WordNet

any of three poisonous colorless isomeric phenols; derived from coal or wood tar; used as a disinfectant (同)methyl phenol

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/02/10 12:33:45」(JST)

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Isomers of Cresol^[1]^[2]^[3]
Skeletal formula
Ball-and-stick model
General
Common name	o-cresol	m-cresol	p-cresol
Systematic name	2-methylphenol	3-methylphenol	4-methylphenol
Other names	ortho-cresol	meta-cresol	para-cresol
Molecular formula	C₇H₈O
SMILES	Oc1c(C)cccc1	Oc1cc(C)ccc1	Oc1ccc(C)cc1
Molar mass	108.14 g/mol
Appearance at room temperature and pressure	colorless crystals	thicker liquid	greasy-looking solid
CAS number	[95-48-7]	[108-39-4]	[106-44-5]
CAS number	mixture of cresols (tricresol): [1319-77-3]
Properties
Density and phase	1.05 g/cm³, solid	1.03 g/cm³, liquid	1.02 g/cm³, liquid
Solubility in pure water 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	29.8 °C (303.0 K)	11.8 °C (285.0 K)	35.5 °C (309.7 K)
Boiling point	191.0 °C (464.2 K)	202.0 °C (475.2 K)	201.9 °C (475.1 K)
Acidity (pK_a)	10.26	10.09	10.26
Viscosity	solid at 25 °C	? cP at 25 °C	solid at 25 °C
Structure
Dipole moment	1.35 D	1.61 D	1.58 D
Hazards
SDS
Main hazards	flammable, ingestion and inhalation toxicity hazard
Flash point	81 °C c.c.	86 °C	86 °C c.c.
R/S statement	R24/25-R34 ((S1/2)-)S36/37/S39-S45
RTECS number
Related compounds
Related phenols	xylenols
Related compounds	bromo cresol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Cresols (also hydroxytoluene) are organic compounds which are methylphenols. They are a widely occurring natural and manufactured group of aromatic organic compounds, which are categorized as phenols (sometimes called phenolics). Depending on the temperature, cresols can be solid or liquid because they have melting points 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 "coal tar" smell. The name cresol reflects their structure, being phenols, and their traditional source, creosote.

Structure and production

In its chemical structure, a molecule of cresol has a methyl group substituted onto the ring of phenol. There are three forms (isomers) of cresol: ortho-cresol (o-cresol), meta-cresol (m-cresol), and para-cresol (p-cresol). These forms occur separately or as a mixture, which can also be called cresol or more specifically, tricresol. About half of the world's supply of cresols are extracted from coal tar.^[4] The rest is produced synthetically, by methylation of phenol or hydrolysis of chlorotoluenes.^[5]

Applications

Cresols are precursors or synthetic intermediates to other compounds and materials, including plastics, pesticides, pharmaceuticals, and dyes.^[5]

Commercial examples

Derivatives of p-cresol include:

Bupranolol, a non-selective beta blocker
Butylated hydroxytoluene, a common antioxidant
Indo-1, a popular calcium indicator

Derivatives of o-cresol include:

MCPA, (4-chloro-2-methylphenoxy)acetic acid
MCPB, 4-(4-chloro-2-methylphenoxy)butanoic acid
Mecoprop, (RS)-2-(4-chloro-2-methylphenoxy)propanoic acid
the amine atomoxetine, (3R)-N-methyl-3-(2-methylphenoxy)-3-phenylpropan-1-amine
the diol mephenesin, 3-(2-methylphenoxy)propane-1,2-diol

Derivatives of m-cresol include:

Amylmetacresol, an antiseptic
Bevantolol, (RS)-[2-(3,4-dimethoxyphenyl)ethyl][2-hydroxy-3-(3-methylphenoxy)propyl]amine
Bromocresol green
Chloro-m-cresol which is used as a household disinfectant
Tolimidone, 5-(3-methylphenoxy)pyrimidin-2(1H)-one

Health effects

Most exposures to cresols are at very low levels that are not harmful. When cresols are inhaled, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, 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 lungs.

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 reproduction.

It is not known what the effects are from long-term ingestion or skin contact with low levels of cresols.

The Occupational Safety and Health Administration has set a permissible exposure limit at 5 ppm (22 mg/m³) over an eight hour time-weighted average, while the National Institute for Occupational Safety and Health recommends a limit of 2.3 ppm (10 mg/m³).^[6]

References

^ o-CRESOL (ICSC)
^ m-CRESOL (ICSC)
^ p-CRESOL (ICSC)
^ http://medical-dictionary.thefreedictionary.com/tricresol. 18 July, 2013.
^ ^a ^b Helmut Fiegein "Cresols and Xylenols" in Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_025
^ Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs) - Cresol (o, m, p isomers)

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Molecular products from the pyrolysis and oxidative pyrolysis of tyrosine.

Kibet JK, Khachatryan L, Dellinger B.SourceDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
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Tubular metal-organic framework-based capillary gas chromatography column for separation of alkanes and aromatic positional isomers.

Fang ZL, Zheng SR, Tan JB, Cai SL, Fan J, Yan X, Zhang WG.SourceInstitute of Special Materials & School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China; School of Basic Science, East China Jiaotong University, Nanchang 330013, China.
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Planar triazinium cations from vanadyl-mediated ring cyclizations: the thiazole species for efficient nuclear staining and photocytotoxicity.

Prasad P, Khan I, Sasmal PK, Koley D, Kondaiah P, Chakravarty AR.SourceDepartment of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560012, India. arc@ipc.iisc.ernet.in.
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