P-Cresol

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p-Cresol
Para-cresol-horizontal-2D-skeletal.png
P-cresol-spaceFilling.png
Names
Preferred IUPAC name
4-Methylphenol
Systematic IUPAC name
4-Methylbenzenol
Other names
4-Cresol
p-Cresol
4-Hydroxytoluene
p-Cresylic acid
1-Hydroxy-4-methylbenzene
Identifiers
3D model (JSmol)
1305151
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.090 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-398-6
2779
KEGG
PubChem CID
RTECS number
  • GO6475000
UNII
  • InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3 Yes check.svgY
    Key: IWDCLRJOBJJRNH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
    Key: IWDCLRJOBJJRNH-UHFFFAOYAN
  • Cc1ccc(O)cc1
Properties
C7H8O
Molar mass 108.13
Appearancecolorless prismatic crystals
Density 1.0347 g/ml
Melting point 35.5 °C (95.9 °F; 308.6 K)
Boiling point 201.8 °C (395.2 °F; 474.9 K)
2.4 g/100 ml at 40 °C
5.3 g/100 ml at 100 °C
Solubility in ethanol miscible
Solubility in diethyl ether miscible
Vapor pressure 0.11 mmHg (25 °C) [1]
−72.1×10−6 cm3/mol
1.5395
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
May be fatal if swallowed, inhaled, or absorbed through skin.
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg
Danger
H201, H311, H314, H351, H370, H372, H373, H401, H412
P201, P202, P260, P264, P270, P273, P280, P281, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P321, P322, P330, P361, P363, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 86.1 °C (187.0 °F; 359.2 K)
Explosive limits 1.1%–? [1]
Lethal dose or concentration (LD, LC):
207 mg/kg (oral, rat, 1969)
1800 mg/kg (oral, rat, 1944)
344 mg/kg (oral, mouse) [2]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 5 ppm (22 mg/m3) [skin] [1]
REL (Recommended)
TWA 2.3 ppm (10 mg/m3) [1]
IDLH (Immediate danger)
250 ppm [1]
Safety data sheet (SDS) External MSDS
Related compounds
Related phenols
o-cresol, m-cresol, phenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

para-Cresol, also 4-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of o-cresol and m-cresol. [3]

Production

Together with many other compounds, p-cresol is conventionally extracted from coal tar, the volatilized materials obtained in the roasting of coal to produce coke. This residue contains a few percent by weight of phenol and cresols. Industrially, p-cresol is currently prepared mainly by a two-step route beginning with the sulfonation of toluene: [4]

CH3C6H5 + H2SO4 → CH3C6H4SO3H + H2O

Basic hydrolysis of the sulfonate salt gives the sodium salt of the cresol:

CH3C6H4SO3H + 2 NaOH → CH3C6H4OH + Na2SO3 + H2O

Other methods for the production of p-cresol include chlorination of toluene followed by hydrolysis. In the cymene-cresol process, toluene is alkylated with propene to give p-cymene, which can be oxidatively dealkylated in a manner similar to the cumene process. [3]

Applications

p-Cresol is consumed mainly in the production of antioxidants, such as butylated hydroxytoluene (BHT). The monoalkylated derivatives undergo coupling to give an extensive family of diphenol antioxidants. These antioxidants are valued because they are relatively low in toxicity and nonstaining. [3] [5] [6]

Natural occurrences

In humans

p-Cresol is produced by bacterial fermentation of protein in the human large intestine. It is excreted in feces and urine, [7] and is a component of human sweat that attracts female mosquitoes. [8] [9]

p-Cresol is a constituent of tobacco smoke. [10]

In other species

p-Cresol is a major component in pig odor. [11] Temporal glands secretion examination showed the presence of phenol and p-cresol during musth in male elephants. [12] [13] It is one of the very few compounds to attract the orchid bee Euglossa cyanura and has been used to capture and study the species. [14] p-Cresol is a component found in horse urine during estrus that can elicit the Flehmen response. [15]

Related Research Articles

<span class="mw-page-title-main">Phenol</span> Organic compound (C6H5OH)

Phenol, or Benzenol, is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Butylated hydroxytoluene</span> Chemical compound

Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidation in fluids and other materials, and the regulations overseen by the U.S. F.D.A.—which considers BHT to be "generally recognized as safe"—allow small amounts to be added to foods. Despite this, and the earlier determination by the National Cancer Institute that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an antiviral drug, but as of December 2022, use of BHT as a drug is not supported by the scientific literature and it has not been approved by any drug regulatory agency for use as an antiviral.

<span class="mw-page-title-main">Xylene</span> Organic compounds with the formula (CH3)2C6H4

In organic chemistry, xylene or xylol are any of three organic compounds with the formula (CH3)2C6H4. They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are substituted determines which of three structural isomers results. It is a colorless, flammable, slightly greasy liquid of great industrial value.

<span class="mw-page-title-main">Butanone</span> Chemical compound

Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

Cresols are a group of aromatic organic compounds. They are widely-occurring phenols which may be either natural or manufactured. They are also categorized as methyl phenols. Cresols commonly occur as either solids or liquids because their melting points are generally close to room temperature. Like other types of phenols, they are slowly oxidized by exposure to air, and the resulting impurities often give the samples a yellow 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" is an adduct of phenol and their traditional source, creosote.

<span class="mw-page-title-main">Pentachlorophenol</span> Chemical compound

Pentachlorophenol (PCP) is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names. It can be found as pure PCP, or as the sodium salt of PCP, the latter of which dissolves easily in water. It can be biodegraded by some bacteria, including Sphingobium chlorophenolicum.

