Benzenoids

苯类化合物
  • 文章类型: Journal Article
    Hanseniasporavineae表现出非凡的积极的酿酒特性,有助于葡萄酒的香气和质地,特别是与常规酵母相比,它能够产生高浓度的苯类和苯丙素化合物。因此,在实践中,连续接种H.vineae和酿酒酵母可以提高葡萄酒的香气质量。在这项工作中,我们评估了增加苯丙氨酸浓度对葡萄酒香气的影响,苯丙素类和苯类的主要氨基酸前体。使用含有150mgN/L酵母可同化氮的霞多丽葡萄汁进行发酵。进行发酵,添加60mg/L的苯丙氨酸而不向果汁中添加任何补充。使用从乌拉圭葡萄园分离的三种不同的H.vineae菌株依次接种Musts,96小时后,接种酿酒酵母以完成该过程。在发酵结束时,通过气相色谱-质谱法和通过专家小组的感官评估来分析葡萄酒的香气。源自芳香族氨基酸的香气根据处理而不同地产生。与不添加苯丙氨酸的对照发酵相比,感官分析显示出更多的花特性和更大的芳香复杂性。此外,发酵在合成必须与纯H.vineae显示,即使酪氨酸可以在没有苯丙氨酸的情况下使用,这种酵母不使用苯丙氨酸合成酪氨酸衍生物。
    Hanseniaspora vineae exhibits extraordinary positive oenological characteristics contributing to the aroma and texture of wines, especially by its ability to produce great concentrations of benzenoid and phenylpropanoid compounds compared with conventional Saccharomyces yeasts. Consequently, in practice, sequential inoculation of H. vineae and Saccharomyces cerevisiae allows to improve the aromatic quality of wines. In this work, we evaluated the impact on wine aroma produced by increasing the concentration of phenylalanine, the main amino acid precursor of phenylpropanoids and benzenoids. Fermentations were carried out using a Chardonnay grape juice containing 150 mg N/L yeast assimilable nitrogen. Fermentations were performed adding 60 mg/L of phenylalanine without any supplementary addition to the juice. Musts were inoculated sequentially using three different H. vineae strains isolated from Uruguayan vineyards and, after 96 h, S. cerevisiae was inoculated to complete the process. At the end of the fermentation, wine aromas were analysed by both gas chromatography-mass spectrometry and sensory evaluation through a panel of experts. Aromas derived from aromatic amino acids were differentially produced depending on the treatments. Sensory analysis revealed more floral character and greater aromatic complexity when compared with control fermentations without phenylalanine added. Moreover, fermentations performed in synthetic must with pure H. vineae revealed that even tyrosine can be used in absence of phenylalanine, and phenylalanine is not used by this yeast for the synthesis of tyrosine derivatives.
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  • 文章类型: Journal Article
    Anibacanelilla(Kunth)Mez精油由于其主要化合物1-硝基-2-苯乙烷(1N2F)而具有许多生物活性,其次是甲基丁香酚,致癌物质.本研究分析了季节性对产量的影响,抗氧化能力,A.canelilla叶和树枝精油的1N2F含量。用加氢蒸馏提取精油(EO),并用气相色谱与质谱联用和火焰离子化检测器进行分析。使用自由基清除方法(DPPH)测量抗氧化能力。进行了化学计量学分析,以验证气候因素对EO的产生和组成的影响。在整个季节期间,1-硝基-2-苯基乙烷是A.canelillaEO的主要成分(68.0-89.9%);未检测到甲基丁香酚。精油产量和1N2F平均值在叶片和树枝的旱季和雨季之间没有统计学上的显着差异。观察到主要化合物与气候因子之间的中等和显着相关性。树枝油(36.0±5.9%)a显示出比叶油(20.4±5.0%)更大的抗氧化能力。PCA和HCA分析显示,旱季和雨季的油样之间没有统计学差异。在所有几个月的研究中都没有甲基黄精,第一次描述,使该标本成为1N2F的可靠来源。
    Aniba canelilla (Kunth) Mez essential oil has many biological activities due to its main compound 1-nitro-2-phenylethane (1N2F), followed by methyleugenol, a carcinogenic agent. This study analyzed the influence of seasonality on yields, antioxidant capacity, and 1N2F content of A. canelilla leaf and twig essential oils. Essential oils (EOs) were extracted with hydrodistillation and analyzed with gas chromatography coupled to mass spectrometry and a flame ionization detector. Antioxidant capacity was measured using the free radical scavenging method (DPPH). Chemometric analyses were carried out to verify the influence of climatic factors on the production and composition of EOs. 1-Nitro-2-phenylethane was the major constituent in A. canelilla EOs throughout the seasonal period (68.0-89.9%); methyleugenol was not detected. Essential oil yields and the 1N2F average did not show a statistically significant difference between the dry and rainy seasons in leaves and twigs. Moderate and significant correlations between major compounds and climate factor were observed. The twig oils (36.0 ± 5.9%) a showed greater antioxidant capacity than the leaf oils (20.4 ± 5.0%). The PCA and HCA analyses showed no statistical differences between the oil samples from the dry and rainy seasons. The absence of methyleugenolin in all months of study, described for the first time, makes this specimen a reliable source of 1N2F.
