L-Lactic acid-1-¹³C - ≥99 atom% 13C,≥98%,≥98%(Chiral Purity,HPLC) , CAS No.727379-97-7

CAS: 727379-97-7 Cat. No.: L465451 Formula: CH₃CH(OH)¹³CO₂H Peso molecolare: 91.07 Numero EC: 687-886-8

Synonyms

Sarcolactic acid-1-13C, (S)-2-Hydroxypropionic acid-1-13C

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Sinonimi

Sarcolactic acid-1-13C, (S)-2-Hydroxypropionic acid-1-13C

Specifiche e purezza

≥99 atom% 13C,≥98%,≥98%(Chiral Purity,HPLC)

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Nomi e identificatori

Sorrisi canonici

C[C@H](O)[13C](O)=O

InChIKey

JVTAAEKCZFNVCJ-NSQKCYGPSA-N

INCHI

1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1/i3+1

Numero UN

3261

Peso molecolare

91.07

Reaxy-Rn

30899946

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=30899946&ln=

Proprietà chimiche e fisiche

• Punto di infiammabilità (°F): 235.4 °F - closed cup
• Punto di infiammabilità (°C): 113 °C - closed cup

Application Protocols

Item-specific validated protocols are not provided for this SKU. The following are general, literature-based starting points tailored to [1-13C]-lactic acid; optimize for your system.

• 13C NMR quantitation in aqueous solution:

  • Prepare a 100–200 mM solution in D2O; neutralize to pD ~7.5 with NaOD to form sodium [1-13C]lactate (reduces exchange broadening).
  • Acquire 13C spectrum with broadband 1H decoupling; 13C carboxyl resonance expected ~175–185 ppm (literature). Use inverse-gated decoupling for qNMR.
  • Include an external or internal 13C standard (e.g., 1,4-dioxane-13C2) if absolute quantitation is required.

• LC–MS isotopic tracer assay (negative ESI):

  • Stock: 10 mM in water. Working: 1–100 µM in 50:50 water:acetonitrile, 5 mM ammonium acetate, pH ~8.
  • Inject onto HILIC or ion-pair reversed-phase column; monitor m/z 91→43 (example transition; adjust to instrument/method) for [1-13C]lactate and m/z 89→43 for unlabeled.
  • Calibrate with mixed labeled/unlabeled standards for isotope dilution quantitation.

• LDH exchange assay (spectrophotometric coupled):

  • Buffer: 50 mM HEPES, pH 7.5; 1 mM NAD+; variable [1-13C]lactate (0.1–10 mM); LDH at catalytic levels.
  • Monitor NADH formation at 340 nm; parallel aliquots taken for 13C NMR or LC–MS to confirm label position in pyruvate.

Note: Parameters above are representative literature starting points. Validate against your instrument and refer to peer-reviewed methods for compliance.

Biological Roles

General biochemical context (literature):

• Central metabolite: L-lactic acid (lactate) is produced from pyruvate by lactate dehydrogenase (LDH) coupled to NADH oxidation; it is interconverted with pyruvate depending on cellular redox and oxygen availability.
• Transport: Translocated across membranes by monocarboxylate transporters (MCTs), often coupled to proton gradients. Intercellular lactate shuttling supports metabolic cooperation between tissues/cell types.
• Pathways impacted: Glycolysis, gluconeogenesis (Cori cycle), anaplerosis via pyruvate carboxylase, and oxidative metabolism via pyruvate dehydrogenase and the TCA cycle.
• Signaling: Lactate can modulate enzyme activities and transcriptional programs via redox state and post-translational modifications (e.g., lysine lactylation; literature under active study).

Role of the 13C label at C1:

• Label fate under PDH vs PC: PDH releases C1 as CO2 (label lost), whereas PC retains C1 into oxaloacetate/malate (label observed in specific TCA positions after scrambling), enabling discrimination of pathway fluxes by 13C NMR or MS isotopomer analysis.
• LDH exchange: Rapid LDH-catalyzed exchange maintains the 13C label at the carboxyl position through the lactate–pyruvate interconversion.
• Fluxomics utility: [1-13C]lactate is a standard probe for quantifying lactate uptake/production rates, exchange with pyruvate, and contributions to gluconeogenic output in cells or extracts.

Note: For research use only. No clinical or diagnostic claims are made or implied.

Buffer Applications

While lactic acid is not a primary Good’s buffer, the lactate/lactic acid system forms a useful buffering pair around its pKa.

