Drupanol

Drupanol is a naturally occurring phenol and phytoandrogen that has been isolated from the seeds of Psoralea drupaceae.[1][2] Although drupanol is sometimes said to be the same compound as bakuchiol, the two compounds are in fact distinct; they have the same molecular formula and weight but different chemical structures and hence are structural isomers.[1] Bakuchiol has been found to possess antiandrogenic activity in vitro.[3]

Drupanol
Identifiers
IUPAC name
  • 4-(3-Ethenyl-3,6-dimethyl-1-methylene-5-heptenyl)phenol
CAS Number
UNII
Chemical and physical data
FormulaC18H24O
Molar mass256.389 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)=CCC(C)(CC(=C)C1=CC=C(O)C=C1)C=C
InChI
  • InChI=1/C18H24O/c1-6-18(5,12-11-14(2)3)13-15(4)16-7-9-17(19)10-8-16/h6-11,19H,1,4,12-13H2,2-3,5H3
  • Key:CRWULAJEYWVGOC-UHFFFAOYNA-N

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 120,473. ISBN 978-1-4757-2085-3.
  2. Golovina LA, Nikonov GK (1973). "The structure of drupanol — A new phenol from Psoralea drupaceae". Chemistry of Natural Compounds. 9 (1): 7–9. doi:10.1007/BF00580876. ISSN 0009-3130. S2CID 4813778.
  3. Miao L, Ma SW, Fan GW, Wang H, Wang YF, Chai LJ (2013). "Bakuchiol inhibits the androgen induced-proliferation of prostate cancer cell line LNCaP through suppression of AR transcription activity". Tianjin Journal of Traditional Chinese Medicine. 5: 012.


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