PTIO - ≥98%(T) , CAS No.18390-00-6

CAS: 18390-00-6 Cat. No.: P160514 Fórmula: C₁₃H₁₇N₂O₂ Peso molecular: 233.29 Número CE: 634-050-5 PubChem CID: 2733513

GRADE & PURITY ≥98%(T)

Synonyms

PTIO | MFCD00059929 | 1H-Imidazol-1-yloxy, 4,5-dihydro-4,4,5,5-tetramethyl-2-phenyl-, 3-oxide | PTIO (2-Phenyl-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl) | A5440 | 4,5-Dihydro-4,4,5,5-tetramethyl-2-phenyl-1H-imidazol-1-yloxy-1-oxide | 2-phenyl-4,4,5,5

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Visão geral

2-phenyl-4, 4, 5, 5,-tetramethylimidazoline-1-oxyl 3-oxide (PTIO) has been used as a nitric oxide (NO) scavenger.

Specifications

Sinónimos

PTIO | MFCD00059929 | 1H-Imidazol-1-yloxy, 4,5-dihydro-4,4,5,5-tetramethyl-2-phenyl-, 3-oxide | PTIO (2-Phenyl-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl) | A5440 | 4,5-Dihydro-4,4,5,5-tetramethyl-2-phenyl-1H-imidazol-1-yloxy-1-oxide | 2-phenyl-4,4,5,5

Especificações e pureza

≥98%(T)

Mecanismos bioquímicos e fisiológicos

2-phenyl-4, 4, 5, 5,-tetramethylimidazoline-1-oxyl 3-oxide (PTIOs) derivatives react with nitric oxide (NO) to yield the corresponding imino nitroxides (PTIs) and nitrogen dioxide (NO2).A stable radical scavenger for nitric oxide; affects NO without affec

Condições de armazenamento de armazenamento

Store at 2-8°C,Protected from light

Enviado em

Wet ice

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Tipo de ação

INHIBITOR

Pureza

≥98%(T)

Nomes e identificadores

• Pubchem Sid: 504761011
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504761011
• Sorrisos canónicos: CC1(C([N+](=C(N1[O])C2=CC=CC=C2)[O-])(C)C)C
• InChIKey: DYUUGILMVYJEHY-UHFFFAOYSA-N
• INCHI: 1S/C13H17N2O2/c1-12(2)13(3,4)15(17)11(14(12)16)10-8-6-5-7-9-10/h5-9H,1-4H3
• SMILES isoméricas: CC1(C([N+](=C(N1[O])C2=CC=CC=C2)[O-])(C)C)C
• PubChem CID: 2733513
• Peso molecular: 233.29
• Reaxy-Rn: 13743042

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzene and substituted derivatives
• Alternative Parents: Imidazolines Nitrones Propargyl-type 1,3-dipolar organic compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Monocyclic benzene moiety - 2-imidazoline - Nitrone - Azacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteromonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Alvos associados (humanos)

TYR Tclin Tyrosinase (717 Activities)

Discover Target: TYR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Alvos associados (não humanos)

PC-12 (7051 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RAW264.7 (28094 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de ação

Propriedades químicas e físicas

• Solubilidade: Soluble in methanol.
• Sensibilidade: heat sensitive；light sensitive
• Peso molecular: 233.290 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 233.129 Da
• Monoisotopic Mass: 233.129 Da
• Topological Polar Surface Area: 33.000 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 316.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referências

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15. Liping Yu, Wang Cheng, Meifen Tian, Zhigang Wu, Xiaoli Wei, Xing Cheng, Mingwei Yang, Xuan Ma.  (2024)  Antioxidant Activity and Volatile Oil Analysis of Ethanol Extract of Phoebe zhennan S. Lee et F. N. Wei Leaves.  Forests,  15  (2): (236).  [PMID:] [10.3390/f15020236]

16. Bin Cheng, Jie Zhou, Xu Wang, Zihan He, Zhengyi Xu, Jian Wang, Junyu Chen, Zhou Zhu, Weifeng Zhao, Qianbing Wan, Xibo Pei.  (2024)  Dual-responsive metal polyphenol network nanosheets for diabetic wound healing.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.153071]