• Relevant constants (literature): pKa ≈ 3.86 at 25 °C; effective buffering range ~2.8–4.8.
• Typical compositions:
  • Lactic acid buffer: prepare lactic acid in water and titrate with NaOH to desired pH within 3–4.5.
  • Sodium lactate buffer: dissolve sodium [1-13C]lactate (formed in situ by neutralizing [1-13C]-lactic acid) to the target molarity; adjust pH with HCl or NaOH.
• Practical recipes (example):
  • 0.1 M lactate buffer, pH 3.8: dissolve 8.6 g lactic acid (FW 90.08; literature FW for unlabeled) in ~800 mL water, adjust to pH 3.8 with ~0.1–0.2 M NaOH, bring to 1 L. For isotopic work, compute using the exact FW from the CoA and minimize dilution steps to preserve concentration accuracy.
• Considerations for isotopic experiments:
  • Use carbonate-free base (fresh NaOH/NaOD) to avoid pH drift and unintended isotopic dilution in 13C quantitation (minor impact but good practice).
  • Avoid elevated temperatures and strong acid catalysis in alcoholic solvents to prevent ester formation, which can alter speciation and analytical response.

If your application does not require buffering near pH 4, prefer a Good’s buffer (e.g., HEPES, MOPS) and add [1-13C]lactate as an analyte within that buffer.

Green Alternatives

Lactic acid is itself a biobased, biodegradable organic acid widely considered a greener alternative to many mineral acids in aqueous processing. For this isotopically labeled variant, the focus is typically on analytical performance rather than bulk processing, but sustainability considerations still apply.

• Greenness profile (general literature):

  • Feedstock: conventionally produced by fermentation of renewable carbohydrates (corn, sugarcane); isotopic labeling may use specialized substrates, which can increase footprint.
  • Biodegradability: readily biodegradable; low persistence.
  • Aqueous usability: effective in water, reducing reliance on hazardous organic solvents for many acidification tasks.

• Alternatives and trade-offs:

  • Lactic acid vs mineral acids (HCl, H2SO4): lactic acid offers milder, buffered acidity and is safer to handle; however, for stoichiometric neutralization/mineralization, strong acids may be required at smaller volumes.
  • Lactic acid vs other α-hydroxy acids (glycolic, mandelic): similar acidity; choice driven by solubility and downstream compatibility. For isotope tracing of central carbon metabolism, lactic acid is uniquely relevant.

• Practical guidance:

  • For tracer studies, minimizing solvent and avoiding halogenated media (e.g., CHCl3) is straightforward because the reagent is water-soluble.
  • Reuse/aliquoting: prepare concentrated aqueous stock solutions and aliquot to reduce waste from repeated thaw/discard cycles.

Note: Green chemistry substitution is less applicable here because the reagent’s identity (lactate) dictates biological relevance; greener practice focuses on solvent choice (water) and right-sizing experiments.

Pharmaceutical Uses

Item-specific regulatory or pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet. This product is designated For research use only.

General formulation roles of lactic acid (literature; not specific to this isotope and not for human/clinical use):

• Excipient functions: pH modifier/acidulant in aqueous formulations; counterion to form lactate salts of APIs (enhancing solubility/stability for some actives).
• Processing aid: ester formation (e.g., ethyl/methyl lactate) used as solvents in topical/non-sterile products; formation of lactate buffers for stability studies.
• Polymer feedstock studies: lactic acid → lactide → polylactide (PLA) for biomedical material research; [1-13C] label can support analytical tracking of degradation in preclinical materials R&D.

Caveats for this SKU:

• Isotopic labeling greatly increases cost; it is atypical for manufacturing scale and is primarily an analytical tool in development laboratories.
• No medical, diagnostic, or therapeutic claims are made for this product. It is not certified to any pharmacopoeial monograph in this listing; verify any compendial needs independently.

Best practices in a development lab setting:

• When used as a pH adjuster or counterion in research formulations, standardize titers by potentiometric titration and account for exact formula weight from the CoA (13C contributes +1.0033 Da relative to natural abundance).

