Chenodeoxycholic acid-d - ≥98% , CAS No.52840-12-7

CAS: 52840-12-7 Cat. No.: C1423512 Formule: C₂₄H₃₅D₅O₄ Poids moléculaire: 397.6 PubChem CID: 71309530

GRADE & PURITY ≥98%

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Vue d’ensemble

Chenodeoxycholic acid-d 5 is the deuterium labeled Chenodeoxycholic Acid. Chenodeoxycholic Acid is a hydrophobic primary bile acid that activates nuclear receptors ( FXR ) involved in cholesterol metabolism.

Specifications

Spécifications et pureté

≥98%

Conditions de stockage de stockage

Store at 2-8°C,Protected from light

Expédié en

Wet ice

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Pureté

≥98%

Noms et identifiants

• Sourires canoniques: CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
• IUPAC Name: (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-2,2,3,4,4-pentadeuterio-3,7-dihydroxy-10,13-dimethyl-1,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• InChIKey: RUDATBOHQWOJDD-FVAYXOGXSA-N
• INCHI: 1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1/i8D2,12D2,16D
• Isomères SMILES: [2H][C@]1(C(C[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3[C@@H](C[C@@H]2C1([2H])[2H])O)CC[C@@H]4[C@H](C)CCC(=O)O)C)C)([2H])[2H])O
• PubChem CID: 71309530
• Poids moléculaire: 397.6

Application Protocols

Example workflow for LC–MS/MS quantification of chenodeoxycholic acid using chenodeoxycholic acid-d as internal standard (general guidance; optimize per lab SOP):

• Stock preparation

  • Dissolve the deuterated standard at 1–5 mg/mL in methanol or DMSO in an amber vial. Store aliquots at low temperature per Storage tab.

• Calibration and QC

  • Prepare calibration standards by spiking fixed IS concentration into blank matrix (e.g., stripped plasma) across the expected range.
  • Include at least 6–8 non-zero calibrators and low/mid/high QCs. Verify linearity and back-calculated accuracy.

• Sample processing (plasma example)

  • Add IS to samples prior to extraction.
  • Perform protein precipitation with 3–4 volumes cold MeOH or ACN; vortex and centrifuge.
  • Optionally conduct SPE (C18 or mixed-mode) for cleanup; elute with MeOH.
  • Dilute/reevaporate and reconstitute in initial LC mobile phase (e.g., 50:50 water/MeOH with volatile buffer).

• LC–MS/MS settings (typical)

  • Chromatography: C18; gradient from aqueous to methanol-rich; column temp 30–40 °C.
  • Ionization: ESI−; monitor MRM transitions for analyte and deuterated IS with appropriate mass offset.

• System suitability

  • Check retention time stability, peak shape, IS response CV (<15%), and absence of significant carryover.

Biological Roles

General literature context for chenodeoxycholic acid (CDCA) biology (not specific to the labeled variant; research use only):

• Physiological function

  • CDCA is a primary bile acid in humans, synthesized from cholesterol in the liver and conjugated with glycine or taurine for secretion into bile.
  • Facilitates intestinal lipid emulsification and absorption through micelle formation.

• Signaling roles

  • Acts as an endogenous ligand for nuclear receptor FXR (NR1H4), modulating bile acid homeostasis, lipid metabolism, and transport gene expression (literature).
  • Interacts with membrane receptor TGR5 (GPBAR1) with downstream cAMP signaling (literature). Potency varies across bile acid species and conjugation state.

• Microbial transformations

  • In the gut, microbiota can deconjugate and transform CDCA (e.g., 7α-dehydroxylation to lithocholic acid), affecting the bile acid pool composition.

• Transport and metabolism

  • Transported by hepatocellular uptake transporters (e.g., NTCP) and effluxed via BSEP/MRP pathways; reabsorbed in the ileum via ASBT (literature).

• Relevance of deuteration (research)

  • Deuterium labeling allows tracing of metabolic flux, pool size, and turnover in in vitro and ex vivo systems without altering receptor specificity materially (small isotope effects possible).

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare pH buffer systems. For aqueous work, it is sometimes converted to its sodium salt to improve solubility, or dissolved in buffered aqueous-organic mixtures for analytical assays. Select buffers that match your analytical method (e.g., ammonium acetate/formate for LC–MS) rather than using the compound itself as a buffer.

Green Alternatives

For this product (a labeled analytical standard), “green alternatives” relate more to solvent systems and derivatization reagents rather than to the molecule itself.

• Greener solvent choices (general guidance)

  • Prefer ethanol or methanol over chlorinated solvents where feasible for dissolution and sample prep.
  • For LC–MS, mobile phases of water with methanol and volatile buffers (ammonium acetate/formate) are generally greener than acetonitrile-heavy methods, though ACN can improve performance; balance is application-specific.

