Paeonol

{{Chembox | ImageFile = Paeonol.svg | ImageSize = 180px | ImageAlt = Chemical structure of paeonol | PIN = 1-(2-Hydroxy-4-methoxyphenyl)ethan-1-one | OtherNames = 2'-Hydroxy-4'-methoxyacetophenone |Section1={{Chembox Identifiers | CASNo = 552-41-0 | CASNo_Ref = <ref>{{Cite web | url=http://www.chemblink.com/products/552-41-0.htm |title = CAS # 552-41-0, Paeonol, 2'-Hydroxy-4'-methoxyacetophenone, 1-(2-hydroxy-4-methoxyphenyl)ethan-1-one}}</ref> | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 3R834EPI82 | PubChem = 11092 | SMILES = CC(=O)C1=C(C=C(C=C1)OC)O | ChemSpiderID = 10621 | InChI = 1/C9H10O3/c1-6(10)8-4-3-7(12-2)5-9(8)11/h3-5,11H,1-2H3 | InChIKey = UILPJVPSNHJFIK-UHFFFAOYAG | StdInChI = 1S/C9H10O3/c1-6(10)8-4-3-7(12-2)5-9(8)11/h3-5,11H,1-2H3 | StdInChIKey = UILPJVPSNHJFIK-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=9|H=10|O=3 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''Paeonol''' is a phenolic compound found in peonies<ref>{{cite journal | last1 = Zhang | first1 = L. | last2 = Li | first2 = D. C. | last3 = Liu | first3 = L. F. | year = 2019 | title = Paeonol: pharmacological effects and mechanisms of action | url = | journal = International immunopharmacology | volume = 72 | issue = | pages = 413–421 | doi = 10.1016/j.intimp.2019.04.033 | pmid = 31030097 }}</ref> such as ''Paeonia suffruticosa'' (moutan cortex),<ref name=Fukuhara>{{Cite journal|title=Paeonol: a bio-antimutagen isolated from a crude drug, moutan cortex|vauthors=Fukuhara Y, Yoshida D|name-list-style=amp |journal= Agricultural and Biological Chemistry|year= 1987| volume= 51|issue= 5| pages= 1441–1442|id= {{INIST|7609719}}|doi=10.1271/bbb1961.51.1441 |doi-access= free}}</ref><ref>{{Cite journal|doi=10.1002/bmc.259|title=Determination of paeonol in rat plasma by high-performance liquid chromatography and its application to pharmacokinetic studies following oral administration of Moutan cortex decoction|year=2003|last1=Wu|first1=Xinan|last2=Chen|first2=Hongli|last3=Chen|first3=Xingguo|last4=Hu|first4=Zhide|journal=Biomedical Chromatography|volume=17|issue=8|pages=504–8|pmid=14648606}}</ref> in ''Arisaema erubescens'',<ref>{{Cite journal|title=Isolation of paeonol from ''Arisaema erubescens''|vauthors= Ducki S, Hadfield JA, Lawrence NJ, Zhang X, McGown AT|name-list-style= amp|journal= Planta Medica|year= 1995| volume =61|id= {{INIST|2920867}}|issue =6|doi=10.1055/s-2006-959390|pmid=8824957|pages=586–587 }}</ref> and in ''Dioscorea japonica''.<ref name=Miyazama>{{Cite journal|doi=10.1021/jf950792u|title=Antimutagenic Activity of (+)-β-Eudesmol and Paeonol from ''Dioscorea japonica''|year=1996|last1=Miyazawa|first1=Mitsuo|last2=Shimamura|first2=Hideo|last3=Nakamura|first3=Sei-Ichi|last4=Kameoka|first4=Hiromu|journal=Journal of Agricultural and Food Chemistry|volume=44|issue=7|pages=1647–1650|bibcode=1996JAFC...44.1647M }}</ref> It is a chemical compound found in some traditional Chinese medicines.<ref>{{Cite journal|doi=10.1016/j.chroma.2005.11.023|title=Development of microwave-assisted extraction followed by headspace single-drop microextraction for fast determination of paeonol in traditional Chinese medicines|year=2006|last1=Deng|first1=Chunhui|last2=Yao|first2=Ning|last3=Wang|first3=Ben|last4=Zhang|first4=Xiangmin|journal=Journal of Chromatography A|volume=1103|pages=15–21|pmid=16309693|issue=1}}</ref>

