On the chemistry of 1-pyrroline in solution and in the gas phase

Abstract 1-Pyrroline has a highly characteristic odor, which is employed by living organisms for chemical signaling and other purposes, but the mechanism whereby this odor is formed remains poorly understood. Here we used a combination of ambient mass spectrometry (AMS) and nuclear magnetic resonanc...

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Autores principales:	Xiaoping Zhang, Konstantin Chingin, Dacai Zhong, Juchao Liang, Yongzhong Ouyang, Huanwen Chen
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/88e6c7faa2d54a46a70bc3d23e1690b3
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spelling	oai:doaj.org-article:88e6c7faa2d54a46a70bc3d23e1690b32021-12-02T16:06:46ZOn the chemistry of 1-pyrroline in solution and in the gas phase10.1038/s41598-017-08217-12045-2322https://doaj.org/article/88e6c7faa2d54a46a70bc3d23e1690b32017-08-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-08217-1https://doaj.org/toc/2045-2322Abstract 1-Pyrroline has a highly characteristic odor, which is employed by living organisms for chemical signaling and other purposes, but the mechanism whereby this odor is formed remains poorly understood. Here we used a combination of ambient mass spectrometry (AMS) and nuclear magnetic resonance (NMR) spectroscopy to experimentally address the mechanistic aspects of 1-pyrroline volatility and other controversies regarding the chemistry of this compound. Our results indicate that in solution the volatility of the monomer species is significantly higher than that of the trimer species, and 1-pyrroline is evaporated mainly in its monomer state. Neat 1-pyrroline is essentially the pure trimer and displays ca. 100-fold lower evaporation rate than the monomer state in solution. In the gas-phase the trimer species is irreversibly decomposed into monomer species. Under equilibrium conditions the vapor of 1-pyrroline entirely consists of monomer species. The evaporation rate of 1-pyrroline in water has a step-wise dependence on the solution pH, the abrupt increase in volatility (>1,000-fold) occurring around the pKa value of 1-pyrroline (6.8). The pronounced step-wise dependence of 1-pyrroline volatility around neutral pH may also be an important evolutionary factor allowing living systems to regulate the odor strength from very weak to very strong with minimal efforts.Xiaoping ZhangKonstantin ChinginDacai ZhongJuchao LiangYongzhong OuyangHuanwen ChenNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-8 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Xiaoping Zhang Konstantin Chingin Dacai Zhong Juchao Liang Yongzhong Ouyang Huanwen Chen On the chemistry of 1-pyrroline in solution and in the gas phase
description	Abstract 1-Pyrroline has a highly characteristic odor, which is employed by living organisms for chemical signaling and other purposes, but the mechanism whereby this odor is formed remains poorly understood. Here we used a combination of ambient mass spectrometry (AMS) and nuclear magnetic resonance (NMR) spectroscopy to experimentally address the mechanistic aspects of 1-pyrroline volatility and other controversies regarding the chemistry of this compound. Our results indicate that in solution the volatility of the monomer species is significantly higher than that of the trimer species, and 1-pyrroline is evaporated mainly in its monomer state. Neat 1-pyrroline is essentially the pure trimer and displays ca. 100-fold lower evaporation rate than the monomer state in solution. In the gas-phase the trimer species is irreversibly decomposed into monomer species. Under equilibrium conditions the vapor of 1-pyrroline entirely consists of monomer species. The evaporation rate of 1-pyrroline in water has a step-wise dependence on the solution pH, the abrupt increase in volatility (>1,000-fold) occurring around the pKa value of 1-pyrroline (6.8). The pronounced step-wise dependence of 1-pyrroline volatility around neutral pH may also be an important evolutionary factor allowing living systems to regulate the odor strength from very weak to very strong with minimal efforts.
format	article
author	Xiaoping Zhang Konstantin Chingin Dacai Zhong Juchao Liang Yongzhong Ouyang Huanwen Chen
author_facet	Xiaoping Zhang Konstantin Chingin Dacai Zhong Juchao Liang Yongzhong Ouyang Huanwen Chen
author_sort	Xiaoping Zhang
title	On the chemistry of 1-pyrroline in solution and in the gas phase
title_short	On the chemistry of 1-pyrroline in solution and in the gas phase
title_full	On the chemistry of 1-pyrroline in solution and in the gas phase
title_fullStr	On the chemistry of 1-pyrroline in solution and in the gas phase
title_full_unstemmed	On the chemistry of 1-pyrroline in solution and in the gas phase
title_sort	on the chemistry of 1-pyrroline in solution and in the gas phase
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/88e6c7faa2d54a46a70bc3d23e1690b3
work_keys_str_mv	AT xiaopingzhang onthechemistryof1pyrrolineinsolutionandinthegasphase AT konstantinchingin onthechemistryof1pyrrolineinsolutionandinthegasphase AT dacaizhong onthechemistryof1pyrrolineinsolutionandinthegasphase AT juchaoliang onthechemistryof1pyrrolineinsolutionandinthegasphase AT yongzhongouyang onthechemistryof1pyrrolineinsolutionandinthegasphase AT huanwenchen onthechemistryof1pyrrolineinsolutionandinthegasphase
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On the chemistry of 1-pyrroline in solution and in the gas phase

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