scholarly journals A Study of the Reaction Between Quinone and 2R4F Cigarette Smoke Condensate

Author(s):  
WM Coleman

AbstractA study using atomic emission detection (AED) as an approach to explore the fate of quinone added into 2R4F cigarette smoke condensate (CSC) have been performed. Both natural isotope quinone and 13C labeled quinone were used in the study. When coupled with a gas chromatographic separation (GC/AED), the AED provided informative new data on 13C isotope enriched products generated following reactions between 2R4F CSC and the quinone. Two 13C containing species were detected by GC/AED. Matching chromatographic separation using gas chromatography/mass selective detection (GC/MSD) allowed for a structural assignment of a relatively minor CSC 13C 6quinone reaction product as nitrohydroquinone (13C6NO2HQ). The chemical mechanism accounting for the formation of 13C6NO2HQ in the CSC was envisioned to be a reaction product between HONO and 13C 6Quinone (13C6Q) to form 13C6NO2Q, followed by reduction of 13C6NO2Q to 13C6NO2HQ. The amount of 13C6NO2HQ accounted for ~6% of the added 13C6Q. Identical trends in reaction chemistries were found for experiments with 12C6Q. The major reaction product detected upon addition of 13C6Q to the 2R4F CSC sample was 13C6HQ. 13C6HQ accounted for, on average, ~47% of the initial 13C6Q concentration. Identical trends in reaction chemistries were found for experiments with 12C6Q. No additional 13C containing species were detected. A 13C AED compound independent calibration (CIC) approach under the operating conditions was not possible. This work further expands the knowledge regarding possible reactions of quinone and hydroquinone in CSC.

Talanta ◽  
2012 ◽  
Vol 95 ◽  
pp. 36-41 ◽  
Author(s):  
Gang Li ◽  
Da Wu ◽  
Wenyan Xie ◽  
Xiangmin Zhang ◽  
Baizhan Liu

Author(s):  
M. E. Snook ◽  
R. F. Severson ◽  
R. F. Arrendale ◽  
H. C. Higman ◽  
O. T. Chortyk

AbstractThe methyl, multi-methyl, and ethyl derivatives of the polynuclear aromatic hydrocarbons (PAH) of cigarette smoke condensate (CSC) were isolated from the neutrals by silicic acid chromatography, solvent partitioning and gel chromatography. The procedure yielded a relatively pure PAH isolate amenable to further identifications. The multi-alkylated PAH were concentrated in the early gel fractions with parent and higher ring PAH found in subsequent gel fractions. It was shown that CSC is very rich in alkylated PAH, and their successful identification required extensive use of gas and liquid chromatography and ultra-violet and GC - mass spectrometric techniques. High-pressure liquid chromatography (HPLC) separated individual isomers of the alkylated PAH in complex GC peaks. PAH from indene to pentamethylchrysene were found. This report concludes our identification studies on the PAH of CSC and complements our two previous reports in this journal. Collectively, our studies have identified approximately 1000 PAH of cigarette smoke condensate and have led to the development of methods for the routine quantitation of PAH in smalI quantities of cigarette smoke condensate.


1963 ◽  
Vol 41 (6) ◽  
pp. 1606-1611 ◽  
Author(s):  
Hans Helmut Baer ◽  
Frank Kienzle

The steric course of the nitromethane cyclization of L′-methoxy-D-hydroxymethyldiglycolic aldehyde was investigated. Methyl 3-nitro-3-deoxy-β-D-galactopyranoside was shown to arise as a second major reaction product in addition to the previously isolated principal stereoisomer, the gluco derivative. The corresponding manno stereoisomer is formed to a smaller extent. The configurations of the new methyl nitrodeoxyglycosides were established by conversion into the corresponding amino derivatives and hydrolysis of these latter to the known 3-amino-3-deoxy-D-galactose and -D-mannose hydrochlorides. All the products were obtained in a crystalline state. The reaction lends itself to a facile preparation of the nitrogenous galactose derivatives.


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