17. Ziwen Wang, Dongdong Wang, Jiaxuan Fang, Zixin Song, Jiman Geng, Jianfei Zhao, Yifan Fang, Changtao Wang, Meng Li.  (2024)  Green and efficient extraction of flavonoids from Perilla frutescens (L.) Britt. leaves based on natural deep eutectic solvents: Process optimization, component identification, and biological activity.  FOOD CHEMISTRY,      [PMID:38733681] [10.1016/j.foodchem.2024.139508]

18. Xiang Li, Wenli Han, Gao He, Jiahao Yang, Jing Li, Hongxia Ma, Shige Wang.  (2024)  Hydrogel-Transformable Antioxidant Poly-γ-Glutamic Acid/Polyethyleneimine Hemostatic Powder for Efficient Wound Hemostasis.  Gels,  10  (1): (68).  [PMID:38247790] [10.3390/gels10010068]

19. Gang Feng, Yifan Wu, Xinzi He, Tingting Ye, Shang Chi, Xiaoxiao Ji, Jiawei Kang, Kaicheng Xu, JinFeng Zhou, Zhihui Xiang, Wei Wang, Yaping Li, Yiying Qi.  (2025)  Lubricated hydrogel with STING-inhibiting EXOs protect the osteoarthritis by suppressing the senescent microenvironment.  Nano Today,      [PMID:] [10.1016/j.nantod.2025.102688]

20. Zhiqing Liu, Tianlong Wang, Lei Zhang, Yiping Luo, Jinhui Zhao, Yixing Chen, Yao Wang, Wentao Cao, Xinyu Zhao, Bingqiang Lu, Feng Chen, Zifei Zhou, Longpo Zheng.  (2024)  Metal–Phenolic Networks-Reinforced Extracellular Matrix Scaffold for Bone Regeneration via Combining Radical-Scavenging and Photo-Responsive Regulation of Microenvironment.  Advanced Healthcare Materials,      [PMID:38319101] [10.1002/adhm.202304158]

21. Zhibin Ren, Xiaoying Liu, Guanghao Lv, Xiaiting Wang, Jingli Wang, Wei Wu, Xingyi Li, Jiaqing Wang.  (2025)  Mitochondrial Localization of Antioxidant Nanodrug Suppresses Ocular Inflammation by Alleviating Oxidative Stress on Cells.  CHEMISTRY-A EUROPEAN JOURNAL,      [PMID:39833114] [10.1002/chem.202402441]

22. Shun Xiao, Xiaozhi Sun, Chong Wang, Jianlie Wu, Kun Zhang, Mingjin Guo, Bing Liu.  (2024)  Nanomicrosphere sustained-release urokinase systems with antioxidant properties for deep vein thrombosis therapy.  RSC Advances,  14  (10): (7195-7205).  [PMID:38419677] [10.1039/D3RA07221E]

23. Liya Fan, Xiaoxuan Xi, Xiaoyan Zhao, Xiao Zhu.  (2024)  Preparation of composite hydrogel with mechanical stability and temperature response for tea polyphenol release.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2024.135831]

24. Enhui Xu, Hainan Yu, Wei Wu, Bolin Ji, Xueling Feng, Hong Xu, Yi Zhong, Bijia Wang, Zhiping Mao.  (2024)  Preparation of high antioxidant nanolignin and its application in cosmetics.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:38797295] [10.1016/j.ijbiomac.2024.132635]

25. Wenjing Ma, Mingjun Tang, Siying Li, Yongqun Ma, Min Ling, Wenqian Sheng.  (2024)  The effect of hydrogen bonding strength in natural deep eutectic solvents on the extraction efficiency of polyphenols.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.112379]

26. Mingjun Tang, Min Ling, Wenjing Ma, Wenqian Sheng, Wenjun Yan.  (2025)  The Elucidation of the Critical Role of HLB value in Microemulsions Formulation.  ChemNanoMat,      [PMID:] [10.1002/cnma.202400554]

27. Yi Wang, Xuemei Liao, Qinglong Guo, Heng Zhang, Lei Ye, Liangchen Yu, Xiaoming Kong, Yicheng Jiang, Peng Zhao, Kaiyong Cai, Hongwei Cheng.  (2025)  Dual-pathway targeted therapy for Parkinson's disease: Biomimetic nanosomes inhibit ferroptosis and pyroptosis through NLRP3 inflammasome regulation.  Bioactive Materials,      [PMID:40678266] [10.1016/j.bioactmat.2025.06.033]

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Application Protocols

No validated application protocols, assay dilutions, or use instructions are provided in the Product Data for this item. Please refer to primary literature and your laboratory’s standard operating procedures when designing experiments with PTIO.

