Naringenin-d4 - ≥98% , CAS No.1192260-78-8

CAS: 1192260-78-8 Cat. No.: N650118 Formula: C₁₅H₈D₄O₅ Molecular Weight: 276.28

GRADE & PURITY ≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Naringenin-d 4 is the deuterated version of Naringenin . Naringenin shows strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

Form:Solid

Specifications

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Naringenin-d 4 is the deuterated version of Naringenin (HY-N0100). Naringenin shows strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

Molecular Weight

276.28

Application Protocols

Isotope-dilution LC–MS(/MS) quantitation of naringenin (general guidance)

1. Stock preparation: Dissolve naringenin-d4 in LC–MS grade methanol or DMSO to 1.0 mg/mL (or convenient concentration). Vortex and sonicate briefly to ensure complete dissolution.
2. Working solutions: Prepare a series of calibrators (e.g., 1–1000 ng/mL naringenin) in 50:50 water:MeOH (0.1% formic acid) and spike each with a fixed concentration of naringenin-d4 (e.g., 50 ng/mL). Maintain constant internal standard concentration across all standards and samples.
3. Sample spiking: Add internal standard to samples at the same concentration used in calibrators prior to extraction or immediately before injection, depending on validation plan (pre- vs post-extraction spike).
4. Extraction (plant/food matrices): Precipitate proteins with 3–4 volumes of ACN or MeOH, vortex, centrifuge, and collect supernatant. Optionally perform SPE cleanup (C18 or HLB). Evaporate and reconstitute in initial mobile phase.
5. LC–MS settings (example, literature): Reversed-phase C18; mobile phase A: water + 0.1% FA; B: ACN or MeOH + 0.1% FA; gradient 10→70% B over 10–15 min; ESI negative or positive mode. Monitor MRM transitions for naringenin and +4 m/z for the IS.
6. Quantitation: Plot analyte/IS peak area ratios vs analyte concentration. Assess linearity, LOD/LOQ, precision, and matrix effects per guidance.

Note: Concentrations and conditions are general literature-style guidance; optimize for your system. Refer to the item’s CoA/SDS for any handling constraints.

Biological Roles

General (literature; for the unlabeled parent naringenin)

• Naringenin is a plant-derived flavanone widely found in citrus and other botanical sources. It participates in plant secondary metabolism, often as a precursor in the flavonoid biosynthetic pathway leading to flavones, anthocyanins, and other polyphenols.
• Its phenolic groups confer redox activity and metal-chelating ability, properties often explored in biochemical assays studying antioxidant capacity and enzyme modulation in vitro.

Relevance of the deuterated isotopologue (analytical focus)

• Naringenin-d4 serves as an internal standard/tracer to quantify uptake, metabolism, and transformation of naringenin in biochemical systems (e.g., enzymatic glucuronidation/sulfation assays) via mass spectrometry, enabling accurate correction for matrix effects and ionization variability.
• The deuterium label does not confer new biological activity; it is primarily a mass tag. Under certain enzyme-catalyzed hydrogen exchange conditions, deuterium at labile positions could exchange—verify isotopic integrity when assays involve strong acids/bases or prolonged incubation.

Note: This product is for research use only. No clinical or therapeutic claims are made or implied.

Buffer Applications

This compound is not a buffering reagent and is not typically used to establish or control pH. For experiments requiring dissolution into aqueous media, a compatible buffer (e.g., phosphate, ammonium formate/acetate for LC–MS) may be used to dilute an organic stock solution of naringenin-d4. Maintain organic co-solvent at low percentages to avoid precipitation and ensure instrument compatibility.

Green Alternatives

Context

• As an isotopically labeled analytical standard, the molecule itself is not replaceable in quantitation of naringenin. However, greener choices can be made in solvents and workflow.

Greener solvent considerations (literature-based)

• Prefer ethanol over methanol when feasible for stock solutions and extractions; comparable solvency with improved safety profile.
• Use water–ethanol or water–acetonitrile mobile phases optimized to minimize organic content while maintaining chromatographic performance.
• Avoid chlorinated solvents (e.g., DCM) for routine dissolution; acetone or EtOAc may suffice for some sample preps.

Comparison (general guidance)

| Use case | Conventional | Greener alternative | Trade-offs | |---|---|---|---| | Stock preparation | Methanol | Ethanol | Slightly reduced solubility; similar LC–MS compatibility at low % | | Extraction | ACN (QuEChERS) | EtOH/H2O (60–90%) | May extract more matrix; requires optimization | | Rinse/cleaning | ACN/MeOH | IPA/EtOH | Evaporation rate and residue may differ |

Operational green practices

• Prepare concentrated stocks to reduce solvent volume; use microliter-scale spiking for standards.
• Employ low-flow LC (microLC) to cut solvent consumption without sacrificing sensitivity.
• Consolidate calibrators and QCs to minimize vial waste and runs.

