Photoanethole

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 mass 240.302 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Photoanethole is a naturally occurring organic compound that is found in anise and fennel.[1][2] It has estrogenic activity, and along with anethole and dianethole, may be responsible for the estrogenic effects of anise and fennel.[1][3][4][5][6] These compounds bear resemblance to the estrogens stilbene and diethylstilbestrol, 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]

  1. ^ a b c d 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. ^ 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.