mechanistic or analytical goals.

Target Specificity

This product is a small-molecule isotopologue and does not possess biological target specificity in the sense of antibodies, enzymes, or receptor ligands supplied as biological reagents.

• No antigen, epitope, clone, isotype, or species reactivity information applies.
• Its “specificity” in practice is analytical: the mass shift relative to unlabeled indolelactic acid enables selective detection and quantification by MS.

For intended analytical selectivity, confirm the mass difference and fragmentation behavior from the CoA and your instrument method.

Frequently Asked 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. Refrigerated storage is required to maintain the specified shelf life.

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 2470130-19-7, the molecular formula is C11H6D5NO3, and the molecular weight is 210.24 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.