• General guidance (non-prescriptive, literature): prepare fresh concentrated stocks in dry DMSO under low light; dilute into the working medium immediately before use. Verify compatibility of any co-solvent with your assay system.

For authoritative, item-specific instructions (if available), consult the lot-specific CoA and SDS, or contact Technical Support with your application details.

Biological Roles

No biological function is assigned to PTIO itself in living systems; it is a synthetic nitronyl nitroxide used as a research tool. The statements below describe common research uses and underlying chemical biology without implying therapeutic application.

• Research role (literature):

  • Acts as a selective nitric oxide (NO) scavenger in chemical/biochemical assays, enabling differentiation between NO-dependent and NO-independent processes.
  • Its EPR-active nitroxide facilitates detection and quantitation of radical species and provides a handle for studying redox environments.

• Mechanistic notes (literature):

  • PTIO consumes NO via radical coupling/electron-transfer pathways, converting to downstream products while reducing free NO concentration.
  • Because NO participates in signaling cascades (guanylate cyclase activation, S-nitrosation, etc.), removing NO with PTIO helps dissect NO’s contribution in vitro.

• Practical considerations for bio-experiments (literature):

  • Aqueous solubility limitations often necessitate co-solvents (e.g., DMSO) or use of the more water-soluble analog cPTIO when low organic content is critical.
  • Reducing environments (e.g., excess ascorbate, thiols) can reduce nitroxides to hydroxylamines, disabling NO scavenging and EPR signals; this should be controlled or accounted for.

Research Use Only: As stated in the Product Data, this product is for research use only and is not intended for use in humans or for clinical/diagnostic purposes.

Buffer Applications

PTIO is not a buffering agent and does not define a useful conjugate acid/base pair for pH control. Consequently, it is not typically used to prepare buffer solutions.

• Practical note (literature): in biological assays where PTIO is employed as an NO scavenger, it is usually introduced into pre-established buffers (e.g., PBS, HEPES, or Krebs-type solutions) via a concentrated stock in DMSO or ethanol. Keep final organic content minimal and verify compatibility with cells/enzymes if applicable.

For pH control and buffering capacity, select conventional buffers (e.g., phosphate, HEPES, Tris) appropriate to your system; PTIO should be treated as an additive rather than a buffer component.

Green Alternatives

From a green chemistry standpoint, considerations focus on solvent choice, reagent selectivity, and waste minimization rather than altering PTIO’s core reactivity.

• Solvent choices (literature):

  • Greener polar organics such as ethanol, 2-propanol, or ethyl acetate may sometimes substitute for DMF/MeCN depending on solubility needs. DMSO, while not “green” in all frameworks, has low volatility and good operator safety when handled properly.

• Alternative NO scavengers (literature comparison):

  | Reagent | Water solubility | Selectivity to NO | Notes | | --- | --- | --- | --- | | PTIO | Limited | High (established) | Strong EPR signal; requires organic co-solvent in aqueous systems | | cPTIO (carboxy-PTIO) | Improved | High | Better for aqueous media; similar mechanism; potentially less organic solvent use | | Hemoproteins (e.g., oxyHb) | Aqueous | High (binding) | Biogenic but protein waste stream; possible side reactions | | TEMPO derivatives | Variable | Lower for NO | Useful radicals but not NO-specific; may not replace PTIO mechanistically |

• Operational greening (general):

  • Use minimal co-solvent loading (≤1–2% DMSO/EtOH) in aqueous studies to reduce VOC and waste.
  • Employ amber glassware and low-light handling to extend solution life and reduce repeat preparations.
  • Scale experiments appropriately; nitroxide radicals are intensely colored, enabling visual confirmation at low concentrations.

Note: Selection should prioritize data quality and safety; greener alternatives must preserve the mechanistic validity of NO scavenging for your system.

Pharmaceutical Uses

No pharmaceutical or clinical uses are claimed or supported for this catalog item. It is supplied strictly for research use only, as noted in the Product Data.

• Formulation/excipient status: PTIO is not a common excipient and is not recognized as a compendial ingredient in pharmacopeias for formulation purposes.

