Isolation and ldentification of 2,6- Dimethyl- and 2,2,6 -Trimethyl-4-piperidone, Artifacts Produced by the Reaction of Cigarette Smoke Condensate and Acetone

Einolf, W. Noel; Ferguson, Rena; Whidby, Jerry F.; Debardeleben, J. F.

doi:10.2478/cttr-2013-0449

Cited by 4 publications

(4 citation statements)

References 12 publications

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“…For the purpose of this study, similar 13 C NMR techniques have been applied that will be shown to provide meaningful information on the nature of the structures of the components that result from reactions of HQ and Q within smoke matrices. Thus, based in part on the information surrounding the characteristics of mainstream cigarette smoke as portrayed by hydroxybenzenes, the chemical complexity of mainstream cigarette smoke, as well as smoke chemistries disclosed within additional reports (38,39), the dynamic reactivity of mainstream cigarette smoke would seem to have been confirmed and well documented. In this report is described yet another reaction between reasonably well known cigarette smoke components.…”

Section: Resumementioning

confidence: 99%

A Diels-Alder Reaction Between A Cigarette Mainstream Smoke Component and Benzoquinone

Coleman¹

2008

Beiträge Zur Tabakforschung International/Contributions to Tobacco Research

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A notable amount of research has been placed toward understanding the roles of benzoquinone (Q) and hydroquinone (HQ) in the chemistry and toxicity of cigarette smoke. To further understanding of the roles of these compounds in cigarette smoke, a series of reactions were performed wherein the levels and chemistries of Q and HQ were monitored after having been added to selected phases of the mainstream smoke from 2R4F cigarettes. Through the application of both fundamental organic chemistry reaction mechanistic principles and qualitative analysis of smoke chemistry, a new reaction pathway for mainstream smoke components was elucidated. During the course of these investigations, the presence of a product from a Diels-Alder reaction between a 2R4F cigarette mainstream smoke component and Q was discovered. Data from carbon-13 nuclear magnetic resonance (13C NMR), gas chromatography-atomic emission detection (GC-AED), and gas chromatography-mass selective detection (GC-MSD) revealed a Diels-Alder reaction product resulting from the reaction of benzoquinone (Q), a dienophile, and 1,3-cyclopentadiene, a diene, to yield tricyclo[6.2.1.02,7] undeca-4,9-diene-3,6-dione, more commonly referred to as cyclopentadienebenzoquinone. The reaction between Q and 1,3-cyclopentadiene was observed to have occurred when fresh mainstream vapor phase smoke (MSVP) from a 2R4F cigarette, captured in acetone, was subsequently treated with Q. Other 13C containing species were detected but inadequate signal to noise values prevented structural assignments. Accompanying the Diels-Alder reaction was an additional reaction of Q to form hydroquinone (HQ). These reactions provide additional information on the complexity of cigarette smoke, particularly as it relates to possible reactions involving Q and HQ and other cigarette smoke components.

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Section: Resumementioning

confidence: 99%

A Diels-Alder Reaction Between A Cigarette Mainstream Smoke Component and Benzoquinone

Coleman¹

2008

Beiträge Zur Tabakforschung International/Contributions to Tobacco Research

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“…Acetone and its mixtures, however, caused discoloration and degradation of nornicotine after storage for 12 h, very probably because of chemical reaction between the secondary amine group on the pyrrolidine ring of nornicotine and the carbonyl group of acetone. With an extra pair of electrons on the nitrogen the pyrrolidine ring has the normal basicity and the nature of a secondary aliphatic amine [9,10]. Because of incomplete miscibility with the aqueous ammonia solution use of 100% dichloromethane or hexane and resulted in a low recovery of some alkaloids.…”

Section: Resultsmentioning

confidence: 99%

Determination of tobacco alkaloids by gas chromatography with nitrogen–phosphorus detection

Yang¹,

Smetena²,

Cb³

2002

Anal Bioanal Chem

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An improved method, gas chromatography (GC) with nitrogen-phosphorus detection (NPD), has been used for determination of alkaloids in green and cured tobacco. Tobacco alkaloids of interest included nicotine, nornicotine, myosmine, anabasine, and anatabine. Tobacco samples were treated with a small quantity of aqueous ammonia solution to "loosen" tobacco tissue and to adjust pH, then extracted with solvent. The composition of the extraction solvent solution affected recoveries of the alkaloids, particularly nornicotine, and also contributed to other phenomena such as carry-over in the injection liner and "quenching" of the nitrogen-phosphorus detector. Use of a packed injection liner (e.g. with Carbowax-KOH on Chromosorb) to reduce carry-over was studied. Quenching of the nitrogen-phosphorus detector was eliminated by reducing the injection volume (i.e. increasing the split ratio), by use of a packed injection liner, and by reducing the amount of pretreatment with aqueous ammonia. A narrow bore capillary column (i.e. 0.18 mm id) was used to improve sensitivity and resolution and to increase the speed of GC analysis. An internal standard, 2,4'-dipyridyl, was used for quantitative measurement of these tobacco alkaloids.

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“…Gel chromatography of dry condensates revealed polymerization being a factor in the changes of condensate composition due to aging. In view of the fact that acetone had become a preferred solvent for taking up cigarette smoke condensate it is noteworthy that EINOLF et al (542) identified three methylated piperidones, which were formed as artifacts by reactions between the solvent, acetone, and two smoke constituents, acetaldehyde and ammonia.…”

Section: The Smoking Machine Sibata Sg-200mentioning

confidence: 99%

Cigarette Mainstream Smoke: The Evolution of Methods and Devices for Generation, Exposure and Collection

Klus¹,

Boenke-Nimphius²,

Müller

2016

Beiträge Zur Tabakforschung International/Contributions to Tobacco Research

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SUMMARYThe objective of this review is to support tobacco scientists when evaluating information published on smoking machines, and on cigarette mainstream smoke (in vivo and in vitro) exposure systems and collection devices. The intriguing development of smoking machines (mainly for cigarettes) is followed for more than 170 years -from the first simple set-ups in the 1840s to the sophisticated and fully automated analytical smoking machines available today. Systems for the large-scale production of smoke (condensate) for preparative work are equally considered. The standardization of machine smoking methods and test pieces has solved several technical problems and produced sensible rules but, at the same time, given rise to new controversies like the compatibility of artificial and human smoking, and the implementation of more intense machine smoking regimes. Adequate space is allotted for the discussion of configurations for in vivo smoke exposure of rodent and non-rodent species and the machines generating the required smoke (condensate). Covered as well is the field of in vitro toxicity testing, including the increasingly informative new techniques of air-liquid interface exposure, which are becoming more and more refined with the use of organotypic cultures and genetic analyses. The review is completed by the examination of the considerable variety of mainstream smoke collection devices (filters and traps) developed over time -some for very specific purposes -and refers to the perpetual problem of artifact formation by aging.

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Isolation and ldentification of 2,6- Dimethyl- and 2,2,6 -Trimethyl-4-piperidone, Artifacts Produced by the Reaction of Cigarette Smoke Condensate and Acetone

Cited by 4 publications

References 12 publications

A Diels-Alder Reaction Between A Cigarette Mainstream Smoke Component and Benzoquinone

A Diels-Alder Reaction Between A Cigarette Mainstream Smoke Component and Benzoquinone

Determination of tobacco alkaloids by gas chromatography with nitrogen–phosphorus detection

Cigarette Mainstream Smoke: The Evolution of Methods and Devices for Generation, Exposure and Collection

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