Physical Properties

Item-specific physical specifications (this catalog lot):

• Boiling point, melting point, density, refractive index, water content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for L-lactic acid (unlabeled; the 13C label does not materially change bulk properties):

• Physical state: typically a low-melting solid or viscous liquid depending on hydration; pure L-lactic acid reported to melt near ~53 °C (literature).
• pKa (25 °C): ~3.86 (carboxyl group; literature), useful for buffer calculations in the pH 2.8–4.8 range.
• Solubility: miscible with water; highly soluble in polar protic solvents (MeOH, EtOH); limited solubility in nonpolar solvents (literature).
• Partitioning: logP (XlogP3, literature) approximately −0.7 to −0.6 indicating high hydrophilicity.
• Boiling behavior: tends to decompose/esterify upon heating; distillation reported at reduced pressure (e.g., ~122 °C at ~15 mmHg; literature). Prolonged heating can cause lactide formation.
• Hygroscopicity: can absorb moisture; aqueous solutions are common in commerce (literature note).

Notes for practitioners:

• For NMR work, 13C-labeled lactic acid is typically prepared as the sodium lactate salt to shift pH >6 and minimize line broadening from exchange; dissolve in D2O for 13C/1H acquisition.
• Exact thermal constants and density are matrix- and hydration-state dependent; consult the item’s CoA for any lot-specific values if required for method validation.

Quality and Grades

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

Considerations specific to isotopically labeled L-lactic acid:

• Isotopic enrichment (atom % 13C at C1): Critical for sensitivity and quantitative tracing in NMR/MS. The exact enrichment for this SKU is not specified; confirm on the CoA when designing quantitative flux studies.
• Chemical purity: Residual solvents, water content, and trace salts can influence NMR baselines and MS ionization. If purity is unspecified, perform a quick QC (1H/13C NMR, qNMR against internal standard, and HRMS) on receipt for critical applications.
• Enantiomeric purity: As an L-isomer reagent, enantiomeric excess (ee%) impacts chiral recognition and enzymatic assays (e.g., LDH). If ee% is not listed, verify with chiral HPLC or enzymatic assay when needed.
• Acidity specification: For buffer or calibration work, titratable acidity and lactate equivalence may be more relevant than nominal weight; standardize by potentiometric titration if a precise normality is required.
• Stabilizers: None indicated for this item. If stabilizers are used in other lots/products, they can add UV or MS background; verify on CoA.

Documentation and compliance:

• CoA should list isotopic enrichment, chemical purity, residual solvents, and storage notes. Request an isotopic distribution spectrum (13C NMR or MS) if your method depends on M+1 abundance calibration.

Reaction and Applications

As [1-13C]-labeled L-lactic acid, this reagent is primarily used as an isotopic tracer rather than a synthetic solvent. Key research applications include:

• Metabolic flux analysis (MFA):
  • Tracing lactate uptake and conversion to pyruvate by lactate dehydrogenase (LDH). The 13C at C1 remains the carboxyl carbon; conversion to pyruvate yields [1-13C]pyruvate, informing LDH directionality and redox coupling.
  • Entry into gluconeogenesis and the TCA cycle via pyruvate carboxylase (PC) or pyruvate dehydrogenase (PDH). Label fate distinguishes decarboxylation (PDH removes C1 as CO2) vs anaplerosis (PC retains 13C in OAA C1/C4 after scrambling; literature concept).
• NMR standardization and quantitation:
  • 13C NMR sensitivity enhancement for calibrating chemical shifts and longitudinal relaxation (T1) in α-hydroxyacids; qNMR internal/external standardization.
• MS calibration and tracer studies:
  • Determination of lactate/pyruvate pool sizes and exchange rates using M+1 isotopologues in LC–MS/GC–MS; supports isotope dilution strategies.
• Enzymology:
  • Kinetic isotope tracing in LDH, lactate oxidase, and lactate monooxygenase assays; track label retention/loss to validate mechanisms.
• Materials and synthesis contexts:
  • Precursor for labeled polylactide (PLA) via lactide; label at the carboxyl carbon enables studies of depolymerization and composting pathways.

Practical tips:

• Maintain defined pH during incubations to prevent non-enzymatic interconversion or esterification.
• Confirm isotopic enrichment by quick 13C NMR (carboxyl ~175–185 ppm) or LC–HRMS before critical experiments.

Reaction Conditions

General laboratory conditions for common lactic acid transformations (literature guidance; adjust to your system and verify experimentally):

• Fischer esterification to alkyl [1-13C]lactates:

  • Reagents: ROH (5–10 equiv), catalytic H2SO4 or p-TsOH (1–5 mol%).
  • Conditions: reflux in the alcohol solvent, Dean–Stark if using higher alcohols; 2–12 h.
  • Notes: Protect the secondary alcohol if selective acylation is required elsewhere; minimize temperature/time to preserve stereochemistry.

