# P-Cresol

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Chemical compound

p-Cresol Skeletal formula of p-cresol 3D model of p-cresol 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 CAS Number 106-44-5 Y 3D model (JSmol) Interactive image Beilstein Reference 1305151 ChEBI CHEBI:17847 Y ChEMBL ChEMBL16645 Y ChemSpider 13839082 Y DrugBank DB01688 Y ECHA InfoCard 100.003.090 EC Number 203-398-6 Gmelin Reference 2779 KEGG C01468 Y PubChem CID 2879 RTECS number GO6475000 UNII 1MXY2UM8NV Y CompTox Dashboard (EPA) DTXSID7021869 InChI InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3 Y Key: IWDCLRJOBJJRNH-UHFFFAOYSA-N Y InChI=1/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3 Key: IWDCLRJOBJJRNH-UHFFFAOYAN SMILES Cc1ccc(O)cc1 Properties Chemical formula C7H8O Molar mass 108.13 Appearance colorless 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) Solubility in water 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] Magnetic susceptibility (χ) −72.1×10−6 cm3/mol Refractive index (nD) 1.5395 Hazards Occupational safety and health (OHS/OSH): Main hazards May be fatal if swallowed, inhaled, or absorbed through skin. GHS labelling: Pictograms Signal word Danger Hazard statements H201, H311, H314, H351, H370, H372, H373, H401, H412 Precautionary statements 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) 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): LD50 (median dose) 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). Y verify (what is YN ?) Infobox references

Chemical compound

***para*-Cresol**, also **4-methylphenol**, is an [organic compound](/source/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](/source/Phenol) and is an isomer of [*o*-cresol](/source/O-Cresol) and [*m*-cresol](/source/M-Cresol).[3]

## Production

Together with many other compounds, *p*-cresol is conventionally extracted from [coal tar](/source/Coal_tar), the volatilized materials obtained in the roasting of [coal](/source/Coal) to produce [coke](/source/Coke_(fuel)). This residue contains a few percent by weight of [phenol](/source/Phenol) and [cresols](/source/Cresol). Industrially, *p*-cresol is currently prepared mainly by a two-step route beginning with the [sulfonation](/source/Sulfonation) of [toluene](/source/Toluene):[4]

- CH3C6H5 + [H2SO4](/source/Sulfuric_acid) → CH3C6H4SO3H + H2O

[Basic](/source/Base_(chemistry)) hydrolysis of the [sulfonate](/source/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](/source/Alkylated) with [propene](/source/Propene) to give [*p*-cymene](/source/P-Cymene), which can be oxidatively dealkylated in a manner similar to the [cumene process](/source/Cumene_process).[3]

## Applications

*p*-Cresol is consumed mainly in the production of [antioxidants](/source/Antioxidant), such as [butylated hydroxytoluene](/source/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](/source/Bacterial_fermentation) of [protein](/source/Protein) in the human [large intestine](/source/Large_intestine). It is excreted in feces and urine,[7] and is a component of human [sweat](/source/Sweat) that attracts female [mosquitoes](/source/Mosquito).[8][9]

*p*-Cresol is a constituent of [tobacco smoke](/source/Tobacco_smoke).[10]

### In other species

*p*-Cresol is a major component in [pig](/source/Pig) odor.[11] Temporal glands secretion examination showed the presence of phenol and *p*-cresol during [musth](/source/Musth) in male [elephants](/source/Elephant).[12][13] It is one of the very few compounds to attract the [orchid bee](/source/Euglossini) *[Euglossa cyanura](https://en.wikipedia.org/w/index.php?title=Euglossa_cyanura&action=edit&redlink=1)* and has been used to capture and study the species.[14] *p*-Cresol is a component found in [horse](/source/Horse) urine during [estrus](/source/Estrus) that can elicit the [Flehmen response](/source/Flehmen_response).[15]

*p*-Cresol is found in numerous [essential oils](/source/Essential_oils) - typically in trace quantities where its intense odour imparts an animalic character.[16]

