DOCSLIB.ORG

Retention Indices for Frequently Reported Compounds of Plant Essential Oils

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Retention Indices for Frequently Reported Compounds of Plant Essential Oils Retention Indices for Frequently Reported Compounds of Plant Essential Oils V. I. Babushok,a) P. J. Linstrom, and I. G. Zenkevichb) National Institute of Standards and Technology, Gaithersburg, Maryland 20899, USA (Received 1 August 2011; accepted 27 September 2011; published online 29 November 2011) Gas chromatographic retention indices were evaluated for 505 frequently reported plant essential oil components using a large retention index database. Retention data are presented for three types of commonly used stationary phases: dimethyl silicone (nonpolar), dimethyl sili- cone with 5% phenyl groups (slightly polar), and polyethylene glycol (polar) stationary phases. The evaluations are based on the treatment of multiple measurements with the number of data records ranging from about 5 to 800 per compound. Data analysis was limited to temperature programmed conditions. The data reported include the average and median values of retention index with standard deviations and confidence intervals. VC 2011 by the U.S. Secretary of Commerce on behalf of the United States. All rights reserved. [doi:10.1063/1.3653552] Key words: essential oils; gas chromatography; Kova´ts indices; linear indices; retention indices; identification; flavor; olfaction. CONTENTS 1. Introduction The practical applications of plant essential oils are very 1. Introduction................................ 1 diverse. They are used for the production of food, drugs, per- fumes, aromatherapy, and many other applications.1–4 The 2. Retention Indices ........................... 2 need for identification of essential oil components ranges 3. Retention Data Presentation and Discussion . 2 from product quality control to basic research. The identifi- 4. Summary.................................. 45 cation of unknown compounds remains a complex problem, in spite of great progress made in analytical techniques over 5. Acknowledgments .......................... 45 the last several decades.3,5,6 Gas chromatography (GC) and 6. References................................. 45 gas chromatography-mass spectrometry (GC/MS) techniques are commonly employed for the identification of essential oil components.1,3,7,8 Measurement of retention indices (RI) of List of Tables chemical compounds and comparison with available reten- tion data collections is the usual approach in the confirmation 1. Cross-reference list of essential oil components of compound identification. Retention data are more useful (common names, other chemical identifiers and in combination with mass spectrometry, because the combi- average retention index values). .............. 4 nation can provide a nearly unambiguous identification of 2. Related enantiomers and racemic mixtures.. 16 isomers, which is difficult using mass spectra alone. Thus 3. Retention indices of essential oil components differences in the structures of branched alkyl substituents for dimethylsilicone stationary phase . ........ 17 and cis/trans isomers, which normally do not result in signif- 4. Retention indices of essential oil components icant mass spectral differences, can be identified with the use for dimethylsilicone stationary phase with 5% of retention data. phenyl groups. ............................. 26 Gas chromatographic retention data are very attractive for 5. Retention indices of essential oil components applications due to the simplicity of the measurements, for polar phase ............................. 35 application, and interpretation. To some extent retention data 6. Averaged standard deviation and confidence are available at no additional cost or effort as a by-product of range size for commonly reported constituents the use of chromatographic separation for mass spectrometry of essential oils............................. 45 measurements. It is known that a large number of compo- 7. The structural assignment of four isomers of nents of plant essential oils are common to many species. farnesol using retention data . ............... 45 Adams7 indicated that the ability to identify 500 compounds would enable one to identify more than 90% of the constitu- a)Electronic mail: [email protected]. ents of an essential oil of most species. Thus a relatively b) On leave from the Chemical Research Institute, St. Petersburg State Uni- small and reliable RI data collection can substantially versity, St. Petersburg, Russia. VC 2011 by the U.S. Secretary of Commerce on behalf of the United States. increase the identification effectiveness in the analysis of All rights reserved. essential oil constituents. 