• Oxidation to [1-13C]pyruvic acid:

  • Options: TEMPO/bleach, Dess–Martin periodinane, or catalytic TEMPO with Oxone under buffered, cold conditions to limit overoxidation.
  • Solvent: aqueous acetonitrile or dichloromethane (for DMP); 0–25 °C.
  • Monitor by 13C NMR (carboxyl ~170–180 ppm; carbonyl ~200–205 ppm) or LC–MS.

• Activation and coupling (ester/amide formation):

  • Reagents: DCC or EDCI (1.1–1.5 equiv), DMAP (5–10 mol%), alcohol/amine nucleophile (1.1–2.0 equiv).
  • Solvent: DCM, DMF, or THF; 0–25 °C, 1–16 h.
  • Caution: Racemization at C2 can occur under strongly basic or high-temperature conditions; maintain mild temperatures and use modern coupling reagents.

• Polymer-related (lactide formation):

  • Pre-polymerization: azeotropic removal of water in toluene with acid catalysis; then cyclization under reduced pressure.
  • Ring-opening polymerization: Sn(Oct)2 (0.01–0.1 mol%), 120–160 °C; monitor for label retention at carbonyl in repeat units.

• Derivatization for GC–MS (example):

  • Convert to methyl [1-13C]lactate (MeOH/HCl, 60–65 °C, 1–2 h), then silylate the hydroxyl (BSTFA + 1% TMCS, 60 °C, 30 min).

Always confirm isotopic integrity by 13C NMR or HRMS after transformations.

Safety and Handling

Item-specific hazard classification (GHS), signal word, H-statements, and pictograms: Not specified for this item; refer to SDS.

General safety information for lactic acid reagents (literature/practice; not a substitute for the SDS):

• Likely hazards: organic acid; can be irritating to skin, eyes, and mucous membranes. Concentrated solutions may cause burns upon prolonged contact.
• PPE: lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a well-ventilated area or fume hood to avoid aerosol/mist exposure.
• Storage incompatibilities: avoid strong oxidizers (e.g., permanganates), strong bases (may neutralize/exotherm), and reactive acylation/dehydration agents. Corrodes some metals at low pH.
• Handling notes for isotopologues:
  • Minimize atmospheric CO2 and moisture exposure if isotopic purity of derived salts must be preserved (cap promptly; use desiccated environment if storing solids).
  • Avoid unnecessary heating to prevent dehydration/oligomerization (lactide formation) that can complicate NMR/MS analysis.
• First aid overview (consult SDS for full guidance):
  • Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: move to fresh air; obtain medical advice if symptoms occur.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Waste: neutralize with base to lactate salts if appropriate and dispose according to institutional and local regulations.

Always consult the product-specific SDS for authoritative hazard and response information.

Solvent Selection

This compound is a small, highly polar organic acid (α-hydroxy acid). As such, it behaves as a hydrophilic solute rather than a solvent.

• Polarity/miscibility (literature):
  • Highly miscible with water; readily soluble in polar protic solvents (MeOH, EtOH) and polar aprotic solvents capable of hydrogen bonding (DMSO, DMF).
  • Poorly soluble in nonpolar media (e.g., hexanes, toluene) unless converted to an appropriate salt or ester.
• Practical dissolution choices by application:
  • NMR (13C/1H): D2O or H2O; adjust to pH 7–8 with NaOD/NaOH to generate sodium [1-13C]lactate for sharper lines and reduced exchange broadening. For 1H decoupled 13C, 50–200 mM is typical.
  • MS tracing: Water or 50:50 water:acetonitrile with 0.1% formic acid or ammonium acetate buffer as required by method; maintain identical matrices for standards and samples to reduce ion suppression.
  • Enzymatic assays (LDH): Aqueous buffer (e.g., phosphate, HEPES) at pH 7–8; convert to lactate salt in situ to avoid acidification of the assay medium.
• When to choose alternatives:
  • If organic media are mandatory, prepare esters (e.g., methyl [1-13C]lactate) to increase solubility in apolar solvents—note that esterification changes biochemical compatibility and may scramble labeling under transesterification.

Brief comparison (literature tendencies):

• Water/D2O: maximal solubility, ideal for spectroscopy and biology.
• MeOH/EtOH: good solubility; may participate in esterification under acidic/heated conditions—avoid for quantitative isotope recovery.

Storage and Reconstitution

• Storage (item-specific): Store at −20 °C (from Product Data). Keep container tightly closed. Protect from moisture and prolonged exposure to air.

• Shipping (item-specific): Shipped in an ice chest with ice pads (from Product Data). Inspect upon arrival and return to recommended storage promptly.

