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Cresols are organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s which are methyl
Methyl group

In chemistry, a methyl group is a hydrophobic alkyl functional group named after methane . It has the chemical formula -3 and is often abbreviated -Me....
phenol
Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
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 chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s which are categorized as phenols
Phenols

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl Functional group attached to an aromatic hydrocarbon group....
 (sometimes called phenolics). Depending on the temperature
Temperature

In physics, temperature is a physical property of a Physical system that underlies the common notions of hot and cold; something that feels hotter generally has the greater temperature....
, cresols can be solid
Solid

A solid object is in the states of matter characterized by resistance to deformation and changes of volume. In other words, it has high values both of Young's modulus and of shear modulus; this contrasts e.g....
 or liquid
Liquid

Liquid is one of the principal states of matter. A liquid is a fluid that has the particles loose and can freely form a distinct surface at the boundaries of its bulk material....
 because they have melting point
Melting point

The melting point of a solid is the temperature range at which it changes states of matter from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium....
s not far from room temperature. Like other types of phenols, they are slowly oxidized by long exposure to air
AIR

Air is the part of Earth's atmosphere that humans breath and as such Air .Air may also refer to:...
 and the impurities often give cresols a yellowish to brownish red tint.






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Encyclopedia


Cresols are organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s which are methyl
Methyl group

In chemistry, a methyl group is a hydrophobic alkyl functional group named after methane . It has the chemical formula -3 and is often abbreviated -Me....
phenol
Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
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 chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s which are categorized as phenols
Phenols

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl Functional group attached to an aromatic hydrocarbon group....
 (sometimes called phenolics). Depending on the temperature
Temperature

In physics, temperature is a physical property of a Physical system that underlies the common notions of hot and cold; something that feels hotter generally has the greater temperature....
, cresols can be solid
Solid

A solid object is in the states of matter characterized by resistance to deformation and changes of volume. In other words, it has high values both of Young's modulus and of shear modulus; this contrasts e.g....
 or liquid
Liquid

Liquid is one of the principal states of matter. A liquid is a fluid that has the particles loose and can freely form a distinct surface at the boundaries of its bulk material....
 because they have melting point
Melting point

The melting point of a solid is the temperature range at which it changes states of matter from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium....
s not far from room temperature. Like other types of phenols, they are slowly oxidized by long exposure to air
AIR

Air is the part of Earth's atmosphere that humans breath and as such Air .Air may also refer to:...
 and the impurities often give cresols a yellowish to brownish red tint. Cresols have an odor
Odor

An odor or odour is a volatilized chemical compound, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction....
 characteristic to that of other simple phenols, reminiscent to some of a "medicine" smell.

Chemical structure

In its chemical structure
Chemical structure

A Chemical structure includes molecular geometry, electronic structure and crystal structure of a chemical compound. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together....
, a cresol molecule
Molecule

In chemistry, a molecule is defined as a sufficiently stable, electric charge neutral group of at least two atoms in a definite arrangement held together by very strong chemical bonds....
 has a methyl group
Methyl group

In chemistry, a methyl group is a hydrophobic alkyl functional group named after methane . It has the chemical formula -3 and is often abbreviated -Me....
 substituted onto the benzene ring of a phenol
Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
 molecule. There are three forms of cresols that are only slightly different in their chemical structure: ortho-cresol (o-cresol
O-Cresol

ortho-Cresol, also 2-methylphenol, is a phenol, with formula C6H4.It is an isomer of P-Cresol, O-Cresol and anisole...
), 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....
). These forms occur separately or as a mixture. The word tricresol can be used as a synonym for cresol where it means a mixture of o-, m- and p-cresols.

Isomers of Cresol
Skeletal formula
Skeletal formula

The skeletal formula of an organic compound is a shorthand representation of its molecular geometry. Skeletal formulae are ubiquitous in organic chemistry because they show complicated structures clearly and they are quick and simple to draw....
Ball-and-stick model
Ball-and-stick model

Ball-and-stick models and space-filling models are three-dimensional space or spatial molecular models which serve to display the structure of chemical products and chemical substance or biomolecules....
General
Common name o-cresol m-cresol p-cresol
Systematic name
IUPAC nomenclature

IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry ....
 2-methylphenol 3-methylphenol 4-methylphenol
Other names ortho-cresol meta-cresol para-cresol
Molecular formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 C7H8O
SMILES
Simplified molecular input line entry specification

The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemistry molecules using short ASCII string ....
 Oc1c(C)cccc1 Oc1cc(C)ccc1 Oc1ccc(C)cc1
Molar mass
Molar mass

Molar mass, symbol M, is the mass of one mole of a substance . It is a physical property which is characteristic of each pure substance. The base SI unit for mass is the kilogram but, for both practical and historical reasons, molar masses are almost always quoted in grams per mole , especially in chemistry....
 108.14 g/mol
Appearance at room
temperature and pressure		 greasy-looking solid
ready to melt
on hot day		 thicker liquid greasy-looking solid
CAS number
CAS registry number