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  • 文章类型: Journal Article
    当前的气候条件可能会导致葡萄物候和成熟度动态发生重大变化,通常与生态气候指标的变化有关。首次研究了连续四年不同气象条件对Grignolino葡萄芳香潜力的影响。样品是从三个葡萄园中收集的,其特征是微气候条件不同,主要与葡萄园的暴露和植物的年龄不同有关。在4年中,观察到了成熟过程中温度和降雨模式的重要差异。葡萄对非生物胁迫的反应,特别强调芳香前体,使用气相色谱与质谱联用进行评估。结果表明,每个葡萄园的年份在浆果重量和芳香前体浓度方面存在显着差异。对于年轻葡萄园的葡萄,与老葡萄园相比,香气化合物的含量在年份之间显示出不同的变异性。在绿色阶段,温度和降雨方面的最佳条件,然后是温暖干燥的后期,直到收获为止,对所有类别的化合物都有利,尤其是主要在老藤本植物的葡萄中的萜类化合物。Veraison之前的高温(>30°C)和低降雨模式导致高的苯类含量和增加的葡萄园之间的差异,例如浆果重量,而凉爽的条件有利于东南方向葡萄园的葡萄中的萜类含量。在丘陵环境中,缺乏降雨和高温,最近表征浆果发育的第二部分似乎有利于Grignolino的葡萄品质,中晚成熟的品种,通过限制束成熟的差异,允许次级代谢产物的更多积累,但同时保持糖/酸度的最佳平衡。
    Current climatic conditions may cause significant changes in grapevine phenology and maturity dynamics linked often with changes to ecoclimatic indicators. The influence exerted by different meteorological conditions during four consecutive years on the aromatic potential of Grignolino grapes was investigated for the first time. The samples were collected from three vineyards characterized by different microclimatic conditions mainly related to the vineyard exposure and by a different age of the plants. Important differences as far as temperature and rainfall patterns are concerned during ripening were observed among the 4 years. Grape responses to abiotic stress, with particular emphasis on aromatic precursors, were evaluated using gas chromatography coupled to mass spectrometry. The results highlighted significant differences among the vintages for each vineyard in terms of the berry weight and the aromatic precursor concentration. For the grapes of the younger-vine vineyard, the content of aroma compounds showed a different variability among the vintages if compared to the old-vine vineyards. Optimal conditions in terms of temperature and rainfall during the green phase followed by a warm and dry post-veraison period until harvest favored all classes of compounds especially terpenoids mainly in the grapes of the old vines. High-temperature (>30°C) and low-rainfall pattern before veraison led to high benzenoid contents and increased differences among vineyards such as berry weight, whereas cooler conditions favored the terpenoid levels in grapes from southeast-oriented vineyards. In a hilly environment, lack of rainfall and high temperature that lately characterize the second part of berry development seem to favor the grape quality of Grignolino, a cultivar of medium-late ripening, by limiting the differences on bunch ripening, allowing a greater accumulation of secondary metabolites but maintaining at the same time an optimum balance sugar/acidity.