Pharmaceutical Uses

No therapeutic or clinical use is implied. In a pharmaceutical R&D and QC context (general/industry practice):

• Isotope-dilution reference standard: Naringenin-d4 can be employed as an internal standard in method development and validation for quantifying naringenin in botanicals, nutraceutical raw materials, and dosage forms using LC–UV or LC–MS(/MS).
• Process and stability studies: Enables tracking of extraction efficiency, degradation pathways, and sample handling losses by spiking at known levels and assessing recovery relative to the analyte.
• System suitability and performance checks: Monitors retention time stability, ionization efficiency, and calibration robustness across batches.

Pharmacopeial status and monographs: Not specified for this item; refer to CoA/Spec Sheet and applicable compendia. Ensure the isotopic labeling pattern and chemical purity meet internal specifications for intended analytical procedures.

Physical Properties

Item-specific properties

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

Literature/general properties (unlabeled naringenin; deuteration has negligible effect on most bulk properties)

• Typical melting point (literature): ~250–253 °C (unlabeled naringenin; deuteration may shift MP slightly).
• Boiling point: Not generally reported due to decomposition before boil (literature note).
• Density: Not widely tabulated; solids typically reported as bulk density only (literature note).
• Solubility (qualitative, literature): sparingly soluble in water; soluble in DMSO, DMF, methanol, ethanol, acetone, and acetonitrile; enhanced solubility in basic aqueous media due to phenolate formation.
• LogP/logD (literature): moderate hydrophobicity; reported logP for naringenin typically ~2.5–3.2 depending on method.
• pKa (phenolic, literature): multiple acidic sites; reported phenolic pKa values in the approximate range pKa1 ~7–8 and pKa2 ~8–10 (method-dependent).
• UV/Vis (literature): phenylchromanone chromophore absorbs in UV; typical maxima near 280–290 nm and a higher-wavelength band upon deprotonation (exact values depend on solvent and pH).

Important: Values above are general literature data for the unlabeled parent compound and are provided for context only. Do not treat them as specifications for SKU N650118. For exact item-specific values, consult the CoA/Spec Sheet.

Quality & Grades

Item-specific quality information

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Isotopic enrichment and labeling positions: Not specified for this item; refer to CoA/Spec Sheet.

What to expect for an isotopically labeled small-molecule standard

• Isotopic purity (literature/industry context): For quantitative LC–MS(/MS) using isotope dilution, deuterium enrichment and the defined labeling pattern are critical to avoid isotopic overlap with native analyte and to ensure coelution. Vendors commonly report %D incorporation per site and overall isotopic distribution—consult the CoA for this SKU.
• Chemical purity: Typically assessed by HPLC/UPLC area %, NMR, and MS. Low levels of unlabeled naringenin should be reported to avoid bias in quantitation.
• Residual solvents, water, and inorganic impurities: Not specified for this item; refer to CoA/Spec Sheet. These can impact weighing accuracy at microgram scales.
• Identity tests: High-resolution MS (accurate mass shift of +4 Da relative to naringenin), 1H/2H NMR showing attenuated or absent signals at labeled positions, and comparative chromatographic retention with the unlabeled reference.

Implications for use

• For internal standard applications, verify: (1) isotopic purity, (2) absence of positional scrambling under your conditions, and (3) chromatographic coelution with analyte. If working near limits of detection, confirm background naringenin in solvents/reagents does not confound blanks.

Reaction & Applications

Primary application (analytical; general guidance)

• Naringenin-d4 is commonly used as an internal standard for quantitative analysis of naringenin in plant extracts, foods, and complex matrices by LC–MS(/MS) and GC–MS (after derivatization). The +4 Da mass shift provides clear MRM transitions while maintaining similar chromatographic behavior to the analyte.
• Suitable for method validation (linearity, recovery, matrix effects) via isotope-dilution protocols. Spike levels are typically matched to expected analyte concentrations to minimize relative error.

Chemical/transformation context (literature)

• Phenolic protection: O-acetylation (Ac2O/pyridine) or O-benzylation (BnBr/K2CO3, acetone) facilitates selective transformations on the flavanone core. Deuterium labels located on aromatic rings are generally retained under these conditions.
• Oxidation/reduction: Flavanone oxidation to flavone (e.g., DDQ, I2/DMSO) or reduction at C4 carbonyl (NaBH4) can occur; verify that labels are not exchanged under protic/acidic conditions that may promote H/D scrambling.
• Conjugation chemistry: Esterification or etherification at phenolic sites enables immobilization on solid supports for affinity or binding studies, preserving the mass label for MS readouts.