• Research/formulation context (literature):

  • In preclinical research settings, PTIO may be used as a chemical tool to modulate NO levels in in vitro systems or ex vivo preparations to elucidate pathways. These are laboratory studies, not medicinal products.
  • When preparing research solutions, typical practice is to dissolve PTIO in a polar organic solvent (e.g., DMSO) and dilute into a suitable aqueous vehicle; ensure solvent levels remain within tolerability limits of the experimental model.

• Manufacturing/handling note: If PTIO-containing solutions are prepared in a laboratory manufacturing setting (e.g., for in vitro kit reagents), quality controls should focus on radical integrity (EPR), concentration verification (UV-Vis/EPR), and absence of reducing contaminants that could quench activity.

No therapeutic, diagnostic, or clinical claims should be inferred from the presence of PTIO in any research system.

Physical Properties

Item-specific specifications are not provided in the Product Data; consult the CoA/Spec Sheet for definitive values.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general information (for context only; not product specifications):

• Typical physical form: orange to deep-red, crystalline solid; intensely colored due to nitroxide chromophore.
• Paramagnetism: EPR-active nitroxide radical; characteristic nitroxide triplet in EPR spectra with hyperfine coupling to 14N.
• Solubility profile: soluble in polar organic solvents (DMSO, DMF, ethanol, acetonitrile); limited aqueous solubility compared with carboxy-PTIO; increased solubility with co-solvents or surfactants.
• Stability: sensitive to strong reducing agents (which can convert the nitroxide to the corresponding hydroxylamine) and to strong acids/bases; light may accelerate degradation—store protected from light (matches Product Data).
• Color changes: reduction to hydroxylamine typically bleaches the orange color (useful qualitative indicator during handling).

Note: Do not treat the above literature values as specifications for this catalog item; always verify relevant properties and suitability for your application experimentally and via the product’s CoA/SDS.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet. In the absence of a declared grade (e.g., ≥98%, HPLC, or ReagentPlus), users should verify assay and impurity profile via the CoA and, where critical, confirm by independent QC (e.g., 1H/13C NMR, HRMS, EPR for nitroxide signal, and chromatographic purity).

• What grade means (general guidance):

  • "Analytical Reagent/AR" or "ACS" grades: meet typical assay and impurity limits suitable for analytical and routine lab work.
  • "HPLC grade" (for solids or solvents): emphasizes low UV-absorbing impurities, suitability for trace analysis; for nitroxides, low paramagnetic contaminants is also relevant for EPR/NMR use.
  • "BioReagent"/"Cell culture" grades: tested for endotoxin/bioburden and sometimes for defined solubility/compatibility in biological buffers.

• PTIO-specific quality considerations (general):

  • Radical integrity: PTIO’s nitroxide should present a strong and clean EPR triplet; partial reduction to hydroxylamine lowers signal intensity. If applications are EPR- or NO-chemistry–sensitive, verify by an EPR spot check.
  • Moisture/redox history: exposure to reducing agents (including some metal surfaces or impure solvents) can degrade PTIO; check for color loss or altered TLC/HPLC profile.
  • Stabilizers: None are listed in Product Data. If present in a particular lot, stabilizers will be noted on the CoA.

Always consult the lot-specific CoA/Spec Sheet for definitive assay, residual solvent, and impurity data.

Reaction and Applications

This compound is primarily employed as a nitric oxide (NO) scavenger and as a paramagnetic probe in radical chemistry and EPR spectroscopy.

• NO scavenging (literature):

  • PTIO reacts with NO in solution, effectively reducing free NO levels. The initial step involves radical–radical coupling or electron transfer within the nitronyl nitroxide framework, ultimately converting PTIO to PTI-like products while consuming NO. This has been used to validate NO-dependent pathways in chemical and biochemical systems.
  • Compared with metal-based NO traps (e.g., hemoproteins), PTIO avoids metal-mediated side chemistry but is less water soluble than cPTIO.

• Radical chemistry probe (literature):

  • EPR-active nitroxide with a characteristic 14N hyperfine pattern, useful for calibration, spin counting, and mechanistic studies.
  • Can participate in radical–radical cross reactions, providing insight into radical fluxes and lifetimes in model systems.

• Practical tips:

  • Prepare fresh solutions under reduced light; assess integrity by color and/or EPR if outcomes are sensitive to scavenger efficacy.
  • Avoid strong reducing agents (ascorbate, dithionite) unless intentional quenching is desired; these rapidly convert nitroxides to hydroxylamines (EPR-silent).
  • In mixed aqueous/organic media, a small percentage of DMSO or ethanol can help achieve homogeneous dosing while maintaining biological compatibility in in vitro systems (verify tolerability for your assay).