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  • 文章类型: Journal Article
    气候变化增加了对光合作用产生负面影响的热浪的频率,并可以改变本构挥发物的排放并引起胁迫挥发物的排放,但是,暴露于轻度温暖的温度如何影响植物对随后的严重高温事件的生理反应仍不清楚,特别是对于具有高而复杂的挥发性防御的芳香植物。我们研究了单独施加热休克(45°C/5分钟)以及暴露于中等热应力(35°C/1h,启动)在72小时的恢复期内对芳香植物Ohangumvulgare的叶片光合作用和挥发性物质的排放。热胁迫降低了光合作用速率和气孔导度,而光合作用的减少主要是由于非气孔因素。在非底漆植物中,热休克诱导的光合活性降低最大,但光合活性在实验结束时完全恢复。在底漆植物中,光合活性受到一定的抑制,表明有持续的启动效应。热休克增加了挥发物的排放,包括脂氧合酶途径挥发物,长链脂肪酸衍生化合物,单萜和倍半萜,香叶基香叶基二磷酸途径挥发物,和苯类化合物,而不同的热处理导致独特的排放混合物。在非底漆植物中,在72小时时恢复了应激引起的排放。在灌注的植物中,挥发性排放物是多相的,第一阶段,在0.5和10小时之间,反映了主要的应激反应,而次要的上升,在24到72小时之间,表明不同防御代谢途径的激活。我们的结果表明,暴露于温和的热量会导致持续的生理应激记忆,从而增强植物对随后的严重热应激事件的抵抗力。
    Climate change enhances the frequency of heatwaves that negatively affect photosynthesis and can alter constitutive volatile emissions and elicit emissions of stress volatiles, but how pre-exposure to mildly warmer temperatures affects plant physiological responses to subsequent severe heat episodes remains unclear, especially for aromatic plants with high and complex volatile defenses. We studied the impact of heat shock (45 °C/5 min) applied alone and after exposure to moderate heat stress (35 °C/1 h, priming) on foliage photosynthesis and volatile emissions in the aromatic plant Origanum vulgare through 72 h recovery period. Heat stress decreased photosynthesis rates and stomatal conductance, whereas the reductions in photosynthesis were primarily due to non-stomatal factors. In non-primed plants, heat shock-induced reductions in photosynthetic activity were the greatest, but photosynthetic activity completely recovered by the end of the experiment. In primed plants, a certain inhibition of photosynthetic activity remained, suggesting a sustained priming effect. Heat shock enhanced the emissions of volatiles including lipoxygenase pathway volatiles, long-chained fatty acid-derived compounds, mono- and sesquiterpenes, geranylgeranyl diphosphate pathway volatiles, and benzenoids, whereas different heat treatments resulted in unique emission blends. In non-primed plants, stress-elicited emissions recovered at 72 h. In primed plants, volatile emissions were multiphasic, the first phase, between 0.5 and 10 h, reflected the primary stress response, whereas the secondary rise, between 24 and 72 h, indicated activations of different defense metabolic pathways. Our results demonstrate that exposure to mild heat leads to a sustained physiological stress memory that enhances plant resistance to subsequent severe heat stress episodes.
