O-Cresol
Encyclopedia
ortho-Cresol, also 2-methylphenol, is a phenol
, with formula (CH3)C6H4(OH).
It is an isomer of p-cresol
, m-cresol
and anisole
s which are methyl
phenol
s. They are a widely occurring natural and manufactured group of aromatic organic compound
s which are categorized as phenols
(sometimes called phenolics). Depending on the temperature
, cresols can be solid
or liquid
because they have melting point
s not far from room temperature. Like other types of phenols, they are slowly oxidized by long exposure to air and the impurities often give cresols a yellowish to brownish red tint. Cresols have an odor
characteristic to that of other simple phenols, reminiscent to some of a "medicine" smell.
In its chemical structure
, a cresol molecule
has a methyl group
substituted onto the benzene ring of a phenol
molecule. There are three forms of cresols that are only slightly different in their chemical structure: ortho-cresol (o-cresol), meta-cresol (m-cresol
), and para-cresol (p-cresol
). These forms occur separately or as a mixture.
other chemicals, as disinfectants and deodorizers, and to make specific chemicals that kill insect
pest
s.
Cresol solutions are used as household cleaners and disinfectants, perhaps most famously under the trade name Lysol
. In the past, cresol solutions have been used as antiseptic
s in surgery
, but they have been largely displaced in this role by less toxic compounds. Lysol was also advertised as a disinfecting vaginal douche
in mid-twentieth century America.
Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar
, and in brown mixtures such as creosote
, cresolene
and cresylic acids, which are wood preservative
s. Small organisms in soil and water produce cresols when they break down materials in the environment.
at very high levels, they can be very harmful. Effects observed in people include irritation
and burning of skin
, eye
s, mouth
, and throat
; abdominal pain and vomiting; heart
damage; anemia
; liver
and kidney
damage; facial paralysis; coma
; and death
.
Breathing high levels of cresols for a short time results in irritation of the nose
and throat. Aside from these effects, very little is known about the effects of breathing cresols, for example, at lower levels over longer times.
Ingesting high levels results in kidney problems, mouth and throat burns, abdominal pain, vomiting, and effects on the blood
and nervous system
.
Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, brain
, and lung
s.
Short-term and long-term studies with animals have shown similar effects from exposure to cresols. No human or animal studies have shown harmful effects from cresols on the ability to have children.
It is not known what the effects are from long-term ingestion or skin contact with low levels of cresols.
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
, with formula (CH3)C6H4(OH).
It is an isomer of p-cresol
P-Cresol
p-Cresol, also 4-methylphenol, is a phenol, with formula C6H4.It is a positional isomer; the other two are m-cresol and o-cresol. P-cresol is a major component in pig odor. . For more information see cresol. 4-methylphenol is a component in human sweat. It is a component of human odour attractive...
, m-cresol
M-Cresol
m-Cresol, also 3-methylphenol, is a phenol, with formula C6H4.Amongst its uses it can be used as a solvent for dissolving polymers, most notably the conducting polymer polyaniline...
and anisole
Anisole
Anisole, or methoxybenzene, is the organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances...
Chemistry
Cresols are organic compoundOrganic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
s which are methyl
Methyl group
Methyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion...
phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
s. They are a widely occurring natural and manufactured group of aromatic organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
s which are categorized as phenols
Phenols
In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group bonded directly to an aromatic hydrocarbon group...
(sometimes called phenolics). Depending on the temperature
Temperature
Temperature is a physical property of matter that quantitatively expresses the common notions of hot and cold. Objects of low temperature are cold, while various degrees of higher temperatures are referred to as warm or hot...
, cresols can be solid
Solid
Solid is one of the three classical states of matter . It is characterized by structural rigidity and resistance to changes of shape or volume. Unlike a liquid, a solid object does not flow to take on the shape of its container, nor does it expand to fill the entire volume available to it like a...
or liquid
Liquid
Liquid is one of the three classical states of matter . Like a gas, a liquid is able to flow and take the shape of a container. Some liquids resist compression, while others can be compressed. Unlike a gas, a liquid does not disperse to fill every space of a container, and maintains a fairly...
because they have melting point
Melting point
The melting point of a solid is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depends on pressure and is usually specified at standard atmospheric pressure...
s not far from room temperature. Like other types of phenols, they are slowly oxidized by long exposure to air and the impurities often give cresols a yellowish to brownish red tint. Cresols have an odor
Odor
An odor or odour is caused by one or more volatilized chemical compounds, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction. Odors are also commonly called scents, which can refer to both pleasant and unpleasant odors...
characteristic to that of other simple phenols, reminiscent to some of a "medicine" smell.
