Expanding the Modular Ester Fermentative Pathways for Combinatorial Biosynthesis of Esters from Volatile Organic Acids
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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. -
Chapter 21 the Chemistry of Carboxylic Acid Derivatives
Instructor Supplemental Solutions to Problems © 2010 Roberts and Company Publishers Chapter 21 The Chemistry of Carboxylic Acid Derivatives Solutions to In-Text Problems 21.1 (b) (d) (e) (h) 21.2 (a) butanenitrile (common: butyronitrile) (c) isopentyl 3-methylbutanoate (common: isoamyl isovalerate) The isoamyl group is the same as an isopentyl or 3-methylbutyl group: (d) N,N-dimethylbenzamide 21.3 The E and Z conformations of N-acetylproline: 21.5 As shown by the data above the problem, a carboxylic acid has a higher boiling point than an ester because it can both donate and accept hydrogen bonds within its liquid state; hydrogen bonding does not occur in the ester. Consequently, pentanoic acid (valeric acid) has a higher boiling point than methyl butanoate. Here are the actual data: INSTRUCTOR SUPPLEMENTAL SOLUTIONS TO PROBLEMS • CHAPTER 21 2 21.7 (a) The carbonyl absorption of the ester occurs at higher frequency, and only the carboxylic acid has the characteristic strong, broad O—H stretching absorption in 2400–3600 cm–1 region. (d) In N-methylpropanamide, the N-methyl group is a doublet at about d 3. N-Ethylacetamide has no doublet resonances. In N-methylpropanamide, the a-protons are a quartet near d 2.5. In N-ethylacetamide, the a- protons are a singlet at d 2. The NMR spectrum of N-methylpropanamide has no singlets. 21.9 (a) The first ester is more basic because its conjugate acid is stabilized not only by resonance interaction with the ester oxygen, but also by resonance interaction with the double bond; that is, the conjugate acid of the first ester has one more important resonance structure than the conjugate acid of the second. -
Transport of Dangerous Goods
ST/SG/AC.10/1/Rev.16 (Vol.I) Recommendations on the TRANSPORT OF DANGEROUS GOODS Model Regulations Volume I Sixteenth revised edition UNITED NATIONS New York and Geneva, 2009 NOTE The designations employed and the presentation of the material in this publication do not imply the expression of any opinion whatsoever on the part of the Secretariat of the United Nations concerning the legal status of any country, territory, city or area, or of its authorities, or concerning the delimitation of its frontiers or boundaries. ST/SG/AC.10/1/Rev.16 (Vol.I) Copyright © United Nations, 2009 All rights reserved. No part of this publication may, for sales purposes, be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, electrostatic, magnetic tape, mechanical, photocopying or otherwise, without prior permission in writing from the United Nations. UNITED NATIONS Sales No. E.09.VIII.2 ISBN 978-92-1-139136-7 (complete set of two volumes) ISSN 1014-5753 Volumes I and II not to be sold separately FOREWORD The Recommendations on the Transport of Dangerous Goods are addressed to governments and to the international organizations concerned with safety in the transport of dangerous goods. The first version, prepared by the United Nations Economic and Social Council's Committee of Experts on the Transport of Dangerous Goods, was published in 1956 (ST/ECA/43-E/CN.2/170). In response to developments in technology and the changing needs of users, they have been regularly amended and updated at succeeding sessions of the Committee of Experts pursuant to Resolution 645 G (XXIII) of 26 April 1957 of the Economic and Social Council and subsequent resolutions. -
Effect of Enzymes on Strawberry Volatiles During Storage, at Different Ripeness
Effect of Enzymes on Strawberry Volatiles During Storage, at Different Ripeness Level, in Different Cultivars and During Eating Thesis Presented in Partial Fulfillment of the Requirements for the Degree Master of Science in the Graduate School of The Ohio State University By Gulsah Ozcan Graduate Program in Food Science and Technology The Ohio State University 2010 Thesis Committee: Sheryl Ann Barringer, Adviser W. James Harper John Litchfield 1 Copyright by Gülşah Özcan 2010 ii ABSTRACT Strawberry samples with enzyme activity and without enzyme activity (stannous chloride added) were measured for real time formation of lipoxygenase (LOX) derived aroma compounds after 5 min pureeing using selected ion flow tube mass spectrometry (SIFT-MS). The concentration of (Z)-3-hexenal and (E)-2-hexenal increased immediately after blending and gradually decreased over time while hexanal concentration increased for at least 5 min in ground strawberries. The formation of hexanal was slower than the formation of (Z)-3-hexenal and (E)-2-hexenal in the headspace of pureed strawberries. The concentration of LOX aldehydes and esters significantly increased during refrigerated storage. Damaging strawberries increased the concentration of LOX aldehydes but did not significantly affect the concentration of esters. The concentrations of many of the esters were strongly correlated to their corresponded acids and/or aldehydes. The concentration of LOX generated aldehydes decreased during ripening, while fruity esters increased. Different varieties had different aroma profiles and esters were the greatest percentage of the volatiles. The aroma release of some of the LOX derived aldehydes in the mouthspace in whole strawberries compared to chopped strawberries showed that these volatiles are formed in the mouth during chewing. -
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Interspecific Hybrids Reveal Increased Fermentation Abilities and a Mosaic Metabolic Profile
Preprints (www.preprints.org) | NOT PEER-REVIEWED | Posted: 9 December 2019 doi:10.20944/preprints201912.0109.v1 Peer-reviewed version available at Fermentation 2020, 6, 14; doi:10.3390/fermentation6010014 Saccharomyces Arboricola and Its Hybrids’ Propensity for Sake Production: Interspecific Hybrids Reveal Increased Fermentation Abilities and a Mosaic Metabolic Profile Matthew J. Winans1,2,*, Yuki Yamamoto1, Yuki Fujimaru1, Yuki Kusaba1, Jennifer E.G. Gallagher2, Hiroshi Kitagaki1 1Saga University of Agriculture, Saga City, Saga, Japan 2West Virginia University, Morgantown, West Virginia, United States of America *Corresponding Author: Matthew J. Winans Email: [email protected] Telephone: (304) 483-1786 Fax: (304) 293-6363 Address: 53 Campus Drive, West Virginia University – Biology Department, Morgantown, W.Va., 26506-6057, USA Abstract The use of interspecific hybrids during the industrial fermentation process has been well established, positioning the frontier of advancement in brewing to capitalize on the potential of Saccharomyces hybridization. Interspecific yeast hybrids used in modern monoculture inoculations benefit from a wide range of volatile metabolites that broaden the organoleptic complexity. This is the first report of sake brewing by Saccharomyces arboricola and its hybrids. S. arboricola x S. cerevisiae direct-mating generated cryotolerant interspecific hybrids which increased yields of ethanol and ethyl hexanoate compared to parental strains, important flavor attributes of fine Japanese ginjo sake rice wine. We used hierarchical clustering heatmapping with principal component analysis for metabolic profiling and found that the low levels of endogenous amino/organic acids clustered S. arboricola apart from the S. cerevisiae industrial strains. In sake fermentations, hybrid strains showed a mosaic profile of parental strains, while metabolic analysis suggested S. -
The Composition of Strawberry Aroma Is Influenced by Cultivar, Maturity, and Storage Charles F
WORKSHOP The Composition of Strawberry Aroma Is Influenced by Cultivar, Maturity, and Storage Charles F. Forney1, Willy Kalt2, and Michael A. Jordan3 Agriculture and Agri-Food Canada, Atlantic Food and Horticulture Research Centre, 32 Main Street, Kentville, N.S., B4N 1J5, Canada Strawberry (Fragaria ×ananassa Duch.) fruit have a unique, they both may contribute to strawberry aroma (Dirinck et al., 1981; highly desirable flavor and are one of the most popular summer fruits. Schreier, 1980). Sugars, acids, and aroma volatiles contribute to the characteristic The volatile profile obtained from strawberry fruit is influenced by strawberry flavor, which is dependent on the proper balance of these the analytical methods used to characterize these compounds. Volatiles chemical constituents. While sugars and acids are responsible for the from whole, intact fruit can be collected using headspace techniques; sweetness and tartness of the fruit, aroma volatiles provide the unique, these samples can be analyzed directly or concentrated using adsor- fruity flavors that characterize a fresh strawberry. bent or cold traps. Volatiles are also collected from homogenized fruit The aroma of fresh strawberries is dependent on many factors. The or juice, using either headspace or solvent extraction techniques. large genetic variability in the nature of strawberry aroma results in Volatile samples are normally analyzed by gas liquid chromatography differences in flavor among cultivars. In addition, the aroma changes using a variety of methods of sample introduction, including liquid dramatically during fruit ripening after harvest; therefore, it is impor- injection, thermal desorption, and cold on-column injection. High tant to preserve and enhance the ripe fruit aroma during postharvest performance liquid chromatography (HPLC) has been used for some handling. -
