113944-48-2Relevant academic research and scientific papers
Pungent principal of Alpinia galangal (L.) Swartz and its applications
Yang, Xiaogen,Eilerman, Robert G.
, p. 1657 - 1662 (1999)
The pungent principal of galangal [Alpinia galangal (L.) Swartz] rhizomes was isolated and identified as 1'-acetoxychavicol acetate (galangal acetate). Galangal acetate exhibits a unique pungent sensation, which is less intense than that of capsaicin and without a lingering effect. Applications of galangal acetate were tested in beverages, sweet goods, dressings, and personal care products. In many applications, galangal acetate is preferred to other pungent ingredients. It can be used as an alcohol enhancer or an alcohol replacer in alcohol and alcohol-free beverages. Galangal acetate is not stable in aqueous solutions and undergoes hydrolysis/isomerization reactions. Therefore, galangal acetate was absent in galangal essential oil obtained by steam distillation. However, galangal acetate was found as one of the major volatile components of the galangal rhizomes by headspace GC analysis. The stability of galangal acetate was studied under various conditions.
Lipase-catalyzed preparation of optically active 1′-acetoxychavicol acetates and their structure-activity relationships in apoptotic activity against human leukemia HL-60 cells
Azuma, Hideki,Miyasaka, Keita,Yokotani, Tsuyoshi,Tachibana, Taro,Kojima-Yuasa, Akiko,Matsui-Yuasa, Isao,Ogino, Kenji
, p. 1811 - 1818 (2007/10/03)
Structure-activity relationships of 1′-acetoxychavicol acetate (ACA) for apoptotic activity against human leukemia HL-60 cells were investigated using optically active ACA and various racemic ACA analogues. Natural-type (or with different acyl group) ACA showed a high apoptotic activity, but the ortho or meta isomers, 4-deacetoxy analogue, and the 2′-3′ dehydrogenated derivative had no effect, or a weak activity. Optically active (R)- and (S)-ACA were prepared by a lipase-catalyzed esterification. Using a mixture of vinyl acetate-tetrahydrofuran (1:1 v/v) as a solvent at refluxing temperature, optically pure (R)- and (S)-ACA were obtained (99.7% ee and 99.1% ee, respectively). The apoptosis-inducing effects of both enantiomers were compared by means of an MTT assay and the detection of typical apoptotic phenomena (DNA fragmentation, caspase-3 activation, and PARP cleavage) and these two activities were almost equal. These results indicate that the essential moieties of ACA for apoptotic activity against HL-60 cells are both the presence of a 4-acetoxyl group and an unsaturated double bond between C-2′ and C-3′, and that the configuration at the 1′-position is unrelated to activity. All rights reserved.
DFRC Method for Lignin Analysis. 1. New Method for β-Aryl Ether Cleavage: Lignin Model Studies
Lu, Fachuang,Ralph, John
, p. 4655 - 4660 (2007/10/03)
A new method for selective and efficient cleavage of arylglycerol-β-aryl (β-O-4) ether linkages in lignins is described and applied to several lignin β-ether models. The term "DFRC" was coined for derivatization followed by reductive cleavage. Derivatization, accompanied by cell wall solubilization, is accomplished with acetyl bromide (AcBr); reductive cleavage of resulting β-bromo ethers utilizes zinc in acetic acid. Degradation monomers, 4-acetoxycinnamyl acetates, from β-ether cleavage by the DFRC method were identified by NMR, GC-MS, and comparison of GC retention times with authentic compounds. Under the conditions used in this study, the β-ether linkage of all models was cleaved in very high (>92%) yield. The DFRC method produces simpler mixtures of monomers with higher yields than alternative hydrolytic methods. Because of its relative simplicity, mild conditions, and exceptional selectivity, this method should become a powerful analytical method for lignin characterization.