• Reconstitution and handling (general best practices for isotopically labeled lactic acid):

  • Solvent: Water or D2O for most applications. For enzymatic or cell-free assays, adjust to neutral pH by titration with NaOH/NaOD to generate the corresponding sodium [1-13C]lactate.
  • Concentrated stocks: Prepare 100–1000 mM stocks, filter-sterilize if needed (0.22 µm), and aliquot into single-use vials to avoid freeze–thaw cycles that can cause concentration drift and contamination.
  • Stability: Store aliquots at −20 °C; for working solutions, 2–8 °C for days to weeks depending on pH (neutral to slightly basic solutions are generally stable; avoid high temperatures and strong acids that promote esterification/dehydration).
  • Isotopic integrity: The 13C label is stable; avoid conditions that cause decarboxylation (strong base + heat) if retention of the label is critical.
  • Documentation: Record exact concentration by weight and pH after neutralization; for quantitative work, standardize by titration or qNMR.

• Thawing/use: Thaw on ice, mix thoroughly, and return unused portions to −20 °C promptly. Do not store in contact with reactive metals; use glass or suitable polymer containers.

• Research Use Note: For research use only (from Product Data).

Structure and Identity

L-Lactic acid-1-13C is the isotopically labeled form of L-lactic acid with the carboxyl carbon (C1) enriched in 13C, enabling 13C tracing by NMR and MS while retaining the native L stereochemistry.

• Item-specific identifiers (from Product Data):

  • CAS: 727379-97-7
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • 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/computed identity (for the L-isomer labeled at C1):

  • Common name: [1-13C]-L-lactic acid (L-2-hydroxypropanoic acid-1-13C)
  • Stereochemistry: L configuration at the α-carbon (C2), corresponding to (S) absolute configuration.
  • Functional groups: α-hydroxy carboxylic acid (one secondary alcohol, one carboxylic acid).
  • Isotopologue composition: 13C1–12C2–H6–O3 (label at the carboxyl carbon).
  • Canonical SMILES (literature): CC@H13CO
  • 2D structural description: a three‑carbon backbone; C2 bears the hydroxyl and methyl substituents (chiral center, L configuration), while C1 is a carboxyl group carrying the 13C label.
  • Exact mass (computed, 13C1): ~91.0351 Da; nominal formula equivalent to C3H6O3 with one 13C atom.

• Structural features of interest:

  • The 13C label at C1 directly reports on carboxyl/pyruvate carbonyl fate in metabolic transformations (e.g., LDH interconversion with pyruvate via hydride transfer at C2 while C1 remains the carboxyl carbon).
  • Retains hydrogen-bond donor/acceptor capability typical of α-hydroxy acids.

Synthetic Utility

Chemically, L-lactic acid is an α-hydroxycarboxylic acid, offering complementary reactivity at the hydroxyl and carboxyl sites. The [1-13C] label at the carboxyl carbon allows positional tracking through transformations.

• Functional handles and typical transformations (literature):
  • Esterification: Fischer esterification with ROH/H+ to give alkyl [1-13C]lactates—useful for GC–MS derivatization or solubility tuning; retain 13C at the carbonyl carbon.
  • Lactide formation: stepwise dehydration/condensation to cyclic dimer (lactide), precursor to PLA; label remains at carbonyl in the repeat unit, enabling polymer degradation studies.
  • Oxidation/reduction: selective oxidation of the secondary alcohol to [1-13C]pyruvic acid; reduction (e.g., catalytic hydrogenation of the acid) can lead to 1,2-propanediol derivatives—note potential label redistribution if decarboxylation pathways are invoked.
  • Salt formation and coupling: generation of lactate salts (Na+, K+, NR4+) and coupling to amines via activated esters (e.g., DCC/DMAP) to form amides or esters.
• Chiral context:
  • The L-(S) stereocenter can be exploited for chiral induction or as a chiral auxiliary in certain esterification or acyl transfer settings; protect the alcohol (e.g., silyl, benzyl) to control chemoselectivity.
• Isotopic integrity considerations:
  • Avoid conditions that decarboxylate the acid (strong heating/base in certain systems), which would eliminate the 13C label as CO2.
  • For MS-based quantitation, derivatize under mild conditions (e.g., silylation of alcohol after esterifying the acid) to prevent exchange or scrambling.

Target Specificity

Not applicable. This product is a small-molecule metabolite (isotopically labeled lactic acid), not a biological affinity reagent or antibody. No antigen/epitope/clone/isotype information applies.