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Revision as of 09:27, 18 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472471033 of page P-Cresol for the Chem/Drugbox validation project (updated: 'ChEBI', 'KEGG').  Latest revision as of 03:01, 9 January 2024 edit Michael7604 (talk | contribs)Extended confirmed users8,895 edits added category 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{DISPLAYTITLE:''p''-Cresol}}
{{use dmy dates|date=November 2022}}
{{chembox {{chembox
| verifiedrevid = 472469178 | verifiedrevid = 477506207
| Name = ''p''-Cresol | Name = ''p''-Cresol
| ImageFile = Para-cresol-horizontal-2D-skeletal.png | ImageFile = Para-cresol-horizontal-2D-skeletal.png
| ImageName = Skeletal formula of para-cresol | ImageName = Skeletal formula of ''p''-cresol
⚫ | ImageFile1 = p-cresol-spaceFilling.png
| ImageSize = 200px
| ImageSize1 = 150px
⚫ | ImageFile1 = p-cresol-spaceFilling.png
⚫ | ImageName1 = 3D model of ''p''-cresol
| ImageSize1 = 150px
⚫ | PIN = 4-Methylphenol
⚫ | ImageName1 = 3D model of p-cresol
| SystematicName = 4-Methylbenzenol
⚫ | IUPACName = 4-Methylphenol
| OtherNames = 4-Cresol<br/>''p''-Cresol<br />4-Hydroxytoluene<br/>''p''-Cresylic acid<br/>1-Hydroxy-4-methylbenzene
| OtherNames = 4-Hydroxytoluene, p-Hydroxytoluene, p-Methylphenol
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 106-44-5 | CASNo = 106-44-5
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 16645 | ChEMBL = 16645
| RTECS = GO6475000 | RTECS = GO6475000
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01688 | DrugBank = DB01688
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1MXY2UM8NV | UNII = 1MXY2UM8NV
| SMILES = Cc1ccc(O)cc1 | SMILES = Cc1ccc(O)cc1
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17847 | ChEBI = 17847
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01468 | KEGG = C01468
| ChemSpiderID = 13839082 | ChemSpiderID = 13839082
| PubChem = 2879
⚫ | InChI = 1/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
| EC_number = 203-398-6
⚫ | InChIKey = IWDCLRJOBJJRNH-UHFFFAOYAN
| Beilstein = 1305151
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| Gmelin = 2779
⚫ | InChI = 1/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
⚫ | InChIKey = IWDCLRJOBJJRNH-UHFFFAOYAN
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3 | StdInChI = 1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IWDCLRJOBJJRNH-UHFFFAOYSA-N | StdInChIKey = IWDCLRJOBJJRNH-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Appearance = colorless prismatic crystals | Appearance = colorless prismatic crystals
| Formula = C<sub>7</sub>H<sub>8</sub>O | Formula = C<sub>7</sub>H<sub>8</sub>O
| MolarMass = 108.13 | MolarMass = 108.13
| BoilingPtC = 201.8 | BoilingPtC = 201.8
| MeltingPtC = 35.5 | MeltingPtC = 35.5
| Density = 1.0347 g/ml | Density = 1.0347 g/ml
| RefractIndex = 1.5395 | RefractIndex = 1.5395
| Solubility = 2.4 g/100 ml at 40 °C<br>5.3 g/100 ml at 100 °C | Solubility = 2.4 g/100 ml at 40&nbsp;°C<br>5.3 g/100 ml at 100&nbsp;°C
| Solubility1 = fully ] | Solubility1 = ]
| Solvent1 = ethanol | Solvent1 = ethanol
| Solubility2 = fully ] | Solubility2 = ]
| Solvent2 = diethyl ether | Solvent2 = diethyl ether
| VaporPressure = 0.11 mmHg (25&nbsp;°C)<ref name=PGCH/>
| Viscosity =
| MagSus = {{val|-72.1e-6|u=cm<sup>3</sup>/mol}}
| Dipole =
}} }}
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
| ExternalSDS =
| ExternalMSDS =
| FlashPt = | FlashPtC = 86.1
| MainHazards = May be fatal if swallowed, inhaled, or absorbed through skin. | MainHazards = May be fatal if swallowed, inhaled, or absorbed through skin.
| NFPA-H = 3 | NFPA-H = 3
| NFPA-F = 1 | NFPA-F = 1
| NFPA-R = 0 | NFPA-R = 0
| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS08}}
| NFPA-O =
| GHSSignalWord = Danger
| RPhrases = {{R34}} {{R24}} {{R25}}
| HPhrases = {{H-phrases|201|311|314|351|370|372|373|401|412}}
| SPhrases = {{S36}} {{S37}} {{S39}} {{S45}}
| PPhrases = {{P-phrases|201|202|260|264|270|273|280|281|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|307+311|308+313|310|312|314|321|322|330|361|363|405|501}}
⚫ }}
| PEL = TWA 5 ppm (22 mg/m<sup>3</sup>) <ref name=PGCH>{{PGCH|0156}}</ref>
⚫ | Section8 = {{Chembox Related
| ExploLimits = 1.1%–?<ref name=PGCH/>
⚫ | Function = ]s
| IDLH = 250 ppm<ref name=PGCH/>
⚫ | OtherFunctn = ], ], ]
| LD50 = 207 mg/kg (oral, rat, 1969)<br/>1800 mg/kg (oral, rat, 1944)<br/>344 mg/kg (oral, mouse)<ref>{{IDLH|cresol|Cresol (o, m, p isomers)}}</ref>
⚫ }}
| REL = TWA 2.3 ppm (10 mg/m<sup>3</sup>)<ref name=PGCH/>
⚫ }}
⚫ | Section8 = {{Chembox Related
⚫ | OtherFunction_label = ]s
⚫ | OtherFunction = ], ], ]
⚫ }}
}} }}

