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Application Protocols
Item-specific tested applications and dilutions: Not specified for this item; refer to CoA/Spec Sheet.
General protocols (research use only)
LC–MS internal standard preparation
Prepare a ~1–10 mM stock in water or 50:50 water:acetonitrile.
Store aliquots at −20 °C; thaw on ice and dilute into mobile phase to 1–100 μM depending on detector sensitivity.
Use in negative ESI mode; monitor [M–H]− at m/z = unlabeled lactate − 1 + 1 (i.e., +1 shift from native).
¹³C/¹H NMR tracer solutions
Dissolve in D2O to 10–100 mM; adjust pD with NaOD/DCl to minimize exchange broadening.
Acquire ¹³C spectra with broadband ¹H decoupling; expect a downfield carbonyl signal from the 3-¹³C label.
Buffer preparation (lactate buffer)
Combine lactic acid with equimolar NaOH to form sodium lactate; adjust to desired pH (3–5 range is typical for lactate buffering).
Notes
Filter solutions (0.22 μm) for bioanalytical applications to remove particulates.
Validate concentration by quantitative NMR (qNMR) or gravimetry for precise isotope-dilution studies.
Always confirm stability and compatibility with your analytical method; refer to CoA for lot-specific guidance.
Biological Roles
General biochemical context (literature)
Central metabolite: L-Lactic acid (lactate) is a key endpoint of anaerobic glycolysis and a substrate in gluconeogenesis (Cori cycle). The L-(S) enantiomer is predominant in human and most mammalian metabolism.
Redox balance: Formation of lactate from pyruvate via lactate dehydrogenase (LDH) regenerates NAD+, sustaining glycolytic ATP production under hypoxia.
Shuttling/signaling: Lactate is transported by monocarboxylate transporters (MCTs) and can act as a metabolic fuel and pH-modulating species in tissue microenvironments (literature).
Isotopic tracing utility: Position-specific 3-¹³C labeling enables tracking of the carboxyl carbon through LDH interconversion with pyruvate, TCA cycle entry (via pyruvate dehydrogenase to acetyl-CoA with CO2 release), and assessment of carbon fate via ¹³C NMR or MS isotopologue analysis.
Enzymatic specificity: LDH stereoselectively processes L-lactate; D-lactate is handled by distinct dehydrogenases in organisms that produce/use it.
Notes for researchers
Use stable isotope-resolved metabolomics to discriminate endogenous lactate from spiked tracer via +1 m/z and distinct ¹³C satellite patterns in NMR.
Control pH carefully in biological incubations; lactate speciation (acid vs lactate anion) affects transport and enzyme kinetics.
This product is for research use only and not for human or veterinary applications.
Buffer Applications
Applicability: L-Lactic acid is commonly used with its conjugate base (lactate) to prepare buffers in the acidic range; isotopic labeling does not affect buffering capacity.
For a 0.1 M lactate buffer at pH 3.8: Combine calculated amounts of lactic acid with NaOH (or directly mix lactic acid with sodium lactate) to achieve the desired Henderson–Hasselbalch ratio; adjust ionic strength as needed.
For NMR work: Prepare in D2O and adjust pD (pD ≈ pH meter reading + 0.4–0.5) to reduce exchange broadening.
Sterility: Filter-sterilize (0.22 μm) if buffer will contact biological samples; store cold to limit microbial growth.
Practical notes
Temperature dependence: pKa shifts modestly with temperature; recalibrate pH at working temperature when high precision is required.
Ionic strength: Add NaCl to mimic physiological ionic strength if needed for transport/enzyme assays.
Isotopic integrity: Neutralization and dilution do not move the ¹³C label; avoid decarboxylating conditions.
Item-specific
Buffer-related specifications for this item are Not specified for this item; refer to CoA/Spec Sheet.
Green Alternatives
Perspective: L-Lactic acid is a bio-based, biodegradable α-hydroxy acid often produced by fermentation, which aligns well with green chemistry principles. For isotopic material, production routes depend on ¹³C source economics and availability.
Green attributes (general)
Renewable feedstock: Conventionally sourced from carbohydrate fermentation (literature).
Low toxicity profile relative to many mineral acids; fully water-miscible enabling aqueous processing.
Biodegradable; participates in natural metabolic cycles.
Greener handling choices
Prefer aqueous media when feasible to reduce VOC emissions.
Use catalytic esterification (e.g., solid acid catalysts) instead of stoichiometric reagents when preparing esters.
For extractions, consider ethyl acetate or 2-MeTHF as greener alternatives to chlorinated solvents when compatible.
Tradeoffs
Aqueous systems may complicate downstream drying and can promote esterification or oligomerization during concentration.
Isotopically enriched ¹³C feedstocks may limit scalability and increase cost/footprint compared with unlabeled acids.
