Vitamin K5 - ≥98% , CAS No.83-70-5

CAS: 83-70-5 Cat. No.: V1073200 Formula: C₁₁H₁₁NO Peso molecolare: 173.210

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Tipo di azione

INHIBITOR

Purezza

≥98%

Nomi e identificatori

• Sorrisi canonici: CC1=C(C2=CC=CC=C2C(=C1)N)O
• IUPAC Name: 4-amino-2-methylnaphthalen-1-ol
• InChIKey: UGQFCTZXVAPVCS-UHFFFAOYSA-N
• INCHI: 1S/C11H11NO/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6,13H,12H2,1H3
• Peso molecolare: 173.210

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Naphthalenes
      • Subclass Naphthols and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Naphthalenes
• Subclass: Naphthols and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthols and derivatives
• Alternative Parents: Primary amines Organopnictogen compounds Organooxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: 1-naphthol - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Amine - Aromatic homopolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 173.210 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 173.084 Da
• Monoisotopic Mass: 173.084 Da
• Topological Polar Surface Area: 46.300 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 183.000
• 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

Application Protocols

No manufacturer-tested application protocols are provided for this SKU. For general laboratory use with hydrophobic small molecules:

• Stock solutions: Prepare 10–50 mM stocks in anhydrous DMSO under low light; filter (0.22 μm PTFE) if particulate is present. Record exact concentration by UV–Vis when feasible.
• Assay dilution: Add stock to the assay medium with rapid mixing to achieve ≤1–2% final DMSO; verify absence of precipitation by visual inspection and UV–Vis/HPLC.
• Analytical QC: Confirm identity/purity by HPLC and MS upon receipt; re-check after prolonged storage.

All procedures should be adapted to your laboratory’s validated methods. Item-specific parameters are Not specified; consult the CoA/SDS.

Biological Roles

No biological/clinical claims are made for this research-use reagent. The following context pertains to the vitamin K chemical class (literature, general):

• Structural class: Vitamin K compounds are naphthoquinone derivatives. In biology, K1 (phylloquinone) and K2 (menaquinones) function as cofactors in carboxylation pathways. Synthetic analogs (K3–K5) share the quinone core but differ in side chains and substituents, which strongly affect solubility, redox potential, and membrane affinity.
• Redox properties: The quinone/hydroquinone couple underlies electron-transfer roles in enzymatic cycles. Substituents modulate standard reduction potentials and reactivity toward nucleophiles.
• Experimental use: In biochemical research, quinone analogs are employed to probe redox enzymes, electron transport, and thiol chemistry due to their defined electrophilicity and chromophoric signatures.
• Stability considerations: Quinone analogs can undergo photoreduction or redox cycling in the presence of light and reducing agents, potentially confounding biological assays if not controlled (e.g., use low-light conditions, oxygen control, and defined co-solvent levels).

Item-specific biological activity and potency are not specified for this SKU. Any use in living systems should be preceded by rigorous pilot testing of stability, aggregation/solubility, and off-target reactivity under the exact assay conditions.

Buffer Applications

This item is not a buffering agent. Quinone-based vitamin K analogs do not typically serve as acid/base buffers.

• Practical note: If preparing aqueous assay solutions, dissolve first in a miscible organic co-solvent (commonly anhydrous DMSO), then dilute into the target buffer with rapid mixing, keeping the final organic content low (often ≤1–2%) to avoid precipitation.
• Avoid common pitfalls: Adsorption to plastics and precipitation may occur at low aqueous organic content; verify concentration by UV–Vis in the final matrix if quantitative dosing is required.

No item-specific buffer recipes or pKa values are provided; refer to the CoA/Spec Sheet and perform small-scale solubility trials.

Green Alternatives

While the compound itself does not have a direct “green” substitute in most research contexts, its handling and transformations can be optimized using greener solvents and conditions (general, literature):

• Prefer greener solvents for dissolution and reactions:
  • Replace chlorinated solvents with ethyl acetate, 2-MeTHF, CPME, or toluene where solubility/reactivity allow.
  • Use ethanol or isopropanol instead of methanol when feasible to lower toxicity.
• Redox and reduction steps:
  • Consider catalytic hydrogenation (H2, Pd/C) under controlled conditions as an atom-efficient alternative to stoichiometric metal reductants, when compatible with the substrate.
  • Employ aqueous biphasic systems with surfactants or micellar catalysis (e.g., TPGS-750-M) to reduce organic solvent usage, provided the quinone’s solubility can be managed.
• Workup and purification:
  • Minimize silica usage by optimizing crystallizations (e.g., EtOAc/hexanes or EtOAc/EtOH). Recycle solvents where possible.
• Energy and light management:
  • Many quinones are light-sensitive; using amberware not only preserves material but reduces degradation waste. Conduct reactions at ambient temperature when kinetics allow.