• Derivatization alternatives

  • Avoid diazomethane where possible due to extreme toxicity/explosivity; TMS-diazomethane or trimethylsilylation (BSTFA/MSTFA) are safer alternatives, though still hazardous.
  • Enzymatic conjugation (e.g., sulfate or glucuronide formation with purified enzymes) can be a milder route to targeted derivatives for research.

• Comparison snapshot (literature, general)

  • Diazomethane methylation: fastest/cleanest, highest hazard profile.
  • TMS-diazomethane: effective methylation with reduced hazard vs CH2N2, still requires strict controls.
  • Direct LC–MS of underivatized bile acids: eliminates derivatization waste; requires optimized negative-mode ESI and chromatographic separation (e.g., C18 with methanol-rich gradients).

Pharmaceutical Uses

No therapeutic claims are made for this product. The following are general formulation-related roles for bile acids (literature context):

• Excipient and formulation functions (general)

  • Solubilizer and emulsifier: bile salts (e.g., sodium chenodeoxycholate) can enhance solubility of hydrophobic actives in research formulations.
  • Permeation/modulation: bile salts have been explored as absorption enhancers and for stabilizing lipid-based drug delivery systems.
  • Crystallization modifier: bile acids may influence nucleation/particle morphology in crystallization studies of steroids and hydrophobes.

• Process considerations

  • Salt form selection (e.g., sodium) improves aqueous processability but can impact stability and compatibility with other excipients.
  • For analytical standards used in pharmaceutical analysis (stability-indicating methods), deuterated analogues support quantitation and recovery tracking.

• Regulatory note

  • Deuterated analytical standards are typically used for method development/validation and quality control; they are not intended as API or excipients in finished dosage forms without appropriate qualification.

Physical Properties

Item-specific physical data were not provided for this deuterated material; consult the CoA/Spec Sheet for exact values relevant to this SKU.

• Item-specific

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.

• Typical properties for non-deuterated chenodeoxycholic acid (literature, for context only)

  • Molecular formula (CDCA): C24H40O4 (literature)
  • Molecular weight (CDCA): ~392.57 g/mol (literature)
  • Form: white to off-white crystalline solid (literature)
  • Melting point: reported in the ~165–170 °C range, decomposition possible (literature)
  • Solubility: sparingly soluble in water as free acid; soluble in polar organic solvents (MeOH, EtOH, DMSO); improved aqueous solubility as bile salt (e.g., sodium chenodeoxycholate) (literature)
  • LogP: high (hydrophobic steroid nucleus balanced by polar groups); exact value depends on ionization state (literature)
  • pKa: carboxyl ~5–6; phenolic/secondary alcohols are non-ionizing under neutral conditions (literature)

• Notes on deuteration (general)

  • Deuterium substitution minimally affects bulk physical properties (mp/bp/solubility) but shifts MS and NMR signals, enabling isotope-dilution quantitation and tracer studies.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• General expectations for deuterated analytical standards

  • Isotopic enrichment: For quantitative LC–MS/GC–MS, isotopic enrichment and labeling pattern (position-specific vs non-specific) critically impact performance. Verify %D and positional labeling on the CoA.
  • Chemical purity: High chemical purity minimizes interference in targeted assays; residual unlabeled analogue percentage should be documented to assess possible chromatographic co-elution.
  • Residual solvents and water: For quantitative work, review CoA for residual solvent profile (GC) and Karl Fischer moisture.

• Stabilizers

  • None specified for this item. If stabilizers are present in a particular lot (e.g., as salts or antioxidants), their identity and level should be declared on the CoA, as they may affect MS response or derivatization efficiency.

• What the grade implies (general guidance)

  • Research/analytical grade deuterated bile acids are typically optimized for mass spectrometry with minimal UV-absorbing impurities. If HPLC/LC–MS grade is noted on the CoA, expect low baseline noise and consistent ionization.

• Recommendation

  • For isotope-dilution assays, match the chemical form (free acid vs salt, derivatized vs underivatized) and retention behavior of the analyte. Confirm with the CoA that the labeling does not undergo H/D exchange under your sample conditions.

Reaction and Applications

This deuterated bile acid is primarily used as a stable-isotope internal standard and tracer in analytical and biochemical studies.

• Analytical applications

  • LC–MS/LC–MS/MS: internal standard for quantifying chenodeoxycholic acid in plasma, bile, feces, and tissue extracts by isotope-dilution. Deuterium labeling provides a defined mass shift for co-eluting correction.
  • GC–MS: after derivatization to methyl ester and/or trimethylsilyl (TMS) ethers, used for profiling bile acid panels.
  • NMR: deuterium labeling assists in assignment and can reduce spectral overlap in complex mixtures.

