Article · Wikipedia archive · Last revised Jul 16, 2026

Dianethole

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

Last revised
Jul 16, 2026
Read time
≈ 2 min
Length
384 w
Citations
17
Source
Wikipedia ↗
Dianethole
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Names
IUPAC name
1-Methoxy-4-[(4E)-5-(4-methoxyphenyl)-4-methylpent-4-en-2-yl]benzene1
Identifiers
3D model (JSmol)
  • InChI=1S/C19H22O2/c1-15(17-9-13-19(21-3)14-10-17)5-4-6-16-7-11-18(20-2)12-8-16/h4,6-15H,5H2,1-3H3
    Key: NWLMIETUAKULHS-UHFFFAOYSA-N
  • C1=CC(=CC=C1C(C)CC=CC2=CC=C(C=C2)OC)OC
Properties
C19H22O21
Molar mass 282.3768 g/mol1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dianethole is a naturally occurring organic compound that is found in anise and fennel.12 It is a dimeric polymer of anethole.134 It has estrogenic activity, and along with anethole and photoanethole, may be responsible for the estrogenic effects of anise and fennel.15678 These compounds bear resemblance to the estrogens stilbene and diethylstilbestrol, which may explain their estrogenic activity.19 In fact, it is said that diethylstilbestrol and related drugs were originally modeled after dianethole and photoanethole.110

See also

See also

References

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.