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  • 文章类型: Journal Article
    Cinnamomumverum(Lauraceae),也被称为“真正的肉桂”或“锡兰肉桂”,长期以来被广泛用于传统的民间医学和烹饪。由于其他Cinnamomum物种之间的遗传变异和形态相似性,C.verum的系统学存在一些困难。本工作旨在寻找来自巴西亚马逊地区的C.verum样品的化学和分子标记。从栽培样品和商业样品中提取叶EO和遗传物质(DNA)。通过主成分分析(PCA)的多变量统计分析将来自培养的C.verum(Cve1-Cve5)和商业(Cve6-c-Cv9-c)样品的精油的化学组成分组。主要化合物富含苯类和苯丙素,如丁香酚(0.7-91.0%),苯甲酸苄酯(0.28-76.51%),(E)-乙酸肉桂酯(0.36-32.1%),和(E)-肉桂醛(1.0-19.73%)。使用matK和rbcL基因的叶绿体区域开发了DNA条形码用于系统发育分析,和psbA-trnH基因间间隔区。psbA-trnH序列提供了更多的核苷酸多样性,MatK证实了C.verum的身份.发现DNA条形码和挥发物谱的组合是区分C.verum品种和检查工业来源真实性的重要工具。
    Cinnamomum verum (Lauraceae), also known as \"true cinnamon\" or \"Ceylon cinnamon\" has been widely used in traditional folk medicine and cuisine for a long time. The systematics of C. verum presents some difficulties due to genetic variation and morphological similarity between other Cinnamomum species. The present work aimed to find chemical and molecular markers of C. verum samples from the Amazon region of Brazil. The leaf EOs and the genetic material (DNA) were extracted from samples cultivated and commercial samples. The chemical composition of the essential oils from samples of C. verum cultivated (Cve1-Cve5) and commercial (Cve6-c-Cv9-c) was grouped by multivariate statistical analysis of Principal Component Analysis (PCA). The major compounds were rich in benzenoids and phenylpropanoids, such as eugenol (0.7-91.0%), benzyl benzoate (0.28-76.51%), (E)-cinnamyl acetate (0.36-32.1%), and (E)-cinnamaldehyde (1.0-19.73%). DNA barcodes were developed for phylogenetic analysis using the chloroplastic regions of the matK and rbcL genes, and psbA-trnH intergenic spacer. The psbA-trnH sequences provided greater diversity of nucleotides, and matK confirmed the identity of C. verum. The combination of DNA barcode and volatile profile was found to be an important tool for the discrimination of C. verum varieties and to examine the authenticity of industrial sources.
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  • 文章类型: Journal Article
    仅食用槟榔,或以槟榔(BQ)的形式,对健康有负面影响,对人类致癌。印度尼西亚是世界上最大的槟榔生产国之一,然而,对印尼槟榔和BQs的生物分子组成知之甚少。我们最近表明,印尼BQs的酚类和生物碱含量表现出明显的地理差异。这里,我们首次使用非靶向气相色谱-质谱(GC-MS)分析对来自印度尼西亚四个地区的BQ成分进行了代谢组学分析。除了众所周知的生物碱,小分子谱分析初步确定了BQ中的92种植物化学物质。这些主要包括苯类和萜类,以及酸,醛类,酒精,和酯类。Safrole,一种潜在的基因毒性苯类,在西巴布亚的槟榔(Piperbetle)花序中大量发现,在除西巴布亚以外的任何印度尼西亚地区的槟榔样品中均未检测到。萜烯主要在槟榔叶和花序/茎中检测到。槟榔,外壳,槟榔叶,花序茎,和BQ混合物表达了独特的代谢物模式,并且在不同地理区域发现代谢物的含量和浓度存在显着差异。总之,这是首次使用GC-MS对BQs进行代谢组学研究。结果表明,BQs的分子成分在地理上有所不同,并表明BQs的鉴别疾病诱导能力可能反映了其独特的化学组成。
    Consumption of areca nut alone, or in the form of betel quid (BQ), has negative health effects and is carcinogenic to humans. Indonesia is one of the largest producers of areca nuts worldwide, yet little is known about the biomolecular composition of Indonesian areca nuts and BQs. We have recently shown that phenolic and alkaloid content of Indonesian BQs exhibits distinct geographical differences. Here, we profiled for the first time the metabolomics of BQ constituents from four regions of Indonesia using non-targeted gas chromatography-mass spectrometry (GC-MS) analysis. In addition to well-known alkaloids, the analysis of small-molecule profiles tentatively identified 92 phytochemicals in BQ. These included mainly benzenoids and terpenes, as well as acids, aldehydes, alcohols, and esters. Safrole, a potentially genotoxic benzenoid, was found abundantly in betel (Piper betle) inflorescence from West Papua and was not detected in areca nut samples from any Indonesian region except West Papua. Terpenes were mostly detected in betel leaves and inflorescence/stem. Areca nut, husk, betel leaf, the inflorescence stem, and BQ mixture expressed distinctive metabolite patterns, and a significant variation in the content and concentration of metabolites was found across different geographical regions. In summary, this was the first metabolomic study of BQs using GC-MS. The results demonstrate that the molecular constituents of BQs vary geographically and suggest that the differential disease-inducing capacity of BQs may reflect their distinct chemical composition.
