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

Last updated
1-Keto-1,2,3,4-tetrahydrophenanthrene
THP-1.svg
Clinical data
Other namesTHP-1; 1,2,3,4-Tetrahydrophenanthren-1-one
Identifiers
  • 3,4-Dihydro-2H-phenanthren-1-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C14H12O
Molar mass 196.249 g·mol−1
3D model (JSmol)
  • C1CC2=C(C=CC3=CC=CC=C23)C(=O)C1
  • 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

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. [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 mixed androgenic and antiandrogenic activity in vitro. [2]

See also

References

  1. 1 2 Virgil Craig Jordan (1986). Estrogen/antiestrogen Action and Breast Cancer Therapy. Univ of Wisconsin Press. pp. 20–. ISBN   978-0-299-10480-1.
  2. 1 2 3 4 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.



This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.