## References

1. ^ [***a***](#cite_ref-PGCH_1-0) [***b***](#cite_ref-PGCH_1-1) [***c***](#cite_ref-PGCH_1-2) [***d***](#cite_ref-PGCH_1-3) [***e***](#cite_ref-PGCH_1-4) NIOSH Pocket Guide to Chemical Hazards. ["#0156"](https://www.cdc.gov/niosh/npg/npgd0156.html). [National Institute for Occupational Safety and Health](/source/National_Institute_for_Occupational_Safety_and_Health) (NIOSH).

1. **[^](#cite_ref-2)** ["Cresol (o, m, p isomers)"](https://www.cdc.gov/niosh/idlh/cresol.html). *Immediately Dangerous to Life or Health Concentrations*. [National Institute for Occupational Safety and Health](/source/National_Institute_for_Occupational_Safety_and_Health).

1. ^ [***a***](#cite_ref-Ullmann_3-0) [***b***](#cite_ref-Ullmann_3-1) [***c***](#cite_ref-Ullmann_3-2) Fiege H (2000). "Cresols and Xylenols". *[Ullmann's Encyclopedia of Industrial Chemistry](/source/Ullmann's_Encyclopedia_of_Industrial_Chemistry)*. Weinheim: Wiley-VCH. [doi](/source/Doi_(identifier)):[10.1002/14356007.a08_025](https://doi.org/10.1002%2F14356007.a08_025). [ISBN](/source/ISBN_(identifier)) [3-527-30673-0](https://en.wikipedia.org/wiki/Special:BookSources/3-527-30673-0).

1. **[^](#cite_ref-4)** W. W. Hartman (1923). "*p*-Cresol". *Organic Syntheses*. **3**: 37. [doi](/source/Doi_(identifier)):[10.15227/orgsyn.003.0037](https://doi.org/10.15227%2Forgsyn.003.0037).

1. **[^](#cite_ref-5)** ["meta- and para-Cresols"](https://web.archive.org/web/20171208161609/https://inchem.org/documents/sids/sids/m-p-cresols.pdf) (PDF). *[International Programme on Chemical Safety](/source/International_Programme_on_Chemical_Safety) (IPCS INCHEM)*. April 2005. Archived from [the original](https://inchem.org/documents/sids/sids/m-p-cresols.pdf) (PDF) on 8 December 2017. Retrieved 4 November 2022.

1. **[^](#cite_ref-hazmap_6-0)** ["p-Cresol - Hazardous Agents"](https://haz-map.com/Agents/16387?#:~:text=used,materials). *[Haz-Map](https://en.wikipedia.org/w/index.php?title=Haz-Map&action=edit&redlink=1): Information on Hazardous Chemicals and Occupational Diseases*. Retrieved 4 November 2022.

1. **[^](#cite_ref-7)** Hamer HM, De Preter V, Windey K, Verbeke K (January 2012). ["Functional analysis of colonic bacterial metabolism: relevant to health?"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3345969). *American Journal of Physiology. Gastrointestinal and Liver Physiology*. **302** (1): G1-9. [doi](/source/Doi_(identifier)):[10.1152/ajpgi.00048.2011](https://doi.org/10.1152%2Fajpgi.00048.2011). [PMC](/source/PMC_(identifier)) [3345969](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3345969). [PMID](/source/PMID_(identifier)) [22016433](https://pubmed.ncbi.nlm.nih.gov/22016433).

1. **[^](#cite_ref-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](/source/Bibcode_(identifier)):[2004Natur.427..212H](https://ui.adsabs.harvard.edu/abs/2004Natur.427..212H). [doi](/source/Doi_(identifier)):[10.1038/427212a](https://doi.org/10.1038%2F427212a). [PMID](/source/PMID_(identifier)) [14724626](https://pubmed.ncbi.nlm.nih.gov/14724626). [S2CID](/source/S2CID_(identifier)) [4419658](https://api.semanticscholar.org/CorpusID:4419658).

