查看“︁偏苯三酚”︁的源代码

{{chembox|Watchedfields=changed|verifiedrevid=443865001|Name=偏三苯酚|ImageFile=Hydroxyhydrochinon.svg|ImageSize=120px|ImageName=Chemical structure of hydroxyquinol|ImageAlt=Chemical structure of hydroxyquinol|PIN=Benzene-1,2,4-triol|OtherNames=羥基氫醌<br>1,2,4-苯三酚<br>1,2,4-三羥基苯<br>4-羥基兒茶酚|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10331
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C02814
| InChIKey = GGNQRNBDZQJCCN-UHFFFAOYAX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GGNQRNBDZQJCCN-UHFFFAOYSA-N
| CASNo = 533-73-3 
| CASNo_Ref = {{cascite|correct|CAS}}= 
| CASNoOther = 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 173O8B04RD
| PubChem = 10787
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16971
| SMILES = Oc1cc(O)c(O)cc1
| InChI = 1/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H
| MeSHName = 
}}|Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>6</sub>O<sub>3</sub>
| MolarMass = 126.11 g/mol
| Appearance = 白色固體
| Density = 
| MeltingPt =
| BoilingPt =
| Solubility = 
}}}}

'''偏苯三酚'''，又稱為'''羥基氫醌 (HHQ) (英文： Hydroxyhydroquinone、Hydroxyquinol)'''<ref>{{Cite web|title=[資訊] 咖啡對血管動脈的影響取決於咖啡中綠原酸(Chlorogenic acid)與羥基氫醌(Hydroxyhydroquinone)的含量|url=http://nehrc.nhri.org.tw/foodsafety/news.php?id=153|access-date=2021-06-06|work=nehrc.nhri.org.tw|archive-date=2021-06-06|archive-url=https://web.archive.org/web/20210606094332/http://nehrc.nhri.org.tw/foodsafety/news.php?id=153}}</ref>是一種[[有机化合物|有機化合物]]。它是[[苯三酚]]三种[[同分異構#位置异构|位置异构物]]的其中之一。该化合物是一种可溶于水的無色固體，但在接觸空氣後會反應生成黑色不溶性固體。 <ref name="Ullmann">{{cite journal|last1=Fiege|first1=Helmut|last2=Heinz-Werner|first2=Voges|last3=Hamamoto|first3=Toshikazu|last4=Umemura|first4=Sumio|last5=Iwata|first5=Tadao|last6=Miki|first6=Hisaya|last7=Fujita|first7=Yasuhiro|last8=Buysch|first8=Hans-Josef|last9=Garbe|first9=Dorothea|last10=Paulus|first10=Wilfried|title=Phenol Derivatives|journal=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|location=Weinheim, Germany|doi=10.1002/14356007.a19_313|isbn=978-3527306732}}</ref>

== 製備 ==
工業上的製備方式是先以[[乙酸酐]]乙酰化[[1,4-苯醌|對苯醌]]，然后水解所產生三乙酸酯来制备。 <ref name="Ullmann"/>

在历史上，偏苯三酚則是通过[[氢氧化钾]]和对[[对苯二酚|氢醌]]的反應而产生。 <ref>{{Cite book|last=Roscoe|first=Henry|title=A treatise on chemistry, Volume 3, Part 3|year=1891|publisher=Macmillan & Co.|location=London|pages=199|url=https://books.google.com/books?id=HEY9AAAAYAAJ&q=hydroxyquinol&pg=PA199|access-date=2021-06-06|archive-date=2021-04-18|archive-url=https://web.archive.org/web/20210418225452/https://books.google.com/books?id=HEY9AAAAYAAJ&q=hydroxyquinol&pg=PA199}}</ref>也可通过[[果糖]][[失水反应|脱水]]製得。 <ref>{{Cite journal|title=Hydrothermal formation of 1,2,4-benzenetriol from 5-hydroxymethyl-2-furaldehyde and D-fructose|last=Luijkx|first=Gerard|last2=Rantwijk|first2=Fred|date=1993|journal=Carbohydrate Research|issue=1|doi=10.1016/0008-6215(93)80027-C|volume=242|pages=131–139|last3=Bekkum|first3=Herman|authorlink3=Herman van Bekkum}}</ref> <ref>{{Cite journal|title=Hydrothermal upgrading of biomass to biofuel; studies on some monosaccharide model compounds|last=Srokol|first=Zbigniew|last2=Anne-Gaëlle|first2=Bouche|date=2004|journal=Carbohydrate Research|issue=10|doi=10.1016/j.carres.2004.04.018|volume=339|pages=1717–1726|pmid=15220081|last3=Estrik|first3=Anton|last4=Strik|first4=Rob|last5=Maschmeyer|first5=Thomas|last6=Peters|first6=Joop}}</ref>

<chem>C6H12O6->3H2O + C6H6O3</chem>

== 在自然中的發現 ==
偏苯三酚是许多芳香族化合物，例如单[[氯苯酚|氯酚]]、[[二氯苯酚|二氯酚]]以及更複雜的物质如農藥[[2,4,5-三氯苯氧乙酸|2,4,5-T]]等 ，在生物降解中常見的[[中间產物]]。 <ref>{{Cite journal|title=Hydroxyquinol pathway for microbial degradation of halogenated aromatic compounds|last=Travkin, Vasili M.; Solyanikova, Inna P.; Golovleva, Ludmila A.|journal=Journal of Environmental Science and Health, Part B|issue=8|doi=10.1080/03601230600964159|year=2006|volume=41|pages=1361–1382|pmid=17090498}}</ref>羟基氫醌通常作为[[儿茶素|兒茶素]]，一種存在於植物中的天然酚（例如在土壤细菌''[[大豆慢生根瘤菌|Bradyrhizobium japonicum]]'' 中）<ref>{{Cite journal|title=Degradation of catechin by Bradyrhizobium japonicum|last=Mahadevan|first=A.|last2=Waheeta|first2=Hopper|date=1997|journal=Biodegradation|issue=3|doi=10.1023/A:1008254812074|volume=8|pages=159–165}}</ref>的[[生物降解]]产物而存在於自然界中。羟基氫醌亦是某些生物体的代謝過程中所產生的[[代謝產物|代谢物]]，例如 [[羟基喹啉1,2-双加氧酶|1,2,4-苯三酚 1,2-雙加氧酶]]這一种[[酶]]就使用偏苯三酚作為[[底物]]與[[氧氣]]反應而产生[[3-羟基-顺，顺-粘康酸盐|3-羟基-顺,顺-粘康酸]]。

== 参考資料 ==
{{Reflist}}
{{芳香族化合物}}

[[Category:偏苯三酚|*]]