Differences in Volatile Ester Composition Between Fragaria Ananassa and F
Scientia Horticulturae 150 (2013) 47–53 Contents lists available at SciVerse ScienceDirect Scientia Horticulturae journa l homepage: www.elsevier.com/locate/scihorti × Differences in volatile ester composition between Fragaria ananassa and F. ଝ vesca and implications for strawberry aroma patterns a,b b c b a,∗ Jing Dong , Yuntao Zhang , Xiaowei Tang , Wanmei Jin , Zhenhai Han a Institute for Horticultural Plants, College of Agronomy and Biotechnology, China Agricultural University, No. 2 Yuanmingyuan West Road, Haidian District, Beijing 100193, PR China b Institute of Forestry and Pomology, Beijing Academy of Agriculture and Forestry Sciences, No. 12 Ruiwangfen, Xiangshan, Haidian District, Beijing 100093, PR China c Beijing Vegetable Research Center, Beijing Academy of Agriculture and Forestry Sciences, Banjin, Haidian District, Beijing 100097, PR China a r t i c l e i n f o a b s t r a c t Article history: Esters are a very important component of strawberry (Fragaria sp.) aroma. In this study, fruit volatiles Received 8 April 2012 were isolated by solid-phase microextraction and analyzed by gas chromatography–mass spectrometry Received in revised form 1 November 2012 (SPME/GC–MS). It was found that F. × ananassa had more esters than F. vesca, but there was no significant Accepted 1 November 2012 difference in average relative content of esters. Twenty five esters were selected as predominant esters, 16 of which were prevalent in F. × ananassa and another 16 in F. vesca. Among them, hexyl acetate, Keywords: octyl acetate, ethyl butyrate, ethyl hexanoate, ethyl octanoate, methyl decanoate, and ethyl decanoate Volatile ester composition were found in both F. -
Estimation of Hydrolysis Rate Constants of Carboxylic Acid Ester and Phosphate Ester Compounds in Aqueous Systems from Molecular Structure by SPARC
Estimation of Hydrolysis Rate Constants of Carboxylic Acid Ester and Phosphate Ester Compounds in Aqueous Systems from Molecular Structure by SPARC R E S E A R C H A N D D E V E L O P M E N T EPA/600/R-06/105 September 2006 Estimation of Hydrolysis Rate Constants of Carboxylic Acid Ester and Phosphate Ester Compounds in Aqueous Systems from Molecular Structure by SPARC By S. H. Hilal Ecosystems Research Division National Exposure Research Laboratory Athens, Georgia U.S. Environmental Protection Agency Office of Research and Development Washington, DC 20460 NOTICE The information in this document has been funded by the United States Environmental Protection Agency. It has been subjected to the Agency's peer and administrative review, and has been approved for publication. Mention of trade names of commercial products does not constitute endorsement or recommendation for use. ii ABSTRACT SPARC (SPARC Performs Automated Reasoning in Chemistry) chemical reactivity models were extended to calculate hydrolysis rate constants for carboxylic acid ester and phosphate ester compounds in aqueous non- aqueous and systems strictly from molecular structure. The energy differences between the initial state and the transition state for a molecule of interest are factored into internal and external mechanistic perturbation components. The internal perturbations quantify the interactions of the appended perturber (P) with the reaction center (C). These internal perturbations are factored into SPARC’s mechanistic components of electrostatic and resonance effects. External perturbations quantify the solute-solvent interactions (solvation energy) and are factored into H-bonding, field stabilization and steric effects. These models have been tested using 1471 reliable measured base, acid and general base-catalyzed carboxylic acid ester hydrolysis rate constants in water and in mixed solvent systems at different temperatures. -
University Microfilms, Inc., Ann Arbor, Michigan BIOCHEMICAL STUDIES of ZOOGLOEA RAMIGERA ISOLATE 115
This dissertation has been microfilmed exactly as received 69-11,658 JOYCE, Gayle Hahn, 1937- BIOCHEMICAL STUDIES OF ZOOGLOEA RAMIGERA ISOLATE 115 WITH EMPHASIS ON ETHYL ALCOHOL METABOLISM. The Ohio State University, Ph.D., 1968 Microbiology University Microfilms, Inc., Ann Arbor, Michigan BIOCHEMICAL STUDIES OF ZOOGLOEA RAMIGERA ISOLATE 115 WITH EMPHASIS ON ETHYL ALCOHOL METABOLISM DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University v * By Gayle hT Joyce, B.S., M.S. ****** The Ohio State University 1968 Approved by / Adviser ' fj . qpobiAcademic Faculty of Miqpobial.qpobiAcademic and Cellular Biology ACKNOWLEDGMENTS The author wishes to express her sincere gratitude to Dr. Patrick R. Dugan for the