Illustrative comparison (general):

• Dichloromethane vs 2-MeTHF: Both dissolve many quinones; 2-MeTHF offers a better environmental profile and can support many conjugate additions and cycloadditions, though it absorbs water and may require drying.

Item-specific solvent compatibility is not specified here—verify experimentally with small-scale trials.

Pharmaceutical Uses

For research use only. No clinical or therapeutic use is claimed or intended for this product.

• Formulation context (general information): Quinone analogs are hydrophobic and, when used as research excipients or actives in preclinical formulation development, often require solubilization strategies such as co-solvents (ethanol, PEG 400, propylene glycol), surfactants (Tween 80, Cremophor), or lipid vehicles. Those strategies are presented here only as general background.
• Compendial status: No pharmacopeial monograph is cited for this specific SKU. Item-specific regulatory grade, residual solvent compliance, and elemental impurity assessments are Not specified; refer to the CoA/Spec Sheet if required for method development.
• Manufacturing handling (general): Protect from light, control oxygen exposure when targeting a defined oxidation state, and use amber glassware. Validate hold times to ensure no redox drift.

Any evaluation of this compound in pharmaceutical research must include independent characterization of identity, purity, stability, and compatibility with excipients under ICH-relevant conditions. This product is supplied for laboratory research only.

Physical Properties

Item-specific specifications are not provided in the Product Data for this SKU.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (literature, vitamin K analogs/naphthoquinones): Typically solid with MP in the 100–200 °C range depending on substitution; exact value for this item not confirmed here.
• Boiling point: Not typically reported for quinones that decompose or sublime; Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general guidance): Vitamin K-type naphthoquinones are sparingly soluble in water and soluble in organic solvents (e.g., DMSO, DMF, ethanol, acetone, chlorinated solvents). Exact solubility for this item: Not specified; determine experimentally or consult CoA.
• LogP/partitioning (literature, general): Quinone analogs are moderately to highly lipophilic; specific logP for Vitamin K5 not provided here.
• UV–Vis (literature, general): Quinone chromophores exhibit strong visible absorption (yellow–orange) with bands near 240–280 nm and 320–450 nm depending on substitution. Item-specific UV cutoff/ε: Not specified.
• Refractive index: Not applicable to a solid; if oil or solution is provided, Not specified for this item.
• pKa: Not generally applicable; quinones are not Brønsted acids/bases, though substituents (e.g., phenolic/amine) can confer acid/base character. Item-specific pKa: Not specified.

Always confirm any property needed for method development by consulting the CoA/SDS or by small-scale measurement.

Quality and Grades

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet for exact assay, related substances, and residual solvent data.
• What to expect in the CoA (typical for small-molecule research reagents):
  • Identity confirmation (e.g., NMR, MS, HPLC/UPLC purity).
  • Water content (Karl Fischer) and residual solvents, if applicable.
  • Assay by HPLC area% or quantitative NMR.
  • Acceptance criteria for appearance and storage.
• Stabilizers: Not specified for this item. Many quinones do not require stabilizers but may be shipped in amber containers to mitigate light exposure. If a stabilizer is present, it will be listed on the CoA/SDS.
• UV-Vis/HPLC suitability: If HPLC suitability is important (e.g., profiling redox state), select lots with low baseline drift and clearly resolved impurity profile. For photometric work, verify extinction coefficients experimentally as item-specific values are not provided here.
• Batch-to-batch considerations (general for quinones): Redox-active materials can show minor lot-to-lot variation in color/absorbance depending on trace redox state. Equilibrate under inert or controlled atmosphere if assay requires a defined oxidation state.
• Documentation: Request the latest CoA and analytical package if you require regulatory-level detail for method validation. This product is intended for research use only.

