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Photoanethole

From Wikipedia, the free encyclopedia
Photoanethole
Names
IUPAC name
1-Methoxy-4-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
Other names
Bianisal; Bianisylidene;p,p′-Dimethoxystilbene; 4,4′-Dimethoxystilbene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C16H16O2/c1-17-15-9-5-13(6-10-15)3-4-14-7-11-16(18-2)12-8-14/h3-12H,1-2H3/b4-3+
    Key: CAWFCZIEFIQKRV-ONEGZZNKSA-N
  • COC1=CC=C(C=C1)/C=C/C2=CC=C(C=C2)OC
Properties
C16H16O2
Molar mass240.302 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Photoanethole is anaturally occurringorganic compound that is found inanise andfennel.[1][2] It hasestrogenic activity, and along withanethole anddianethole, may be responsible for the estrogenic effects of anise and fennel.[1][3][4][5][6] These compounds bear resemblance to the estrogensstilbene anddiethylstilbestrol, which may explain their estrogenic activity.[1][7] In fact, it is said that diethylstilbestrol and related drugs were originally modeled after photoanethole and dianethole.[1][8]

See also

[edit]

References

[edit]
  1. ^abcdAlbert-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. ^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.
  4. ^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.
  5. ^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.
  6. ^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.
  7. ^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.
  8. ^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.


ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown


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