<span class="mw-page-title-main">Catechol</span> Organic compound (C6H4(OH)2); benzene with two adjacent –OH groups

Catechol, also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances.

<span class="mw-page-title-main">Hydroquinone</span> Chemical compound

Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a para position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843.

<span class="mw-page-title-main">Hippuric acid</span> Chemical compound

Hippuric acid is a carboxylic acid and organic compound. It is found in urine and is formed from the combination of benzoic acid and glycine. Levels of hippuric acid rise with the consumption of phenolic compounds. The phenols are first converted to benzoic acid, and then to hippuric acid and excreted in urine.

<span class="mw-page-title-main">2,4-Dinitrotoluene</span> Organic chemical compound

2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.

<i>m</i>-Cresol Chemical compound

meta-Cresol, also 3-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless, viscous liquid that is used as an intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and o-cresol.

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

Toluene toxicity refers to the harmful effects caused by toluene on the body.

<span class="mw-page-title-main">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

<span class="mw-page-title-main">Benzene</span> Hydrocarbon compound consisting of a 6-sided ring

Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.

<span class="mw-page-title-main">4-Nitrochlorobenzene</span> Chemical compound

4-Nitrochlorobenzene is the organic compound with the formula ClC6H4NO2. It is a pale yellow solid. 4-Nitrochlorobenzene is a common intermediate in the production of a number of industrially useful compounds, including antioxidants commonly found in rubber. Other isomers with the formula ClC6H4NO2 include 2-nitrochlorobenzene and 3-nitrochlorobenzene.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

ortho-Cresol (IUPAC name: 2-methylphenol, also known as 2-hydroxytoluene or ortho-Toluenol) is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and m-cresol.

<span class="mw-page-title-main">Methylhippuric acid</span> Chemical compound

Methylhippuric acid is a carboxylic acid and organic compound. Methylhippuric acid has three isomers. The isomers include 2-, 3-, and 4-methylhippuric acid.

References

  1. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0156". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ "Cresol (o, m, p isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 3 Fiege H (2000). "Cresols and Xylenols". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_025.
  4. ↑ W. W. Hartman (1923). "p-Cresol". Organic Syntheses. 3: 37. doi:10.15227/orgsyn.003.0037.
  5. ↑ "meta- and para-Cresols" (PDF). International Programme on Chemical Safety (IPCS INCHEM). April 2005. Archived from the original (PDF) on 8 December 2017. Retrieved 4 November 2022.
  6. ↑ "p-Cresol - Hazardous Agents". Haz-Map: Information on Hazardous Chemicals and Occupational Diseases. Retrieved 4 November 2022.
  7. ↑ Hamer HM, De Preter V, Windey K, Verbeke K (January 2012). "Functional analysis of colonic bacterial metabolism: relevant to health?". American Journal of Physiology. Gastrointestinal and Liver Physiology. 302 (1): G1-9. doi:10.1152/ajpgi.00048.2011. PMC   3345969 . PMID   22016433.
  8. ↑ Hallem EA, Nicole Fox A, Zwiebel LJ, Carlson JR (January 2004). "Olfaction: mosquito receptor for human-sweat odorant". Nature. 427 (6971): 212–213. Bibcode:2004Natur.427..212H. doi:10.1038/427212a. PMID   14724626. S2CID   4419658.
  9. ↑ Linley JR (October 1989). "Laboratory tests of the effects of p-cresol and 4-methylcyclohexanol on oviposition by three species of Toxorhynchites mosquitoes". Medical and Veterinary Entomology. 3 (4): 347–52. doi:10.1111/j.1365-2915.1989.tb00241.x. PMID   2577519. S2CID   1641506.
  10. ↑ Talhout R, Schulz T, Florek E, van Benthem J, Wester P, Opperhuizen A (February 2011). "Hazardous compounds in tobacco smoke". International Journal of Environmental Research and Public Health. 8 (2): 613–28. doi: 10.3390/ijerph8020613 . PMC   3084482 . PMID   21556207.
  11. ↑ Borrell, Brendan (5 March 2009). "Why study pig odor?". Scientific American. Archived from the original on 20 March 2021. Retrieved 9 March 2009.
  12. ↑ Rasmussen LE, Perrin TE (October 1999). "Physiological correlates of musth: lipid metabolites and chemical composition of exudates". Physiology & Behavior. 67 (4): 539–49. doi:10.1016/S0031-9384(99)00114-6. PMID   10549891. S2CID   21368454.
  13. ↑ Ananth D (May 2000). "Musth in elephants". Zoos' Print Journal. 15 (5): 259–62. doi: 10.11609/jott.zpj.14.4.259-62 .
  14. ↑ Williams NH, Whitten WM (June 1983). "Orchid Floral Fragrances and Male Euglossine Bees: Methods and Advances in the Last Sesquidecade". Biological Bulletin. 164 (3): 355–95. doi:10.2307/1541248. JSTOR   1541248. Archived from the original on 5 June 2020. Retrieved 10 November 2021.
  15. ↑ Būda V, Mozūraitis R, Kutra J, Borg-Karlson AK (July 2012). "p-Cresol: a sex pheromone component identified from the estrous urine of mares". Journal of Chemical Ecology. 38 (7): 811–3. doi:10.1007/s10886-012-0138-2. PMID   22592336. S2CID   14558317.
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