1-Keto-1,2,3,4-tetrahydrophenanthrene

Chemical compound 3,4-Dihydro-2H-phenanthren-1-one THP-1.svg skin-invert-image 225px correct CAS 573-22-8 225683 196209 correct FDA RAN6R458LN 88130 14 12 1 C1CC2=C(C=CC3=CC=CC=C23)C(=O)C1 1S/C14H12O/c15-14-7-3-6-12-11-5-2-1-4-10(11)8-9-13(12)14/h1-2,4-5,8-9H,3,6-7H2 KBARGPSSEIXDQU-UHFFFAOYSA-N THP-1; 1,2,3,4-Tetrahydrophenanthren-1-one 1-Keto-1,2,3,4-tetrahydrophenanthrene (THP-1), or 1,2,3,4-tetrahydrophenanthren-1-one, is a synthetic steroid-like compound which was reported to be the first xenoestrogen.Virgil Craig Jordan Estrogen/antiestrogen Action and Breast Cancer Therapy https://books.google.com/books?id=7WmLZfGXST0C&pg=PA20 1986 Univ of Wisconsin Press 978-0-299-10480-1 20– Ashby J, Odum J, Paton D, Lefevre PA, Beresford N, Sumpter JP Re-evaluation of the first synthetic estrogen, 1-keto-1,2,3, 4-tetrahydrophenanthrene, and bisphenol A, using both the ovariectomised rat model used in 1933 and additional assays Toxicol. Lett. 115 3 231–8 2000 10814893 10.1016/s0378-4274(00)00198-3 http://bura.brunel.ac.uk/handle/2438/384 It was first synthesized in 1933 by Cook et al. and was tested due to its similarity to the presumed chemical structure of estrone. Upon reassessment many decades later, the compound was found to bind only weakly to the estrogen receptors, and, unexpectedly, did not actually have functional activity as an estrogen or antiestrogen in vitro or in vivo. It did, however, show some mixed androgenic and antiandrogenic activity in vitro. See also Estrin References 2 Category:Ketones Category:Phenanthrenes Category:Synthetic estrogens Category:Substances discovered in the 1930s