Dianethole

Dianethole is a naturally occurring organic compound that is found in anise and fennel.[1][2] It is a dimeric polymer of anethole.[1][3][4] It has estrogenic activity, and along with anethole and photoanethole, may be responsible for the estrogenic effects of anise and fennel.[1][5][6][7][8] These compounds bear resemblance to the estrogens stilbene and diethylstilbestrol, which may explain their estrogenic activity.[1][9] In fact, it is said that diethylstilbestrol and related drugs were originally modeled after dianethole and photoanethole.[1][10]

Dianethole
Names
IUPAC name
1-Methoxy-4-[(4E)-5-(4-methoxyphenyl)-4-methylpent-4-en-2-yl]benzene[1]
Identifiers
3D model (JSmol)
InChI
  • InChI=1/C20H24O2/c1-15(14-17-5-9-19(21-3)10-6-17)13-16(2)18-7-11-20(22-4)12-8-18/h5-12,14,16H,13H2,1-4H3/b15-14+[1]
    Key: \WTUWQYSUWFERGB-CCEZHUSRNA-N[1]
SMILES
  • C1=CC(=CC=C1C(C)CC=CC2=CC=C(C=C2)OC)OC
Properties
Chemical formula
 C19H22O2[1]
Molar mass 282.3768 g/mol[1]
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. Albert-Puleo, Michael (1980). "Fennel and anise as estrogenic agents". Journal of Ethnopharmacology. 2 (4): 337–344. doi:10.1016/S0378-8741(80)81015-4. ISSN 0378-8741. PMID 6999244.
  2. James A. Duke (10 November 2000). Handbook of Phytochemical Constituents of GRAS Herbs and Other Economic Plants: Herbal Reference Library. CRC Press. pp. 257, 458. ISBN 978-0-8493-3865-6.
  3. K. V. Peter (21 September 2012). Handbook of Herbs and Spices. Elsevier Science. pp. 142–. ISBN 978-0-85709-568-8.
  4. Finn Sandberg; Desmond Corrigan (4 October 2001). Natural Remedies: Their Origins and Uses. CRC Press. pp. 124–. ISBN 978-0-415-27202-5.
  5. Steven Foster (12 November 2012). Tyler's Honest Herbal: A Sensible Guide to the Use of Herbs and Related Remedies. Routledge. pp. 157–. ISBN 978-1-136-74501-0.
  6. Thomas DeBaggio; Arthur O. Tucker (1 September 2009). The Encyclopedia of Herbs: A Comprehensive Reference to Herbs of Flavor and Fragrance. Timber Press. pp. 240–. ISBN 978-1-60469-134-4.
  7. Ikhlas A. Khan; Ehab A. Abourashed (21 September 2011). Leung's Encyclopedia of Common Natural Ingredients: Used in Food, Drugs and Cosmetics. John Wiley & Sons. pp. 3–. ISBN 978-1-118-21306-3.
  8. T. K. Lim (2 February 2013). Edible Medicinal And Non-Medicinal Plants: Volume 5, Fruits. Springer Science & Business Media. pp. 50–. ISBN 978-94-007-5653-3.
  9. Kerry Bone; Simon Y. Mills (2013). Principles and Practice of Phytotherapy,Modern Herbal Medicine,2: Principles and Practice of Phytotherapy. Elsevier Health Sciences. pp. 559–. ISBN 978-0-443-06992-5.
  10. Jordan, V. C. (2009). "A Century of Deciphering the Control Mechanisms of Sex Steroid Action in Breast and Prostate Cancer: The Origins of Targeted Therapy and Chemoprevention". Cancer Research. 69 (4): 1243–1254. doi:10.1158/0008-5472.CAN-09-0029. ISSN 0008-5472. PMID 19208829.


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