Next Article in Journal
Antianhedonic and Antidepressant Effects of Affron®, a Standardized Saffron (Crocus Sativus L.) Extract
Previous Article in Journal
Dried Urine Microsampling Coupled to Liquid Chromatography—Tandem Mass Spectrometry (LC–MS/MS) for the Analysis of Unconjugated Anabolic Androgenic Steroids

Scalable Green Approach Toward Fragrant Acetates

Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237 Bratislava, Slovakia
Author to whom correspondence should be addressed.
Molecules 2020, 25(14), 3217;
Received: 18 June 2020 / Revised: 9 July 2020 / Accepted: 13 July 2020 / Published: 14 July 2020
(This article belongs to the Section Flavours and Fragrances)
The advantageous properties of ethylene glycol diacetate (EGDA) qualify it as a useful substitute for glycerol triacetate (GTA) for various green applications. We scrutinised the lipase-mediated acetylation of structurally diverse alcohols in neat EGDA furnishing the range of naturally occurring fragrant acetates. We found that such enzymatic system exhibits high reactivity and selectivity towards activated (homo) allylic and non-activated primary/secondary alcohols. This feature was utilised in the scalable multigram synthesis of fragrant (Z)-hex-3-en-1-yl acetate in 70% yield. In addition, the Lipozyme 435/EGDA system was also found to be applicable for the chemo-selective acetylation of (hydroxyalkyl) phenols as well as for the kinetic resolution of chiral secondary alcohols. Lastly, its discrimination power was demonstrated in competitive experiments of equimolar mixtures of two isomeric alcohols. This enabled the practical synthesis of 1-pentyl acetate isolated as a single product in 68% yield from the equimolar mixture of 1-pentanol and 3-pentanol. View Full-Text
Keywords: enzymatic acetylation; green solvents; chemo-selectivity enzymatic acetylation; green solvents; chemo-selectivity
Show Figures

Graphical abstract

MDPI and ACS Style

Puchl’ová, E.; Szolcsányi, P. Scalable Green Approach Toward Fragrant Acetates. Molecules 2020, 25, 3217.

AMA Style

Puchl’ová E, Szolcsányi P. Scalable Green Approach Toward Fragrant Acetates. Molecules. 2020; 25(14):3217.

Chicago/Turabian Style

Puchl’ová, Eva, and Peter Szolcsányi. 2020. "Scalable Green Approach Toward Fragrant Acetates" Molecules 25, no. 14: 3217.

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

Back to TopTop