0047-2689/2011/40(4)/043101/47/$47.00043101-1 J. Phys. Chem. Ref. Data, Vol. 40, No. 4, 2011 This article is copyrighted as indicated in the article. Reuse of AIP content is subject to the terms at: http://scitation.aip.org/termsconditions. Downloaded to IP: 129.6.105.191 On: Tue, 30 Dec 2014 17:37:42 043101-2 BABUSHOK, LINSTROM, AND ZENKEVICH 0 0 0 0 The purpose of this communication is to evaluate retention Ix ¼ 100n þ 100½logðtxÞlogðtnÞ=½logðtnþ1ÞlogðtnÞ; (1) indices for the most frequently reported components of essential 9–13 0 0 oils using the retention data from the NIST data-collection. where tn and tnþ1 are adjusted retention times of the refer- A large body of gas chromatographic retention data exists for ence n-alkane hydrocarbons eluting immediately before and the compounds of essential oils, thus reliable values of RI data after compound “X,” and tx is the adjusted retention time of can be provided. The goal was to evaluate retention data for compound “X.” Linear indices (nonisothermal indices in about 500 commonly identified components of essential oils. accord with the definition of Van den Dool and Kratz32 from We undertake the analysis of data distributions of multiple (rep- temperature-programming measurements) are defined by the licate) measurements to provide statistically justified RI values. following: Retention indices also find applications in the characteriza- tion of selectivity of stationary phases, in structural analysis, Ix ¼ 100n þ 100ðtx À tnÞ=ðtnþ1 À tnÞ; (2) and in studies of physico-chemical properties of analytes and 5,14 stationary phases. Relationships between Kova´ts indices where tn,tnþ1, and tx are net retention times. and thermodynamic properties are used for determination of A large volume of retention data is available for essential vapor pressures, enthalpies, and entropies of adsorption and oil compounds. Thus 1967 data records for limonene can be vaporization of different analytes.15–28 Zabiegala et al.29 found in the last release of the NIST database. The observed employed retention indices for the estimation of the calibra- RI data distributions are the result of several factors includ- tion constants of permeation passive samplers with polydime- ing small variations in stationary phase polarity, temperature thylsiloxane membranes. RI is also used as an aid in the conditions, and ratios between amounts of characterized ana- development of new medical and perfume formulations.8,30 lytes and reference compounds.34 The observed data spread The current status of retention data collections and of the is also the result of errors in measurements and compound development of computerized databases has been summar- misidentification.35 Discussion of retention data distributions ized by Babushok et al.9 The collection and processing of can be found in Refs. 9, 10, 35, and 36. gas chromatographic properties of chemical compounds began at NIST in the late 1990s with the aim of developing a 3. Retention Data Presentation and comprehensive and evaluated database of retention indi- Discussion ces.9,13 Currently the collection contains 346 757 data records for 70 839 compounds measured on nonpolar and po- A list of the most frequently reported compounds was gen- lar stationary phases (a data record corresponds to a single erated based on the number of data records available for dif- RI measurement for chemical compound). Data were ferent compounds in the NIST database.9,11,12 At first, the extracted from original papers, technical reports, conference list of compounds was determined based on the number of proceedings, and Internet sources (1958–2011). The collec- all available data records in the database. This list was tion contains over 10 000 sources of gas chromatographic adjusted in accord with the frequency of data reporting in the properties. The third release of the RI database is available journals publishing the results of research related to the as a part of NIST/EPA/NIH Mass Spectral database (June, essential oils, such as “Journal of Essential Oil Research,” 2011),11 as well as on the Internet (NIST Chemistry Web- “Flavor and Fragrance Journal,” “Phytochemistry,” and Book).12 The database allows one to study and evaluate “Biochemical Systematics and Ecology.” Additionally, we retention index variability for different chemical compounds. verified the presence of these compounds in the available This variability results from the differences in the column collections of data for essential oil compounds.6,7,37–39 As properties (brand, column size, etc.), differences in the con- the result, the list of frequently reported components of ditions of measurements, and experimental errors. essential oils was determined (Table 1). We limited our anal- ysis to the 505 commonly identified compounds. Only com- 2. Retention Indices pounds with at least five data-records were included in the final list. The retention index system suggested first by Kova´ts,31 The following describes our procedure for the treatment of and
