Methoxyeugenol

Methoxyeugenol

Names
IUPAC name 2,6-dimethoxy-4-prop-2-enylphenol
Identifiers
CAS Number	6627-88-9  Y
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]

See also

• Acetyleugenol

References

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.
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.
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.
4. 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.