Quinones
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Category：Organic Chemicals Own Brand：MT /MOQ:100KG /From China/ B2B only.
Introduction
Definition & Structure
Quinones are cyclic diketones derived from aromatic compounds (e.g., benzene, naphthalene) with two carbonyl (C=O) groups in conjugated positions.
- General Formula:
- Benzoquinone: C₆H₄O₂ (1,4- or 1,2-isomers)
- Naphthoquinone: C₁₀H₆O₂ (e.g., Vitamin K)
- Key Feature: Redox-active, forming hydroquinones (C₆H₄(OH)₂) upon reduction.
Classification & Examples
| Type | Structure | Example | Role |
|---|---|---|---|
| 1,4-Benzoquinone |  |
Ubiquinone (CoQ10) | Electron transport in mitochondria |
| 1,2-Naphthoquinone |  |
Lawsone (Henna dye) | Natural pigment, hair dye |
| Anthraquinone |  |
Alizarin (textile dye) | Red dye, pH indicator |
Key Properties
| Property | Value/Behavior | Application Implication |
|---|---|---|
| Redox Potential | +0.1 to +0.7 V (vs. SHE) | Electron shuttles in batteries |
| Color | Yellow to red (conjugated C=O) | Dye and pigment synthesis |
| Solubility | Low in water, high in organics | Requires polar aprotic solvents |
Industrial Applications
| Industry | Use Case | Example Quinone |
|---|---|---|
| Polymers | Crosslinking agent for polyurethanes | Chloranil (C₆Cl₄O₂) |
| Pharmaceuticals | Anticancer drugs (e.g., Mitomycin C) | Anthracycline antibiotics |
| Energy Storage | Cathode material in flow batteries | AQDS (9,10-anthraquinone-2,7-disulfonic acid) |
| Food & Cosmetics | Antioxidants, natural dyes | Emodin (rhubarb pigment) |
Biological & Natural Roles
- Photosynthesis: Plastoquinone in chloroplast electron transport.
- Enzyme Cofactors: Vitamin K (blood clotting).
- Defense Mechanisms: Toxic quinones in insect secretions (e.g., bombardier beetle).
Synthesis Methods
| Method | Reaction | Example |
|---|---|---|
| Oxidation of Phenols | C₆H₅OH + [O] → C₆H₄O₂ | Hydroquinone → 1,4-Benzoquinone |
| Diels-Alder | Diene + Quinone → Polycyclic product | Synthesis of steroid frameworks |
Safety & Handling
| Risk | Precaution | Example |
|---|---|---|
| Toxicity | Carcinogenic (e.g., benzene-1,4-diol derivatives) | PPE required |
| Skin Staining | Wear gloves (lawsone dyes skin) | Henna-based tattoos |
| Environmental | Persistent in soil (anthraquinones) | Biodegradation studies |
Disclaimer: The above content is for reference and communication only among industry insiders, and does not guarantee its accuracy or completeness. According to relevant laws and regulations and the regulations of this website, units or individuals who purchase related items should obtain valid qualifications and qualification conditions.
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