166733-97-7Relevant academic research and scientific papers
Structural Reassignment of rel-(3′ Z,3 R,6 R,7 R,3a′ R,6′ R)-3,8-Dihydrodiligustilide and the Activity of Diligustilide and 3,8-Dihydro- A nd 3,8,7′,7a′-Tetrahydrodiligustilides as Progestins
ávila, José Luis,Almeida-Aguirre, Ericka K. P.,Méndez-Cuesta, Carlos A.,Toscano, Rubén A.,Cerbón Cervantes, Marco A.,Delgado, Guillermo
, p. 7460 - 7465 (2019)
Several phthalides were semisynthesized, including a 3,8-dihydrodiligustilide with progesterone-like activity, previously isolated from Ligusticum chuanxiong, the structure of which was earlier assigned to a semisynthetic product with nonidentical spectroscopic constants. The structure of this natural phthalide was reassigned with a proposal of its absolute configuration. Phthalides acted as progestins in cell viability assays, immunofluorescence microscopy, and docking analysis. Therefore, the structures for natural and semisynthetic phthalides with potential use in hormone-related therapies were reassigned.
Asymmetric synthesis and sensory evaluation of sedanenolide
Oguro, Daichi,Watanabe, Hidenori
, p. 1502 - 1505 (2011/11/04)
The synthesis and sensory evaluation of enantiomeric sets of sedanenolide (1) and 3-butylphthalide (3) are described. The asymmetric synthesis was achieved via the intramolecular Diels-Alder reaction of chiral propargylester (5) which was prepared from optically active propargyl alcohol (4) and 2,4-pentadienoic acid. The sensory evaluation of these enantiomers revealed that there were distinct differences between their aroma character and odor threshold.