• Related tools: carboxy-PTIO (more hydrophilic NO scavenger), TEMPO derivatives (general nitroxides, less NO-selective), and metal–porphyrin NO binders (different selectivity profile).

Reaction Conditions

No item-specific reaction protocols are provided in the Product Data. The following are general literature-based conditions relevant to PTIO’s common uses; adapt to your system and consult primary sources.

• NO scavenging in solution (literature):

  • Solvent: buffered aqueous media with 0.1–2% DMSO or ethanol; or purely organic media (DMSO, MeCN, EtOH) for chemical studies.
  • Temperature: ambient (20–25°C) is typical; lower temperatures can slow side reactions and improve control in kinetic studies.
  • Atmosphere: air or inert; degassing can be helpful when tracking radical kinetics.
  • Stoichiometry: employ PTIO in molar excess relative to the expected NO flux to ensure effective scavenging; exact ratios depend on NO generation rate and matrix.
  • Monitoring: EPR to monitor nitroxide signal; UV-Vis may track characteristic nitroxide absorbance; chemiluminescence or Griess assay to quantify NO/NOx changes.

• Redox control experiments (literature):

  • Intentional reduction with ascorbate or other reductants can be used as a negative control (loss of EPR and NO-scavenging capacity), verifying PTIO-dependent effects.

• Workup/compatibility:

  • Avoid strong acids/bases and strong reductants that degrade PTIO during the experiment unless mechanistically intended.
  • Use amberware or limit light exposure to reduce photodegradation.

These guidelines are conceptual starting points; optimize concentrations, timing, and detection methods for each assay or chemical system.

Safety and Handling

Authoritative safety information must be taken from the SDS. Product Data for this item does not list GHS or H-statements.

• GHS/CLP (item-specific):

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

• Known hazard considerations (literature/general):

  • Nitroxide radicals may cause skin/eye irritation and are harmful if swallowed or inhaled. PTIO can react with nitric oxide and other radicals; avoid uncontrolled contact with strong oxidants or reductants.
  • May be harmful to aquatic life; avoid release to the environment.

• Handling practices (general laboratory):

  • Use in a chemical fume hood. Wear appropriate PPE: lab coat, safety glasses or face shield, and chemical-resistant gloves (e.g., nitrile). Avoid dust generation and inhalation.
  • Avoid contact with strong acids, strong bases, strong reducing agents (which quench the nitroxide to a hydroxylamine), and strong oxidants.
  • Light sensitivity: minimize light exposure during weighing and solution prep (amber glassware recommended), consistent with Product Data.

• First aid (general):

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

• Fire response: Use CO2, dry chemical, or foam. Combustion may produce NOx; firefighters should wear self-contained breathing apparatus.

Solvent Selection

PTIO is a moderately polar organic radical that is typically dissolved in polar aprotic solvents; aqueous solubility is limited relative to carboxylated analogs.

• Practical solubility guidance (literature):

  • Good: DMSO, DMF, acetonitrile, ethanol, methanol, ethyl acetate.
  • Limited/variable: water, phosphate-buffered saline (PBS); solubility improves with co-solvent (e.g., ≤1–2% DMSO) or cyclodextrins/surfactants.
  • Avoid: highly basic media or strong reducing environments that quench the nitroxide.

• Polarity and behavior (literature):

  • Nitroxide function imparts polarity and hydrogen-bond accepting capability; the phenyl and tert-alkyl-like substituents impart hydrophobicity. Net behavior: organophilic with measurable polarity.

• Choosing vs alternatives (literature perspective):

  • For aqueous biological systems, consider carboxy-PTIO (cPTIO) due to superior water solubility and comparable NO-scavenging behavior.
  • For strictly organic-phase mechanistic studies or spin-labeling contexts, PTIO in DMSO/MeCN offers high solubility and stability.

• Working tips:

  • Prepare concentrated stocks in anhydrous DMSO under low light; dilute into buffered media immediately before use. Use amber vials and minimize repeated freeze–thaw cycles.
  • Degassed solvents reduce side reactions with dissolved O2-derived radicals when mechanistic control is critical.

Storage and Reconstitution

• Item-specific storage (from Product Data):

  • Store at 2–8°C.
  • Protect from light.
  • Shipped on wet ice.