Comparison (literature-based, qualitative)
Mineral acids (HCl/H2SO4): Stronger acid strength but corrosive and hazardous; lactic acid offers milder, safer acidity for pH adjustment in research settings.
Organic solvents for derivatization: 2-MeTHF/EtOAc preferable to DCM/CHCl3 when making lactate esters; monitor water content to control equilibrium.
Pharmaceutical Uses
Scope: No clinical claims are made. The notes below concern general formulation and manufacturing roles of lactic acid; the isotopically labeled product is intended for research/analytical use only.
Excipient roles (literature/general)
pH adjustment/acidulant: Used to acidify aqueous formulations, cleaning-in-place (CIP) solutions, and as a counter-ion for basic APIs.
Solubilization aid: Conversion of basic drugs to lactate salts can enhance aqueous solubility.
Polymer precursor: Lactic acid derivatives are precursors to polylactide (PLA); isotopically labeled variants may serve in degradation/trace studies, not routine manufacture.
Analytical/validation uses of 3-¹³C-labeled material
Internal standards: Isotope dilution LC–MS/GC–MS quantification of lactic acid in formulations and process streams.
Stability studies: Tracking lactate formation/degradation pathways by mass balance using the distinctive +1 m/z label.
Regulatory and quality notes
Pharmacopeial monographs exist for unlabeled lactic acid in major compendia; however, isotopically labeled versions are typically supplied under research-use documentation. Confirm acceptance criteria with your QA unit.
Item-specific
Grade, compendial status, residual solvent limits, and metal content: Not specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific properties
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (reference values for lactic acid; isotopic labeling has negligible effect on bulk physico-chemical behavior)
State/appearance: Colorless to pale syrupy liquid/solid depending on purity and hydration (literature)
Melting point: ~53 °C (for anhydrous crystalline lactic acid; literature)
Boiling point: Decomposes; reported ~122 °C at 20 mmHg (literature)
Density: ~1.20 g/mL at 20 °C (literature; concentration/purity dependent)
Refractive index (n20D): ~1.43 (literature; concentration dependent)
pKa (25 °C): ~3.86 for the carboxylic acid (literature)
LogP (octanol/water): ~−0.7 (literature)
Solubility: Miscible with water, ethanol, and many polar protic/apyrotic solvents; low solubility in nonpolar hydrocarbons (literature)
Hygroscopicity: Can absorb moisture; forms oligomers/esters upon heating or under dehydrating conditions (literature)
Notes for practitioners
The ¹³C enrichment does not materially change melting/boiling behavior, pKa, or miscibility; use standard lactic acid handling assumptions for method development.
Physical constants vary with water content (free acid vs aqueous solutions) and enantiopurity; verify with CoA for lot-specific data when critical.
Quality and Grades
Item-specific details
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Isotopic enrichment (¹³C at C-3): Not specified for this item; refer to CoA/Spec Sheet.
Context and expectations for isotopically labeled small molecules (general guidance)
Isotopic purity: For quantitative NMR or MS tracer work, suppliers commonly offer >98–99 atom% ¹³C at the labeled position. Verify exact enrichment and any ¹²C residual content on the CoA for quantitative work (e.g., isotope dilution MS).
Chemical purity: High chemical purity minimizes background signals and matrix effects in analytical workflows. Check residual solvent, water content, and optical purity (ee) when chiral discrimination is relevant.
Optical purity: As an L-(S) reagent, enantiomeric excess is often specified for chiral pool or stereochemical studies. If not stated, request an ee certificate.
Trace contaminants: For bioanalytical standards, low levels of inorganic ions and metal catalysts are preferred. Item-specific metal limits are Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Typically none are added for lactic acid, but if present they can influence UV background and derivatizations. Stabilizers for this item are Not specified for this item; refer to CoA/Spec Sheet.
Documentation
For regulated or quantitative studies, retain the CoA, lot-specific Spec Sheet, and isotopic enrichment statement. Recalibrate analytical methods if changing lots.
Reaction and Applications
Primary use domains
Isotopic tracing: The 3-¹³C label at the carboxyl carbon makes this compound ideal for metabolic flux analysis (MFA), stable isotope-resolved metabolomics (SIRM), and ¹³C NMR/MS studies of glycolysis, fermentation, and the Cori cycle.
Internal standards: Serves as an isotope-labeled internal standard for quantifying lactic acid in biological and industrial samples by LC–MS/GC–MS.
Synthetic/chemical applications (general)
Esterification: Fischer esterification to form methyl/ethyl 3-¹³C-lactate; preserves label at the carbonyl carbon.
Salt formation: Generation of sodium/potassium 3-¹³C-lactate for buffer systems or analytical calibrants.
Protection strategies: Hydroxyl protection (e.g., TBDMS, TBDPS) to enable selective acylation or coupling at the carboxylate without scrambling the label.
