10482-56-1Relevant articles and documents
Comparison of enzymatic and acid hydrolysis of bound flavor compounds in model system and grapes
Dziadas, Mariusz,Jeleń, Henryk H.
, p. 412 - 418 (2016)
Four synthesized terpenyl-β-D-glycopyranosides (geranyl, neryl, citronellyl, myrtenyl) were subjected to enzymatic (AR 2000, pH 5.5) and acid (citric buffer, pH 2.5) hydrolysis. Decrease of glycosides was measured by HPLC and the volatiles released - by comprehensive gas chromatography-mass spectrometry (GC x GC-ToF-MS). Enzymatic hydrolysis performed for 21 h yielded 100% degree of hydrolysis for all glycosides but citronellyl (97%). Degree of acid hydrolysis was highly dependent on type of aglycone and the conditions. The highest degree was achieved for geraniol, followed by citronellol and nerol. Myrtenylo-β-D-glycopyranoside was the most resistant glycoside to hydrolysis. Acid hydrolysis degree was also related to temperature/time combination, the highest being for 100 °C and 2 h. In a result of enzymatic hydrolysis 85-91% of total peak areas was terpene aglycone, whereas for acid hydrolysis the area of released terpene aglycone did not exceed 1.3% of total peak area indicating almost complete decomposition/transformation of terpenyl aglycone.
Galloylglucosides from berries of Pimenta dioica
Kikuzaki, Hiroe,Sato, Akemi,Mayahara, Yoko,Nakatani, Nobuji
, p. 749 - 752 (2000)
Three new galloylglucosides, (4S)-α-terpineol 8-O-β-D-(6-O- galloyl)glucopyranoside (1); (4R)-α-terpineol 8-O-β-D-(6-O- galloyl)glucopyranoside (2), and 3-(4-hydroxy-3-methoxyphenyl)propane-1,2- diol 2-O-β-D-(6-O-galloyl)glucopyranoside (3), were isolated from the berries of Pimenta dioica together with three known compounds, gallic acid (4), pimentol (5), and eugenol 4-O-β-D-(6-O-galloyl)glucopyranoside (6). The structures of 1-3 were elucidated on the basis of MS and NMR spectral data and enzymatic hydrolysis. These galloylglucosides (1-3, 5, and 6) showed radical-scavenging activity nearly equivalent to that of gallic acid (4) against 1,1-diphenyl-2-picrylhydrazyl radical.
Synthesis of antimalarial yingzhaosu A analogues by the peroxidation of dienes with Co(II)/O2/Et3SiH
Tokuyasu, Takahiro,Kunikawa, Shigeki,Abe, Manabu,Masuyama, Araki,Nojima, Masatomo,Kim, Hye-Sook,Begum, Khurshida,Wataya, Yusuke
, p. 7361 - 7367 (2003)
Co(II)-catalyzed peroxidation of dienes including (S)-limonene in the presence of molecular oxygen and triethylsilane provided in each case the corresponding 2,3-dioxabicyclo[3.3.1]nonane derivatives via the intramolecular cyclization of the unsaturated peroxy radical intermediates. The product composition was remarkably influenced by the structure of the dienes, the nature of the solvents, and the concentration of the substrates and the catalyst. Some of the yingzhaosu A analogues obtained in this study showed notable antimalarial activities in vitro.
Amine and thiazole substituted γ-butyrolactones from naturally occurring limonene
Kaur, Pushpinder,Das, Pralay,Chaudhary, Abha,Singh, Bikram
, p. 639 - 644 (2011)
Substituted γ-butyrolactones are important structural motifs in several natural products and pharmaceuticals. In this paper, we report the synthesis of novel γ-butyrolactone amine and thiazole derivatives from naturally occurring limonene. Regioselective bromination followed by nucleophilic substitution with different amines and thiourea gave desired products in moderate yield.
Enantioselective synthesis of α-terpineol and nephthenol by intramolecular acyloxazolidinone enolate alkylations
Jin, Yinghua,Coates, Robert M.
, p. 2902 - 2904 (2008/09/18)
Enolate anions generated from norterpenyl bromides bearing oxazolidinone chiral auxiliaries at the chain termini underwent efficient, stereo-biased cyclizations to form 6- and 14-membered rings in novel synthetic routes to α-terpineol and nephthenol enantiomers. The Royal Society of Chemistry 2006.