CAS registry numbers are unique numerical identifiers for chemical elements, chemical compound, polymers, biological sequences, mixtures and alloys....
 [95-48-7] [108-39-4] [106-44-5]
mixture of cresols: [1319-77-3]
Properties
Density
Density

The density of a material is defined as its mass per unit volume. The symbol of density is ....
 and phase
Phase (matter)

In the physical sciences, a phase is a region of space , throughout which all physical properties of a material are essentially uniform. Examples of physical properties include density, refractive index, and chemical composition....
 1.05 g/cm3, solid 1.03 g/cm3, liquid 1.02 g/cm3, liquid
Solubility in pure water
Water (molecule)

File:Blue-water-pool.jpgWater is the most abundant molecule on Earth's surface, constituting about 70% of the Earth's surface in liquid, solid, and gaseous states....

at 20-25°C		 2.5 g/100 ml 2.4 g/100 ml 1.9 g/100 ml
soluble in strongly alkaline water
Melting point
Melting point

The melting point of a solid is the temperature range at which it changes states of matter from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium....
 29.8 °C (303.0 K) 11.8 °C (285.0 K) 35.5 °C (309.7 K)
Boiling point
Boiling point

The boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid....
 191.0 °C (464.2 K) 202.0 °C (475.2 K) 201.9 °C (475.1 K)
Acidity
Acid dissociation constant

An acid dissociation constant, Ka, is a quantitative measure of the strong acid in solution. It is the equilibrium constant for a chemical reaction known as Dissociation in the context of acid-base reactions....
 (pKa)		 10.26 10.99 10.26
Viscosity
Viscosity

Viscosity is a measure of the Drag of a fluid which is being deformed by either shear stress or extensional stress. In everyday terms , viscosity is "thickness"....
 solid at 25 °C ? cP
Poise

The poise is the unit of dynamic viscosity in the centimetre gram second system of units. It is named after Jean Louis Marie Poiseuille.The analogous unit in the SI is the pascal second :...
 at 25 °C		 solid at 25 °C
Structure
Dipole moment
Dipole

In physics, there are two kinds of dipoles :*An electric dipole is a separation of positive and negative charge. The simplest example of this is a pair of electric charges of equal magnitude but opposite sign, separated by some, usually small, distance....
 1.35 D
Debye

The debye is a non-SI, CGS unit of electric dipole moment. It is defined as 1 statcoulomb centimeter . In SI units, 1 D equals approximately 3.33564 coulomb-meter ....
 1.61 D
Debye

The debye is a non-SI, CGS unit of electric dipole moment. It is defined as 1 statcoulomb centimeter . In SI units, 1 D equals approximately 3.33564 coulomb-meter ....
 1.58 D
Debye

The debye is a non-SI, CGS unit of electric dipole moment. It is defined as 1 statcoulomb centimeter . In SI units, 1 D equals approximately 3.33564 coulomb-meter ....
Hazards
MSDS
Material safety data sheet

A material safety data sheet is a form containing data regarding the properties of a particular substance. An important component of product stewardship and workplace safety, it is intended to provide workers and emergency personnel with procedures for handling or working with that substance in a safe manner, and includes information such...
 External MSDS ? ?
Main hazards flammable, ingestion and inhalation toxicity hazard
Flash point
Flash point

The flash point of a flammability liquid is the lowest temperature at which it can form an ignitable mixture in air. At this temperature the vapour may cease to burn when the source of ignition is removed....
 81°C c.c. 86 °C 86 °C c.c.
R/S statement
Risk and Safety Statements

Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds....
 - (-)/-
RTECS
RTECS

Registry of Toxic Effects of Chemical Substances is a database of toxicity information compiled from the open scientific literature without reference to the validity or usefulness of the studies reported....
 number		 ? ? ?
Supplementary data page
Structure & properties n
Refractive index

The refractive index of a medium is a measure for how much the speed of light is reduced inside the medium. For example, typical soda-lime glass has a refractive index of 1.5, which means that in glass, light travels at times the speed of light in a vacuum....
, er
Dielectric constant

The relative static permittivity of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux....
, etc.
Thermodynamic data Phase behaviour
Solid, liquid, gas
Spectral data UV, IR
Infrared spectroscopy

Infrared spectroscopy is the subset of spectroscopy that deals with the infrared region of the electromagnetic spectrum. It covers a range of techniques, the most common being a form of absorption spectroscopy....
, NMR
NMR spectroscopy

Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei....
, MS
Mass spectrometry

Mass spectrometry is an analytical technique for the determination of the elemental composition of a sample or molecule. It is also used for elucidating the chemical structures of molecules, such as peptides and other chemical compounds....
Related compounds
Related phenols
Phenols

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl Functional group attached to an aromatic hydrocarbon group....
 phenol
Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
, xylenols
Related compounds ?
Except where noted otherwise, data are given for
materials in their standard state (at 25°C, 100 kPa)
Standard state

In chemistry, the standard state of a material is a reference point used to calculate its properties under different conditions. In principle, the choice of standard state is arbitrary, although the International Union of Pure and Applied Chemistry recommends a conventional set of standard states for general use....

