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Chemical Compound Review

Esdragol     1-methoxy-4-prop-2-enyl- benzene

Synonyms: Esdragon, Estragol, Tarragon, Terragon, Esdragole, ...
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Disease relevance of Chavicyl methyl ether

  • Estragole induced hepatocellular carcinomas by 15 months in 23 and 39% of the mice that received total doses of 4.4 and 5.2 mumoles, respectively, and lived to an age of 12 months or more [1].
  • The 2',3'-oxides of safrole and estragole and their 1'-hydroxy derivatives likewise had little or no activity for the induction of lung adenomas in female A/J mice or for the induction of tumors on repetitive injections s.c. in male Fischer rats [2].
  • Estragole was not positive in a chromosomal aberration test with V79 cells either via direct treatment, with rat liver S9 mix or with rat hepatocytes as source of metabolism [3].
  • The ex vivo UDS test led to clearly elevated DNA repair for estragole and basil oil in rats treated orally with doses up to 2 g/kg body weight [3].
  • Our results also have toxicogenetic significance, as UGT2B7 is polymorphic and could potentially result in genetic differences in glucuronidation of 1'-HE and, hence, toxicity of estragole [4].

Psychiatry related information on Chavicyl methyl ether

  • Estragole, a relatively nontoxic terpenoid ether, is an important constituent of many essential oils with widespread applications in folk medicine and aromatherapy and known to have potent local anesthetic activity [5].

High impact information on Chavicyl methyl ether


Chemical compound and disease context of Chavicyl methyl ether


Biological context of Chavicyl methyl ether

  • Feeding experiments of [2-(2)H]- and [4'-(2)H]phenylalanine in Artemisia dracunculus validate the hypothesis that the marked difference in deuterium content at the natural abundance level between the aromatic carbons of estragole (1) is due to an NIH shift during the hydroxylation of the benzene ring [11].
  • Effects of estragole on the compound action potential of the rat sciatic nerve [5].
  • At 4.0 mM, estragole significantly altered PPA, conduction velocity, chronaxy, and rheobase (P < or = 0.05, ANOVA; N = 5) to 49.3 +/- 6.21 and 77.7 +/- 3.84, 125.9 +/- 10.43 and 116.7 +/- 4.59%, of control, respectively [5].