== Biological effects == A number of biological effects of paeonol ''in vitro'' or in animal models have been observed. Paeonol increases levels of cortical cytochrome oxidase and vascular actin and improves behavior in a rat model of Alzheimer's disease.<ref>{{Cite journal|pmid=21377451|doi=10.1016/j.brainres.2011.02.064|title=Paeonol increases levels of cortical cytochrome oxidase and vascular actin and improves behavior in a rat model of Alzheimer's disease|year=2011|last1=Zhou|first1=Jun|last2=Zhou|first2=Li|last3=Hou|first3=Deren|last4=Tang|first4=Jiaochun|last5=Sun|first5=Juanjuan|last6=Bondy|first6=Stephen C.|journal=Brain Research|volume=1388|pages=141–7|s2cid=12668336 |url=https://cloudfront.escholarship.org/dist/prd/content/qt1qs126j6/qt1qs126j6.pdf}}</ref> Paeonol also reduced cerebral infarction involving the superoxide anion and microglia activation in ischemia-reperfusion injured rats.<ref>{{Cite journal|doi=10.1016/j.jep.2005.12.027|title=Paeonol reduced cerebral infarction involving the superoxide anion and microglia activation in ischemia-reperfusion injured rats|year=2006|last1=Hsieh|first1=Ching-Liang|last2=Cheng|first2=Chin-Yi|last3=Tsai|first3=Tung-Hu|last4=Lin|first4=I-Hsin|last5=Liu|first5=Chung-Hsiang|last6=Chiang|first6=Su-Yin|last7=Lin|first7=Jaung-Geng|last8=Lao|first8=Chih-Jui|last9=Tang|first9=Nou-Ying|journal=Journal of Ethnopharmacology|volume=106|issue=2|pages=208–15|pmid=16458462}}</ref>

Paeonol shows antimutagenic activities.<ref name=Fukuhara/><ref name=Miyazama/> It also has anti-inflammatory and analgesic effects in carrageenan-evoked thermal hyperalgesia.<ref>{{Cite journal|doi=10.1038/sj.bjp.0705360|title=Anti-inflammatory and analgesic effects of paeonol in carrageenan-evoked thermal hyperalgesia|year=2003|last1=Chou|first1=Tz-Chong|journal=British Journal of Pharmacology|volume=139|issue=6|pages=1146–52|pmid=12871833|pmc=1573952}}</ref> Paeonol inhibits anaphylactic reaction by regulating histamine and TNF-α.<ref>{{Cite journal|doi=10.1016/j.intimp.2003.12.013|title=Paeonol inhibits anaphylactic reaction by regulating histamine and TNF-α|year=2004|last1=Kim|first1=Sung Hoon|last2=Kim|first2=Seung-Ae|last3=Park|first3=Mi-Kyung|last4=Kim|first4=Seung-Hyung|last5=Park|first5=Young-Doo|last6=Na|first6=Ho-Jeong|last7=Kim|first7=Hyung-Min|last8=Shin|first8=Min-Kyu|last9=Ahn|first9=Kyoo-Seok|journal=International Immunopharmacology|volume=4|issue=2|pages=279–87|pmid=14996419}}</ref>

Paeonol has weak MAO-A and MAO-B inhibiting effects with IC₅₀ values of 54.6 μM and 42.5 μM respectively.<ref name="Konga2004">{{cite journal |title=Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones |journal=Journal of Ethnopharmacology |volume=91 |issue=2–3 |year=2004 |pages=351–355 |doi=10.1016/j.jep.2004.01.013 |last1=Kong |first1=L.D. |last2=Cheng |first2=Christopher H.K. |last3=Tan |first3=R.X. |pmid=15120460 }}</ref>

== Metal complex == Metal complexes of paeonol shows tetrahedral and octahedral coordination geometry in the absence and presence of solvent pyridine respectively.<ref>{{cite journal |last1=Patel |first1=Mahesh kumar |title=Solvent effect on neutral Co (II) complexes of paeonol derivative equalitative and quantitative studies from energy frame work and Hirshfeld surface analysis |journal=Journal of Molecular Structure |volume=1196 |pages=119–131 |doi=10.1016/j.molstruc.2019.06.050 |year=2019 |bibcode=2019JMoSt1196..119P |s2cid=197231895 }}</ref>

== References == {{Reflist}}

Category:Aromatic ketones Category:O-methylated phenols