many helpful suggestions and guidance given during the course of this study and in the preparation of this manuscript. Her appreciation is expressed to the graduate students of the Faculty of Microbial and Cellular Biology, particularly to Mr. Jon Tuttle, for their helpful discussions and assistance, to Mrs. John Olenzak for her technical assistance, and to Mr. Robert Joyce for his patience during the course of this study. The use of the facilities of the Water Resources Center of The Ohio State University is appreciated. The research was supported in part by Research Grant No. WP-00713 from the Federal Water Pollution Control Administration, U.S. Department of the Interior. VITA September 10, 1937 Born - Cleveland, Ohio 1959 ....... B.S., Kent State University, Kent, Ohio 1959-1961 ........ Research Assistant, Department of Microbiology, The Pennsylvania State University, University Park, Pennsylvania 1961 ...... -
Comprehensive Characterization of Toxicity of Fermentative Metabolites on Microbial Growth Brandon Wilbanks1 and Cong T
Wilbanks and Trinh Biotechnol Biofuels (2017) 10:262 DOI 10.1186/s13068-017-0952-4 Biotechnology for Biofuels RESEARCH Open Access Comprehensive characterization of toxicity of fermentative metabolites on microbial growth Brandon Wilbanks1 and Cong T. Trinh1,2* Abstract Background: Volatile carboxylic acids, alcohols, and esters are natural fermentative products, typically derived from anaerobic digestion. These metabolites have important functional roles to regulate cellular metabolisms and broad use as food supplements, favors and fragrances, solvents, and fuels. Comprehensive characterization of toxic efects of these metabolites on microbial growth under similar conditions is very limited. Results: We characterized a comprehensive list of thirty-two short-chain carboxylic acids, alcohols, and esters on microbial growth of Escherichia coli MG1655 under anaerobic conditions. We analyzed toxic efects of these metabo- lites on E. coli health, quantifed by growth rate and cell mass, as a function of metabolite types, concentrations, and physiochemical properties including carbon number, chemical functional group, chain branching feature, energy density, total surface area, and hydrophobicity. Strain characterization revealed that these metabolites exert distinct toxic efects on E. coli health. We found that higher concentrations and/or carbon numbers of metabolites cause more severe growth inhibition. For the same carbon numbers and metabolite concentrations, we discovered that branched chain metabolites are less toxic than the linear chain ones. Remarkably, shorter alkyl esters (e.g., ethyl butyrate) appear less toxic than longer alkyl esters (e.g., butyl acetate). Regardless of metabolites, hydrophobicity of a metabolite, gov- erned by its physiochemical properties, strongly correlates with the metabolite’s toxic efect on E. coli health. -
Esterification for Butyl Butyrate Formation Using Candida
Arabian Journal of Chemistry (2013) xxx, xxx–xxx King Saud University Arabian Journal of Chemistry www.ksu.edu.sa www.sciencedirect.com ORIGINAL ARTICLE Esterification for butyl butyrate formation using Candida cylindracea lipase produced from palm oil mill effluent supplemented medium Aliyu Salihu a,b,*, Md. Zahangir Alam a, M. Ismail AbdulKarim a, Hamzah M. Salleh a a Bioenvironmental Engineering Research Unit (BERU), Department of Biotechnology Engineering, Faculty of Engineering, International Islamic University Malaysia (IIUM), 50728 Kuala Lumpur, Gombak, Malaysia b Department of Biochemistry, Ahmadu Bello University, Zaria, Nigeria Received 1 September 2011; accepted 16 August 2013 KEYWORDS Abstract The ability of Candida cylindracea lipase produced using palm oil mill effluent (POME) Lipase; as a basal medium to catalyze the esterification reaction for butyl butyrate formation was investi- Butyl butyrate; gated. Butyric acid and n-butanol were used as substrates at different molar ratios. Different con- Esterification; version yields were observed according to the affinity of the produced lipase toward the substrates. Palm oil mill effluent The n-butanol to butyric acid molar ratio of 8 and lipase concentration of 75 U/mg gave the highest butyl butyrate formation of 63.33% based on the statistical optimization using face centered central composite design (FCCCD) after 12 h reaction. The esterification potential of the POME based lipase when compared with the commercial lipase from the same strain using the optimum levels was found to show a similar pattern. It can be concluded therefore that the produced lipase pos- sesses appropriate characteristics to be used as a biocatalyst in the esterification reactions for butyl butyrate formation.