Phenolic Acid

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What are Phenolic Acids?

Phenolic acids, which are also called s phenol carboxylic acids, are the aromatic acids that hold a carboxyl functional group and a phenolic ring.

Phenolic acids and Flavonoids constitute one of the most widespread groups of plant phenolics. Due to their significance in human health and plants, a deeper understanding of the flavonoid concentration and biological activities can suggest their potential as therapeutic agents, including predicting and monitoring the medicinal herbs' quality as well, would be useful.

Thus, these compounds contain at least one hydroxy group, one carboxyl group, and one aromatic ring. Salicylic acid is also given as one of the simplest phenolic acids.

Structure of Salicylic Acid

The structure of salicylic acid, which is given as a common phenolic acid, can be illustrated as follows.

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Some other important naturally occurring phenolic acids can be given as hydroxybenzoic acids and hydroxycinnamic acids. Hydroxybenzoic acids are derived from the benzoic acid molecules, which are non-phenolic, whereas the Hydroxycinnamic acids are derived from the acid molecules, which are non-phenolic cinnamic.

Occurrences of Phenolic Acid

Phenolic acids are found in several plant species. Their content present in the dried fruits can be high.

Natural phenols in the horse grams (which is Macrotyloma uniflorum) are mostly given as phenolic acids, which are namely p-hydroxybenzoic, 3,4-dihydroxy benzoic, vanillic, p-coumaric, caffeic, ferulic, sinapinic acids, and syringic.

Phenolic acids are also found in the species of mushroom Basidiomycetes. It is a part of the humic substances, which are given as the major organic constituents of soil humus.

Several phenolic acids are also found in human urine.

Uses of Phenolic Acid

  • Phenolic compounds are the ones among the phytochemicals that are present in cereals that promote health. Despite their antioxidant properties, phenolic compounds receive more attention. The most common types of phenolic compounds found in whole grains are given as flavonoids and phenolic acids.

  • Phenolic acids are the most abundant compounds found in cereals, and the flavonoids also exist in grains. The total flavonoid and phenolic content of 20 genotypes of very small grain cereals, including durum wheat, bread wheat, rye, hulless oat, and hull-less barley, were analyzed. These phytochemicals consisted of the highest content in hull-less barley, followed by the rye, durum wheat, bread wheat, and hulless oat.

  • The role of gut microbiota in bio-transformation of the phytochemicals, along with the phenolic acid, is widely accepted, causing the circulation of food-derived metabolites excreted in the urine.

Medicinal Uses of Phenol

Phenol was also used for skin cleaning and itching reducing. Phenol is also used in drugs such as Chloraseptic to treat pharyngitis as an oral analgesic or anaesthetic. Phenol and its related compounds are also used in the diagnosis of a surgical ingrown toenail, a procedure called phenolization.

Deciding the Acidic Nature of Phenols

Acidic strength is always directly proportional to the conjugate base's stability, which means the more stable is the conjugate base and more acidic is the compound. And, in phenols, once H+ leaves Phenol, a negative charge is acquired by the Oxygen atom. Hence, there is no problem with that as the Oxygen is much more electronegative, containing a value of 3.5. Therefore, it won't raise any issues if it contains a negative charge on it.

Secondly, the most important thing is given as resonance, as the negative charge on the Oxygen atom and π bonds of the Carbon present in the ring are in conjugation, which is given as the basis of resonance. And, resonance lessens oxygen's negative charge by pulling its negative charge towards itself as in a benzene ring. Also, carbon atoms can effectively hold a negative charge where the negative charge is circulated throughout the ring and on oxygen as well, which lessens the compound's energy adding to its stability.

Natural Occurrences of Phenolic Acids

Let us understand a few of the natural occurrences of the phenolic acids as listed below:

  • Many of the dried fruits hold phenolic acids.

  • Phenolic acids are also found in the horse grams.

  • The Basidiomycetes species of the mushroom is much known to hold these organic compounds.

  • These aromatic acids are also found in the soil humus. 

  • Finally, human urine also comprises some phenolic acids.

Why is Acetic Acid Said to Be Stronger Than Phenol?

Acetic acid (with the chemical form, CH3-CO-OH) is defined as a typical carboxylic acid. In carboxylic acids, the OH hydrogen release as a proton is much facilitated by the electron-withdrawing carbonyl group. There is no such type of feature available in phenol, and it majorly depends on the stability of resultant phenoxide ions to release OH proton.

Therefore, acetic acid is described as a much stronger acid than the other.

Examples of Phenolic Acids

A few of the examples of phenolic acids can be listed as follows:

  • p-hydroxybenzoic acid (PHBA)

  • Protocatechuic acid (PCA)

  • Caffeic acid

  • Vanillic acid

  • Ferulic acid

  • p-Coumaric acid

  • Sinapinic acid

  • Syringic acid

FAQ (Frequently Asked Questions)

1. What is phenolic acid used for?

Phenolic acids are the ones, which are readily absorbed via the walls of our intestinal tract, which can also be beneficial to human health because they serve as antioxidants, which avoids cellular damage because of the free-radical oxidation reactions. If we intake these regularly, they can also promote anti-inflammatory conditions of the body.

2. What does phenol do to the human body?

If the concentrated phenol has applied to the skin, it can cause serious skin damage. And, when exposed to this element on a short-term basis to high levels in animals, it has caused twitching of the muscles and respiratory tract irritation. In animals, long-term exposure to the high phenol levels caused damage to the kidneys, lungs, liver, and even to the heart.

3. Explain the medicinal uses of phenol?

Phenol was used to ease itching and to disinfect the skin. Also, phenol can be used in products like Chloraseptic as an anaesthetic or oral analgesic to treat pharyngitis. Besides, phenol, including its related compounds, can be used in the treatment of surgically grown toenails, which is a procedure known as phenolization.

4. Explain the difference between phenol and alcohol?

Alcohol is defined as an organic compound where its molecule is formed up of either one or more groups of hydroxyl, further attached to a carbon atom. On the other hand, phenol is a compound, a group of hydroxyls bound directly to a hydrocarbon's aromatic group.