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  • 文章类型: Journal Article
    发现长链非编码RNA(lncRNA)在转录中起重要作用,转录后,以及各种生物过程中的表观遗传基因调控。然而,lncRNAs及其调控作用在园艺植物中的研究仍然很少。玫瑰在经济上很重要,不仅因为它们广泛用作花园和切花,而且是香水和化妆品行业天然香料的重要来源。但是目前对花香产生的调节机制知之甚少。在本文中,使用链特异性文库进行RNA-Seq分析,对不同开花期的玫瑰花进行了研究。有香味的品种“Tianmidemeng”(罗莎杂交)被用作植物材料。通过挖掘RNA-Seq数据鉴定了总共13,957个lncRNAs,包括10,887个注释的lncRNAs和3070个新的lncRNAs。其中,预测10,075个lncRNAs共有29,622个靶基因,包括54个合成酶基因和24个与花香合成相关的转录因子。425个lncRNAs在开花过程中差异表达,其中19个在所有三个开花期中差异表达。使用加权相关网络分析(WGCNA),我们将差异表达的lncRNAs与单个花香化合物的合成相关联。此外,使用VIGS方法在玫瑰中验证了一种候选lncRNA对花香合成的调节功能。在这项研究中,我们能够证明lncRNAs可能在玫瑰花香产生中起重要作用。这项研究还提高了我们对植物如何通过lncRNAs调节其次生代谢的理解。
    Long non-coding RNAs (lncRNAs) were found to play important roles in transcriptional, post-transcriptional, and epigenetic gene regulation in various biological processes. However, lncRNAs and their regulatory roles remain poorly studied in horticultural plants. Rose is economically important not only for their wide use as garden and cut flowers but also as important sources of natural fragrance for perfume and cosmetics industry, but presently little was known about the regulatory mechanism of the floral scent production. In this paper, a RNA-Seq analysis with strand-specific libraries, was performed to rose flowers in different flowering stages. The scented variety \'Tianmidemeng\' (Rosa hybrida) was used as plant material. A total of 13,957 lncRNAs were identified by mining the RNA-Seq data, including 10,887 annotated lncRNAs and 3070 novel lncRNAs. Among them, 10,075 lncRNAs were predicted to possess a total of 29,622 target genes, including 54 synthase genes and 24 transcription factors related to floral scent synthesis. 425 lncRNAs were differentially expressed during the flowering process, among which 19 were differentially expressed among all the three flowering stages. Using weighted correlation network analysis (WGCNA), we correlate the differentially-expressed lncRNAs to synthesis of individual floral scent compounds. Furthermore, regulatory function of one of candidate lncRNAs for floral scent synthesis was verified using VIGS method in the rose. In this study, we were able to show that lncRNAs may play important roles in floral scent production in the rose. This study also improves our understanding of how plants regulate their secondary metabolism by lncRNAs.
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  • 文章类型: Journal Article
    花卉气味对花卉产业中的玫瑰生产具有很高的观赏和经济价值。在过去的二十年里,已经研究了玫瑰花香产生的分子基础及其遗传。取得了一些重大成就,例如全面的玫瑰基因组和在植物中发现了一种新的香叶醇合成酶。在这次审查中,我们总结了现代玫瑰中花香的成分,关注花香产生和排放的分子机制的最新进展,以及玫瑰气味分子育种和代谢工程的最新进展。它可以为研究和改善玫瑰中的花香提供有用的信息。
    Floral scents possess high ornamental and economic values to rose production in the floricultural industry. In the past two decades, molecular bases of floral scent production have been studied in the rose as well as their genetic inheritance. Some significant achievements have been acquired, such as the comprehensive rose genome and the finding of a novel geraniol synthase in plants. In this review, we summarize the composition of floral scents in modern roses, focusing on the recent advances in the molecular mechanisms of floral scent production and emission, as well as the latest developments in molecular breeding and metabolic engineering of rose scents. It could provide useful information for both studying and improving the floral scent production in the rose.