In its chemical structure
Chemical structure
A chemical structure includes molecular geometry, electronic structure and crystal structure of molecules. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. Molecular geometry can range from the very simple, such as...
, a cresol molecule
Molecule
A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...
has a methyl group
Methyl group
Methyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion...
substituted onto the benzene ring of a phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
molecule. There are three forms of cresols that are only slightly different in their chemical structure: ortho-cresol (o-cresol), meta-cresol (m-cresol
M-Cresol
m-Cresol, also 3-methylphenol, is a phenol, with formula C6H4.Amongst its uses it can be used as a solvent for dissolving polymers, most notably the conducting polymer polyaniline...
), and para-cresol (p-cresol
P-Cresol
p-Cresol, also 4-methylphenol, is a phenol, with formula C6H4.It is a positional isomer; the other two are m-cresol and o-cresol. P-cresol is a major component in pig odor. . For more information see cresol. 4-methylphenol is a component in human sweat. It is a component of human odour attractive...
). These forms occur separately or as a mixture.
Applications
Cresols are used to dissolveSolvation
Solvation, also sometimes called dissolution, is the process of attraction and association of molecules of a solvent with molecules or ions of a solute...
other chemicals, as disinfectants and deodorizers, and to make specific chemicals that kill insect
Insect
Insects are a class of living creatures within the arthropods that have a chitinous exoskeleton, a three-part body , three pairs of jointed legs, compound eyes, and two antennae...
pest
Pest (animal)
A pest is an animal which is detrimental to humans or human concerns. It is a loosely defined term, often overlapping with the related terms vermin, weeds, parasites and pathogens...
s.
Cresol solutions are used as household cleaners and disinfectants, perhaps most famously under the trade name Lysol
Lysol
Lysol is a trade name for common household cleanersLysol may also refer to:* Lysol , a 1992 album by The Melvins* Lysol , Actor muMs da Schemer played Lysol in The Mad Real World skit on Chappelle's Show....
. In the past, cresol solutions have been used as antiseptic
Antiseptic
Antiseptics are antimicrobial substances that are applied to living tissue/skin to reduce the possibility of infection, sepsis, or putrefaction...
s in surgery
Surgery
Surgery is an ancient medical specialty that uses operative manual and instrumental techniques on a patient to investigate and/or treat a pathological condition such as disease or injury, or to help improve bodily function or appearance.An act of performing surgery may be called a surgical...
, but they have been largely displaced in this role by less toxic compounds. Lysol was also advertised as a disinfecting vaginal douche
Douche
A douche is a device used to introduce a stream of water into the body for medical or hygienic reasons, or the stream of water itself.Douche usually refers to vaginal irrigation, the rinsing of the vagina, but it can also refer to the rinsing of any body cavity. A douche bag is a piece of...
in mid-twentieth century America.
Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar
Coal tar
Coal tar is a brown or black liquid of extremely high viscosity, which smells of naphthalene and aromatic hydrocarbons. Coal tar is among the by-products when coal iscarbonized to make coke or gasified to make coal gas...
, and in brown mixtures such as creosote
Creosote
Creosote is the portion of chemical products obtained by the distillation of a tar that remains heavier than water, notably useful for its anti-septic and preservative properties...
, cresolene
Cresolene
Cresolene is a dark liquid with a pungent smell made from coal tar used in the 19th and early 20th century as a disinfectant and to treat various ailments such as colds and measles. There was also a special 'Vapo-Cresolene' lamp used to heat the substance so that the fumes could be inhaled-External...
and cresylic acids, which are wood preservative
Preservative
A preservative is a naturally occurring or synthetically produced substance that is added to products such as foods, pharmaceuticals, paints, biological samples, wood, etc. to prevent decomposition by microbial growth or by undesirable chemical changes....
s. Small organisms in soil and water produce cresols when they break down materials in the environment.
