Identification of oxidation products of solanesol produced during air sampling for tobacco smoke by electrospray mass spectrometry and HPLC

被引:16
作者
Tucker, SP [1 ]
Pretty, JR [1 ]
机构
[1] NIOSH, Cincinnati, OH 45226 USA
关键词
D O I
10.1039/b505328e
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Solanesol, a 45-carbon, trisesquiterpenoid alcohol found in tobacco leaves and tobacco smoke, has been used as a quantitative marker for tobacco smoke for years. However, solanesol appears to be unreliable as a quantitative marker for tobacco smoke during environmental air sampling because it can be degraded substantially when present as a component of tobacco smoke and by as much as 100% when present as pure solanesol on fortified filters during air sampling. Since there is strong evidence that ozone is the agent responsible for the degradation, solanesol appears to be unreliable as a quantitative marker during indoor air sampling when indoor levels of ozone are greater than about 15 ppb. The degree of loss of pure solanesol is directly proportional to the concentration of ozone and the length of the sampling period and depends on the type of 37 mm membrane filter used for air sampling ( PTFE or quartz fiber). While the degree of loss of solanesol is inversely proportional to the relative humidity of the air at a sampling rate of 1.7 L min(-1), the degree of loss is virtually independent of relative humidity at a lower sampling rate; i.e., 0.25 L min(-1). A curve of loss of solanesol on a filter versus concentration of ozone from an ozone generator is virtually identical to a curve segment based on atmospheric ozone under the same conditions of air sampling. Oxidation of solanesol by ozone to approximately 25 to 60% completion produces at least three series of products for a total of at least 26 compounds: ( 1) isoprenoid acetones, ( 2) omega-hydroxyisoprenoid acetaldehydes, and ( 3) isoprenoid oxoaldehydes. All products in each series were tentatively identified as their derivatives with 2-(p-aminophenyl) ethanol (APE) by electrospray mass spectrometry (ES-MS). Ten ozonation products were detected as their 2,4-dinitrophenylhydrazine derivatives by HPLC at 360 nm: 4-oxopentanal and nine isoprenoid acetones ( acetone, 6-methyl-5-hepten-2-one, geranylacetone, farnesylacetone, tetraprenylacetone, geranylfarnesylacetone, farnesylfarnesylacetone, farnesylgeranylgeranylacetone and bombiprenone.
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页码:1414 / 1424
页数:11
相关论文
共 46 条
[1]  
[Anonymous], 1991, ENV SAMPLING ANAL PR
[2]  
[Anonymous], 2003, 181442003 ISO
[3]  
*ASTM, 2004, D627104 ASTM
[4]   KINETICS AND MECHANISMS OF THE GAS-PHASE REACTIONS OF OZONE WITH ORGANIC-COMPOUNDS UNDER ATMOSPHERIC CONDITIONS [J].
ATKINSON, R ;
CARTER, WPL .
CHEMICAL REVIEWS, 1984, 84 (05) :437-470
[5]   Indoor air quality in homes, offices and restaurants in Korean urban areas - Indoor/outdoor relationships [J].
Baek, SO ;
Kim, YS ;
Perry, R .
ATMOSPHERIC ENVIRONMENT, 1997, 31 (04) :529-544
[6]   CHEMICAL-COMPOSITION OF ENVIRONMENTAL TOBACCO-SMOKE .2. PARTICULATE-PHASE COMPOUNDS [J].
BENNER, CL ;
BAYONA, JM ;
CAKA, FM ;
TANG, HM ;
LEWIS, L ;
CRAWFORD, J ;
LAMB, JD ;
LEE, ML ;
LEWIS, EA ;
HANSEN, LD ;
EATOUGH, DJ .
ENVIRONMENTAL SCIENCE & TECHNOLOGY, 1989, 23 (06) :688-699
[7]  
Burkart JA, 1986, APPL IND HYG, V1, P153
[8]   The effects of smoking status and ventilation on environmental tobacco smoke concentrations in public areas of UK pubs and bars [J].
Carrington, J ;
Watson, AFR ;
Gee, IL .
ATMOSPHERIC ENVIRONMENT, 2003, 37 (23) :3255-3266
[9]   Variations in the estimation of the contribution of environmental tobacco smoke (ETS) to respirable (≤5 μm) indoor air particulates obtained by the use of different analytical methods [J].
Douce, DS ;
Clench, MR ;
Frost, B .
JOURNAL OF ENVIRONMENTAL MONITORING, 2001, 3 (03) :295-301
[10]   HYDROLYSIS OF SIMPLE FURANS . PRODUCTS OF SECONDARY CONDENSATION [J].
EFTAX, DSP ;
DUNLOP, AP .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (04) :1317-&