Reaction and Applications

This product is a research-grade small molecule; no manufacturer applications were provided. The following outlines common laboratory uses of vitamin K-type naphthoquinones (literature, general):

• Redox probes and electron acceptors: Quinones reversibly cycle between quinone/hydroquinone states, useful in studying redox processes, catalysis, and electron-transfer phenomena.
• Michael acceptor chemistry: The 1,4-quinone ring undergoes conjugate addition with soft nucleophiles (thiols, amines, enolates). Substitution modulates electrophilicity and selectivity.
• Diels–Alder dienophiles: Activated quinones participate in [4+2] cycloadditions with electron-rich dienes, enabling access to complex bicyclic frameworks. Subsequent rearrangements or reductions elaborate products.
• Photochemistry: Quinones can engage in photoinduced electron transfer; care with light exposure is necessary to control side reactions.
• Reductive functionalization: Stepwise reduction to the hydroquinone (e.g., Na2S2O4, Zn/AcOH, catalytic hydrogenation) enables protection/deprotection strategies, differential reactivity, and subsequent ether/ester formation from the diol.
• Analytical calibration standards: Quinone chromophores offer defined absorbance bands for method development in UV–Vis and HPLC (verify extinction coefficients experimentally for this exact item).

Practical tips:

• Exclude strong bases or nucleophiles unless desired—over-addition can occur.
• Degas and use inert atmosphere for sensitive transformations; avoid prolonged bright light.
• Monitor by TLC/HPLC with amber lighting or red filters to minimize photo-effects.

Reaction Conditions

General laboratory conditions for reactions involving vitamin K-type naphthoquinones (literature guidance; optimize for your substrate and this SKU):

• Conjugate (Michael) additions:
  • Solvent: Dry THF, MeCN, 2-MeTHF, or toluene; for polar nucleophiles, MeOH/EtOH may be used.
  • Base/nucleophile: Thiols or amines (0.5–2.0 equiv); for C–C additions, use enolates (e.g., LDA) or organocuprates at −78 to 0 °C.
  • Temperature/time: −78 to 25 °C, 0.5–16 h depending on nucleophile strength.
  • Notes: Avoid excess strong base to prevent over-reduction or polymerization; exclude oxygen for sensitive substrates.
• Diels–Alder cycloadditions:
  • Solvent: Toluene, xylene, or 2-MeTHF.
  • Conditions: 60–140 °C (thermal) or Lewis acid catalysis (e.g., BF3·OEt2) at lower temperatures.
  • Workup: Reductive or oxidative post-treatments tailor product oxidation states.
• Reductions to hydroquinones:
  • Reagents: Na2S2O4 (aq./biphasic), Zn/AcOH, SnCl2, or catalytic hydrogenation (H2, Pd/C at 1–3 bar).
  • Solvent: Alcohols, AcOH, or mixed aqueous-organic systems.
  • Caution: Control stoichiometry to avoid complete deoxygenation/aromatization.
• Analytical monitoring:
  • TLC/HPLC under amber light; UV–Vis bands facilitate quick monitoring.
  • Quench samples with a small amount of antioxidant (e.g., BHT) if redox drift is observed during analysis.

Expected yields and exact parameters are substrate-dependent and not specified for this item; begin with small-scale screens.

Safety and Handling

• GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to the SDS for authoritative hazard classification.
• Anticipated hazards (general for quinones/vitamin K analogs; literature): May cause skin/eye irritation. Quinones can be redox-active and may generate reactive oxygen species in the presence of reductants; avoid inhalation of dust and prolonged exposure. Some quinones are light-sensitive.
• PPE: Laboratory coat, nitrile gloves, safety glasses as a minimum. Use a certified chemical fume hood to avoid dust/vapor exposure.
• Handling: Avoid contact with oxidizing or strong reducing agents unless intended; prevent dust formation. Use amber glassware or minimize light exposure if the compound is photo-labile (common for quinones).
• Incompatibilities (general): Strong bases/nucleophiles may add to the quinone via Michael addition; strong reducing agents may over-reduce to hydroquinones. Strong oxidants may degrade the aromatic system.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: Use CO2, dry chemical, or foam. Combustion may produce irritating fumes; firefighters should wear SCBA.
• Spill response: Avoid dust formation; collect with inert absorbent; dispose per local regulations.

For research use only. Consult the SDS for detailed and legally binding safety information.

Solvent Selection

Vitamin K-type naphthoquinones are generally hydrophobic and benefit from polar aprotic or moderately polar organic solvents for dissolution.