Coupling: Carbodiimide-mediated ester/amide formation (DCC/EDC + DMAP/NHS) to incorporate 3-¹³C-lactyl residues into polymers or small molecules.
Oxidation: Alcohol oxidation (e.g., TEMPO, Dess–Martin) to 3-¹³C-pyruvic acid; useful as a labeled keto-acid standard.
Analytical tips
¹³C NMR: The labeled carbonyl resonates downfield (~170–185 ppm; literature), simplifying assignment. Use proton-decoupling to enhance signal-to-noise.
MS behavior: In negative ESI, lactate [M–H]− is strong; the +1 m/z shift cleanly differentiates from unlabeled analyte. Monitor potential 44→43 CO2 loss pathways in fragmentation while noting the ¹³C retention.
Avoid label scrambling: Maintain mild temperatures and avoid decarboxylation conditions to preserve the ¹³C at C-3.
Reaction Conditions
General conditions (literature guidance for α-hydroxy acids; adjust per substrate and objective)
Fischer esterification (to 3-¹³C-lactate esters)
Solvent: Neat alcohol (MeOH, EtOH) or toluene with Dean–Stark
Catalyst: p-TsOH or H2SO4 (catalytic)
Temperature/time: Reflux, 2–12 h depending on water removal
Notes: Remove water to drive equilibrium; protect the OH if over-esterification is an issue.
Carbodiimide coupling (ester/amide formation)
Solvent: DCM, DMF, or MeCN
Reagents: DCC or EDC·HCl (1.1–1.5 eq), DMAP or HOBt/NHS additives
Temperature/time: 0–25 °C, 1–16 h
Notes: Filter urea byproducts; control base to limit epimerization at C-2.
Alcohol protection (silylation)
Solvent: DMF or DCM (dry)
Reagents: TBDMS-Cl (1.2–1.5 eq), imidazole or Et3N
Reagents: TEMPO (5–10 mol%), NaClO (bleach), KBr (co-catalyst) or Dess–Martin periodinane
Temperature/time: 0–25 °C, 0.5–4 h
Notes: Monitor closely to avoid overoxidation; maintain pH ~8–9 in TEMPO protocol.
Salt formation/buffer prep
Solvent: Water or alcohols
Base: NaOH, KOH, or amines (1.0 eq)
Temperature/time: 0–25 °C, minutes
Notes: Gentle addition with cooling to dissipate heat; isotopic label remains at C-3.
Yields are substrate- and setup-dependent; consult primary literature for your specific transformation.
Safety and Handling
Item-specific hazard information
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 safety considerations for α-hydroxy carboxylic acids (literature/good practice)
Hazards: Organic acids can be irritating to skin, eyes, and mucous membranes; concentrated solutions may cause burns. Inhalation of mists may irritate respiratory tract.
PPE: Use lab coat, safety glasses/goggles, and appropriate chemically resistant gloves (e.g., nitrile). Employ splash protection when preparing concentrated solutions.
Engineering controls: Handle in a fume hood to avoid inhalation of vapors/aerosols. Ensure access to eyewash and safety shower.
Incompatibilities: Strong oxidizers (risk of exotherm), strong bases (vigorous neutralization), reactive acylating agents, dehydrating agents (esterification/oligomerization). Avoid contact with reactive metals if acidic media can generate H2.
Spill/cleanup: Absorb small spills with inert material; neutralize cautiously with sodium bicarbonate and collect for disposal. Prevent release to drains without proper neutralization.
First aid (overview; defer to SDS):
Skin/eye contact: Rinse immediately with copious water for ≥15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
Ingestion/inhalation: Rinse mouth; move to fresh air; do not induce vomiting; obtain medical advice.
Special notes: Not prone to peroxide formation. Hygroscopic; wipe closures, purge headspace when feasible, and re-cap promptly to limit water uptake and microbial contamination.
Waste: Dispose as organic acid waste per institutional and local regulations.
Solvent Selection
Relevance: L-Lactic acid-3-¹³C is a polar, strongly hydrogen-bonding α-hydroxy acid; it is typically handled as neat material or in polar solvents.
Limited solubility: Acetonitrile (improves with small amounts of water), acetone.
Poor solubility: Nonpolar hydrocarbons (hexanes, toluene) unless converted to esters/salts.
Dielectric context: Water (ε ~80) and DMSO (ε ~47) efficiently solvate the ionic/associated forms; protic solvents can promote esterification under acidic/dehydrating conditions.
Selection tips by application
NMR standards/tracers: D2O or DMSO-d6 for ¹H/¹³C NMR; adjust pD/pH with NaOD/NaOH or DCl/HCl to reduce line broadening from exchange.
LC–MS reference solutions: Water or water:acetonitrile with 0–0.1% formic acid; avoid high organic at low pH if lactate anion response is desired in negative ESI.
