4-hydroxy Benzyl Alcohol from SAMIR123's blog

4-hydroxy Benzyl Alcoholis an organic compound commonly used in chemical and pharmaceutical research. It is a phenolic derivative of benzyl alcohol, containing both a hydroxyl group (-OH) and a benzyl alcohol functional group. These features make it a versatile compound for various synthetic and biological applications.

Chemical Structure and Properties

Chemical Name: 4-Hydroxybenzyl alcohol
Other Names: Para-hydroxybenzyl alcohol, Tyrosol
Molecular Formula: C₇H₈O₂
Molecular Weight: 124.14 g/mol
CAS Number: 623-05-2

Physical Properties:

PropertyDescriptionAppearanceWhite to off-white crystalline solid or powderMelting Point85–87°CBoiling Point285°CSolubilitySoluble in water, ethanol, and other polar solventsOdorMild phenolic odor

The compound's chemical structure features a benzene ring substituted with a hydroxyl group at the para position and a primary alcohol group on the benzyl side chain.

Synthesis

4-Hydroxybenzyl alcohol can be synthesized through various methods, including:

1. Reduction of 4-Hydroxybenzaldehyde: The reduction of 4-hydroxybenzaldehyde using a mild reducing agent such as sodium borohydride (NaBH₄) or catalytic hydrogenation produces 4-hydroxybenzyl alcohol.

   C6H4(OH)CHO+H2→C6H4(OH)CH2OHC₆H₄(OH)CHO + H₂ → C₆H₄(OH)CH₂OHC6​H4​(OH)CHO+H2​→C6​H4​(OH)CH2​OH

2. Biotechnological Synthesis: It can also be produced via microbial or enzymatic pathways, particularly from tyrosine or related precursors, using engineered microorganisms.

Applications

1. Pharmaceutical Research:

   • 4-Hydroxybenzyl alcohol is a biologically active compound known for its antioxidant and anti-inflammatory properties.
   • It serves as a model compound for studying phenolic antioxidants and their role in preventing oxidative stress.
   • It is found in natural sources, including olives, and is studied for its cardioprotective and neuroprotective effects.

2. Chemical Synthesis:

   • It is a precursor in the synthesis of various fine chemicals, including polymers, agrochemicals, and fragrances.
   • The hydroxyl group on the aromatic ring provides reactivity for substitution and coupling reactions.

3. Biomimetic Studies:

   • 4-Hydroxybenzyl alcohol is a structural analog of tyrosol, a naturally occurring antioxidant in olive oil. It is used in research focused on mimicking the beneficial properties of Mediterranean diets.

4. Material Science:

   • It is used in the preparation of phenolic resins and other polymeric materials.
   • It serves as a building block for advanced materials requiring phenolic functionality.

5. Antimicrobial Applications:

   • Due to its phenolic nature, it exhibits antimicrobial properties and is explored as an additive in formulations requiring biostatic effects.

Safety and Handling

4-Hydroxybenzyl alcohol is generally regarded as safe when handled under standard laboratory conditions, but caution should still be exercised.

Safety Precautions:

• Wear appropriate personal protective equipment (PPE) such as gloves, safety glasses, and lab coats.
• Work in a well-ventilated area or under a fume hood to avoid inhaling any dust or vapors.

Storage:

• Store in a cool, dry place, away from heat and direct sunlight.
• Keep the container tightly closed to prevent moisture uptake, as it may degrade over time.

First Aid:

• In case of skin contact: Wash thoroughly with soap and water.
• In case of eye contact: Rinse eyes with water for several minutes and seek medical attention if irritation persists.
• If ingested or inhaled: Seek immediate medical attention.

Environmental Impact

4-Hydroxybenzyl alcohol is not considered highly toxic to the environment, but care should be taken during disposal. Waste material should be handled according to local regulations to prevent contamination of water or soil.

Conclusion

4-Hydroxybenzyl alcohol is a versatile compound with applications spanning pharmaceuticals, material science, and organic synthesis. Its phenolic and alcohol functional groups make it reactive and adaptable for various industrial and research uses. Proper handling and storage ensure its stability and effectiveness, while its biological activities continue to make it a focus of scientific investigation.