18374-76-0Relevant articles and documents
GUAIANE SESQUITERPENES FROM AGARWOOD
Ishihara, Masakazu,Tsuneya, Tomoyuki,Uneyama, Kenji
, p. 3343 - 3347 (1991)
Key Word Index - Aquilaria agallocha; Thymelaeaceae; agarwood; sesquiterpenes; (-)-guaia-1(10),11-dien-15-ol; (-)-guaia-1(10),11-diene-15-carboxylic acid; methyl guaia-1(10),11-diene-15-carboxylate; (+)-guaia-1(10),11-dien-9-one; (-)-1,10-epoxyguai-11-ene; (-)-guaia-1(10),11-dien-15,2-olide; (-)-rotundone.Seven new sesquiterpenes, all of which have a guaiane skeleton, i.e. (-)-guaia-1(10),11-dien-15-ol, (-)-guaia-1(10),11-diene-15-carboxylic acid, methyl guaia-1(10),11-diene-15-carboxylate, (+)-guaia-1(10),11-dien-9-one, (-)-1,10-epoxyguai-11-ene, (-)-guaia-1(10),11-dien-15,2-olide and (-)-rotundone, have been isolated from Aquilaria agallocha (agarwood).Their structures have been established on the bases of detailed spectroscopic analyses and synthesis.
Development of a synthesis method for odor sesquiterpenoid, (?)-rotundone, using non-heme Fe2+-chelate catalyst and ferric-chelate reductase
Umezawa, Satoru,Konishi, Shunsuke,Kino, Kuniki
, p. 1875 - 1883 (2019)
(?)-Rotundone, a sesquiterpenoid that has a characteristic woody and peppery odor, is a key aroma component of spicy foodstuffs, such as black pepper and Australian Shiraz wine. (?)-Rotundone shows the lowest level of odor threshold in natural compounds and remarkably improves the quality of various fruit flavors. To develop a method for the synthesis of (?)-rotundone, we focused on non-heme Fe2+-chelates, which are biomimetic catalysts of the active center of oxygenases and enzymatic supply and regeneration of those catalysts. That is, we constructed a unique combination system composed of the oxidative synthesis of (?)-rotundone using the non-heme Fe2+-chelate catalyst, Fe(II)-EDTA, and the enzymatic supply and regeneration of Fe2+-chelate by ferric-chelate reductase, YqjH, from Escherichia coli. In addition, we improved the yield of (?)- rotundone by the application of cyclodextrin and glucose dehydrogenase to this system, and thus established a platform for efficient (?)-rotundone production.
IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS
-
Page/Page column 8; 9; 10, (2019/06/23)
An allylic oxidation process comprising: forming a mixture containing α-Guaiene and an iron (III)-X porphyrin complex catalyst in a sustainable solvent, introducing molecular oxygen into the mixture, and effecting allylic oxidation to produce an α,?-unsaturated ketone, Rotundone.
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 (2017/06/13)
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.
