3/20/2019

PHENOLS AND THEIR

DERIVATIVES
‫ فرج ال ُمختــار ع ُمـــوش‬.‫أ‬
‫الفصل الرابع صيدلـــة‬

PHENOLS AND THEIR DERIVATIVES

• Phenol, USP, remains the standard to which the
activity of most germicidal substances is
compared.

• The phenol coefficient is defined as the ratio of a

dilution of a given test disinfectant to the dilution
of phenol that is required to kill (to the same
extent) a strain of Salmonella typhi under
carefully controlled time and temperature
conditions.

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PHENOLS & THEIR DERIVATIVES

• As an example, if the dilution of a test disinfectant is 10-
fold greater than the dilution of phenol, the phenol
coefficient is 10.

• Obviously, the phenol coefficient of phenol itself is 1.

• The phenol coefficient test has many drawbacks )‫ (عوائق‬.

• Phenols and other germicides do not kill microorganisms

uniformly, so variations in the phenol coefficient will occur.

PHENOLS &THEIR DERIVATIVES

• Alkylated phenols and resorcinols are less
toxic than the parent compounds while
retaining bactericidal properties.

• Phenols denature bacterial proteins at low

concentrations, whereas lysis of bacterial cell
membranes occurs at higher concentrations

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PHENOLS &THEIR DERIVATIVES

• Several phenols are actually more bactericidal

than phenol itself.

• Substitution )‫ (بديل‬with alkyl, aryl, and halogen

(especially in the para position) groups increases
bactericidal activity.

• Straight-chain alkyl groups enhance bactericidal

activity more than branched groups.

Phenol (carbolic acid)

• Phenol (carbolic acid) is a colorless to pale-pink ‫( وردي‬
)‫ شاحب‬crystalline material with a characteristic
“medicinal odor.”

• It is soluble to the extent of 1 part to 15 parts water,

very soluble in alcohol, and soluble in methanol and
salol (phenyl salicylate).

• Phenol exhibits germicidal activity (general

protoplasmic poison), is caustic to skin )‫(حارق للجلد‬,
exerts local anesthetic effects, and must be diluted to
avoid tissue destruction and dermatitis.

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Phenol (carbolic acid)

• Sir Joseph Lister introduced phenol as a surgical antiseptic
in 1867,

• and it is still used occasionally )‫ (من حين ألخر‬as an

antipruritic in phenolated calamine lotion (0.1%–1%
concentrations).

• A 4% solution of phenol in glycerin has been used to

cauterize )‫ (كوي‬small wounds.

• Phenol is almost obsolete )‫ ( ملغي تقريبا‬as an antiseptic and

disinfectant.

Liquified Phenol
• Liquified phenol is simply phenol containing 10%
water.
• The liquid form is convenient for adding phenol
to various pharmaceutical preparations because
it can be measured and transferred easily.

• The water content, however, precludes )‫(يُمنع‬its

use in fixed oils or liquid petrolatum, because
the solution is not miscible with lipophilic
ointment bases.

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p- Chlorophenol

• p- Chlorophenol is used in combination with

camphor in liquid petrolatum as an external
antiseptic and anti-irritant.

• The compound has a phenol coefficient of

about 4.

p-Chloro-m-xylenol (Dettol)

• p-Chloro-m-xylenol (PC-MX; Dettol) is a nonirritating

antiseptic agent with broad- spectrum antibacterial
and antifungal properties.

• It is marketed in a 2% concentration as a shampoo.

• It has also been used topically for the treatment of

tinea (ringworm) infections such as athlete’s foot
(tinea pedis) and jock itch (tinea cruris).

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Hexachlorophene

• Hexachlorophene, 2,2-methylenebis (3,4,6-

trichlorophenol); 2,2-dihydroxy-3,5,6,3,5, 6-
hexachlorodiphenylmethane is a white to
light-tan crystalline powder that is insoluble
in water but is soluble in alcohol and most
other organic solvents.

Hexachlorophene
• A biphenol such as hexachlorophene will, in
general, possess greater potency than a
monophenol.

