methoxyeugenol

{{Chembox

| ImageFile = Methoxyeugenol.svg

| ImageFile_Ref =

| ImageAlt = Methoxyeugenol

| ImageSize = 180

| IUPACName = 2,6-dimethoxy-4-prop-2-enylphenol

| Section1={{Chembox Identifiers

| index_label =

| CASNo = 6627-88-9

| CASNo_Ref = {{Cascite|correct|CAS}}

| ChemSpiderID = 196968

| ChemSpiderID_Ref =

| ChEBI = 86562

| ChEMBL = 2059292

| EC_number = 229-600-2

| EC_number_Comment =

| StdInChI = 1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3

| StdInChIKey = FWMPKHMKIJDEMJ-UHFFFAOYSA-N

| SMILES = COC1=CC(=CC(=C1O)OC)CC=C

| PubChem = 226486

| UNII = 8VF00YWP89

| UNII_Ref =

}}

|Section2={{Chembox Properties

| C = 11 | H = 14 | O = 3

}}

|Section7={{Chembox Hazards

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|317|319|335}}

| PPhrases = {{P-phrases|261|264|271|272|280|302+352|304+340|305+351+338|312|321|332+313|333+313|337+313|362|363|403+233|405|501}}

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Methoxyeugenol is a natural occurring allylbenzene and eugenol derivative. It is found in toxic Japanese star anise pericarp{{cite journal |vauthors=Howes MJ, Kite GC, Simmonds MS |title=Distinguishing chinese star anise from Japanese star anise using thermal desorption-gas chromatography-mass spectrometry |journal=Journal of Agricultural and Food Chemistry |volume=57 |issue=13 |pages=5783–9 |date=July 2009 |pmid=19507874 |doi=10.1021/jf9009153 |url= |issn=}} and leaves.{{cite journal |vauthors=Koeduka T, Sugimoto K, Watanabe B, Someya N, Kawanishi D, Gotoh T, Ozawa R, Takabayashi J, Matsui K, Hiratake J |title=Bioactivity of natural O-prenylated phenylpropenes from Illicium anisatum leaves and their derivatives against spider mites and fungal pathogens |journal=Plant Biology |volume=16 |issue=2 |pages=451–6 |date=March 2014 |pmid=23889818 |doi=10.1111/plb.12054 |url= |issn=}} as well as in nutmeg crude extract but not in nutmeg essential oil.{{cite journal |vauthors=Oo T, Saiboonjan B, Srijampa S, Srisrattakarn A, Sutthanut K, Tavichakorntrakool R, Chanawong A, Lulitanond A, Tippayawat P |title=Inhibition of Bacterial Efflux Pumps by Crude Extracts and Essential Oil from Myristica fragrans Houtt. (Nutmeg) Seeds against Methicillin-Resistant Staphylococcus aureus |journal=Molecules (Basel, Switzerland) |volume=26 |issue=15 |date=July 2021 |page=4662 |pmid=34361815 |pmc=8348620 |doi=10.3390/molecules26154662 |url= |issn=|doi-access=free }} It also activates PPAR-gamma in vivo.{{cite journal |vauthors=de Souza Basso B, Haute GV, OrtegaRibera M, Luft C, Antunes GL, Bastos MS, Carlessi LP, Levorse VG, Cassel E, Donadio MV, Santarém ER, GraciaSancho J, Rodrigues de Oliveira J |title=Methoxyeugenol deactivates hepatic stellate cells and attenuates liver fibrosis and inflammation through a PPAR-ɣ and NF-kB mechanism |journal=Journal of Ethnopharmacology |volume=280 |issue= |pages=114433 |date=July 2021 |pmid=34280502 |doi=10.1016/j.jep.2021.114433 |url= |issn=|doi-access=free |hdl=10923/18540 |hdl-access=free }}