Load more

Recommended publications
  • Acetoin Acetate Natural
    aurochemicals.com Safety Data Sheet HEALTH 0 FLAMMABILITY 2 REACTIVITY 0 Section 1: PRODUCT AND COMPANY IDENTIFICATION 1.1 Product identifiers Product Name Acetoin Acetate, Natural Product Number 0352600 CAS-No. 4906-24-5 1.2 Product Recommended Use Flavorings 1.3 Preparation Information Company Aurochemicals 7 Nicoll Street Washingtonville, NY 10992- USA Telephone 845-496-6065 Fax 845-496-6248 1.4 Emergency Telephone Number 1-800-535-5053 International - 1-352-323-3500 collect Section 2: HAZARD(s) IDENTIFICATION 2.1 Classification of substance or mixture GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) Combustible Liquid (Category 4) H227 Skin irritation (Category 2) H315 Eye Irritation (Category 2A) H319 Specific Target Organ Toxicity -Single Exposure -Respiratory irritation H335 2.2 GHS Label Elements, Including precautionary statements Pictogram Signal Statement Warning Hazard Statement(s) H227 Combustible liquid H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation Precautionary Statement(s) PREVENTION P210 Keep away from flames and hot surfaces - No smoking P216 Avoid breathing dust/fumes/gas/mist/vapors/spray P280 Wear protective gloves/protective clothing/face protection 3526 ACETOIN ACETATE Nat sds.doc Printed: April 17, 2019 Page 1 of 7 aurochemicals.com Safety Data Sheet RESPONSE P305+351+338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing. STORAGE P405 Store locked up DISPOSAL P501 Dispose of contents/container to an approved waste disposal plant 2.3 HNOC (Hazards not otherwise None classified or not covered by GHS Section 3: COMPOSITION / INFORMATION ON INGREDIENTS 3.1 Substances Synonym 2-Acetoxy-3-Butanone Formula C6H10O3 Molecular Weight 130.14 g/mol CAS-No 4906-24-5 EC-No 200-580-7 Hazardous Components Does not contain any hazardous substances Section 4: FIRST AID MEASURES 4.1 Description of first aid measures General Advice Consult a physician.
    [Show full text]
  • Anticarcinogenic and Antiplatelet Effects of Carvacrol S
    Experimental Oncology �� ������� ��� ���ne ��� Exp Oncol ��� �� � ������� ANTICARCINOGENIC AND ANTIPLATELET EFFECTS OF CARVACROL S. Karkabounas1, *, O. K Kostoula1, 5, T. Daskalou1, P. Veltsistas2, M. Karamouzis4, I. Zelovitis1, A. Metsios1, P. Lekkas1, A. M. Evangelou1, N. Kotsis1, I. Skoufos3 1Laboratory of Physiology, Faculty of Medicine, University of Ioannina, Ioannina, Greece 2Laboratory of Analytical Chemistry, Department of Chemistry, University of Ioannina, Ioannina, Greece 3Laboratory of Infectious Diseases and Hygiene of Animals, Department of Animal Production, Technological Education Institute of Epirus, Arta, Greece 4Laboratory of Biological Chemistry, Faculty of Medicine, University of Thessalonica, Greece 5Department of Biological Applications and Technology, University of Ioannina, Ioannina, Greece Aim: To investigate the effect of carvacrol on chemical carcinogenesis, cancer cell proliferation and platelet aggregation, and to find possible correlation between all these processes and the antioxidant properties of carvacrol. Materials and Methods: 3,4-benzopyrene-induced carcinogenesis model using Wistar rats was used. Leiomyosarcoma cells from Wistar rats were used to study carvacrol antiproliferative activity in vitro. The carvacrol antiplatelet properties were investigated with platelet aggregation assay and flow cytometry technique. The production of thromboxane B2, final metabolite of platelet aggregation, was evaluated by radioimmunoassay. Results: Our study revealed significant anticarcinogenic properties of carvacrol. We observed 30% decrease of 3,4 benzopyrene carcinogenic activity in vivo. Antiproliferative activity of carvacrol (IC50) was 90 μM and 67 μΜ for 24 h and 48 h of incubation of cells, respectively. Carvacrol possessed also mild antiplatelet effect, inducing the decrease of thromboxane A2 production in platelets and as a result — restrictive expression of the GPIIb/IIIa platelet receptor. Conclusion: Our data demon- strated that carvacrol possesses anticarcinogenic, antiproliferative and antiplatelet properties.
