134-28-1Relevant academic research and scientific papers
From wine to pepper: Rotundone, an obscure sesquiterpene, is a potent spicy aroma compound
Wood, Claudia,Siebert, Tracey E.,Parker, Mango,Capone, Dimitra L.,Elsey, Gordon M.,Pollnitz, Alan P.,Eggers, Marcus,Meier, Manfred,Voessing, Tobias,Widder, Sabine,Krammer, Gerhard,Sefton, Mark A.,Herderich, Markus J.
, p. 3738 - 3744 (2008)
An obscure sesquiterpene, rotundone, has been identified as a hitherto unrecognized important aroma impact compound with a strong spicy, peppercorn aroma. Excellent correlations were observed between the concentration of rotundone and the mean 'black pepper' aroma intensity rated by sensory panels for both grape and wine samples, indicating that rotundone is a major contributor to peppery characters in Shiraz grapes and wine (and to a lesser extent in wine of other varieties). Approximately 80% of a sensory panel were very sensitive to the aroma of rotundone (aroma detection threshold levels of 16 ng/L in red wine and 8 ng/L in water). Above these concentrations, these panelists described the spiked samples as more 'peppery' and 'spicy'. However, approximately 20% of panelists could not detect this compound at the highest concentration tested (4000 ng/L), even in water. Thus, the sensory experiences of two consumers enjoying the same glass of Shiraz wine might be very different. Rotundone was found in much higher amounts in other common herbs and spices, especially black and white peppercorns, where it was present at ～10000 times the level found in very 'peppery' wine. Rotundone is the first compound found in black or white peppercorns that has a distinctive peppery aroma. Rotundone has an odor activity value in pepper on the order of 50000-250000 and is, on this criterion, by far the most powerful aroma compound yet found in that most important spice.
Identification of Rotundone as a Potent Odor-Active Compound of Several Kinds of Fruits
Nakanishi, Akira,Fukushima, Yusuke,Miyazawa, Norio,Yoshikawa, Keisuke,Maeda, Tomoko,Kurobayashi, Yoshiko
, p. 4464 - 4471 (2017)
An investigation of the aromas of grapefruit, orange, apple, and mango revealed the presence of an odor-active compound that gave off a strong woody odor when assessed by gas chromatography-olfactometry. We isolated the compound from a high-boiling fraction of an orange essential oil, and subsequent nuclear magnetic resonance analyses of the isolated compound identified it as rotundone. Mass spectra and retention indices obtained from aroma concentrates of grapefruit, apple, and mango were identical to those of rotundone, which was therefore determined to be the common woody compound in these fruits. Sensory analyses were performed to assess the effects of rotundone on model beverages of the various fruits. It was revealed that rotundone added at even subthreshold levels to model beverages did not confer directly the woody odor, but had significant effects on the overall flavors of the beverages, helping them to better approximate the natural flavors of the fruits.
Synthesis of guaia-4(5)-en-11-ol, guaia-5(6)-en-11-ol, aciphyllene, 1- epi -melicodenones C and E, and other guaiane-type sesquiterpenoids via the diastereoselective epoxidation of guaiol
Huang, An-Cheng,Sumby, Christopher J.,Tiekink, Edward R.T.,Taylor, Dennis K.
, p. 2522 - 2536 (2015/01/09)
The diastereomeric ratio of epoxidation of the internally bridged carbon-carbon double bond of guaiol (1a) is strongly influenced by the combined effects of the types of remote protecting groups on the hydroxyisopropyl side chain, choice of solvent, and e