Derivatization chemistry: Use anhydrous alcohols (MeOH, EtOH) with catalytic acid for Fischer esterification; remove water to drive equilibrium.
Chiral synthesis: Non-aqueous polar solvents (MeCN, THF, toluene with co-solvent) may be preferable after converting to esters to enhance solubility.
Alternatives: If water sensitivity is critical, employ protected derivatives (e.g., O-silyl esters of lactate) in anhydrous aprotic media, then deprotect.
Storage and Reconstitution
Item-specific instructions (from Product Data)
Storage Conditions: Store at -20°C.
Shipped In: Ice chest + Ice pads.
Additional guidance (general best practice)
Container: Store in tightly sealed, chemically compatible vials (e.g., glass with PTFE-lined caps) to minimize moisture uptake and atmospheric CO2 interaction.
Light/moisture: Protect from prolonged exposure to light and ambient humidity; lactic acid is hygroscopic and can absorb water, altering concentration.
Aliquoting: To avoid repeated freeze–thaw cycles, prepare single-use aliquots upon receipt; purge headspace with inert gas if long-term storage is planned.
Reconstitution/stock solutions
Solvents: Water, D2O (for NMR), or polar organics (MeOH, EtOH, DMSO) as compatible with your application.
Typical concentrations: 1–100 mM for analytical standards; adjust to fit instrument response (general guidance).
pH adjustment: Use NaOH/KOH (or NaOD/DCl in D2O) to prepare lactate salts/buffers; record final pH/pD.
Stability
Chemical stability and shelf-life: Not specified for this item; refer to CoA/Spec Sheet.
Avoid elevated temperatures and dehydrating acids that can promote esterification/oligomerization.
Handling after thaw
Thaw on ice, mix thoroughly to ensure homogeneity, and verify concentration if hygroscopic gain is a concern (e.g., by qNMR or titration).
Research Use Note: For research use only.
Structure and Identity
Brief description: L-Lactic acid-3-¹³C is the isotopically enriched form of (S)-2-hydroxypropanoic acid with the carboxyl (C-3) carbon labeled with ¹³C. It serves as a tracer/standard in NMR and MS-based studies and as a chiral, α-hydroxy acid building block.
Item-specific (from Product Data)
SKU: L474072
Product Name: L-Lactic acid-3-¹³C
CAS: 155307-62-3
InChIKey: 171399 (as provided)
Storage Conditions: Store at -20°C
Shipped In: Ice chest + Ice pads
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identity details (for reference; not product specifications)
InChI (conceptual): includes isotopic specification at the carboxyl carbon; specific key will differ from the unlabeled compound.
2D structural description (general)
A three-carbon backbone: C-1 methyl (CH3) – C-2 chiral center bearing OH and H – C-3 carboxylate carbon (here ¹³C). The hydroxyl and carboxyl groups are vicinal (α-hydroxy acid), enabling intramolecular H-bonding and facile ester/salt formation.
Synthetic Utility
Functional group perspective
Bifunctional synthon: Carboxylic acid (at 3-¹³C) and secondary alcohol at the α-position enable orthogonal transformations.
Chirality: L-(S) center offers chiral pool access to enantioenriched intermediates without asymmetric catalysis.
Typical transformations (literature)
Ester/amide formation: DCC/EDC-mediated couplings to generate 3-¹³C-lactate esters and amides; DMAP or HOBt/NHS may be used to improve efficiency and suppress racemization.
Protection/deprotection: Silylation (TBDMS-Cl, imidazole) or acylation (Ac2O) of the alcohol; formation of benzyl/allyl esters at the acid for temporary protection of the labeled carbonyl.
Oxidation/reduction: Oxidize the α-hydroxyl to yield 3-¹³C-pyruvate (e.g., TEMPO/bleach, Dess–Martin) or reduce the acid to 1,2-propanediol derivatives via borane or LiAlH4 pathways while conserving the ¹³C label position.
Cyclization/derivatization: Formation of lactides or cyclic carbonates from lactate derivatives for polymer studies with site-specific ¹³C markers.
Isotopic considerations
Label integrity: Avoid decarboxylation and harsh conditions that could exchange or eliminate the carboxyl carbon. Esterification, amidation, and most OH protections preserve the ¹³C at C-3.
Spectroscopic utility: The ¹³C label simplifies ¹³C NMR assignment and enhances sensitivity at the carbonyl, facilitating kinetic and mechanistic studies in situ.
Practical tips
Employ anhydrous conditions for acylations/esterifications to minimize oligomerization.
Monitor ee if any steps risk epimerization at C-2; use mild bases and low temperatures.
Target Specificity
Not applicable. This product is a small-molecule metabolite (isotopically labeled) and is not an antibody, enzyme, or affinity reagent. No target, epitope, clone, isotype, or species reactivity information applies.
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