    [Show full text]
  • The Following Carcinogenic Essential Oils Should Not Be Used In
    Aromatherapy Undiluted- Safety and Ethics Copyright © Tony Burfield and Sylla Sheppard-Hanger (2005) [modified from a previous article “A Brief Safety Guidance on Essential Oils” written for IFA, Sept 2004]. Intro In the last 20 years aromatherapy has spread its influence to the household, toiletries and personal care areas: consumer products claiming to relax or invigorate our psyche’s have invaded our bathrooms, kitchen and living room areas. The numbers of therapists using essential oils in Europe and the USA has grown from a handful in the early 1980’s to thousands now worldwide. We have had time to add to our bank of knowledge on essential oils from reflecting on many decades of aromatherapeutic development and history, the collection of anecdotal information from practicing therapists, as well as from clinical & scientific investigations. We have also had enough time to consider the risks in employing essential oils in therapy. In the last twenty years, many more people have had accidents, been ‘burnt’, developed rashes, become allergic, and become sensitized to our beloved tools. Why is this? In this paper, we hope to shed light on this issue, clarify current safety findings, and discuss how Aromatherapists and those in the aromatherapy trade (suppliers, spas, etc.) can interpret this data for continued safe practice. After a refresher on current safety issues including carcinogenic and toxic oils, irritant and photo-toxic oils, we will look at allergens, oils without formal testing, pregnancy issues and medication interactions. We will address the increasing numbers of cases of sensitization and the effect of diluting essential oils.
    [Show full text]
  • Borneol - Camphor - Isoborneol
    EXP. 35 A & B OXIDATION-REDUCTION SCHEME: BORNEOL - CAMPHOR - ISOBORNEOL LEARNING OBJECTIVES: To illustrate the concepts of oxidation and reduction in organic chemistry, to illustrate the stereochemical effects of these reactions in certain systems, to use IR spectroscopy to characterize diastereomers and monitor reactions. QUIZ PREPARATION: Recitation notes and readings assigned in the syllabus. OXIDATION AND REDUCTION IN ORGANIC CHEMISTRY The concepts of oxidation and reduction in chemistry are fundamentally related to the loss and gain of electrons, respectively. For a specific atom, oxidation brings about an increase in the oxidation number, whereas reduction does the opposite. This is of course true in organic reactions as well, but it is frequently less clear where the gain or loss of electrons is taking place. For this reason, the concepts of oxidation and reduction are addressed from a different perspective in organic chemistry. Since carbon is the most important element in organic chemistry, we can define oxidation as a process whereby carbon gains bonds to more electronegative atoms. These can be any atoms more electronegative than carbon, such as chlorine or sulphur, but the most commonly seen in organic oxidations is oxygen. The more bonds to oxygen, the higher the oxidation state of the carbon involved. Examples of oxidation reactions are those that convert alkanes into alcohols, or alcohols into carbonyl compounds. The functional groups that contain the most highly oxidized form of carbon in organic compounds are the carboxylic acids and their derivatives. Reduction is the opposite of oxidation. We can define reduction as a process whereby carbon adds bonds to less electronegative atoms.
