Methoxyeugenol

Methoxyeugenol is a naturall 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]

Methoxyeugenol
Methoxyeugenol
Names
IUPAC name
2,6-dimethoxy-4-prop-2-enylphenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.026.910
EC Number
  • 229-600-2
UNII
  • 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
  • COC1=CC(=CC(=C1O)OC)CC=C
Properties
C11H14O3
Molar mass 194.230 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H317, H319, H335
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

See also

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. PMID 34280502.


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