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Drupanol

Identifiers
IUPAC name 4-(3-Ethenyl-3,6-dimethyl-1-methylene-5-heptenyl)phenol
CAS Number	42041-17-8 ((+)-isomer)
UNII	U4JU7QTN2Q
Chemical and physical data
Formula	C18H24O
Molar mass	256.389 g·mol
3D model (JSmol)	Interactive image
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

Drupanol is a naturally occurring phenol that has been isolated from the seeds of Psoralea drupaceae. 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. Bakuchiol has been found to possess antiandrogenic activity in vitro.

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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