Photoanethole

{{Chembox  | ImageFile = Photoanethole.svg | ImageClass = skin-invert-image | ImageSize = 250px | ImageAlt =  | IUPACName = 1-Methoxy-4-[(''E'')-2-(4-methoxyphenyl)ethenyl]benzene | OtherNames = Bianisal; Bianisylidene; ''p'',''{{prime|p}}''-Dimethoxystilbene; 4,4{{prime}}-Dimethoxystilbene  | Section1 = {{Chembox Identifiers | CASNo = 15638-14-9 | CASNo1_Ref = {{cascite|correct|CAS}} | CASNo1 = 4705-34-4 | CASNo1_Comment = (non-specific) | UNII_Ref = {{fdacite|correct|FDA}} | UNII = AME9HMB99F | ChemSpiderID = 556587 | PubChem = 641296 | StdInChI = 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+ | StdInChIKey = CAWFCZIEFIQKRV-ONEGZZNKSA-N | SMILES = COC1=CC=C(C=C1)/C=C/C2=CC=C(C=C2)OC }} | Section2 = {{Chembox Properties | C=16 | H=16 | O=2 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''Photoanethole''' is a naturally occurring organic compound that is found in anise and fennel.<ref name="Albert-Puleo1980">{{cite journal|last1=Albert-Puleo|first1=Michael|title=Fennel and anise as estrogenic agents|journal=Journal of Ethnopharmacology|volume=2|issue=4|year=1980|pages=337–344|issn=0378-8741|doi=10.1016/S0378-8741(80)81015-4|pmid=6999244}}</ref><ref name="Duke2000">{{cite book|author=James A. Duke|title=Handbook of Phytochemical Constituents of GRAS Herbs and Other Economic Plants: Herbal Reference Library|url=https://books.google.com/books?id=R5AhRgbW8UIC&pg=PA458|date=10 November 2000|publisher=CRC Press|isbn=978-0-8493-3865-6|pages=257, 458}}</ref> It has estrogenic activity, and along with anethole and dianethole, may be responsible for the estrogenic effects of anise and fennel.<ref name="Albert-Puleo1980" /><ref name="Foster2012">{{cite book|author=Steven Foster|title=Tyler's Honest Herbal: A Sensible Guide to the Use of Herbs and Related Remedies|url=https://books.google.com/books?id=WQBbOjN0T64C&pg=PA157|date=12 November 2012|publisher=Routledge|isbn=978-1-136-74501-0|pages=157–}}</ref><ref name="DeBaggioTucker2009">{{cite book|author1=Thomas DeBaggio|author2=Arthur O. Tucker|title=The Encyclopedia of Herbs: A Comprehensive Reference to Herbs of Flavor and Fragrance|url=https://books.google.com/books?id=7_KPgxEglHAC&pg=PA240|date=1 September 2009|publisher=Timber Press|isbn=978-1-60469-134-4|pages=240–}}</ref><ref name="KhanAbourashed2011">{{cite book|author1=Ikhlas A. Khan|author2=Ehab A. Abourashed|title=Leung's Encyclopedia of Common Natural Ingredients: Used in Food, Drugs and Cosmetics|url=https://books.google.com/books?id=kIP2Lf9H4dkC&pg=RA3-PA35|date=21 September 2011|publisher=John Wiley & Sons|isbn=978-1-118-21306-3|pages=3–}}</ref><ref name="Lim2013">{{cite book|author=T. K. Lim|title=Edible Medicinal And Non-Medicinal Plants: Volume 5, Fruits|url=https://books.google.com/books?id=_ZZEAAAAQBAJ&pg=PA50|date=2 February 2013|publisher=Springer Science & Business Media|isbn=978-94-007-5653-3|pages=50–}}</ref> These compounds bear resemblance to the estrogens stilbene and diethylstilbestrol, which may explain their estrogenic activity.<ref name="Albert-Puleo1980" /><ref name="BoneMills2013">{{cite book|author1=Kerry Bone|author2=Simon Y. Mills|title=Principles and Practice of Phytotherapy,Modern Herbal Medicine,2: Principles and Practice of Phytotherapy|url=https://books.google.com/books?id=5V1QlqHazcwC&pg=PA559|year=2013|publisher=Elsevier Health Sciences|isbn=978-0-443-06992-5|pages=559–}}</ref> In fact, it is said that diethylstilbestrol and related drugs were originally modeled after photoanethole and dianethole.<ref name="Albert-Puleo1980" /><ref name="Jordan2009">{{cite journal|last1=Jordan|first1=V. C.|title=A Century of Deciphering the Control Mechanisms of Sex Steroid Action in Breast and Prostate Cancer: The Origins of Targeted Therapy and Chemoprevention|journal=Cancer Research|volume=69|issue=4|year=2009|pages=1243–1254|issn=0008-5472|doi=10.1158/0008-5472.CAN-09-0029|pmid=19208829|doi-access=}}</ref>

==See also== * Anol * Hexestrol

==References== {{Reflist|2}}

Category:Phytoestrogens Category:Stilbenoids