Methoxyeugenol

Methoxyeugenol
Names
	IUPAC name 2,6-dimethoxy-4-prop-2-enylphenol
Identifiers
CAS Number	6627-88-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:86562;
ChEMBL	ChEMBL2059292;
ChemSpider	196968;
ECHA InfoCard	100.026.910
EC Number	229-600-2;
PubChem CID	226486;
UNII	8VF00YWP89;
CompTox Dashboard (EPA)	DTXSID30216470 ;
	InChI InChI=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 Key: FWMPKHMKIJDEMJ-UHFFFAOYSA-N;
	SMILES COC1=CC(=CC(=C1O)OC)CC=C;
Properties
Chemical formula	C11H14O3
Molar mass	194.230 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319, H335
Precautionary statements	P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methoxyeugenol is a natural occurring allylbenzene and eugenol derivative. It is found in toxic Japanese star anise pericarp^[1] and leaves.^[2] as well as in nutmeg crude extract but not in nutmeg essential oil.^[3] It also activates PPAR-gamma in vivo.^[4]

References

^ Howes MJ, Kite GC, Simmonds MS (July 2009). "Distinguishing chinese star anise from Japanese star anise using thermal desorption-gas chromatography-mass spectrometry". Journal of Agricultural and Food Chemistry. 57 (13): 5783–9. doi:10.1021/jf9009153. PMID 19507874.
^ Koeduka T, Sugimoto K, Watanabe B, Someya N, Kawanishi D, Gotoh T, Ozawa R, Takabayashi J, Matsui K, Hiratake J (March 2014). "Bioactivity of natural O-prenylated phenylpropenes from Illicium anisatum leaves and their derivatives against spider mites and fungal pathogens". Plant Biology. 16 (2): 451–6. doi:10.1111/plb.12054. PMID 23889818.
^ Oo T, Saiboonjan B, Srijampa S, Srisrattakarn A, Sutthanut K, Tavichakorntrakool R, Chanawong A, Lulitanond A, Tippayawat P (July 2021). "Inhibition of Bacterial Efflux Pumps by Crude Extracts and Essential Oil from Myristica fragrans Houtt. (Nutmeg) Seeds against Methicillin-Resistant Staphylococcus aureus". Molecules (Basel, Switzerland). 26 (15): 4662. doi:10.3390/molecules26154662. PMC 8348620. PMID 34361815.
^ 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 (July 2021). "Methoxyeugenol deactivates hepatic stellate cells and attenuates liver fibrosis and inflammation through a PPAR-ɣ and NF-kB mechanism". Journal of Ethnopharmacology. 280: 114433. doi:10.1016/j.jep.2021.114433. hdl:10923/18540. PMID 34280502.

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[pmid19507874-1] Howes MJ, Kite GC, Simmonds MS (July 2009). "Distinguishing chinese star anise from Japanese star anise using thermal desorption-gas chromatography-mass spectrometry". Journal of Agricultural and Food Chemistry. 57 (13): 5783–9. doi:10.1021/jf9009153. PMID 19507874.

[pmid23889818-2] Koeduka T, Sugimoto K, Watanabe B, Someya N, Kawanishi D, Gotoh T, Ozawa R, Takabayashi J, Matsui K, Hiratake J (March 2014). "Bioactivity of natural O-prenylated phenylpropenes from Illicium anisatum leaves and their derivatives against spider mites and fungal pathogens". Plant Biology. 16 (2): 451–6. doi:10.1111/plb.12054. PMID 23889818.

[pmid34361815-3] Oo T, Saiboonjan B, Srijampa S, Srisrattakarn A, Sutthanut K, Tavichakorntrakool R, Chanawong A, Lulitanond A, Tippayawat P (July 2021). "Inhibition of Bacterial Efflux Pumps by Crude Extracts and Essential Oil from Myristica fragrans Houtt. (Nutmeg) Seeds against Methicillin-Resistant Staphylococcus aureus". Molecules (Basel, Switzerland). 26 (15): 4662. doi:10.3390/molecules26154662. PMC 8348620. PMID 34361815.

[pmid34280502-4] 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 (July 2021). "Methoxyeugenol deactivates hepatic stellate cells and attenuates liver fibrosis and inflammation through a PPAR-ɣ and NF-kB mechanism". Journal of Ethnopharmacology. 280: 114433. doi:10.1016/j.jep.2021.114433. hdl:10923/18540. PMID 34280502.

[1]

[2]

[3]

[4]

See also

References