'''''para''-Cresol''', also '''4-methylphenol''', is an ] with the formula CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of ] and is an isomer of ] and ].<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a08_025 |title=Cresols and Xylenols |year=2000 |last1=Fiege |first1=Helmut | name-list-style = vanc |isbn=3-527-30673-0}}</ref>

==Production==
Together with many other compounds, ''p''-cresol is conventionally extracted from ], the volatilized materials obtained in the roasting of ] to produce ]. This residue contains a few percent by weight of ] and ]s. Industrially, ''p''-cresol is currently prepared mainly by a two-step route beginning with the ] of ]:<ref>{{cite journal|doi=10.15227/orgsyn.003.0037|title=''p''-Cresol|journal=Organic Syntheses|volume=3|pages=37|year=1923|author=W. W. Hartman}}</ref>
:CH<sub>3</sub>C<sub>6</sub>H<sub>5</sub> + ] → CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>3</sub>H + H<sub>2</sub>O
] hydrolysis of the ] salt gives the sodium salt of the cresol:
:CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>SO<sub>3</sub>H + 2 NaOH → CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>OH + Na<sub>2</sub>SO<sub>3</sub> + H<sub>2</sub>O
Other methods for the production of ''p''-cresol include chlorination of toluene followed by hydrolysis. In the cymene-cresol process, toluene is ] with ] to give ], which can be oxidatively dealkylated in a manner similar to the ].<ref name=Ullmann/>

== Applications ==
''p''-Cresol is consumed mainly in the production of ]s, such as ] (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.<ref name=Ullmann/><ref>{{Cite web |date=April 2005 |title=meta- and para-Cresols |url=https://inchem.org/documents/sids/sids/m-p-cresols.pdf |url-status=dead |archive-url=https://web.archive.org/web/20171208161609/https://inchem.org/documents/sids/sids/m-p-cresols.pdf |archive-date=2017-12-08 |access-date=2022-11-04 |website=] (IPCS INCHEM)}}</ref><ref name="hazmap">{{Cite web |title=p-Cresol - Hazardous Agents |url=https://haz-map.com/Agents/16387?#:~:text=used,materials |access-date=2022-11-04 |website=]: Information on Hazardous Chemicals and Occupational Diseases}}</ref>