Infobox disclaimer and references


Applications


Cresols are used to dissolve
Solvation

Solvation, commonly 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 the biggest class of arthropods and the only ones with wings. They are the most diverse group of animals on the planet. They are most diverse at the equator and their diversity declines toward the poles....
 pest
Pest (animal)

A pest is an organism which has characteristics that are regarded by humans as injurious or unwanted. This is most often because it causes damage to agriculture through feeding on crops or parasitising livestock, such as codling moth on apples, or boll weevil on cotton....
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....
. Cresol solutions can also be found in photographic developers. In the past, cresol solutions have been used as antiseptic
Antiseptic

Antiseptics are antimicrobials that are applied to living biological tissue/skin to reduce the possibility of infection, sepsis, or putrefaction....
s in surgery
Surgery

Surgery is a 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, to help improve bodily function or appearance, or sometimes for some other reason....
, 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....
 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 high viscosity, which smells of naphthalene and aromatic hydrocarbons. Coal tar is among the by-products when coal is...
, and in brown mixtures such as creosote
Creosote

Creosote is the name used for a variety of products including wood creosote and coal tar creosote. Wood creosote is created by high temperature treatment of beech and other woods, or from the resin of the Creosote bush....
, 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....
 and cresylic acids, which are wood preservative
Preservative

A preservative is a natural or synthetic chemical compound that is added to products such as foods, pharmaceuticals, paints, biological samples, wood, etc....
s. Small organisms in soil and water produce cresols when they break down materials in the environment. Cresols are also a chemical component found in Sharpie Markers
Sharpie (marker)

Sharpie is a brand name for a line of permanent markers manufactured by Sanford sold in the United States, Canada, the United Kingdom, Latin America, Australia, and parts of Europe ....
.

Xylenol
Xylenol

Xylenol or dimethylphenol is an arene compound with two methyl groups and a hydroxyl group. 6 isomers exist of xylenol of which 2,6-xylenol with both methyl group in an arene substitution patterns with respect to the hydroxyl group is the most important....
s are dimethylphenols, or they can be thought of as methylcresols.

p-cresol is one of the very few compounds to attract the orchid bee
Euglossini

Euglossine bees, also called orchid bees, are the only group of pollen basket bees whose non-parasitic members do not all possess eusociality....
 Euglossa
Euglossa

Euglossa is a genus of orchid bees . Like all their close relatives, they are native to the Neotropics; an introduced population exists in Florida....
 cyanura, and has been used to capture and study the species.

Health effects


Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skin
Skin

The skin is the outer covering of the body, also known as the epidermis. It is the largest organ of the integumentary system made up of multiple layers of epithelial biological tissue, and guards the underlying muscles, bones, ligaments and organ s....
 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, eye
Eye

Eyes are Organ that detect light, and send signals along the optic nerve to the visual system and other areas of the brain. Complex optical systems with resolving power have come in ten fundamentally different forms, and 96% of animal species possess a complex optical system....
s, mouth
Mouth

The mouth, buccal cavity, or oral cavity is the first portion of the alimentary canal that receives food and begins digestion by mechanically breaking up the solid food particles into smaller pieces and mixing them with saliva....
, and throat
Throat

In anatomy, the throat is the anterior part of the neck, in front of the vertebrae. It consists of the pharynx and larynx. An important feature of the throat is the epiglottis, a flap which separates the esophagus from the vertebrate trachea and prevents inhalation of food or drink....
; abdominal pain and vomiting; heart
Heart

The heart is a muscle organ in all vertebrates responsible for pumping blood through the blood vessels by repeated, rhythmic contractions, or a similar structure in annelids, mollusks, and arthropods....
 damage; anemia
Anemia

Anemia or an?mia/anaemia is defined as a qualitative or quantitative deficiency of hemoglobin, a protein found inside red blood cells ....
; liver
Liver

The liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, a few of which are detoxification, protein synthesis, and production of biochemicals necessary for digestion....
 and kidney
Kidney

The kidneys are Organ that have numerous biological roles. Their primary role is to maintain the homeostasis balance of bodily fluids by filtering and secreting Metabolomics#Metabolitess and minerals from the blood and excreting them, along with water , as urine....
 damage; facial paralysis; coma
Coma

In medicine, a coma is a profound state of unconsciousness. A comatose person cannot be awakened, fails to respond normally to pain or light, does not have sleep-wake cycles, and does not take voluntary actions....
; and death
Death

Death is the permanent termination of the biological functions that define a life organism. It refers to both a particular event and to the condition that results thereby....
.

Breathing high levels of cresols for a short time results in irritation of the nose
Nose

Anatomically, a nose is a protuberance in vertebrates that houses the nostrils, or nares, which admit and expel air for Respiration in conjunction with the mouth....
 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 that delivers necessary substances to the body's Cell s ? such as nutrients and oxygen ? and transports waste products away from those same cells....
 and nervous system
Nervous system

The nervous system is a Neural network of specialized cells that communicate information about an animal's surroundings and itself. It processes this information and causes reactions in other parts of the body....
.

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. Some primitive animals such as cnidarian and echinoderm have a decentralized nervous system without a brain, while sponges lack any nervous system at all....
, and lung
Lung

The lung is the essential respiration organ in 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 in the chest 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.

Footnotes