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Chemical Compound Review

ANETHOLE     1-methoxy-4-[(E)-prop-1- enyl]benzene

Synonyms: Anethol, Monasirup, Aniskampfer, Isoestragole, E-anethole, ...
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Disease relevance of NSC4018


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Chemical compound and disease context of NSC4018


Biological context of NSC4018


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Gene context of NSC4018


Analytical, diagnostic and therapeutic context of NSC4018

  • Identification and quantitation of a metabolite of anethol dithiolthione in rat and mouse urine using high-performance liquid chromatography [20].
  • The diol metabolites were isolated by HPLC from the urine of rats administered [1'-14C] trans-anethole and their stereochemistry determined after derivatization to their camphanyl esters [16].
  • The influence of dose size on the metabolic fate of the naturally occurring food flavouring trans-anethole has been investigated in human volunteers, using the [methoxy-14C]-labelled compound [21].
  • Metabolism of the monoterpenoid thymol and the phenylpropanoid trans-anethole, both constituents of essential oils, was investigated following topical and oral administration of the compounds to the tobacco cutworm (Spodoptera litura) and the cabbage looper (Trichoplusia ni) [17].
  • The essential oil characterization by gas liquid chromatography revealed that the level of anethol was significantly enhanced on mycorrhization [22].


  1. The trans-anethole degradation pathway in an Arthrobacter sp. Shimoni, E., Baasov, T., Ravid, U., Shoham, Y. J. Biol. Chem. (2002) [Pubmed]
  2. New studies on trans-anethole oxide and trans-asarone oxide. Kim, S.G., Liem, A., Stewart, B.C., Miller, J.A. Carcinogenesis (1999) [Pubmed]
  3. Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells. Nakagawa, Y., Suzuki, T. Biochem. Pharmacol. (2003) [Pubmed]
  4. Pathways of metabolism of [1'-14C]-trans-anethole in the rat and mouse. Bounds, S.V., Caldwell, J. Drug Metab. Dispos. (1996) [Pubmed]
  5. Chemical and transient spectroscopic evidence for C2-C3 cleavage of 2,3-diaryloxetane radical cations. Miranda, M.A., Izquierdo, M.A. Chem. Commun. (Camb.) (2003) [Pubmed]
  6. Spontaneous hydrolysis reactions of cis- and trans-beta-methyl-4-methoxystyrene oxides (Anethole oxides): buildup of trans-anethole oxide as an intermediate in the spontaneous reaction of cis-anethole oxide. Mohan, R.S., Gavardinas, K., Kyere, S., Whalen, D.L. J. Org. Chem. (2000) [Pubmed]
  7. Genotoxicity of trans-anethole in vitro. Gorelick, N.J. Mutat. Res. (1995) [Pubmed]
  8. The genotoxic potential in vitro and in vivo of the allyl benzene etheric oils estragole, basil oil and trans-anethole. Müller, L., Kasper, P., Müller-Tegethoff, K., Petr, T. Mutat. Res. (1994) [Pubmed]
  9. The mutagenicities of safrole, estragole, eugenol, trans-anethole, and some of their known or possible metabolites for Salmonella typhimurium mutants. Swanson, A.B., Chambliss, D.D., Blomquist, J.C., Miller, E.C., Miller, J.A. Mutat. Res. (1979) [Pubmed]
  10. Anti-genotoxicity of trans-anethole and eugenol in mice. Abraham, S.K. Food Chem. Toxicol. (2001) [Pubmed]
  11. Effects of the naturally occurring alkenylbenzenes eugenol and trans-anethole on drug-metabolizing enzymes in the rat liver. Rompelberg, C.J., Verhagen, H., van Bladeren, P.J. Food Chem. Toxicol. (1993) [Pubmed]
  12. The FEMA GRAS assessment of trans-anethole used as a flavouring substance. Flavour and Extract Manufacturer's Association. Newberne, P., Smith, R.L., Doull, J., Goodman, J.I., Munro, I.C., Portoghese, P.S., Wagner, B.M., Weil, C.S., Woods, L.A., Adams, T.B., Lucas, C.D., Ford, R.A. Food Chem. Toxicol. (1999) [Pubmed]
  13. Molecular and pharmacological analysis of an octopamine receptor from American cockroach and fruit fly in response to plant essential oils. Enan, E.E. Arch. Insect Biochem. Physiol. (2005) [Pubmed]
  14. Fumigant activity of (E)-anethole identified in Illicium verum fruit against Blattella germanica. Chang, K.S., Ahn, Y.J. Pest Manag. Sci. (2002) [Pubmed]
  15. DPPH radical-scavenging effect of several phenylpropanoid compounds and their glycoside derivatives. Tominaga, H., Kobayashi, Y., Goto, T., Kasemura, K., Nomura, M. Yakugaku Zasshi (2005) [Pubmed]
  16. Stereochemical aspects of the hydration of trans-anethole epoxide in the rat. Ishida, T., Bounds, S.V., Caldwell, J. Chirality. (1995) [Pubmed]
  17. Metabolism of thymol and trans-anethole in larvae of Spodoptera litura and Trichoplusia ni (Lepidoptera: Noctuidae). Passreiter, C.M., Wilson, J., Andersen, R., Isman, M.B. J. Agric. Food Chem. (2004) [Pubmed]
  18. Plant extracts affect in vitro rumen microbial fermentation. Busquet, M., Calsamiglia, S., Ferret, A., Kamel, C. J. Dairy Sci. (2006) [Pubmed]
  19. Effects of essential oils from fennel (Foeniculi aetheroleum) and caraway (Carvi aetheroleum) in pigs. Sch??ne, F., Vetter, A., Hartung, H., Bergmann, H., Biert??mpfel, A., Richter, G., M??ller, S., Breitschuh, G. Journal of animal physiology and animal nutrition (2006) [Pubmed]
  20. Identification and quantitation of a metabolite of anethol dithiolthione in rat and mouse urine using high-performance liquid chromatography. Masoud, A.N., Bueding, E. J. Chromatogr. (1983) [Pubmed]
  21. Influence of dose size on the disposition of trans-[methoxy-14C]anethole in human volunteers. Caldwell, J., Sutton, J.D. Food Chem. Toxicol. (1988) [Pubmed]
  22. Improved growth and essential oil yield and quality in Foeniculum vulgare mill on mycorrhizal inoculation supplemented with P-fertilizer. Kapoor, R., Giri, B., Mukerji, K.G. Bioresour. Technol. (2004) [Pubmed]
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