4-Hydroxybenzyl alcohol
[CAS# 623-05-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic alcohol
• Name: 4-Hydroxybenzyl alcohol
• Synonyms: 4-hydroxybenzenemethanol
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.14
• CAS Registry Number: 623-05-2
• EC Number: 210-768-0
• SMILES: C1=CC(=CC=C1CO)O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 114-122 °C (Expl.)
• Index of Refraction: 1.596, Calc.^*
• Boiling Point: 252.0±0.0 °C (760 mmHg), Calc.^*, 251-253 °C (Expl.)
• Flash Point: 145.8±15.0 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-Hydroxybenzyl alcohol (C7H8O2), also known as para-hydroxybenzyl alcohol, is a phenolic compound found in various natural sources, including plants and fungi. It is a colorless to pale yellow liquid at room temperature and has a pleasant, slightly floral odor. This compound is structurally related to other phenolic compounds, particularly to hydroxyphenyl alcohol derivatives, and is recognized for its antioxidant, antimicrobial, and anti-inflammatory properties. The discovery of 4-hydroxybenzyl alcohol and its subsequent study has led to its increasing use in both pharmaceutical and industrial applications.

4-Hydroxybenzyl alcohol was first isolated from various plant species in the early 20th century. It was initially studied for its presence in lignin, a complex polymer found in plant cell walls, particularly in the wood and bark of trees. Over time, researchers have identified its potential for numerous applications beyond its role in plant metabolism. It has been found to play an important role as a precursor for the synthesis of various important compounds, including drugs and fragrances.

The compound is used in a range of applications, particularly in the cosmetic and pharmaceutical industries. In cosmetics, 4-hydroxybenzyl alcohol is used as an active ingredient in formulations targeting skin care and anti-aging. Its antioxidant properties help to protect the skin from oxidative stress, which is a key factor in aging and the development of skin conditions such as wrinkles and dark spots. Its ability to scavenge free radicals makes it an effective addition to formulations aimed at preventing or reducing the visible effects of skin aging. Additionally, 4-hydroxybenzyl alcohol has been shown to possess anti-inflammatory properties, which further enhance its role in soothing and protecting the skin.

In the pharmaceutical sector, 4-hydroxybenzyl alcohol has shown potential as an antimicrobial agent. Research has demonstrated its ability to inhibit the growth of various bacteria and fungi, which could make it a useful compound in the treatment of infections. Its effectiveness as an antimicrobial agent is attributed to its capacity to interact with microbial cell walls, disrupting their integrity and inhibiting their proliferation. This activity suggests that it could be a valuable component in formulations for topical use, especially in wound healing and the prevention of bacterial infections.

Moreover, 4-hydroxybenzyl alcohol is also of interest in the field of drug development due to its potential in treating oxidative stress-related diseases, including cardiovascular diseases and neurodegenerative conditions such as Alzheimer's disease. Its antioxidant and anti-inflammatory properties have been shown to protect cells from damage caused by reactive oxygen species (ROS) and other stressors. By reducing oxidative damage to cells, the compound may help to mitigate the symptoms and progression of these chronic diseases.

In addition to its biological and pharmaceutical activities, 4-hydroxybenzyl alcohol is also used in the synthesis of various chemicals, including flavoring agents, fragrances, and resins. Its mild, pleasant odor makes it a useful additive in perfumes and other fragrance products, contributing to the formulation of floral and woodsy scents.

Overall, the discovery and subsequent applications of 4-hydroxybenzyl alcohol highlight its versatility and potential as a valuable compound in a range of industries. Although more research is needed to explore its full therapeutic potential, current findings suggest that it could play a significant role in promoting skin health, preventing oxidative damage, and serving as an antimicrobial agent. As such, it continues to attract attention in both academic and industrial settings for its diverse and beneficial properties.

References

2024. Hierarchical Co3O4/TSCN Nanocapsules as Green Photocatalyst for Oxidation of Alcohols. Catalysis Letters.
DOI: 10.1007/s10562-024-04688-w

2024. Neue Perspektiven der Aromaforschung: pilzliche O(S)-Methyltransferasen. BIOspektrum.
DOI: 10.1007/s12268-024-2259-x

2024. Synthesis of Collagen Mimetic Peptides. Collagen Mimetic Peptides and Their Biophysical Characterization.
DOI: 10.1007/978-981-10-1941-8_4