    [Show full text]
  • Visible-Light-Driven Photooxidation of Alcohols Using Surface-Doped Graphitic Carbon Nitride
    Electronic Supplementary Material (ESI) for Green Chemistry. This journal is © The Royal Society of Chemistry 2017 Visible-Light-Driven Photooxidation of alcohols using surface-doped graphitic carbon nitride Wuyuan Zhang, Anna Bariotaki, Ioulia Smonou, and Frank Hollmann* Material and Methods Materials Unless stated otherwise all chemicals were purchased from Sigma-Aldrich, Fluka, Acros or Alfa-Aesar with the highest purity available and used without further treatment. Synthesis of g-C3N4 and carbon nanodots doped (CD-C3N4) The g-C3N4 was synthesized via the simple calcination (Carbolite furnace; CWF 12/5, 2400 W) of urea (10.0 g) at 600 °C for 4 h (5 °C/min), a yellowish powder was obtained after the cooling to room temperature.1 The carbon nanodots were synthesized via the thermal decomposition of sucrose with slight modification.2 Briefly, 0.75 g of sucrose was dissolved in 30 mL of MilliQ water and stirred at room temperature for 0.5 h. The solution was transferred into a 45 mL Teflon-lined stainless steel autoclave reactor, and heated at 180 °C for 5 h (10 °C/min). After cooling the reactor to room temperature, a brown mixture was obtained. The mixture was centrifuged (8000 rpm for 20 min), and the pellet was washed with water (3×) and freeze-dried. 3 In order to deposit carbon nanodots to the surface of g-C3N4, Liu et al’s procedures were adopted. Firstly, a stock solution of carbon nanodots (1 mg in 25mL water) was prepared. 15.0 mL of this stock solution was mixed with 15.0 mL of NH4OH (28 %) and sealed in a 45 mL Teflon-lined autoclave reactor.
    [Show full text]
  • Anti-Eczema Mechanism of Action of Nigella Sativa for Atopic Dermatitis: Computer-Aided Prediction and Pathway Analysis Based on Protein-Chemical Interaction Networks
    68 BIOMOLECULAR AND HEALTH SCIENCE JOURNAL 2019 OCTOBER, VOL 02 (02) ORIGINAL ARTICLE Anti-eczema Mechanism of Action of Nigella sativa for Atopic Dermatitis: Computer-aided Prediction and Pathway Analysis Based on Protein-chemical Interaction Networks Meidyta Sinantryana Widyaswari1, Iis Noventi2, Herdiantri Sufriyana3,4* 1Department of Dermatology and Venereology, College of Medicine, University of Nahdlatul Ulama Surabaya, Indonesia 2Department of Medical-Surgical Nursing, College of Nursing and Midwifery, University of Nahdlatul Ulama Surabaya, Indonesia 3Department of Medical Physiology, College of Medicine, University of Nahdlatul Ulama Surabaya, Surabaya, Indonesia 4Graduate Institute of Biomedical Informatics, College of Medical Science and Technology, Taipei Medical University, Taipei, Taiwan A R T I C L E I N F O A B S T R A C T Article history: Introduction: Black cumin (Nigella sativa) is widely used to treat various diseases. It is also Received 26 August 2019 believed to relief skin conditions accompanied by itching symptom, such as atopic dermatitis Received in revised form 14 (AD) or eczema. However, the anti-eczema mechanism of action is still unclear. The aims of this October 2019 syudy was to identify anti-eczema mechanism of action of N. sativa for AD using computer aided Accepted 21 October 2019 prediction and pathway analysis based on protein-chemical networks. Available online 31 October 2019 Methods: We utilized dataset consisting chemical compounds of N. sativa from KNApSAcK. It is a comprehensive species-metabolite relationship database. Using canonical SMILES strings that Keywords: encode molecular structures of each compound, we predicted the probabilities of activity (Pa) for Nigella sativa, anti-eczema effect based on PASS algorithms.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 7,576,170 B2 Perry Et Al