• In addition, as expected, the increased degree

of chlorination of hexachlorophene increases
its antiseptic potency further.

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Hexachlorophene
• Hexachlorophene is easily adsorbed onto the skin and
enters the sebaceous glands. Because of this, topical
application elicits a prolonged antiseptic effect, even in
low concentrations.

• Hexachlorophene is used in concentrations of 2% to 3%

in soaps, detergent creams, lotions, and shampoos for
various antiseptic uses.

• It is, in general, effective against Gram-positive bacteria,

but many Gram-negative bacteria are resistant.

Cresol
• Cresol is actually a mixture of three isomeric
methylphenols:

• The mixture occurs as a yellow to brownish

yellow liquid that has a characteristic odor of
creosote)‫( الطالء‬.

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Cresol
• Cresol is obtained from coal tar or petroleum by alkaline
extraction into aqueous medium, acidification, and
fractional distillation.

• The mixture is an inexpensive antiseptic and disinfectant.

• It possesses a phenol coefficient of 2.5. Cresol is

sparingly soluble in water, although alcohols and other
organic solvents will solubilize it.

• The drawback to its use as an antiseptic is its unpleasant

odor.

Chlorocresol

• 4-Chloro-3-methylphenol occurs as colorless

crystals.
• Chlorocresol is only slightly soluble in water.

• At the low concentration that can be achieved

in aqueous media, the compound is only
useful as a preservative.

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Thymol
• Isopropyl m-cresol is extracted from oil of
Thymus vulgaris (thyme, of the mint family)
by partitioning into alkaline aqueous medium
followed by acidification.

• The crystals obtained from the mother liquor

are large and colorless, with a thyme like
odor.

Thymol
• Thymol is only slightly soluble in water, but it
is extremely soluble in alcohols and other
organic solvents.

• Thymol has mild fungicidal properties and is

used in alcohol solutions and in dusting
powders for the treatment of tinea
(ringworm) infections .

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Eugenol

• 4-Allyl-2-methoxyphenol is obtained primarily

from clove oil.

• It is a pale-yellow liquid with a strong aroma of

cloves and a pungent taste.

• Eugenol is only slightly soluble in water but is

miscible with alcohol and other organic solvents.

Eugenol

• Eugenol possesses both local anesthetic and

antiseptic activity and can be directly applied on
a piece of cotton to relieve toothaches.

• Eugenol is also used in mouthwashes because of

its antiseptic property and pleasant taste.

• The phenol coefficient of eugenol is 14.4.

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Resorcinol
• m-Dihydroxybenzene (resorcin), or resorcinol, is
prepared synthetically.

• It crystallizes as white needles or as an amorphous

powder that is soluble in water and alcohol.

• Resorcinol is light sensitive and oxidizes readily, so it

must be stored in tight, light-resistant containers.

• It is much less stable in solution, especially at alkaline

pH.

Resorcinol
• Resorcinol is only a weak antiseptic (phenol
coefficient 0.4).
• Nevertheless, it is used in 1% to 3% solutions and in
ointments and pastes in concentrations of 10% to 20%
for the treatment of skin conditions such as ringworm,
eczema, psoriasis, and seborrheic dermatitis.
• In addition to its antiseptic action, resorcinol is a
keratolytic agent.
• This property causes the stratum corneum of the skin
to slough, opening the barrier to penetration for
antifungal agents.

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Hexylresorcinol
• 4-Hexylresorcinol, or “hexylresorcinol,” is a white
crystalline substance with a faint phenolic odor.

• When applied to the tongue it produces a

sensation of numbness.

• It is freely soluble in alcohol but only slightly

soluble in water (1–20,000 parts).

• Hexylresorcinol is an effective antiseptic,

possessing both bactericidal and fungicidal
properties.

Hexylresorcinol
• The phenol coefficient of hexylresorcinol against
S. aureus is 98.

• As is typical for alkylated phenols,

hexylresorcinol possesses surfactant properties.

• The compound also has local anesthetic activity.

• Hexylresorcinol is formulated into throat

lozenges because of its local anesthetic and
antiseptic properties.

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