• Biochemical applications (research use only)

  • Tracer studies of bile acid synthesis, enterohepatic circulation, microbial biotransformations (e.g., 7α-dehydroxylation), and transporter interactions (e.g., NTCP/OATP, general literature context).

• Practical tips

  • Minimize H/D exchange: avoid prolonged exposure to protic solvents at elevated temperatures or strong acid/base if the label is at exchangeable positions.
  • Match matrix: spike internal standard before extraction to correct for recovery and ion suppression.
  • Derivatization: for GC–MS, form methyl ester with diazomethane or TMS-diazomethane under cold, anhydrous conditions; silylate hydroxyls with BSTFA + 1% TMCS or MSTFA.

• Related chemistry (general)

  • Conjugation: amide or ester formation at C24 enables probe synthesis (e.g., fluorophores or affinity tags) for mechanistic studies.
  • Enzymatic studies: substrate or inhibitor analog in assays of bile acid-CoA ligases or amidation enzymes (literature).

Reaction Conditions

General conditions from literature for common manipulations of bile acids (apply analogously to chenodeoxycholic acid-d; confirm compatibility with labeling):

• Esterification (methyl ester for GC–MS)

  • Reagent/solvent: TMS-diazomethane in hexane/MeOH or ether; or catalytic HCl/MeOH (reflux) for non-quantitative prep.
  • Conditions: 0–25 °C for TMS-CH2N2, minutes to completion; quench excess with acetic acid. Avoid water.

• Silylation of hydroxyls

  • Reagent: BSTFA (or MSTFA) + 1% TMCS in dry acetonitrile or pyridine.
  • Conditions: 60–70 °C, 20–60 min in sealed vial; exclude moisture to prevent back-hydrolysis.

• Amide coupling at C24

  • Reagents: EDC·HCl (1.1–1.5 equiv) + HOBt or HOAt; or HATU with DIPEA.
  • Solvent: DMF or DCM; 0–25 °C, 2–16 h. Monitor by TLC/LC–MS.

• Oxidation/reduction at hydroxyl positions (to access analogs)

  • Oxidation: Dess–Martin periodinane or PCC (DCM) at 0–25 °C; protect carboxyl as ester to avoid side reactions.
  • Stereoselective reduction: NaBH4 or hydride reagents with chelation control; verify retention of deuterium if adjacent positions are labeled.

• LC–MS conditions (analytical guidance)

  • Column: C18 or phenyl-hexyl; mobile phase water/methanol with 2–10 mM ammonium acetate or 0.1% formic acid.
  • Detection: ESI negative mode, MRM transitions offset by the deuterium mass shift; ensure co-elution of analyte and IS.

Safety and Handling

• GHS and hazard information

  • Signal Word: Not specified for this item; refer to CoA/Spec Sheet and SDS.
  • H-Statements / Pictograms / GHS Classification: Not specified for this item; refer to SDS.

• General safety guidance (good laboratory practice)

  • Handle in a chemical fume hood to minimize dust/aerosol exposure.
  • Wear appropriate PPE: lab coat, safety glasses, and suitable gloves (e.g., nitrile). Avoid skin/eye contact and inhalation.
  • Prevent ingestion; wash hands thoroughly after handling.
  • Avoid generating dust; use antistatic precautions when weighing fine powders.

• Incompatibilities and stability (general for bile acids)

  • Avoid strong oxidizers and strong bases/acids when purity of analytical standards must be preserved; esterification or salt formation can occur under harsh conditions.
  • Protect from light as provided; some bile acids can undergo slow photo/oxidative changes in solution.

• First-aid overview (consult SDS for definitive instructions)

  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting; obtain medical attention.

• Waste disposal

  • Dispose of unused material and contaminated disposables in accordance with institutional and local regulations. For LC–MS residues, collect organic solutions for halogen-free organic waste unless otherwise classified.

Solvent Selection

Chenodeoxycholic acid-d is amphiphilic yet overall hydrophobic as the free acid. Solvent choice depends strongly on ionization state and application.

• Miscibility and polarity (literature, general)

  • Water: sparingly soluble as free acid; substantially more soluble as the sodium salt (bile salt micelles).
  • Alcohols: soluble in methanol, ethanol, isopropanol; commonly used for LC–MS stock solutions.
  • Polar aprotics: highly soluble in DMSO and DMF; DMSO is often preferred for concentrated stocks.
  • Nonpolar solvents: limited solubility in hexanes; solubility improves in chlorinated solvents (e.g., CH2Cl2) for preparative chemistry.