• Polarity/miscibility (general, literature):
  • Poor water solubility; good solubility in DMSO, DMF, acetone, ethyl acetate, ethanol/isopropanol (moderate), and chlorinated solvents (e.g., CH2Cl2, CHCl3).
  • For biological assay stock solutions, anhydrous DMSO is commonly used, followed by dilution into assay buffer with appropriate co-solvent levels (<1–2% DMSO), pending compound stability.
• Selection guidance:
  • For analytical HPLC: ACN–water or MeOH–water with 0.1% acid (e.g., formic) often resolves quinones; protect from strong light to minimize on-column redox.
  • For synthesis: Choose dry, oxygen-controlled solvents when performing nucleophilic additions or reductions to prevent side reactions.
  • For crystallization: Ethanol/ethyl acetate or hexanes/ethyl acetate combinations are frequently effective for quinone derivatives; screen based on TLC polarity.
• Comparison (general):
  • DMSO vs ethanol: DMSO offers higher solubility and stability for stock solutions; ethanol is preferred when lower toxicity solvents are required, though solubility can be limiting.
  • Chlorinated solvents: Excellent solubility and inertness toward many transformations but consider environmental and safety burdens.

Item-specific solubility limits and UV cutoff are not specified; determine empirically at small scale and refer to the CoA for any available guidance.

Storage and Reconstitution

• Storage conditions (as provided): Room temperature.
• Container: Store in tightly closed, amber glass to minimize light exposure. Purge headspace with inert gas (e.g., nitrogen or argon) after opening if long-term storage is anticipated, as quinones can undergo redox changes.
• Stability: Item-specific stability and shelf life are Not specified; refer to CoA/SDS. As a general precaution for quinones, limit exposure to bright light, moisture, and strong reducing/oxidizing atmospheres.
• Reconstitution/stock preparation (general):
  • Dissolve in anhydrous DMSO, DMF, ethanol, or other suitable organic solvent to prepare concentrated stocks (e.g., 10–50 mM for screening use), then dilute into the working medium.
  • If aqueous media are required, use co-solvent systems or formulate with surfactants to maintain solubility. Filter sterilize through 0.22 μm PTFE if sterility is needed for cell-free assays.
• Freeze–thaw: Typically not required when stored as dry solid at room temperature. If aliquots of solution stocks are frozen (e.g., −20 °C), minimize freeze–thaw cycles; store aliquots protected from light.
• Shipped in: Not specified for this item; refer to product label.

Always consult the product label and CoA/SDS for definitive storage and handling guidance for this specific SKU.

Structure and Identity

• Item name: Vitamin K5 (SKU: V1073200); cataloged in the Small Molecules & Compound Library category.
• CAS: 83-70-5; PubChem CID: 6754 (literature identifier for a vitamin K analog; confirm identity against CoA/SDS for this specific lot).
• 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.
• Structural features (general, literature): Vitamin K family members are naphthoquinone derivatives. Vitamin K5 is commonly described in the literature as a para-quinone-based vitamin K analog with an electron-deficient 1,4-quinone core capable of redox cycling and conjugate addition. Verify the exact substitution pattern in the Certificate of Analysis.
• 2D description (general): A fused bicyclic aromatic framework (naphthalene) bearing two carbonyls at the para positions (1,4) creates an electrophilic quinone ring; substituents on the ring modulate redox potential and solubility.
• Synonym notes (literature): Vitamin K analogs are variably named (K1/K2/K3/K4/K5). Always match names to CAS and structure in primary documentation for this product.

Synthetic Utility

Quinone-based vitamin K analogs are valuable synthetic linchpins owing to their electrophilicity and tunable redox properties (literature, general):

• Conjugate additions: Facilitate C–C and C–X bond formation via 1,4-additions of enolates, thiols, and amines. Stereocontrol can be induced using chiral organocatalysts for Michael additions to activated quinones.
• Diels–Alder reactions: Serve as dienophiles with electron-rich dienes to afford bicyclic adducts; downstream manipulations (oxidation, aromatization, or reductive opening) diversify scaffolds for medicinal chemistry.
• Reductive transformations: Stepwise reduction to hydroquinones allows O-functionalization (alkylation/acylation) and subsequent reoxidation to tailored quinones.
• Nucleophilic aromatic substitution (on activated positions): Certain ring positions adjacent to carbonyls can be displaced after activation, enabling substitution patterns not accessible via direct electrophilic aromatic substitution.
• Photoredox/ET chemistry: Quinones act as electron shuttles or H-atom abstractors under photoredox conditions, enabling net dehydrogenations or coupling processes.
• Protecting group logic: The quinone/hydroquinone toggle can serve as a temporary protection strategy for dihydroxy naphthalene motifs in multistep synthesis.

Design considerations:

• Substituent effects on reduction potential and LUMO energy govern reactivity; verify kinetics/selectivity experimentally for the specific analog.
• Control moisture/oxygen and light to suppress undesired side reactions and polymerization.

Target Specificity

Not applicable. This product is a small-molecule chemical standard and is not an antibody, enzyme, or biologic. No antigen/epitope or species reactivity applies.