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

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 synthetic estrogen, or the first synthetic compound identified with estrogenic activity.[1][2] It was first synthesized in 1933 by Cook et al. and was tested due to its similarity to the presumed chemical structure of estrone.[1][2] 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.[2] It did, however, show some androgenic and antiandrogenic activity in vitro.[2]

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

Clinical data
Other names	THP-1; 1,2,3,4-Tetrahydrophenanthren-1-one
Identifiers
IUPAC name 3,4-Dihydro-2H-phenanthren-1-one
CAS Number	573-22-8
PubChem CID	225683
ChemSpider	196209
ChEMBL	ChEMBL88130
CompTox Dashboard (EPA)	DTXSID50280072
Chemical and physical data
Formula	C14H12O2
Molar mass	212.248 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C1CC2=C(C=CC3=CC=CC=C23)C(=O)C1
InChI InChI=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 Key:KBARGPSSEIXDQU-UHFFFAOYSA-N

See also

• Estrin

References

1. Virgil Craig Jordan (1986). Estrogen/antiestrogen Action and Breast Cancer Therapy. Univ of Wisconsin Press. pp. 20–. ISBN 978-0-299-10480-1.
2. Ashby J, Odum J, Paton D, Lefevre PA, Beresford N, Sumpter JP (2000). "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. doi:10.1016/s0378-4274(00)00198-3. PMID 10814893.