| 词条 | P-Cresol |
| 释义 |
| verifiedrevid = 477506207 | Name = p-Cresol | ImageFile = Para-cresol-horizontal-2D-skeletal.png | ImageName = Skeletal formula of para-cresol | ImageFile1 = p-cresol-spaceFilling.png | ImageSize1 = 150px | ImageName1 = 3D model of p-cresol | IUPACName = 4-Methylphenol | OtherNames = 4-Hydroxytoluene, p-Hydroxytoluene, p-Methylphenol, 4-Cresol, p- acid, 1-Hydroxy-4-methylbenzene |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 106-44-5 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 16645 | RTECS = GO6475000 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01688 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 1MXY2UM8NV | SMILES = Cc1ccc(O)cc1 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 17847 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C01468 | ChemSpiderID = 13839082 | PubChem = 2879 | EC_number = 203-398-6 | Beilstein = 1305151 | 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = IWDCLRJOBJJRNH-UHFFFAOYSA-N |Section2={{Chembox Properties | Appearance = colorless prismatic crystals | Formula = C7H8O | MolarMass = 108.13 | BoilingPtC = 201.8 | MeltingPtC = 35.5 | Density = 1.0347 g/ml | RefractIndex = 1.5395 | Solubility = 2.4 g/100 ml at 40 °C 5.3 g/100 ml at 100 °C | Solubility1 = fully miscible | Solvent1 = ethanol | Solubility2 = fully miscible | Solvent2 = diethyl ether | Viscosity = | Dipole = | VaporPressure = 0.11 mmHg (25°C)[1] | MagSus = -72.1·10−6 cm3/mol |Section7={{Chembox Hazards | ExternalSDS = External MSDS | FlashPtC = 86.1 | MainHazards = May be fatal if swallowed, inhaled, or absorbed through skin. | NFPA-H = 3 | NFPA-F = 1 | NFPA-R = 0 | NFPA-S = | GHSPictograms = {{GHS05}}{{GHS06}}{{GHS08}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|201|311|314|318|351|370|372|373|401|412}} | 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/m3) [skin][1] | ExploLimits = 1.1%-?[1] | IDLH = 250 ppm[1] | LD50 = 207 mg/kg (oral, rat, 1969) 1800 mg/kg (oral, rat, 1944) 344 mg/kg (oral, mouse)[2] | REL = TWA 2.3 ppm (10 mg/m3)[1] |Section8={{Chembox Related | OtherFunction_label = phenols | OtherFunction = o-cresol, m-cresol, phenol }}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] ProductionTogether 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. p-Cresol is currently prepared industrially mainly by a two step route beginning with the sulfonation of toluene: CH3C6H5 + H2SO4 → CH3C6H4SO3H + H2O Base 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 propylene to give p-cymene, which can be oxidatively dealkylated in a manner similar to the Cumene process.[3] Applicationsp-Cresol is consumed mainly in the production of antioxidants, e.g., 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]Natural occurrencesIn humansp-Cresol is produced by bacterial fermentation of protein in the human large intestine. It is excreted in the feces and urine,[4] and is a component of human sweat that is attractive to female mosquitoes.[5][6]p-Cresol is a constituent of tobacco smoke.[7]In other speciesp-Cresol is a major component in pig odor.[8]Temporal glands secretion examination showed the presence of phenol and p-cresol during musth in male elephants.[9][10] p-Cresol is one of the very few compounds to attract the orchid bee Euglossa cyanura and has been used to capture and study the species.[11]References1. ^1 2 3 4 {{PGCH|0156}} {{DEFAULTSORT:Cresol, p-}}2. ^{{IDLH|cresol|Cresol (o, m, p isomers)}} 3. ^1 2 {{cite book |doi=10.1002/14356007.a08_025 |chapter=Cresols and Xylenols |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2000 |last1=Fiege |first1=Helmut |isbn=3-527-30673-0}}{{pn|date=February 2015}} 4. ^{{cite journal|last1=Hamer|first1=H. M.|last2=De Preter|first2=V.|last3=Windey|first3=K.|last4=Verbeke|first4=K.|title=Functional analysis of colonic bacterial metabolism: relevant to health?|journal=AJP: Gastrointestinal and Liver Physiology|volume=302|issue=1|year=2011|pages=G1–G9|issn=0193-1857|doi=10.1152/ajpgi.00048.2011|pmc=3345969}} 5. ^{{cite journal |doi=10.1038/427212a|pmid=14724626|title=Olfaction: Mosquito receptor for human-sweat odorant|journal=Nature|volume=427|issue=6971|pages=212–3|year=2004|last1=Hallem|first1=Elissa A.|last2=Nicole Fox|first2=A.|last3=Zwiebel|first3=Laurence J.|last4=Carlson|first4=John R.|bibcode=2004Natur.427..212H}} 6. ^{{cite journal |doi=10.1111/j.1365-2915.1989.tb00241.x|pmid=2577519|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|year=1989|last1=Linley|first1=John R.}} 7. ^{{cite journal|last1=Talhout|first1=Reinskje|last2=Schulz|first2=Thomas|last3=Florek|first3=Ewa|last4=Van Benthem|first4=Jan|last5=Wester|first5=Piet|last6=Opperhuizen|first6=Antoon|title=Hazardous Compounds in Tobacco Smoke|journal=International Journal of Environmental Research and Public Health|volume=8|issue=12|year=2011|pages=613–628|issn=1660-4601|doi=10.3390/ijerph8020613|pmid=21556207|pmc=3084482}} 8. ^http://www.sciam.com/article.cfm?id=why-study-pig-odor{{full|date=February 2015}} 9. ^{{cite journal |doi=10.1016/S0031-9384(99)00114-6|pmid=10549891|title=Physiological Correlates of Musth: Lipid Metabolites and Chemical Composition of Exudates|journal=Physiology & Behavior|volume=67|issue=4|pages=539–49|year=1999|last1=Rasmussen|first1=L.E.L|last2=Perrin|first2=Thomas E}} 10. ^{{cite journal |title=Musth in elephants |first1=Deepa |last1=Ananth |journal=Zoos' Print Journal |volume=15 |issue=5 |pages=259–62 |url=http://www.zoosprint.org/ZooPrintJournal/2000/May/259-262.pdf |doi=10.11609/jott.zpj.14.4.259-62}} 11. ^{{cite journal |first1=Norris H. |last1=Williams |first2=W. Mark |last2=Whitten |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}} 2 : Cresols|Alkylphenols |
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