Homovanillyl alcohol

Homovanillyl alcohol (4-(3-Hydroxy-4-methoxyphenyl)butan-2-ol), also known as 3-Methoxy-4-hydroxyphenethyl alcohol, is a naturally occurring organic compound in the phenethyl alcohol family. It is a minor component of the vanilla flavor and is found in small quantities in the vanilla bean (Vanilla planifolia). Homovanillyl alcohol is also a metabolite of dopamine, indicating its presence in biological systems, particularly in the human body where it plays a role in the metabolism of certain neurotransmitters.

Chemical Properties

Homovanillyl alcohol has the chemical formula C_10H_14O_3 and a molecular weight of 182.22 g/mol. It is characterized by its hydroxy and methoxy functional groups, which contribute to its solubility in water and its reactivity. This compound is a type of phenol with a phenethyl backbone, which is a common structural motif in many natural products and pharmaceuticals.

Biosynthesis and Metabolism

In plants, homovanillyl alcohol is synthesized through the phenylpropanoid pathway, which is responsible for the production of a wide range of phenolic compounds. In humans, it is a metabolite of dopamine, produced through the action of the enzyme catechol-O-methyltransferase (COMT) on 3,4-dihydroxyphenethylamine. This metabolic pathway is significant in the study of neurological diseases and conditions where dopamine regulation is affected.

Biological Significance

Homovanillyl alcohol has been studied for its antioxidant properties. Its ability to scavenge free radicals suggests potential health benefits, including neuroprotective effects. Research into its role in the human body is ongoing, with interest in its implications for diseases characterized by oxidative stress and dopamine dysregulation, such as Parkinson's disease and schizophrenia.

Applications

While homovanillyl alcohol is not widely used in its pure form, its presence in vanilla and its role as a dopamine metabolite make it of interest in both the food industry and medical research. In the food industry, it contributes to the complex flavor profile of vanilla. In medical research, its study may lead to insights into the treatment of neurological disorders.

Safety and Toxicology

As a naturally occurring compound and a minor component of food flavors, homovanillyl alcohol is generally considered safe. However, detailed toxicological studies specific to homovanillyl alcohol are limited, and its safety profile is primarily inferred from its structural relatives and its low concentration in consumable products.

See Also

• Vanillin
• Dopamine
• Phenethyl alcohol
• Catechol-O-methyltransferase

External Links

• PubChem Entry for Homovanillyl Alcohol
• NCBI Database