    US00757617OB2 (12) United States Patent (10) Patent No.: US 7,576,170 B2 Perry et al. (45) Date of Patent: Aug. 18, 2009 (54) CYCLIC SILOXANE COMPOSITIONS FOR 6,046,156 A 4/2000 Perry THE RELEASE OF ACTIVE INGREDIENTS 6,054,547 A 4/2000 Perry et al. 6,063,365 A 5, 2000 Schefer et al. (75) Inventors: Robert J. Perry, Niskayuna, NY (US); 6,075,111 A 6/2000 Perry et al. Mark D. Leatherman, Elmsford, NY 6,077.923 A 6/2000 Perry et al. (US); Shahid Murtuza, Albany, NY 6,083,901 A 7/2000 Perry et al. (US) 6,121,343 A 9/2000 Hongo et al. 6,143,309 A 11/2000 Legrow et al. (73) Assignee: Momentive Performance Materials, 6,153,578 A 11/2000 Perry Albany, NY (US) 6,200,949 B1 3/2001 Reijmer et al. 6,228,380 B1 5, 2001 LeGrow et al. (*) Notice: Subject to any disclaimer, the term of this 6,262,287 B1 7/2001 Anderson et al. patent is extended or adjusted under 35 6,267,977 B1 7/2001 LeGrow et al. U.S.C. 154(b) by 993 days. 6,309,715 B1 10/2001 Lindauer et al. 6,322,777 B1 1 1/2001 Perry et al. (21) Appl. No.: 10/742,415 6,325,274 B2 12/2001 Esumi et al. 6,325,859 B1 12/2001 De Roos et al. (22) Filed: Dec. 19, 2003 6,435,423 B2 8/2002 Hurry et al. (65) Prior Publication Data 6,624,136 B2 9, 2003 Guerinet al.
    [Show full text]
  • Carvacrol and Cinnamaldehyde Inactivate Antibiotic-Resistant <I
    234 Journal of Food Protection, Vol. 73, No. 2, 2010, Pages 234–240 Carvacrol and Cinnamaldehyde Inactivate Antibiotic-Resistant Salmonella enterica in Buffer and on Celery and Oysters SADHANA RAVISHANKAR,1* LIBIN ZHU,1 JAVIER REYNA-GRANADOS,1 BIBIANA LAW,1 LYNN JOENS,1 AND MENDEL FRIEDMAN2 1Department of Veterinary Science and Microbiology, University of Arizona, 1117 East Lowell Street, Tucson, Arizona 85721; and 2U.S. Department of Agriculture, Agricultural Research Service, Western Regional Research Center, Produce Safety and Microbiology Research, 800 Buchanan Street, Albany, California 94710, USA Downloaded from http://meridian.allenpress.com/jfp/article-pdf/73/2/234/1679919/0362-028x-73_2_234.pdf by guest on 27 September 2021 MS 09-228: Received 20 May 2009/Accepted 25 September 2009 ABSTRACT The emergence of antibiotic-resistant Salmonella is of concern to food processors. The objective of this research was to identify antimicrobial activities of cinnamaldehyde and carvacrol against antibiotic-resistant Salmonella enterica in phosphate- buffered saline (PBS) and on celery and oysters. Twenty-three isolates were screened for resistance to seven antibiotics. Two resistant and two susceptible strains were chosen for the study. S. enterica cultures (105 CFU/ml) were added to different concentrations of cinnamaldehyde and carvacrol (0.1, 0.2, 0.3, and 0.4% [vol/vol]) in PBS, mixed, and incubated at 37uC. Samples were taken at 0, 1, 5, and 24 h for enumeration. Celery and oysters were inoculated with S. enterica (106–7 CFU/ml), treated with 1% cinnamaldehyde or 1% carvacrol, incubated at 4uC, and then sampled for enumeration on days 0 and 3.