• Selection by application

  • LC–MS internal standard: prepare a primary stock at 1–10 mg/mL in MeOH or DMSO; dilute into 50:50 water/MeOH (0.1% formic acid or ammonium acetate) to match mobile phase.
  • Derivatization for GC–MS: dissolve in anhydrous MeOH for methyl ester formation or in dry acetonitrile/DMF for silylation (BSTFA + 1% TMCS).
  • Aqueous biology assays: consider converting to sodium salt or using co-solvent (≤1–2% DMSO) with surfactant if needed.

• Comparison (general)

  • Free acid vs sodium salt: free acid favors organic media; sodium salt improves aqueous handling but may alter chromatographic retention and ionization.
  • MeOH vs ACN for LC–MS: MeOH often yields stronger negative-mode ESI for bile acids; ACN can sharpen peaks but may reduce solubility at low percentages.

Storage and Reconstitution

• Item-specific storage conditions

  • Storage: Store at 2–8 °C, protected from light.
  • Shipped in: Wet ice.

• Reconstitution and working solutions (general guidance)

  • Preferred solvents: methanol or DMSO for primary stocks; ethanol is also suitable. Use amber glassware/vials to minimize photodegradation.
  • Concentrations: prepare concentrated stocks (e.g., 1–10 mg/mL) and dilute into assay/mobile phase shortly before use.
  • Aliquoting: divide into single-use aliquots to avoid repeated freeze–thaw and adsorption losses.

• Stability tips

  • Protect from light during storage and handling. Limit exposure to elevated temperatures.
  • For long-term storage of solutions, keep at ≤−20 °C in tightly sealed, headspace-minimized vials. Verify stability and isotopic integrity periodically by LC–MS.
  • Avoid strongly basic or acidic aqueous solutions if label positions are exchangeable; keep solutions near neutral pH unless method requires otherwise.

• Documentation

  • Record preparation date, solvent, concentration, and lot/CoA reference on each aliquot. Review the lot-specific CoA for any additional handling instructions or known incompatibilities.

• Research Use Note

  • For research use only.

Structure and Identity

Chenodeoxycholic acid-d is a deuterium-labeled analogue of chenodeoxycholic acid (CDCA), a primary bile acid with a steroidal cholane backbone.

• Item-specific identifiers (as provided)

  • SKU: C1423512
  • Product Name: Chenodeoxycholic acid-d
  • CAS: 52840-12-7
  • InChIKey: 326089 (as provided)
  • 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.

• Structural features (general chemistry/literature description)

  • Core scaffold: tetracyclic steroid nucleus (5β-cholane framework) with a cis-fused A/B ring junction and trans-fused B/C and C/D rings.
  • Functional groups: carboxylic acid at C24 on the side chain; two axial/eq hydroxyl groups at 3α and 7α (chenodeoxycholate pattern).
  • Stereochemistry: multiple defined stereocenters typical of bile acids (5β configuration introduces a bent steroid geometry).
  • Deuteration: one or more hydrogen atoms are replaced by deuterium (2H); the exact labeling positions/extent are product-specific and should be verified from the CoA.

• 2D structure in words (general): A four-ring steroid nucleus bearing hydroxyl substituents on rings A and B, with an aliphatic side chain terminating in a carboxylic acid; deuterium label(s) incorporated at specified positions (not provided here).

Synthetic Utility

Although primarily employed as an analytical standard, chenodeoxycholic acid scaffolds are valuable synthetic building blocks (general literature context):

• Functional group handles

  • Carboxylic acid at C24: amenable to esterification, amidation, and activation (e.g., acid chlorides, NHS esters) for conjugation to dyes, polymers, or linkers.
  • Secondary alcohols at 3α and 7α: can be selectively protected (e.g., TBDMS, acetates) and derivatized to tune hydrophilicity or to build supramolecular receptors.

• Transformations

  • Ester/amide coupling using EDC/HOBt, HATU, or DCC to generate conjugates or pro-derivatives.
  • Oxidation at 7α to ketone (or 3α) followed by stereoselective reductions to access iso-bile acid analogues.
  • Sulfation or glucuronidation (chemical or enzymatic) to mimic Phase II metabolites for standards.

• Utility in materials and supramolecular chemistry

  • The facially amphiphilic steroid framework supports self-assembly into gels/micelles; used to craft chiral hosts, organogels, and membrane mimetics.

• Notes for deuterated variants

  • Maintain labeling integrity: avoid protic exchange at labeled positions during protection/deprotection. Choose neutral coupling conditions and dry, aprotic solvents when possible.

Target Specificity

Not applicable. This product is a small-molecule bile acid standard, not an antibody or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity data are relevant.