Anatomical context of Chavicyl methyl ether


Associations of Chavicyl methyl ether with other chemical compounds


Gene context of Chavicyl methyl ether


Analytical, diagnostic and therapeutic context of Chavicyl methyl ether


  1. Hepatocarcinogenicity of estragole (1-allyl-4-methoxybenzene) and 1'-hydroxyestragole in the mouse and mutagenicity of 1'-acetoxyestragole in bacteria. Drinkwater, N.R., Miller, E.C., Miller, J.A., Pitot, H.C. J. Natl. Cancer Inst. (1976) [Pubmed]
  2. Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. Miller, E.C., Swanson, A.B., Phillips, D.H., Fletcher, T.L., Liem, A., Miller, J.A. Cancer Res. (1983) [Pubmed]
  3. 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]
  4. Glucuronidation of 1'-hydroxyestragole (1'-HE) by human UDP-glucuronosyltransferases UGT2B7 and UGT1A9. Iyer, L.V., Ho, M.N., Shinn, W.M., Bradford, W.W., Tanga, M.J., Nath, S.S., Green, C.E. Toxicol. Sci. (2003) [Pubmed]
  5. Effects of estragole on the compound action potential of the rat sciatic nerve. Leal-Cardoso, J.H., Matos-Brito, B.G., Lopes-Junior, J.E., Viana-Cardoso, K.V., Sampaio-Freitas, A.B., Brasil, R.O., Coelho-De-Souza, A.N., Albuquerque, A.A. Braz. J. Med. Biol. Res. (2004) [Pubmed]
  6. Immunochemical identification of hepatic protein adducts derived from estragole. Wakazono, H., Gardner, I., Eliasson, E., Coughtrie, M.W., Kenna, J.G., Caldwell, J. Chem. Res. Toxicol. (1998) [Pubmed]
  7. Metabolism of allylbenzene 2',3'-oxide and estragole 2',3'-oxide in the isolated perfused rat liver. Luo, G., Guenthner, T.M. J. Pharmacol. Exp. Ther. (1995) [Pubmed]
  8. The metabolic activation and nucleic acid adducts of naturally-occurring carcinogens: recent results with ethyl carbamate and the spice flavors safrole and estragole. Miller, J.A., Miller, E.C. Br. J. Cancer (1983) [Pubmed]
  9. Mutagenicity of trans-anethole, estragole, eugenol, and safrole in the Ames Salmonella typhimurium assay. To, L.P., Hunt, T.P., Andersen, M.E. Bulletin of environmental contamination and toxicology. (1982) [Pubmed]
  10. Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction. Vassão, D.G., Gang, D.R., Koeduka, T., Jackson, B., Pichersky, E., Davin, L.B., Lewis, N.G. Org. Biomol. Chem. (2006) [Pubmed]
  11. Evidence for an NIH shift as the origin of the apparently anomalous distribution of deuterium in estragole from Artemisia dracunculus. Manitto, P., Monti, D., Speranza, G. J. Nat. Prod. (2000) [Pubmed]
  12. Effects of essential oil of Croton zehntneri, and of anethole and estragole on skeletal muscles. Albuquerque, A.A., Sorenson, A.L., Leal-Cardoso, J.H. Journal of ethnopharmacology. (1995) [Pubmed]
  13. The side-chain epoxidation and hydroxylation of the hepatocarcinogens safrole and estragole and some related compounds by rat and mouse liver microsomes. Swanson, A.B., Miller, E.C., Miller, J.A. Biochim. Biophys. Acta (1981) [Pubmed]
  14. Composition of the Essential Oil of Agastache foeniculum. Nykänen, I., Holm, Y., Hiltunen, R. Planta Med. (1989) [Pubmed]
  15. Investigation of the role of the 2',3'-epoxidation pathway in the bioactivation and genotoxicity of dietary allylbenzene analogs. Guenthner, T.M., Luo, G. Toxicology (2001) [Pubmed]
  16. Safety assessment of allylalkoxybenzene derivatives used as flavouring substances - methyl eugenol and estragole. Smith, R.L., Adams, T.B., Doull, J., Feron, V.J., Goodman, J.I., Marnett, L.J., Portoghese, P.S., Waddell, W.J., Wagner, B.M., Rogers, A.E., Caldwell, J., Sipes, I.G. Food Chem. Toxicol. (2002) [Pubmed]
  17. The metabolic disposition of [methoxy-14C]-labelled trans-anethole, estragole and p-propylanisole in human volunteers. Sangster, S.A., Caldwell, J., Hutt, A.J., Anthony, A., Smith, R.L. Xenobiotica (1987) [Pubmed]
  18. A chemical investigation by headspace SPME and GC-MS of volatile and semi-volatile terpenes in various olibanum samples. Hamm, S., Bleton, J., Connan, J., Tchapla, A. Phytochemistry (2005) [Pubmed]
  19. Determination of the chemical composition and antioxidant activity of the essential oil of Artemisia dracunculus and of the antifungal and antibacterial activities of Turkish Artemisia absinthium, A. dracunculus, Artemisia santonicum, and Artemisia spicigera essential oils. Kordali, S., Kotan, R., Mavi, A., Cakir, A., Ala, A., Yildirim, A. J. Agric. Food Chem. (2005) [Pubmed]
  20. Contact and fumigant activities of constituents of Foeniculum vulgare fruit against three coleopteran stored-product insects. Kim, D.H., Ahn, Y.J. Pest Manag. Sci. (2001) [Pubmed]
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