Transformation of Tobacco Alkaloids

Transformation of Tobacco Alkaloids

Chemical transformation: In air oxidation of nicotine at room temperature, N´-methylmyosmine, which is supposed to be an active intermediate of degradation, cotinine, nicotine-N´-oxide, nicotyrine, myosmine, 3-pyridylpropyI ketone, 3-pyridylmethyI ketone, nicotinic acid, methylamine and ammonia were...

Full description

Bibliographic Details
Main Authors: Kisaki T., Maeda S., Koiwai A., Mikami Y., Sasaki T., Matsushita H.
Format: Article
Language:English
Published: Sciendo 1978-12-01
Series:Beiträge zur Tabakforschung International
Online Access:https://doi.org/10.2478/cttr-2013-0461
id doaj-e4852a445b644c5bb74ed97fe0b105ac
record_format Article
spelling doaj-e4852a445b644c5bb74ed97fe0b105ac2021-09-06T19:22:11ZengSciendoBeiträge zur Tabakforschung International1612-92371978-12-019530831610.2478/cttr-2013-0461Transformation of Tobacco AlkaloidsKisaki T.0Maeda S.1Koiwai A.2Mikami Y.3Sasaki T.4Matsushita H.5Central Research Institute, The Japan Tobacco and Salt Public Corporation, Yokohama, JapanCentral Research Institute, The Japan Tobacco and Salt Public Corporation, Yokohama, JapanCentral Research Institute, The Japan Tobacco and Salt Public Corporation, Yokohama, JapanCentral Research Institute, The Japan Tobacco and Salt Public Corporation, Yokohama, JapanCentral Research Institute, The Japan Tobacco and Salt Public Corporation, Yokohama, JapanCentral Research Institute, The Japan Tobacco and Salt Public Corporation, Yokohama, JapanChemical transformation: In air oxidation of nicotine at room temperature, N´-methylmyosmine, which is supposed to be an active intermediate of degradation, cotinine, nicotine-N´-oxide, nicotyrine, myosmine, 3-pyridylpropyI ketone, 3-pyridylmethyI ketone, nicotinic acid, methylamine and ammonia were isolated. N´-Methylmyosmine was first characterized by 1H-NMR. When N´-methylmyosmine was heated, N-methylnicotinamide and nicotyrine were obtained in addition to a large amount of polymerized resinous substances. 2´(S)-nicotine-1´-N-oxide was rearranged to acetyl pseudooxynicotine by reaction with acetyl chloride or acetyl anhydride. This rearrangement could be generally useful for the preparation of Δ1-pyrrolines or Δ1-piperideines. When appropriate acetyl groups were used, the products were effective in improving tobacco taste.https://doi.org/10.2478/cttr-2013-0461
collection DOAJ
language English
format Article
sources DOAJ
author Kisaki T.
Maeda S.
Koiwai A.
Mikami Y.
Sasaki T.
Matsushita H.
spellingShingle Kisaki T.
Maeda S.
Koiwai A.
Mikami Y.
Sasaki T.
Matsushita H.
Transformation of Tobacco Alkaloids
Beiträge zur Tabakforschung International
author_facet Kisaki T.
Maeda S.
Koiwai A.
Mikami Y.
Sasaki T.
Matsushita H.
author_sort Kisaki T.
title Transformation of Tobacco Alkaloids
title_short Transformation of Tobacco Alkaloids
title_full Transformation of Tobacco Alkaloids
title_fullStr Transformation of Tobacco Alkaloids
title_full_unstemmed Transformation of Tobacco Alkaloids
title_sort transformation of tobacco alkaloids
publisher Sciendo
series Beiträge zur Tabakforschung International
issn 1612-9237
publishDate 1978-12-01
description Chemical transformation: In air oxidation of nicotine at room temperature, N´-methylmyosmine, which is supposed to be an active intermediate of degradation, cotinine, nicotine-N´-oxide, nicotyrine, myosmine, 3-pyridylpropyI ketone, 3-pyridylmethyI ketone, nicotinic acid, methylamine and ammonia were isolated. N´-Methylmyosmine was first characterized by 1H-NMR. When N´-methylmyosmine was heated, N-methylnicotinamide and nicotyrine were obtained in addition to a large amount of polymerized resinous substances. 2´(S)-nicotine-1´-N-oxide was rearranged to acetyl pseudooxynicotine by reaction with acetyl chloride or acetyl anhydride. This rearrangement could be generally useful for the preparation of Δ1-pyrrolines or Δ1-piperideines. When appropriate acetyl groups were used, the products were effective in improving tobacco taste.
url https://doi.org/10.2478/cttr-2013-0461
work_keys_str_mv AT kisakit transformationoftobaccoalkaloids
AT maedas transformationoftobaccoalkaloids
AT koiwaia transformationoftobaccoalkaloids
AT mikamiy transformationoftobaccoalkaloids
AT sasakit transformationoftobaccoalkaloids
AT matsushitah transformationoftobaccoalkaloids
_version_ 1717772525500366848

Similar Items