112375-54-9Relevant articles and documents
Isolation of coniferyl esters from Capsicum baccatum L., and their enzymatic preparation and agonist activity for TRPV1
Kobata, Kenji,Tate, Hitomi,Iwasaki, Yusaku,Tanaka, Yoshiyuki,Ohtsu, Keigo,Yazawa, Susumu,Watanabe, Tatsuo
, p. 1179 - 1184 (2008/09/20)
Coniferyl esters-capsiconiate and dihydrocapsiconiate-were isolated from the fruits of the pepper, Capsicum baccatum L. var. praetermissum. Their structures were determined by spectroscopic methods to be coniferyl (E)-8-methyl-6-nonenoate (capsiconiate) a
A general and stereoselective synthesis of the capsaicinoids via the orthoester Claisen rearrangement
Kaga, Harumi,Goto, Kouhei,Takahashi, Tomiki,Hino, Masao,Tokuhashi, Takashi,Orito, Kazuhiko
, p. 8451 - 8470 (2007/10/03)
Capsaicin, a main pungent principle of hot pepper, and its 15 analogs have been efficiently synthesized. The key step of this synthetic scheme is the orthoester Claisen rearrangement, which transformed allylic alcohols 2A-C to (E)-alkenoates 3A-C (E/Z > 100) in a highly stereoselective manner. The subsequent carbon chain elongations on 3 based on the cyanation or the malonic acid ester synthesis afforded (E)-alkenoic acids 8, which were converted to the corresponding acid chloride and then coupled with vanillylamine to give capsaicinoids. HPLC and CE (capillary electrophoresis) analyses of these capsaicinoids were also carried out.