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
CAS Number	15638-14-9 4705-34-4 (non-specific) Y
3D model (JSmol)	Interactive image
ChemSpider	556587
PubChem CID	641296
UNII	AME9HMB99F  Y
InChI 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
SMILES COC1=CC=C(C=C1)/C=C/C2=CC=C(C=C2)OC
Properties
Chemical formula	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). Infobox references

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]}

See also

• Anol
• Hexestrol

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. 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.