Drupanol

Drupanol

Identifiers
IUPAC name 4-(3-Ethenyl-3,6-dimethyl-1-methylene-5-heptenyl)phenol
CAS Number	42041-17-8  Y ((+)-isomer)
PubChem CID	129685892
ChemSpider	6702812
UNII	U4JU7QTN2Q
Chemical and physical data
Formula	C18H24O
Molar mass	256.389 g·mol−1
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. ^{[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]

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. Bibcode:1973CNatC...9....7G. 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.