Practical tips

• Limit exposure to strong acids/bases and elevated temperatures in protic media to avoid H/D exchange. Validate isotopic integrity by MS before/after any chemical step.
• For LC–MS/MS, choose transitions offset by +4 m/z relative to the analyte and verify coelution over gradient changes.

Reaction Conditions

The following are general literature conditions for transformations relevant to the naringenin scaffold. They are provided for context only and are not specifications for this item.

• O-Acetylation (phenolic protection): naringenin, acetic anhydride (3–6 equiv), pyridine or DMAP (cat.), 0–25 °C, 1–3 h; typical isolated yields 80–95% for triacetate. Deuterium at non-labile aryl positions generally retained.
• O-Benzylation: BnBr (1.2–1.5 equiv per OH), K2CO3 (3–4 equiv), dry acetone or DMF, 25–50 °C, 2–16 h; yields 70–90%. Ensure anhydrous conditions to minimize side reactions.
• Flavanone → Flavone oxidation: I2/DMSO (1.1–2 equiv I2), 80–120 °C, 2–8 h, or DDQ (1.2–2 equiv) in toluene/CH2Cl2, rt–reflux; yields variable (40–85%) depending on protection.
• Reduction of C4 carbonyl: NaBH4 (1–2 equiv) in MeOH/EtOH at 0–25 °C, minutes to 1 h, furnishing diastereomeric flavan-4-ols; quench carefully to limit H/D exchange in protic media.
• Esterification: Acyl chloride or EDCI/DMAP coupling (rt–40 °C) in DCM/DMF; 70–95% yields commonly reported for mono- or polyesters with controlled stoichiometry.

Analytical integrity: After any reaction, confirm mass shift (+4 Da) and the absence of scrambling via HRMS and comparison of diagnostic NMR signals. Avoid extended exposure to strong acids/bases in protic solvents to preserve deuterium labels.

Safety & Handling

Hazard classification (item-specific)

• GHS classification: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.
• Hazard (H) statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General handling guidance (for flavonoid solids; always defer to SDS for authoritative information)

• Personal protective equipment: use lab coat, safety glasses, and nitrile gloves; handle powders in a fume hood or with local extraction to minimize inhalation of dust.
• Avoid generation of dust/aerosols; prevent contact with strong oxidizers and strong bases/acids when not intended, as phenolic compounds can undergo oxidation and base-catalyzed transformations.
• First aid (general): if inhaled, move to fresh air; if on skin, wash with soap and water; if in eyes, rinse cautiously with water for several minutes; if ingested, rinse mouth—seek medical advice in all cases. Provide SDS to medical personnel.
• Fire safety: organic solid; treat as combustible. Suitable extinguishing media include CO2, dry chemical, or foam. Combustion may form CO/CO2 and phenolic/irritant vapors.
• Spill response: avoid dust; sweep up gently and place in a suitable container for disposal according to institutional and governmental regulations.

Storage conditions (item-specific)

• Store at −20 °C (as provided). Protect from light and moisture. Keep container tightly closed. For long-term stability, minimize freeze–thaw by aliquoting upon first opening.

Solvent Selection

General solvent behavior (literature)

• Polarity/functional group profile: polyphenolic flavanone; forms H-bonds and deprotonates under basic conditions. Poorly soluble in water at neutral pH; readily soluble in polar aprotic organics and alcohols.
• Practical stock solutions: DMSO (typical 10–50 mg/mL), methanol or ethanol (1–10 mg/mL depending on need), or acetonitrile. For aqueous work, prepare organic stock then dilute into buffer (≤1–2% DMSO or ≤5–10% MeOH/EtOH v/v) to limit precipitation.

Miscibility and dissolution tips

• Sonication and gentle warming (≤40 °C) can speed dissolution in MeOH/EtOH/ACN. Avoid prolonged high heat to minimize oxidation.
• Deprotonation with dilute base (e.g., ≤10 mM NaOH) can enhance solubility in water by forming phenolates; re-adjust pH after dilution if biological compatibility is needed.

Comparison (literature-based)

• DMSO: maximal solvating power; best for concentrated standards; may suppress ESI if injected at high %.
• Methanol: LC–MS friendly, volatile; good for calibration standards.
• Ethanol: greener alternative to MeOH; slightly lower elution strength vs MeOH.
• Acetonitrile: LC–MS grade common; combines with water to form mobile phases; lower proticity may stabilize some phenolates.