• Stability considerations (general/literature):

  • PTIO is a nitroxide radical that may degrade upon prolonged exposure to light, heat, strong acids/bases, or reducing agents. Maintain in amber, tightly sealed containers. Limit headspace to reduce oxidative changes to co-formulated components.

• Reconstitution/stock preparation (general):

  • Use anhydrous, oxygen-stable polar organic solvents such as DMSO or acetonitrile to prepare concentrated stocks. Filter if particulate is present, avoiding reactive filter media (use PTFE/PP).
  • For aqueous applications, dilute the organic stock into buffer immediately prior to use; keep final organic content as low as practicable while maintaining solubility and homogeneity.
  • Prepare small aliquots to avoid multiple freeze–thaw cycles; store aliquots at 2–8°C protected from light for short-term use. For longer-term storage, some users keep aliquots at ≤−20°C in amber vials; verify stability empirically for your system.

• Inspection before use:

  • Check for color changes (loss of orange hue) that may indicate reduction to the hydroxylamine, and confirm integrity by EPR or quick analytical check if critical.

Always defer to the lot-specific CoA/SDS for binding guidance on storage limits and conditions.

Structure and Identity

PTIO is widely recognized in the literature as 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide, a nitronyl nitroxide radical used as a nitric oxide (NO) scavenger and spin probe.

• Item-specific identifiers (Product Data):

  • SKU: P160514
  • Product Name: PTIO
  • CAS: 18390-00-6
  • PubChem CID: 2733513
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists "76391", which is not a standard InChIKey format.)
  • 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 class and features (literature):

  • Core ring system: imidazoline N-oxide framework bearing a persistent nitroxide (N–O•) and an N→O oxide (N–O) grouping (nitronyl nitroxide).
  • Substitution pattern: phenyl substituent at the 2-position; geminal dimethyl groups at C4 and C5 (four methyls total).
  • Radical character: one unpaired electron delocalized over the N–O system; EPR active.
  • 2D description (literature): an imidazoline ring with adjacent N–O functionalities (one as nitroxide radical, one as N-oxide), a phenyl ring attached to C2, and two methyl groups on each of C4 and C5 (tetrasubstitution producing steric protection of the nitroxide). No stereocenters.

• Naming (literature): often abbreviated PTIO; distinct from carboxy-PTIO (cPTIO), a carboxylated, more water-soluble analog.

Synthetic Utility

Although PTIO is primarily a functional probe rather than a generic building block, it occupies a distinct niche in synthesis and mechanistic chemistry due to its persistent nitroxide character.

• Functional groups and reactivity (literature):

  • Nitronyl nitroxide core features an N–O• radical and an N→O bond; the unpaired electron enables selective radical–radical coupling and serves as an EPR-visible handle.
  • Susceptible to one- or two-electron reduction to the corresponding hydroxylamine (EPR silent), providing a redox-switchable tag.

• Applications in synthesis/mechanistic studies (literature):

  • Radical trapping and kinetic studies: PTIO can quench transient NO and related radicals, enabling rate measurements and product analysis.
  • Spin-labeling surrogate: while not a typical covalent spin label like methanethiosulfonate nitroxides, PTIO’s paramagnetism is useful for calibrating EPR setups and benchmarking spin concentrations.
  • Probe for NO balance in catalytic systems where NO is a byproduct or intermediate, helping to validate proposed mechanisms.

• Retrosynthetic relevance: Limited, since PTIO is not commonly transformed into other scaffolds in stepwise syntheses; however, its controlled redox conversion (radical ↔ hydroxylamine) allows access to reference materials useful for calibration and control experiments.

• Practical notes:

  • Maintain radical integrity by avoiding strong reductants, metals that catalyze reduction, and acidic/basic extremes.
  • For quantitative mechanistic work, standardize PTIO stock concentration spectroscopically (EPR spin counting or UV-Vis if an extinction coefficient is available from literature) before use.

Target Specificity

This product is a small-molecule nitroxide, not a biological macromolecule or antibody. There are no antigen/epitope or species-specific attributes.

• Item-specific data: Not applicable; no target-binding specificity is provided in the Product Data.

• Functional selectivity (literature): PTIO is used as a chemical scavenger for nitric oxide (NO) in solution. While relatively selective for NO compared with many radicals, it can participate in broader radical chemistry under certain conditions; appropriate controls are necessary to attribute effects specifically to NO scavenging.