1. **[^](#cite_ref-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](/source/Doi_(identifier)):[10.1111/j.1365-2915.1989.tb00241.x](https://doi.org/10.1111%2Fj.1365-2915.1989.tb00241.x). [PMID](/source/PMID_(identifier)) [2577519](https://pubmed.ncbi.nlm.nih.gov/2577519). [S2CID](/source/S2CID_(identifier)) [1641506](https://api.semanticscholar.org/CorpusID:1641506).

1. **[^](#cite_ref-10)** Talhout R, Schulz T, Florek E, van Benthem J, Wester P, Opperhuizen A (February 2011). ["Hazardous compounds in tobacco smoke"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3084482). *International Journal of Environmental Research and Public Health*. **8** (2): 613–28. [doi](/source/Doi_(identifier)):[10.3390/ijerph8020613](https://doi.org/10.3390%2Fijerph8020613). [PMC](/source/PMC_(identifier)) [3084482](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3084482). [PMID](/source/PMID_(identifier)) [21556207](https://pubmed.ncbi.nlm.nih.gov/21556207).

1. **[^](#cite_ref-11)** Borrell, Brendan (5 March 2009). ["Why study pig odor?"](http://www.sciam.com/article.cfm?id=why-study-pig-odor). *Scientific American*. [Archived](https://web.archive.org/web/20210320042122/https://www.scientificamerican.com/article/why-study-pig-odor/) from the original on 20 March 2021. Retrieved 9 March 2009.

1. **[^](#cite_ref-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](/source/Doi_(identifier)):[10.1016/S0031-9384(99)00114-6](https://doi.org/10.1016%2FS0031-9384%2899%2900114-6). [PMID](/source/PMID_(identifier)) [10549891](https://pubmed.ncbi.nlm.nih.gov/10549891). [S2CID](/source/S2CID_(identifier)) [21368454](https://api.semanticscholar.org/CorpusID:21368454).

1. **[^](#cite_ref-13)** Ananth D (May 2000). ["Musth in elephants"](https://doi.org/10.11609%2Fjott.zpj.14.4.259-62). *Zoos' Print Journal*. **15** (5): 259–62. [doi](/source/Doi_(identifier)):[10.11609/jott.zpj.14.4.259-62](https://doi.org/10.11609%2Fjott.zpj.14.4.259-62).

1. **[^](#cite_ref-14)** Williams NH, Whitten WM (June 1983). ["Orchid Floral Fragrances and Male Euglossine Bees: Methods and Advances in the Last Sesquidecade"](https://www.biodiversitylibrary.org/part/35261). *Biological Bulletin*. **164** (3): 355–95. [doi](/source/Doi_(identifier)):[10.2307/1541248](https://doi.org/10.2307%2F1541248). [JSTOR](/source/JSTOR_(identifier)) [1541248](https://www.jstor.org/stable/1541248). [Archived](https://web.archive.org/web/20200605121541/https://www.biodiversitylibrary.org/part/35261) from the original on 5 June 2020. Retrieved 10 November 2021.

1. **[^](#cite_ref-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](/source/Doi_(identifier)):[10.1007/s10886-012-0138-2](https://doi.org/10.1007%2Fs10886-012-0138-2). [PMID](/source/PMID_(identifier)) [22592336](https://pubmed.ncbi.nlm.nih.gov/22592336). [S2CID](/source/S2CID_(identifier)) [14558317](https://api.semanticscholar.org/CorpusID:14558317).

1. **[^](#cite_ref-16)** ["para-cresol"](https://scentsandflavors.com/database/9dbb4f60-e83f-443a-a0c6-f23c3e02fbce). *scentsandflavors.com*. Retrieved 15 May 2026.

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Adapted from the Wikipedia article [P-Cresol](https://en.wikipedia.org/wiki/P-Cresol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/P-Cresol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.