Classification The terpene phenols (Carvacrol, Eugenol Catechin, Thymol, Protocatechuic Acid)

2.6.5.5.3 Classification The terpene phenols

are classified into the following categories, namely:

(i) Monohydric phenols and

(ii) Dihydric phenols.

The above categories of phenols shall be discussed briefly as under:

2.6.5.5.3.1 Monohydric Phenols

The typical examples of monohydric phenols are: carvacrol, eugenol, thymol.

A. Carvacrol

Chemical Structure 2-Methyl-5-(1-methylethyl)-phenol.

Occurrence It occurs in the essential oil origanum (Origanum vulgare Linn., Family: Labiatae); oil of thyme (Thymus serphyllum Linn., and T. vulgaris Linn., Family: Labiatae); oil of marjoram and oil of summer savory.

Characteristic Features It is a liquid oil having strong thymol odour. Its physical properties are as follows: d²⁰₄ 0.976; bp₇₆₀ 237-238°C; mp ~ °C; n²⁰_D 1.52295.

It is practically insoluble in water and freely soluble in alcohol and ether.

Uses

1. It is mostly employed as a disinfectant.

2. It is also used as an anthelmintic (Nematodes).

B. Eugenol Please see section 5.2.6.1.4.3 in this chapter.

C. Thymol Please see section 5.2.1.4 in this chapter.

2.6.5.5.3.2 Dihydric Phenols 

The various dihydric phenols found in natural products are namely:

Catechin (catechol). A few of these constituents shall be dealt with here under:

A. Catechin (Catechol)

Chemical Structure (2R-trans)-2-(3, 4-Dihydroxyphenyl)-3, 4-dihydro-4H-1-benzopyran-3, 5, 7-triol.

Occurrence It is a flavonoid found primarily in higher woody plants as (–)-catechin along with (–)-epicatechin (cis-form). It is also found in catechu (gambir and acacia), mahogany wood etc. Besides, it occurs in a variety of medicinal-plants, such as: Argimonia eupatoria L., (Rosaceae)-agrimony; Areca catechu L., (Arecaceae)-areca-nut, betel-nut palm; Camellia sinensis (L.) Kuntze (Theaceae)-tea; Catha edulis Vahl (Celastaceae)-khat; Cola acuminata (Beauv.) Schott & Endl. (Sterculaceae)-kola nuts, cola, guru; Caratadegus oxyacantha L. (Rosaceae)-hawthorn; Ephedra gerardiana Wall. ex Stapf (Ephedraceae)-Paskistani ephedra; Eucalyptus globulus Labill. (Myrataceae)-eucalypt, tasmanium bluegum; Leonurus cardiaca L., (Lamiaceae)-motherwort; Malus sylvestris Mill., (Rosaceae)-apple; Paullinia cupana Kunth. ex H.B.K. (Sapindaceae)-guarana, ubano, Brazilian cocoa; Polygonum aviculare L., (Polygunaceae)-prostrate knotweed; Rheum officanale Bail. (Polygonaceae)-Chinese rhubarb, Canton rhubarb, Shensi rhubarb; Santolina chamaecyparissus L. (Asteraceae)-Lavendar-cotton; Solidago virgaureae L. (Asteraceae)-European goldenrod, woundwort; Uncaria gambir (Hunter) Roxo. (Rubiaceae)-gombir, pale catechu; Vanilla planifolia Andr. (Orchidaceae)-vanilla.

Isolation The areca nut or kola nut is cut into small chips mechanically and filled into the extractors. The steam is passed through the drug profusely to affect maximum extraction. The crude extract is filtered and concentrated under vacuum. The concentrated extract is chilled in deep-freezer when catechin separates as its hydrated product (mp: 93-96°C) and its anhydrous product (mp: 175-177°C).

Characteristic Features Its needles obtained from water and acetic acid give rise to its hydrate form having m.p. 93-96°C, whereas its anhydrous form registers mp 175–177°C, and [α]¹⁸_D + 16° to + 18.4°. The physical parameters of l-form and dl-form are stated below.

Note Catechin is called catechol (flaran) to distinguish it from catechol (pyrocatechol q.v).

Identification

1. Catechin on being treated with HCl yields phluroglucinol, that burns along with lignin to produce purple or magnata colour. The tannin extract is taken on the tip of a match-stick, dipped in HCl and burnt in the blue-flame of the Bunsen-burner.

2. It reacts with vanillin and HCl to produce a pink or red colour.

Uses

1. It is used as an antidiarrheal agent.

2. It is also employed for dycing and tanning.

B. Protocatechuic Acid

Chemical Structure 3,4-Dihydroxybenzoic acid.

Occurrence It is found in the dried fruit of Illicium verum Hook. f. (Magnoliaceae)-star anise, Chinese anise; in the leaves and seeds of Perilla frutescens (L.) Britt. (Lamiaceae)-beef-steak plant, perilla, wild coleus; and in the timbers of Tabebuia Spp. (Bignoniaceae)-Pao D’Arco. However, minute amounts are found in wheat grains and also in wheat seedlings.

Characteristic Features It is white to brownish crystalline powder. It undergoes discolouration on exposure to air. Its mp ~ 200°C and d 1.54. It is soluble in 50 parts of water and freely soluble in ether and alcohol.

Source:Pharmacognosy And Pharmacobiotechnology By Ashutosh Kar