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Quantification of the Geranium Essential Oil, Palmarosa foods Article Quantification of the Geranium Essential Oil, Palmarosa Essential Oil and Phenylethyl Alcohol in Rosa damascena Essential Oil Using ATR-FTIR Spectroscopy Combined with Chemometrics Nur Cebi Department of Food Engineering, Faculty of Chemical and Metallurgical Engineering, Yıldız Technical University, Istanbul˙ 34210, Turkey; [email protected] Abstract: Rosa damascena essential oil is an essential oil that has the greatest industrial importance due to its unique quality properties. The study used ATR-FTIR (attenuated total reflectance-Fourier trans- form infrared) spectroscopy coupled with chemometrics of PLSR (partial least squares regression) and PCR (principal component regression) for quantification of probable adulterants of geranium essential oil (GEO), palmarosa essential oil (PEO) and phenyl ethyl alcohol (PEOH). Hierarchical cluster analysis was performed to observe the classification pattern of Rosa damascena essential oil, spiked samples and adulterants. Rosa damascena essential oil was spiked with each adulterant at con- centrations of 0–100% (v/v). Excellent R2 (regression coefficient) values (≥0.96) were obtained in all Citation: Cebi, N. Quantification of PLSR and PCR cross-validation models. The SECV (standard error of cross-validation) values ranged the Geranium Essential Oil, between 0.43 and 4.15. The lowest SECV and bias values were observed in the PLSR and PCR models, Palmarosa Essential Oil and which were built by using the raw FTIR spectra of all samples. Hierarchical cluster analysis through Phenylethyl Alcohol in Rosa Ward’s algorithm and Euclidian distance had high potential to observe the classification pattern of damascena Essential Oil Using all adulterated and authentic samples. In conclusion, the combination of ATR-FTIR spectroscopy ATR-FTIR Spectroscopy Combined with multivariate analysis can be used for rapid, cost-effective, easy, reliable and high-throughput with Chemometrics. Foods 2021, 10, detection of GEO, PEO and PEOH in Rosa damascena essential oil. 1848. https://doi.org/10.3390/ foods10081848 Keywords: FTIR; Rosa damascena essential oil; PLSR; PCR; HCA; PCA; adulteration; geranium essential oil; palmarosa essential oil; phenyl ethyl alcohol Academic Editors: Francesco Longobardi and Ana María Jiménez Carvelo Received: 5 July 2021 1. Introduction Accepted: 4 August 2021 Rosa damascena (Damask rose) is one of the most important species of the genus Rosa, Published: 11 August 2021 which consists of at least 200 species. It is known as a unique type of oil-bearing rose with its intense and pungent scent [1]. Rosa damascena is mainly cultivated in Turkey and Bulgaria; Publisher’s Note: MDPI stays neutral rose oil, concrete and absolute are the major products obtained from Rosa damascena [2]. with regard to jurisdictional claims in Turkey is the main rose oil producer in the world and provides approximately 50% of the published maps and institutional affil- supply [1]. iations. Rosa damascena essential oil is defined as: essential oil obtained by steam distillation of the flowers of Rosa damascena Miller of the Rosaceae family, cultivated in Turkey, Morocco and Bulgaria according to the international standard [3]. The blooming of Rosa damascena starts in early May and continues to the beginning of July, in Isparta (Turkey). In the Copyright: © 2021 by the author. flowering season, the roses are picked in the very early hours of the morning and then they Licensee MDPI, Basel, Switzerland. are transferred to the distillation facilities [4]. Previous studies reported that 3500–4000 kg This article is an open access article of rose flowers are needed to produce 1 kg of rose essential oil by the distillation process in distributed under the terms and the industrial facilities [5]. conditions of the Creative Commons Rosa damascena essential oil is a type of rose oil that has the highest economic value for Attribution (CC BY) license (https:// the perfume, cosmetics, pharmaceutical and food industries with its sharp and intense scent creativecommons.org/licenses/by/ making it distinctive among other scented rose types [1]. It is widely included in cosmetic 4.0/). Foods 2021, 10, 1848. https://doi.org/10.3390/foods10081848 https://www.mdpi.com/journal/foods Foods 2021, 10, 1848 2 of 15 products such as creams, shampoos, soaps, lotions and more, and is also used in foodstuffs such as puddings, jellies, candies, delights and chocolate [6]. Previous studies reported that Rosa damascena is known as fluid gold due its high price and economic importance [7]. The chemical composition of Rosa damascena includes monoterpene alcohols (e.g., citronellol, geraniol, nerol), the pyran class of monoterpenes (e.g., rose oxide), metabolites related with the shikimic