    [Show full text]
  • Electrooxidation Enables Highly Regioselective Dearomative Annulation of Indole and Benzofuran Derivatives
    ARTICLE https://doi.org/10.1038/s41467-019-13829-4 OPEN Electrooxidation enables highly regioselective dearomative annulation of indole and benzofuran derivatives Kun Liu1, Wenxu Song1, Yuqi Deng1, Huiyue Yang1, Chunlan Song1, Takfaoui Abdelilah1, Shengchun Wang 1, Hengjiang Cong 1, Shan Tang1 & Aiwen Lei1* 1234567890():,; The dearomatization of arenes represents a powerful synthetic methodology to provide three-dimensional chemicals of high added value. Here we report a general and practical protocol for regioselective dearomative annulation of indole and benzofuran derivatives in an electrochemical way. Under undivided electrolytic conditions, a series of highly functio- nalized five to eight-membered heterocycle-2,3-fused indolines and dihydrobenzofurans, which are typically unattainable under thermal conditions, can be successfully accessed in high yield with excellent regio- and stereo-selectivity. This transformation can also tolerate a wide range of functional groups and achieve good efficiency in large-scale synthesis under oxidant-free conditions. In addition, cyclic voltammetry, electron paramagnetic resonance (EPR) and kinetic studies indicate that the dehydrogenative dearomatization annulations arise from the anodic oxidation of indole into indole radical cation, and this process is the rate- determining step. 1 College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, P. R. China. *email: aiwenlei@whu. edu.cn NATURE COMMUNICATIONS | (2020) 11:3 | https://doi.org/10.1038/s41467-019-13829-4 | www.nature.com/naturecommunications 1 ARTICLE NATURE COMMUNICATIONS | https://doi.org/10.1038/s41467-019-13829-4 reaking the aromatic systems of electron-rich arenes or fused indolines (Fig. 1a)39–44. Therefore, it is highly appealing to heteroarenes provides three-dimensional chemicals of high develop efficient approaches to allow for their preparation.
    [Show full text]
  • Oenological Impact of the Hanseniaspora/Kloeckera Yeast Genus on Wines—A Review
    fermentation Review Oenological Impact of the Hanseniaspora/Kloeckera Yeast Genus on Wines—A Review Valentina Martin, Maria Jose Valera , Karina Medina, Eduardo Boido and Francisco Carrau * Enology and Fermentation Biotechnology Area, Food Science and Technology Department, Facultad de Quimica, Universidad de la Republica, Montevideo 11800, Uruguay; [email protected] (V.M.); [email protected] (M.J.V.); [email protected] (K.M.); [email protected] (E.B.) * Correspondence: [email protected]; Tel.: +598-292-481-94 Received: 7 August 2018; Accepted: 5 September 2018; Published: 10 September 2018 Abstract: Apiculate yeasts of the genus Hanseniaspora/Kloeckera are the main species present on mature grapes and play a significant role at the beginning of fermentation, producing enzymes and aroma compounds that expand the diversity of wine color and flavor. Ten species of the genus Hanseniaspora have been recovered from grapes and are associated in two groups: H. valbyensis, H. guilliermondii, H. uvarum, H. opuntiae, H. thailandica, H. meyeri, and H. clermontiae; and H. vineae, H. osmophila, and H. occidentalis. This review focuses on the application of some strains belonging to this genus in co-fermentation with Saccharomyces cerevisiae that demonstrates their positive contribution to winemaking. Some consistent results have shown more intense flavors and complex, full-bodied wines, compared with wines produced by the use of S. cerevisiae alone. Recent genetic and physiologic studies have improved the knowledge of the Hanseniaspora/Kloeckera species. Significant increases in acetyl esters, benzenoids, and sesquiterpene flavor compounds, and relative decreases in alcohols and acids have been reported, due to different fermentation pathways compared to conventional wine yeasts.
