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Drupanol

From Wikipedia, the free encyclopedia
Drupanol
Identifiers
  • 4-(3-Ethenyl-3,6-dimethyl-1-methylene-5-heptenyl)phenol
CAS Number
UNII
Chemical and physical data
FormulaC18H24O
Molar mass256.389g·mol−1
3D model (JSmol)
  • CC(C)=CCC(C)(CC(=C)C1=CC=C(O)C=C1)C=C
  • 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

Drupanolis anaturally occurringphenolthat has been isolated from the seeds ofPsoralea drupaceae.[1][2]Although drupanol is sometimes said to be the same compound asbakuchiol,the two compounds are in fact distinct; they have the samemolecular formulaandweightbut differentchemical structuresand hence arestructural isomers.[1]Bakuchiol has been found to possessantiandrogenicactivityin vitro.[3]

References

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  1. ^abElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies.Springer. p. 120,473.ISBN978-1-4757-2085-3.
  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.ISSN0009-3130.S2CID4813778.
  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.