Dianethole

Dianethole
Names
IUPAC name 1-Methoxy-4-benzene
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+Key: \WTUWQYSUWFERGB-CCEZHUSRNA-N
SMILES
  • C1=CC(=CC=C1C(C)CC=CC2=CC=C(C=C2)OC)OC
Properties
Chemical formula C19H22O2
Molar mass 282.3768 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

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.

See also

References

  1. ^ a b c d e f g h i j 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.
Estrogen receptor modulators
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
  • Coregulator-binding modulators: ERX-11
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
See also Receptor/signaling modulators Estrogens and antiestrogens Androgen receptor modulators Progesterone receptor modulators List of estrogens


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