pathway (e.g., methyl eugenol and phenyl ethyl alcohol), long- chain hydrocarbons (nonadecane, nonadecene, eicosane and heneicosane), and metabolites resulting from carotenoids’ degradation (damascenones and β-ionones) [8]. A number of studies reported that high-value natural product Rosa damascena essential oil has an- timicrobial, antioxidant, relaxant, anti-inflammatory and insecticidal properties due to the biologically active compounds such as citronellol, geraniol, nerol, linalool and phenyl ethyl alcohol in its composition [8]. The high production costs, limited production quantity and wide industrial applica- tions of Rosa damascena essential oil are the biggest pressures driving economically moti- vated adulteration. This essential oil is one of the most expensive in the essential oil market and this situation makes it highly prone to adulteration with cheaper oils or synthetic materials. Adulteration of natural products such as essential oils may cause dishonest trading, exploitation of consumers, deterioration of the authentic product, food-safety related problems and health risks. Previous studies reported that adulteration of Rosa damascena essential oil (REO) is implemented by blending it with geranium oil (GEO), palmarosa oil (PEO) and phenyl ethyl alcohol (PEOH) [9]. Geranium essential oil is mainly composed of citronellol (30.2%), citronellyl formate (9.3%) and geraniol (7.6%) [10]. Additionally, major volatile compounds of the palmarosa essential oil are linalool (2.6–3.8%), geraniol (91.8–92.8%) and geranial (1.8–2.0%) [11]. There is a need for new methodologies for the detection and quantification of such adulterants in its composition. The FTIR (Fourier transform infrared) spectroscopy tech- nique provides fast, efficient, trustable, easy, eco-friendly and economical determination of fingerprinting data related to the overall chemistry of the material investigated [12]. Such FTIR analyses could be performed using either no or only minimum sample preparation with very small amounts of essential oil. It is now well-established from a variety of studies that essential oil quality can be successfully evaluated using Fourier transform infrared spectroscopy combined with chemometric techniques [13]. Previous studies reported that vibrational spectroscopy combined with chemometric models were effectively used for the determination of quality in lavender oils [14]. Similarly, Raman and ATR-FTIR (attenuated total reflectance-Fourier transform infrared) spectroscopy techniques were successfully ap- plied for quality evaluation of eucalyptus essential oil [15]. Sandasi et al. (2011) presented that vibrational spectroscopy and chemometrics can be used for the quality assessment of rose-scented geranium [16]. Some recent studies showed that various adulterants could be successfully quantified in lemon essential oil and mentha piperita essential oil by using FTIR spectroscopy combined with chemometrics [12,17]. To the best of our knowledge, the current research is the first attempt at the detection and quantification of PEO, GEO and PEOH in Rosa damascena essential oil by using FTIR spectroscopy combined with the chemometrics of partial least squares regression (PLSR) and principal component regression (PCR). Additionally, hierarchical cluster analysis (HCA) and principal component analysis (PCA) was applied for visualization of the cluster pattern of adulterants, adulterated samples and Rosa damascena essential oil. Foods 2021, 10, 1848 3 of 15 2. Materials and Methods 2.1. Apparatus A Bruker Tensor 27 FTIR spectrometer equipped with an attenuated total reflectance (ATR) accessory was used for spectral acquisition at the spectral range of 4000–650 cm−1. The FTIR spectrometer had a KBr beamsplitter and DLaTGS detector. The attenuated total re- flectance (ATR) unit was used in combination with the FTIR spectrometer. Spectral acquisition and instrument control was assured by OPUS Version 7.2 (Bruker, Karlsruhe, Germany). 2.2. Essential Oils and Spiked Samples Original Rosa damascena essential oils (REO1, REO2, REO3), geranium essential oils (GEO1, GEO2, GEO3) and palmarosa essential oils (PEO1, PEO2, PEO3) were purchased from well-known companies (Istanbul, Turkey). Phenyl ethyl alcohol (PEOH) was pur- chased from Sigma-Aldrich (Darmstadt, Germany). Spiked (adulterated) samples were diligently prepared at the adulteration levels of 0, 2%, 4%, 8%, 16%, 32%, 64% and 100% v/v for each adulterant. Forty-two spiked samples were prepared in total. Cross-validation graphs were drawn using eight levels of concentration. All of the samples were stored at 4 ◦C in dark vials until the FTIR measurements. 2.3. ATR-FTIR Measurements The FTIR spectra of all samples (authentic essential oils, spiked samples and adulter- ants) were measured at the spectral range
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