Health effects
Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skinHuman skin
The human skin is the outer covering of the body. In humans, it is the largest organ of the integumentary system. The skin has multiple layers of ectodermal tissue and guards the underlying muscles, bones, ligaments and internal organs. Human skin is similar to that of most other mammals,...
at very high levels, they can be very harmful. Effects observed in people include irritation
Irritation
Irritation or exacerbation, in biology and physiology, is a state of inflammation or painful reaction to allergy or cell-lining damage. A stimulus or agent which induces the state of irritation is an irritant...
and burning of skin
Human skin
The human skin is the outer covering of the body. In humans, it is the largest organ of the integumentary system. The skin has multiple layers of ectodermal tissue and guards the underlying muscles, bones, ligaments and internal organs. Human skin is similar to that of most other mammals,...
, eye
Human eye
The human eye is an organ which reacts to light for several purposes. As a conscious sense organ, the eye allows vision. Rod and cone cells in the retina allow conscious light perception and vision including color differentiation and the perception of depth...
s, mouth
Mouth
The mouth is the first portion of the alimentary canal that receives food andsaliva. The oral mucosa is the mucous membrane epithelium lining the inside of the mouth....
, and throat
Throat
In vertebrate anatomy, the throat is the anterior part of the neck, in front of the vertebral column. It consists of the pharynx and larynx...
; abdominal pain and vomiting; heart
Human heart
The human heart is a muscular organ that provides a continuous blood circulation through the cardiac cycle and is one of the most vital organs in the human body...
damage; anemia
Anemia
Anemia is a decrease in number of red blood cells or less than the normal quantity of hemoglobin in the blood. However, it can include decreased oxygen-binding ability of each hemoglobin molecule due to deformity or lack in numerical development as in some other types of hemoglobin...
; liver
Liver
The liver is a vital organ present in vertebrates and some other animals. It has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...
and kidney
Kidney
The kidneys, organs with several functions, serve essential regulatory roles in most animals, including vertebrates and some invertebrates. They are essential in the urinary system and also serve homeostatic functions such as the regulation of electrolytes, maintenance of acid–base balance, and...
damage; facial paralysis; coma
Coma
In medicine, a coma is a state of unconsciousness, lasting more than 6 hours in which a person cannot be awakened, fails to respond normally to painful stimuli, light or sound, lacks a normal sleep-wake cycle and does not initiate voluntary actions. A person in a state of coma is described as...
; and death
Death
Death is the permanent termination of the biological functions that sustain a living organism. Phenomena which commonly bring about death include old age, predation, malnutrition, disease, and accidents or trauma resulting in terminal injury....
.
Breathing high levels of cresols for a short time results in irritation of the nose
Human nose
The visible part of the human nose is the protruding part of the face that bears the nostrils. The shape of the nose is determined by the ethmoid bone and the nasal septum, which consists mostly of cartilage and which separates the nostrils...
and throat. Aside from these effects, very little is known about the effects of breathing cresols, for example, at lower levels over longer times.
Ingesting high levels results in kidney problems, mouth and throat burns, abdominal pain, vomiting, and effects on the blood
Blood
Blood is a specialized bodily fluid in animals that delivers necessary substances such as nutrients and oxygen to the cells and transports metabolic waste products away from those same cells....
and nervous system
Nervous system
The nervous system is an organ system containing a network of specialized cells called neurons that coordinate the actions of an animal and transmit signals between different parts of its body. In most animals the nervous system consists of two parts, central and peripheral. The central nervous...
.
Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, brain
Brain
The brain is the center of the nervous system in all vertebrate and most invertebrate animals—only a few primitive invertebrates such as sponges, jellyfish, sea squirts and starfishes do not have one. It is located in the head, usually close to primary sensory apparatus such as vision, hearing,...
, and lung
Lung
The lung is the essential respiration organ in many air-breathing animals, including most tetrapods, a few fish and a few snails. In mammals and the more complex life forms, the two lungs are located near the backbone on either side of the heart...
s.
Short-term and long-term studies with animals have shown similar effects from exposure to cresols. No human or animal studies have shown harmful effects from cresols on the ability to have children.
It is not known what the effects are from long-term ingestion or skin contact with low levels of cresols.