Note: Choose solvent considering your downstream method (e.g., UV vs LC–MS), sample matrix, and instrument compatibility.

Storage & Reconstitution

Item-specific storage

• Storage conditions: Store at −20 °C (as provided). Protect from light and moisture. Keep container tightly closed.
• Shipping conditions: Shipped in an ice chest with ice pads (as provided).

Reconstitution (general guidance)

• Recommended solvents: LC–MS grade DMSO, methanol, ethanol, or acetonitrile. Begin with small volumes (e.g., 100–500 µL) to prepare a concentrated stock; then dilute as needed.
• Concentration: Not specified for this item; refer to CoA/Spec Sheet. Select concentration to suit assay sensitivity and solubility (commonly 0.1–10 mg/mL for analytical standards).
• Aliquoting: To avoid repeated freeze–thaw, dispense single-use aliquots upon first dissolution. Store aliquots at −20 °C in amber vials or foil-wrapped containers to limit photodegradation.
• Freeze–thaw: Minimize cycles. If precipitate forms upon cooling, warm gently to room temperature and vortex/sonicate to redissolve.
• Aqueous dilutions: Prepare from organic stock into buffer while vortexing to prevent local supersaturation. Keep final organic solvent below instrument and assay limits (e.g., ≤1–2% DMSO in LC–MS injections).

Stability notes (general)

• Phenolic flavonoids can slowly oxidize; limit exposure to air and strong light. Use inert atmosphere (N2/Ar) for long-term storage of solids or concentrated solutions when feasible. Verify integrity periodically by LC–MS.

Structure & Identity

Item-specific identifiers

• CAS: 1192260-78-8 (as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: 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.

General/literature description (for naringenin-d4 isotopologue)

• Naringenin is a flavanone (4′,5,7-trihydroxyflavanone) comprising a chromanone (flavanone) core bearing phenolic groups at 5 and 7 on the A-ring and a 4′-phenol on the B-ring. The deuterated isotopologue (naringenin-d4) contains four deuterium atoms substituted for hydrogens at defined positions (commonly on the aromatic ring(s)); exact labeling sites vary by product specification (consult CoA).
• Typical unlabeled naringenin formula: C15H12O5 (literature). A d4 isotopologue would be higher in mass by approximately +4.03 Da relative to the unlabeled compound (literature/computed), but the exact monoisotopic mass depends on labeling pattern.
• Structural features: one heterocyclic saturated center at C2 (flavanone), a conjugated carbonyl at C4, two phenolic sites on the A-ring (positions 5,7), and one phenolic site on the para position of the B-ring. The 2D structure can be described as a benzopyran-4-one (A/C rings) fused system with a pendant para-hydroxyphenyl B-ring at C2.

Note: All exact structure identifiers and labeling positions pertinent to this specific SKU should be confirmed from the item’s CoA/Spec Sheet.

Synthetic Utility

General synthetic behavior (literature; flavanone chemistry)

• Functional groups: one conjugated ketone (C4), three phenolic OH groups (4′,5,7), and an aryl–aryl linkage. These enable O-acylation/alkylation, ether/ester formation, metal-catalyzed cross-couplings (after halogenation), and oxidative rearrangements (flavanone → flavone).
• Protecting group strategies: Phenols protected as acetates, benzyl ethers, or silyl ethers to control regioselectivity; carbonyl can be transiently protected as ketal if needed.
• Late-stage diversification: Electrophilic aromatic substitution after appropriate activation; directed ortho-metalation has limited scope due to phenols but can be enabled via protecting groups.

Considerations specific to deuterated isotopologues

• Preserving isotopic labels: Avoid conditions that promote H/D exchange at labeled sites (strong acid/base, metal hydrides in protic media, high temperature). Verify by HRMS and 1H/2H NMR post-transformation.
• Use as mechanistic probe: Deuterium kinetic isotope effects can be probed when labels are at positions involved in rate-determining C–H bond cleavage. Confirm labeling site from the CoA to design experiments appropriately.

While naringenin-d4 is primarily an analytical standard, it can participate in the same suite of transformations as the parent flavanone when isotopic integrity is maintained.

Target Specificity

Not applicable. This product is a small-molecule isotopically labeled standard, not a biological targeting reagent (e.g., antibody, inhibitor with defined protein target panel). Any observed interactions in biochemical assays pertain to the unlabeled parent compound’s chemistry rather than specific binding attributes of this SKU.