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  • 文章类型: Journal Article
    热胁迫是全球气候变化下植物面临的重要非生物胁迫之一。植物暴露于非生物或生物胁迫可以提高其对随后相同或不同胁迫(胁迫引发)的严重事件的耐受性。但是到目前为止,关于不同非生物和生物诱导子的预暴露如何改变植物对严重热胁迫的抗性的比较信息有限。我们暴露了多年生草本植物MelilotusalbusMedik。,一个富含次生代谢物的物种,适度的热应激(35°C)和温室粉虱(西TrialeurodesexapariorumWest。)侵染,以比较确定两种预处理是否都可以增强植物对随后的热激(45°C)胁迫的耐受性。通过72h恢复,通过光合特性和挥发性有机化合物的排放来表征植物对胁迫的生理响应。热休克处理降低了所有植物的净同化率(A)和气孔导度,但是热引发植物的A恢复速度明显快于其他植物。到恢复期结束时,在三个热休克应激组中,没有一个恢复到控制水平,但在粉虱侵染的植物中,它达到了热休克前的水平。在热引发的植物中,热休克处理与单萜排放的快速增加有关,以及在白粉虱侵染的植物中,苯类排放和总酚含量增加。
    Heat stress is one of the most important abiotic stresses confronted by plants under global climate change. Plant exposure to abiotic or biotic stress can improve its tolerance to subsequent severe episodes of the same or different stress (stress priming), but so far there is limited comparative information about how pre-exposures to different abiotic and biotic elicitors alter plant resistance to severe heat stress. We exposed the perennial herb Melilotus albus Medik., a species rich in secondary metabolites, to moderate heat stress (35 °C) and greenhouse whitefly (Trialeurodes vaporariorum West.) infestation to comparatively determine whether both pre-treatments could enhance plant tolerance to the subsequent heat shock (45 °C) stress. Plant physiological responses to stress were characterized by photosynthetic traits and volatile organic compound emissions through 72 h recovery. Heat shock treatment reduced net assimilation rate (A) and stomatal conductance in all plants, but heat-primed plants had significantly faster rates of recovery of A than other plants. By the end of the recovery period, A in none of the three heat shock-stressed groups recovered to the control level, but in whitefly-infested plants it reached the pre-heat shock level. In heat-primed plants, the heat shock treatment was associated with a fast rise of monoterpene emissions, and in whitefly-infested plants with benzenoid emissions and an increase in total phenolic content.
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  • 文章类型: Journal Article
    苯和类似芳香族化合物在民用环境中的存在是由于人为作用,也是由于天然来源。天然气由通常存在苯和相关化合物的气体混合物组成。因此,天然气管道中这些化合物的检测以及浓度水平的控制至关重要,必须保持在法律同意的限度以下。在这方面,工程师能够通过自动和连续的远程控制来检测这些化合物的设备引起了极大的兴趣。这里,我们讨论了用于测量天然气管道中硫化加臭剂的光学装置的应用,旨在检测和测量苯,甲苯,和二甲苯(BTX)在相同的上下文中。该仪器由一个定制的紫外分光光度计连接到一个自动控制系统能够提供现场检测BTX通过气体混合物的连续和远程检查。相对于苯,该仪器的特征在于LOD(检测水平)和LOQ(定量水平)的值分别等于0.55和1.84mg/Sm3。对于甲苯和二甲苯也发现了类似的限制(甲苯的LOD为0.81、1.05、1.41和1.00mg/Sm3,元-,正交-,和对二甲苯,分别)。
    The presence of benzene and similar aromatic compounds in civil environments is due to anthropic actions but also to natural sources. Natural gas consists of a gas mixture where benzene and related compounds are usually presents. Thus, the detection of these compounds in natural gas pipelines is of the utmost importance as well as the control of the concentration level, which must remain below the limits consented by law. In this regard, it is of striking interest to engineer devices able to detect these compounds by automatic and continuous remote control. Here, we discuss the application of an optical device designed for the measurement of sulfured odorizing agents in natural gas pipelines aiming at the detection and the measurement of benzene, toluene, and xylenes (BTX) in the same contexts. The instrument consists of a customized UV spectrophotometer connected to an automatic control system able to provide in-field detections of BTX through a continuous and remote check of the gaseous mixture. Relatively to benzene, the instrument is characterized by values of LOD (level of detection) and LOQ (level of quantification) equal to 0.55 and 1.84 mg/Sm3, respectively. Similar limits are found for toluene and xylenes (LOD of 0.81, 1.05, 1.41, and 1.00 mg/Sm3 for toluene, meta-, ortho-, and para-xylene, respectively).
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