== Natural occurrences ==
=== In humans ===
''p''-Cresol is produced by ] of ] in the human ]. It is excreted in feces and urine,<ref>{{cite journal | vauthors = Hamer HM, De Preter V, Windey K, Verbeke K | title = Functional analysis of colonic bacterial metabolism: relevant to health? | journal = American Journal of Physiology. Gastrointestinal and Liver Physiology | volume = 302 | issue = 1 | pages = G1-9 | date = January 2012 | pmid = 22016433 | pmc = 3345969 | doi = 10.1152/ajpgi.00048.2011}}</ref> and is a component of human ] that attracts female ]es.<ref>{{cite journal | vauthors = Hallem EA, Nicole Fox A, Zwiebel LJ, Carlson JR | title = Olfaction: mosquito receptor for human-sweat odorant | journal = Nature | volume = 427 | issue = 6971 | pages = 212–213 | date = January 2004 | pmid = 14724626 | doi = 10.1038/427212a | bibcode = 2004Natur.427..212H| s2cid = 4419658 }}</ref><ref>{{cite journal | vauthors = Linley JR | title = Laboratory tests of the effects of ''p''-cresol and 4-methylcyclohexanol on oviposition by three species of ''Toxorhynchites'' mosquitoes | journal = Medical and Veterinary Entomology | volume = 3 | issue = 4 | pages = 347–52 | date = October 1989 | pmid = 2577519 | doi = 10.1111/j.1365-2915.1989.tb00241.x| s2cid = 1641506 }}</ref>

''p''-Cresol is a constituent of ].<ref>{{cite journal | vauthors = Talhout R, Schulz T, Florek E, van Benthem J, Wester P, Opperhuizen A | title = Hazardous compounds in tobacco smoke | journal = International Journal of Environmental Research and Public Health | volume = 8 | issue = 2 | pages = 613–28 | date = February 2011 | pmid = 21556207 | pmc = 3084482 | doi = 10.3390/ijerph8020613| doi-access = free }}</ref>

=== In other species ===
''p''-Cresol is a major component in ] odor.<ref>{{Cite web | first = Brendan | last = Borrell | date = 5 March 2009 | url = http://www.sciam.com/article.cfm?id=why-study-pig-odor | title = Why study pig odor? | work = Scientific American | access-date = 9 March 2009 | archive-date = 20 March 2021 | archive-url = https://web.archive.org/web/20210320042122/https://www.scientificamerican.com/article/why-study-pig-odor/ | url-status = live }}</ref> Temporal glands secretion examination showed the presence of phenol and ''p''-cresol during ] in male ]s.<ref>{{cite journal | vauthors = Rasmussen LE, Perrin TE | title = Physiological correlates of musth: lipid metabolites and chemical composition of exudates | journal = Physiology & Behavior | volume = 67 | issue = 4 | pages = 539–49 | date = October 1999 | pmid = 10549891 | doi = 10.1016/S0031-9384(99)00114-6| s2cid = 21368454 }}</ref><ref>{{cite journal |title=Musth in elephants |first1=Deepa |last1=Ananth | name-list-style = vanc|journal=Zoos' Print Journal |volume=15 |issue=5 |pages=259–62 |doi=10.11609/jott.zpj.14.4.259-62|date=May 2000 |doi-access=free}}</ref> It is one of the very few compounds to attract the ] '']'' and has been used to capture and study the species.<ref>{{cite journal |vauthors=Williams NH, Whitten WM |date=June 1983 |title=Orchid Floral Fragrances and Male Euglossine Bees: Methods and Advances in the Last Sesquidecade |journal=Biological Bulletin |volume=164 |issue=3 |pages=355–95 |jstor=1541248 |doi=10.2307/1541248 |url=https://www.biodiversitylibrary.org/part/35261 |access-date=2021-11-10 |archive-date=2020-06-05 |archive-url=https://web.archive.org/web/20200605121541/https://www.biodiversitylibrary.org/part/35261 |url-status=live }}</ref> ''p''-Cresol is a component found in ] urine during ] that can elicit the ].<ref>{{cite journal | vauthors = Būda V, Mozūraitis R, Kutra J, Borg-Karlson AK | title = ''p''-Cresol: a sex pheromone component identified from the estrous urine of mares | journal = Journal of Chemical Ecology | volume = 38 | issue = 7 | pages = 811–3 | date = July 2012 | pmid = 22592336 | doi = 10.1007/s10886-012-0138-2| s2cid = 14558317 }}</ref>

== References ==
{{Reflist}}

{{DEFAULTSORT:Cresol, p-}}
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