    [Show full text]
  • Benzofuran Synthesis Through Iodocyclization Reactions: Recent Advances
    MOJ Bioorganic & Organic Chemistry Mini Review Open Access Benzofuran synthesis through iodocyclization reactions: recent advances Abstract Volume 1 Issue 7 - 2017 Recent advancements (2014-17) in the benzofuran synthesis through iodocyclization Saurabh Mehta have been summarized. The successful use of various iodinating agents, bases, additives Department of Applied Chemistry, Delhi Technological etc. make iodocyclization a versatile and efficient methodology. The methodology has University, India been applied for the synthesis of more complex benzofuran derivatives, and may open interesting avenues in the area of heterocyclic chemistry (Figure 1). Correspondence: Saurabh Mehta, Department of Applied O-LG Chemistry, Delhi Technological University, Bawana Road, Delhi, + O R1 I 1 2 110042 India, Tel +9188 0066 5868, R R Email [email protected], [email protected] R2 I Received: December 17, 2017 | Published: December 29, 2017 LG = H, Me or other Protecting group 1 R = H, Me, OMe, I, CO2Me, etc. R2 = H, aryl, alkyl, alkenyl, etc. Figure 1 Keywords: annulations, alkyne, benzofuran, iodocyclization, heterocycle Introduction derivatives were obtained in high yields (84%−100%) under mild conditions. The authors demonstrated that the choice of bis(2,4,6- Benzo[b]furan is a privileged heterocyclic scaffold. Several collidine)iodonium hexafluorophosphate [I(coll)2PF6] as the compounds containing this scaffold have interesting biological iodinating agent was necessary for the success of the reaction. Also, 1 activities, such as anti-cancer, anti-viral, anti-inflammatory, etc. Few the ethoxyethyl ether group acted as a protecting group as well as a 2 derivatives are even used as commercial drugs, such as Amiodarone, good leaving group.
    [Show full text]
  • RIFM Fragrance Ingredient Safety Assessment, 2-Isopropyl-4- Methylanisole, CAS Registry Number 31574-44-4
    Food and Chemical Toxicology 110 (2017) S545eS551 Contents lists available at ScienceDirect Food and Chemical Toxicology journal homepage: www.elsevier.com/locate/foodchemtox Short review RIFM fragrance ingredient safety assessment, 2-isopropyl-4- methylanisole, CAS Registry Number 31574-44-4 * A.M. Api a, , D. Belsito b, D. Botelho a, D. Browne a, M. Bruze c, G.A. Burton Jr. d, J. Buschmann e, M.L. Dagli f, M. Date a, W. Dekant g, C. Deodhar a, M. Francis a, A.D. Fryer h, K. Joshi a,S.LaCavaa, A. Lapczynski a, D.C. Liebler i,D.O’Brien a, R. Parakhia a,A.Patela, T.M. Penning j, G. Ritacco a, J. Romine a, D. Salvito a, T.W. Schultz k, I.G. Sipes l, Y. Thakkar a, E.H. Theophilus a, A.K. Tiethof a, Y. Tokura m, S. Tsang a, J. Wahler a a Research Institute for Fragrance Materials, Inc., 50 Tice Boulevard, Woodcliff Lake, NJ 07677, USA b Columbia University Medical Center, Department of Dermatology, 161 Fort Washington Ave., New York, NY 10032, USA c Malmo University Hospital, Department of Occupational & Environmental Dermatology, Sodra Forstadsgatan 101, Entrance 47, Malmo SE-20502, Sweden d School of Natural Resources & Environment, University of Michigan, Dana Building G110, 440 Church St., Ann Arbor, MI 58109, USA e Fraunhofer Institute for Toxicology and Experimental Medicine, Nikolai-Fuchs-Strasse 1, 30625 Hannover, Germany f University of Sao Paulo, School of Veterinary Medicine and Animal Science, Department of Pathology, Av. Prof. dr. Orlando Marques de Paiva, 87, Sao Paulo CEP 05508-900, Brazil g University of Wuerzburg, Department of Toxicology, Versbacher Str.
    [Show full text]